Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect
ACS Publications. Most Trusted. Most Cited. Most Read
2-Imino-thiazolidin-4-one Derivatives as Potent, Orally Active S1P1 Receptor Agonists

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Med. Chem. 2010, 53, 10, 4198-4211
    Article

    2-Imino-thiazolidin-4-one Derivatives as Potent, Orally Active S1P1 Receptor Agonists
    Click to copy article linkArticle link copied!

    View Author Information
    Drug Discovery Chemistry, Actelion Pharmaceuticals Ltd., Gewerbestrasse 16, CH-4123 Allschwil, Switzerland
    *To whom correspondence should be addressed. Phone: + 41 61 565 65 70. Fax: + 41 61 565 65 00. E-mail: [email protected]
    Other Access OptionsSupporting Information (1)

    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2010, 53, 10, 4198–4211
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm100181s
    Published May 6, 2010
    Copyright © 2010 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Sphingosine-1-phosphate (S1P) is a widespread lysophospholipid which displays a wealth of biological effects. Extracellular S1P conveys its activity through five specific G-protein coupled receptors numbered S1P1 through S1P5. Agonists of the S1P1 receptor block the egress of T-lymphocytes from thymus and lymphoid organs and hold promise for the oral treatment of autoimmune disorders. Here, we report on the discovery and detailed structure−activity relationships of a novel class of S1P1 receptor agonists based on the 2-imino-thiazolidin-4-one scaffold. Compound 8bo (ACT-128800) emerged from this series and is a potent, selective, and orally active S1P1 receptor agonist selected for clinical development. In the rat, maximal reduction of circulating lymphocytes was reached at a dose of 3 mg/kg. The duration of lymphocyte sequestration was dose dependent. At a dose of 100 mg/kg, the effect on lymphocyte counts was fully reversible within less than 36 h. Pharmacokinetic investigation of 8bo in beagle dogs suggests that the compound is suitable for once daily dosing in humans.

    Copyright © 2010 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    Experimental details on the synthesis and characterization, including biological assays, of the 2-imino-thiazolidin-4-one scaffolds 3, 4, 5, 6, additional 2-imino-thiazolidin-4-one scaffolds, and target compounds 8 prepared for this study. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 156 publications.

    1. Emma L. McInturff, Scott P. France, Carolyn A. Leverett, Andrew C. Flick, Erick A. Lindsey, Simon Berritt, Daniel W. Carney, Jacob C. DeForest, Hong X. Ding, Sarah J. Fink, Tony S. Gibson, Kaitlyn Gray, Aran K. Hubbell, Amber M. Johnson, Yiyang Liu, Subham Mahapatra, Indrawan J. McAlpine, Rebecca B. Watson, Christopher J. O’Donnell. Synthetic Approaches to the New Drugs Approved During 2021. Journal of Medicinal Chemistry 2023, 66 (15) , 10150-10201. https://doi.org/10.1021/acs.jmedchem.3c00501
    2. Yiting Wang, Xianfu Fang, Huilin Liao, Gong Zhang, Yangfeng Li, Yizhou Li. DNA-Compatible Synthesis of Thiazolidione Derivatives via Three-Component Annulation and Knoevenagel Condensation. Organic Letters 2023, 25 (24) , 4473-4477. https://doi.org/10.1021/acs.orglett.3c01482
    3. Erika Araujo, Ian M. Bell, Alexander BurckleDennis C. KoesterJames R. Manning, Richard D. Caldwell, Georgette CastanedoSamantha A. GreenMingshuo Zeng, Laurent Debien, T. G. Murali Dhar, Natalie Holmberg-DouglasEric R. Welin, J. Robert Merritt, Kevin M. Peese, Denise C. Grünenfelder, Julian C. Lo. TO MARKET, TO MARKET–2021: SMALL MOLECULES. , 587-731. https://doi.org/10.1021/mc-2022-vol57.ch24
    4. Mark Bell, David Foley, Claire Naylor, Gavin Wood, Colin Robinson, Jennifer Riley, Ola Epemolu, Lucy Ellis, Paul Scullion, Yoko Shishikura, Maria Osuna-Cabello, Liam Ferguson, Erika Pinto, Daniel Fletcher, Elad Katz, W. H. Irwin McLean, Paul Wyatt, Kevin D Read, Andrew Woodland. Discovery of Soft-Drug Topical Tool Modulators of Sphingosine-1-phosphate Receptor 1 (S1PR1). ACS Medicinal Chemistry Letters 2019, 10 (3) , 341-347. https://doi.org/10.1021/acsmedchemlett.8b00616
    5. Wei Guo, Mingming Zhao, Wen Tan, Lvyin Zheng, Kailiang Tao, Lingxiu Liu, Xinyu Wang, Deliang Chen, and Xiaolin Fan . Visible Light-Promoted Three-Component Tandem Annulation for the Synthesis of 2-Iminothiazolidin-4-ones. The Journal of Organic Chemistry 2018, 83 (3) , 1402-1413. https://doi.org/10.1021/acs.joc.7b02940
    6. Haruto Kurata, Kensuke Kusumi, Kazuhiro Otsuki, Ryo Suzuki, Masakuni Kurono, Takaki Komiya, Hiroshi Hagiya, Hirotaka Mizuno, Hiroki Shioya, Takeji Ono, Yuka Takada, Tatsuo Maeda, Norikazu Matsunaga, Tetsu Kondo, Sachiko Tominaga, Ken-ici Nunoya, Hidekazu Kiyoshi, Masaharu Komeno, Shinji Nakade, and Hiromu Habashita . Discovery of a 1-Methyl-3,4-dihydronaphthalene-Based Sphingosine-1-Phosphate (S1P) Receptor Agonist Ceralifimod (ONO-4641). A S1P1 and S1P5 Selective Agonist for the Treatment of Autoimmune Diseases. Journal of Medicinal Chemistry 2017, 60 (23) , 9508-9530. https://doi.org/10.1021/acs.jmedchem.7b00785
    7. Alaric J. Dyckman . Modulators of Sphingosine-1-phosphate Pathway Biology: Recent Advances of Sphingosine-1-phosphate Receptor 1 (S1P1) Agonists and Future Perspectives. Journal of Medicinal Chemistry 2017, 60 (13) , 5267-5289. https://doi.org/10.1021/acs.jmedchem.6b01575
    8. Hai-Yun Xiao, Scott H. Watterson, Charles M. Langevine, Anurag S. Srivastava, Soo S. Ko, Yanlei Zhang, Robert J. Cherney, Wei-Wei Guo, John L. Gilmore, James E. Sheppeck, II, Dauh-Rurng Wu, Peng Li, Duraisamy Ramasamy, Piramanayagam Arunachalam, Arvind Mathur, Tracy L. Taylor, David J. Shuster, Kim W. McIntyre, Ding-Ren Shen, Melissa Yarde, Mary Ellen Cvijic, Anthony M. Marino, Praveen V. Balimane, Zheng Yang, Dana M. Banas, Georgia Cornelius, Celia J. D’Arienzo, Bethanne M. Warrack, Lois Lehman-McKeeman, Luisa M. Salter-Cid, Jenny Xie, Joel C. Barrish, Percy H. Carter, Alaric J. Dyckman, and T. G. Murali Dhar . Identification of Tricyclic Agonists of Sphingosine-1-phosphate Receptor 1 (S1P1) Employing Ligand-Based Drug Design. Journal of Medicinal Chemistry 2016, 59 (21) , 9837-9854. https://doi.org/10.1021/acs.jmedchem.6b01099
    9. Nicholas A. Meanwell . 2015 Philip S. Portoghese Medicinal Chemistry Lectureship. Curing Hepatitis C Virus Infection with Direct-Acting Antiviral Agents: The Arc of a Medicinal Chemistry Triumph. Journal of Medicinal Chemistry 2016, 59 (16) , 7311-7351. https://doi.org/10.1021/acs.jmedchem.6b00915
    10. T. G. Murali Dhar, Hai-Yun Xiao, Jenny Xie, Lois D. Lehman-McKeeman, Dauh-Rurng Wu, Marta Dabros, Xiaoxia Yang, Tracy L. Taylor, Xia D. Zhou, Elizabeth M. Heimrich, Rochelle Thomas, Kim W. McIntyre, Bethanne Warrack, Hong Shi, Paul C. Levesque, Jia L. Zhu, James Hennan, Praveen Balimane, Zheng Yang, Anthony M. Marino, Georgia Cornelius, Celia J. D’Arienzo, Arvind Mathur, Ding Ren Shen, Mary Ellen Cvijic, Luisa Salter-Cid, Joel C. Barrish, Percy H. Carter, and Alaric J. Dyckman . Identification and Preclinical Pharmacology of BMS-986104: A Differentiated S1P1 Receptor Modulator in Clinical Trials. ACS Medicinal Chemistry Letters 2016, 7 (3) , 283-288. https://doi.org/10.1021/acsmedchemlett.5b00448
    11. Emmanuel H. Demont, James M. Bailey, Rino A. Bit, Jack A. Brown, Colin A. Campbell, Nigel Deeks, Simon J. Dowell, Colin Eldred, Pam Gaskin, James R. J. Gray, Andrea Haynes, David J. Hirst, Duncan S. Holmes, Umesh Kumar, Mary A. Morse, Greg J. Osborne, Jessica F. Renaux, Gail A. L. Seal, Chris A. Smethurst, Simon Taylor, Robert Watson, Robert Willis, and Jason Witherington . Discovery of Tetrahydropyrazolopyridine as Sphingosine 1-Phosphate Receptor 3 (S1P3)-Sparing S1P1 Agonists Active at Low Oral Doses. Journal of Medicinal Chemistry 2016, 59 (3) , 1003-1020. https://doi.org/10.1021/acs.jmedchem.5b01512
    12. Adrian D. Hobson, Christopher M. Harris, Elizabeth L. van der Kam, Sean C. Turner, Ayome Abibi, Ana L. Aguirre, Peter Bousquet, Tegest Kebede, Donald B. Konopacki, Gary Gintant, Youngjae Kim, Kelly Larson, John W. Maull, Nigel S. Moore, Dan Shi, Anurupa Shrestha, Xiubo Tang, Peng Zhang, and Kathy K. Sarris . Discovery of A-971432, An Orally Bioavailable Selective Sphingosine-1-Phosphate Receptor 5 (S1P5) Agonist for the Potential Treatment of Neurodegenerative Disorders. Journal of Medicinal Chemistry 2015, 58 (23) , 9154-9170. https://doi.org/10.1021/acs.jmedchem.5b00928
    13. Yogesh B. Wagh, Anil S. Kuwar, Dipak R. Patil, Yogesh A. Tayade, Asha D. Jangale, Santosh S. Terdale, Darshak R. Trivedi, Judith Gallucci, and Dipak S. Dalal . Highly Efficient Regioselective Synthesis of 2-Imino-4-oxothiazolidin-5-ylidene Acetates via a Substitution-Dependent Cyclization Sequence under Catalyst-Free Conditions at Ambient Temperature. Industrial & Engineering Chemistry Research 2015, 54 (40) , 9675-9682. https://doi.org/10.1021/acs.iecr.5b01746
    14. Martin H. Bolli, Jörg Velker, Claus Müller, Boris Mathys, Magdalena Birker, Roberto Bravo, Daniel Bur, Ruben de Kanter, Patrick Hess, Christopher Kohl, David Lehmann, Solange Meyer, Oliver Nayler, Markus Rey, Michael Scherz, and Beat Steiner . Novel S1P1 Receptor Agonists - Part 2: From Bicyclo[3.1.0]hexane-Fused Thiophenes to Isobutyl Substituted Thiophenes. Journal of Medicinal Chemistry 2014, 57 (1) , 78-97. https://doi.org/10.1021/jm401456d
    15. Martin H. Bolli, Stefan Abele, Magdalena Birker, Roberto Bravo, Daniel Bur, Ruben de Kanter, Christopher Kohl, Julien Grimont, Patrick Hess, Cyrille Lescop, Boris Mathys, Claus Müller, Oliver Nayler, Markus Rey, Michael Scherz, Gunther Schmidt, Jürgen Seifert, Beat Steiner, Jörg Velker, and Thomas Weller . Novel S1P1 Receptor Agonists − Part 3: From Thiophenes to Pyridines. Journal of Medicinal Chemistry 2014, 57 (1) , 110-130. https://doi.org/10.1021/jm4014696
    16. Martin H. Bolli, Claus Müller, Boris Mathys, Stefan Abele, Magdalena Birker, Roberto Bravo, Daniel Bur, Patrick Hess, Christopher Kohl, David Lehmann, Oliver Nayler, Markus Rey, Solange Meyer, Michael Scherz, Gunther Schmidt, Beat Steiner, Alexander Treiber, Jörg Velker, and Thomas Weller . Novel S1P1 Receptor Agonists – Part 1: From Pyrazoles to Thiophenes. Journal of Medicinal Chemistry 2013, 56 (23) , 9737-9755. https://doi.org/10.1021/jm4014373
    17. Feng Ren, Guanghui Deng, Hailong Wang, Linbo Luan, Qinghua Meng, Qiongfeng Xu, Heng Xu, Xuesong Xu, Haibo Zhang, Baowei Zhao, Chengyong Li, Taylor B. Guo, Jiansong Yang, Wei Zhang, Yonggang Zhao, Qiantao Jia, Hongtao Lu, Jia-Ning Xiang, John D. Elliott, and Xichen Lin . Discovery of Novel 1,2,4-Thiadiazole Derivatives as Potent, Orally Active Agonists of Sphingosine 1-Phosphate Receptor Subtype 1 (S1P1). Journal of Medicinal Chemistry 2012, 55 (9) , 4286-4296. https://doi.org/10.1021/jm2016107
    18. Orazio A. Attanasi, Silvia Bartoccini, Gianfranco Favi, Gianluca Giorgi, Francesca Romana Perrulli, and Stefania Santeusanio . Powerful Approach to Heterocyclic Skeletal Diversity by Sequential Three-Component Reaction of Amines, Isothiocyanates, and 1,2-Diaza-1,3-dienes. The Journal of Organic Chemistry 2012, 77 (2) , 1161-1167. https://doi.org/10.1021/jo2021949
    19. Emmanuel H. Demont, Sandra Arpino, Rino A. Bit, Colin A. Campbell, Nigel Deeks, Sapna Desai, Simon J. Dowell, Pam Gaskin, James R. J. Gray, Lee A. Harrison, Andrea Haynes, Tom D. Heightman, Duncan S. Holmes, Philip G. Humphreys, Umesh Kumar, Mary A. Morse, Greg J. Osborne, Terry Panchal, Karen L. Philpott, Simon Taylor, Robert Watson, Robert Willis, and Jason Witherington . Discovery of a Brain-Penetrant S1P3-Sparing Direct Agonist of the S1P1 and S1P5 Receptors Efficacious at Low Oral Dose. Journal of Medicinal Chemistry 2011, 54 (19) , 6724-6733. https://doi.org/10.1021/jm200609t
    20. Emmanuel H. Demont, Benjamin I. Andrews, Rino A. Bit, Colin A. Campbell, Jason W. B. Cooke, Nigel Deeks, Sapna Desai, Simon J. Dowell, Pam Gaskin, James R. J. Gray, Andrea Haynes, Duncan S. Holmes, Umesh Kumar, Mary A. Morse, Greg J. Osborne, Terry Panchal, Bela Patel, Alcide Perboni, Simon Taylor, Robert Watson, Jason Witherington, and Robert Willis . Discovery of a Selective S1P1 Receptor Agonist Efficacious at Low Oral Dose and Devoid of Effects on Heart Rate. ACS Medicinal Chemistry Letters 2011, 2 (6) , 444-449. https://doi.org/10.1021/ml2000214
    21. Jeffrey L. Romine, Denis R. St. Laurent, John E. Leet, Scott W. Martin, Michael H. Serrano-Wu, Fukang Yang, Min Gao, Donald R O’Boyle, II, Julie A. Lemm, Jin-Hua Sun, Peter T. Nower, Xiaohua (Stella) Huang, Milind S. Deshpande, Nicholas A. Meanwell, and Lawrence B. Snyder . Inhibitors of HCV NS5A: From Iminothiazolidinones to Symmetrical Stilbenes. ACS Medicinal Chemistry Letters 2011, 2 (3) , 224-229. https://doi.org/10.1021/ml1002647
    22. Daosong Dong, Xue Yu, Xueshu Tao, Qian Wang, Lin Zhao. S1P/S1PR1 signaling is involved in the development of nociceptive pain. Frontiers in Pharmacology 2024, 15 https://doi.org/10.3389/fphar.2024.1407347
    23. Son Nguyen Thi, Duc Nguyen Van, Linh Nguyen Nhat Thuy, Anh Pham Nam, Boi Luu Van, Hoang Do Huy. Microwave-supported one-pot reaction for the synthesis of 5-alkyl/arylidene-2-(morpholin/thiomorpholin-4-yl)-1,3-thiazol-4( 5H )-one derivatives over MgO solid base. Green Processing and Synthesis 2024, 13 (1) https://doi.org/10.1515/gps-2024-0054
    24. Alexander Treiber, Swen Seeland, Jérôme Segrestaa, Cyrille Lescop, Martin H. Bolli. Reversible oxidation/reduction steps in the metabolic degradation of the glycerol side chain of the S1P 1 modulator ponesimod. Xenobiotica 2024, 54 (4) , 182-194. https://doi.org/10.1080/00498254.2024.2319812
    25. Yu-Xin Xie, Hui Yao, Jin-Fu Peng, Dan Ni, Wan-Ting Liu, Chao-Quan Li, Guang-Hui Yi. Insight into modulators of sphingosine-1-phosphate receptor and implications for cardiovascular therapeutics. Journal of Drug Targeting 2024, 32 (3) , 300-310. https://doi.org/10.1080/1061186X.2024.2309577
    26. Wanxing Liu, Zhehui Mao, Daohuang Chong, Zhaoxue Wang, Keying Zhang, Lingang Wu, Lei Xie. Lewis base-catalyzed [3 + 2] annulation of β-oxo-acrylamides with acyl isothiocyanates: Facile access to 2-iminothiazolidin-4-one derivatives. Tetrahedron Letters 2024, 21 , 155022. https://doi.org/10.1016/j.tetlet.2024.155022
    27. Shreyash D. Kadam, Denni Mammen, Vishwanath Zunjar, Rahul R. Bagul, . Novel fluorinated thiazolidin-4-one derivatives: synthesis and anti-cancer potential against HepG2 and HCT116 cell lines. Australian Journal of Chemistry 2024, 77 (9) https://doi.org/10.1071/CH23123
    28. Yunxuan Li, Guanglei Nan, Xianxin Hou, Yechao Yan, Yajun Yang, Ying Yang, Ke Li, Zhiyan Xiao. Non-peptidic immunoproteasome β5i-selective inhibitor as potential treatment for idiopathic pulmonary fibrosis: Virtual screening, hit evolution and lead identification. European Journal of Medicinal Chemistry 2023, 261 , 115856. https://doi.org/10.1016/j.ejmech.2023.115856
    29. Terra M. Kruger, Belén Valenzuela, Charles D. Thompson, Sivi Ouwerkerk-Mahadevan, Juan Jose Perez Ruixo. Clinical Pharmacokinetics of Ponesimod, a Selective S1P1 Receptor Modulator, in the Treatment of Multiple Sclerosis. Clinical Pharmacokinetics 2023, 62 (11) , 1533-1550. https://doi.org/10.1007/s40262-023-01308-5
    30. Sandra Bien-Möller, Fan Chen, Yong Xiao, Hanjo Köppe, Gabriele Jedlitschky, Ulrike Meyer, Céline Tolksdorf, Markus Grube, Sascha Marx, Mladen V. Tzvetkov, Henry W. S. Schroeder, Bernhard H. Rauch. The Putative S1PR1 Modulator ACT-209905 Impairs Growth and Migration of Glioblastoma Cells In Vitro. Cancers 2023, 15 (17) , 4273. https://doi.org/10.3390/cancers15174273
    31. Kihang Choi. The Structure-property Relationships of GPCR-targeted Drugs Approved between 2011 and 2021. Current Medicinal Chemistry 2023, 30 (31) , 3527-3549. https://doi.org/10.2174/1573399819666221102113217
    32. Yasuyuki Kihara, Jerold Chun. Molecular and neuroimmune pharmacology of S1P receptor modulators and other disease-modifying therapies for multiple sclerosis. Pharmacology & Therapeutics 2023, 246 , 108432. https://doi.org/10.1016/j.pharmthera.2023.108432
    33. Elham Sardari, Ahmad Ebadi, Nima Razzaghi-Asl. In silico repurposing of CNS drugs for multiple sclerosis. Multiple Sclerosis and Related Disorders 2023, 73 , 104622. https://doi.org/10.1016/j.msard.2023.104622
    34. Omid Jamshidi Kandjani, Shadi Yaqoubi, Samad Shams Vahdati, Behnam Borhannejad, Siavoush Dastmalchi, Ali Akbar Alizadeh. S1PR1 modulators in multiple sclerosis: Efficacy, safety, comparison, and chemical structure insights. European Journal of Medicinal Chemistry 2023, 250 , 115182. https://doi.org/10.1016/j.ejmech.2023.115182
    35. Mingming Zhao, Yiming Guo, Qi Wang, Lanqi Liu, Shujie Zhang, Wei Guo, Lin-Ping Wu, Fayang G. Qiu. Synthesis of 2-iminothiazolidin-4-ones via copper-catalyzed [2 + 1 + 2] tandem annulation. RSC Advances 2023, 13 (4) , 2220-2224. https://doi.org/10.1039/D2RA07872D
    36. Zilin Gao, Wenbo Huang, Manli Liu, Yu Chen, Liqiao Shi, Zhigang Zhang, Fei Yang, Xiufang Cao, Kaimei Wang, Shaoyong Ke. Highly efficient construction of multi-substituted aminopyrazoles derivatives via iodine-mediated three-components reaction as potential anticancer agents. Green Chemistry Letters and Reviews 2023, 16 (1) https://doi.org/10.1080/17518253.2023.2264324
    37. Shuo Yuan, Dan-Shu Wang, Hui Liu, Sheng-Nan Zhang, Wei-Guang Yang, Meng Lv, Yu-Xue Zhou, Sai-Yang Zhang, Jian Song, Hong-Min Liu. New drug approvals for 2021: Synthesis and clinical applications. European Journal of Medicinal Chemistry 2023, 245 , 114898. https://doi.org/10.1016/j.ejmech.2022.114898
    38. David Baker, Eugenia Forte, Gareth Pryce, Angray S. Kang, Louisa K. James, Gavin Giovannoni, Klaus Schmierer. The impact of sphingosine-1-phosphate receptor modulators on COVID-19 and SARS-CoV-2 vaccination. Multiple Sclerosis and Related Disorders 2023, 69 , 104425. https://doi.org/10.1016/j.msard.2022.104425
    39. Stanley Cohan, Chiayi Chen. Sphingosine-1-phosphate, its receptors, and their role in multiple sclerosis. 2023, 145-173. https://doi.org/10.1016/B978-0-443-18578-6.00009-X
    40. Huan He, Mengting Xie, Mengting Zhang, Haiqin Zhang, Huan Zhu, Yuxian Fang, Zihao Shen, Rui Wang, Zhenjiang Zhao, Lili Zhu, Xuhong Qian, Honglin Li. Design, Synthesis and Biological Evaluation of Potent and Selective S1PR1 Agonists for the Treatment of Ulcerative Colitis. Chinese Journal of Chemistry 2022, 40 (22) , 2625-2632. https://doi.org/10.1002/cjoc.202200392
    41. Belén Valenzuela, Per Olsson Gisleskog, Italo Poggesi, Tatiana Sidorenko, Michel Burcklen, Hilke Kracker, Juan Jose Pérez‐Ruixo. An exposure‐response analysis of ponesimod clinical efficacy in a randomized phase III study in patients with relapsing multiple sclerosis. CPT: Pharmacometrics & Systems Pharmacology 2022, 11 (10) , 1294-1304. https://doi.org/10.1002/psp4.12778
    42. Ihab Adnan Salman Al-Janabi, Sevtap Çağlar Yavuz, Semiha Köprü, Michael Tapera, Hüseyin Kekeçmuhammed, Senem Akkoç, Burak Tüzün, Şaban Patat, Emin Sarıpınar. Antiproliferative activity and molecular docking studies of new 4-oxothiazolidin-5-ylidene acetate derivatives containing guanylhydrazone moiety. Journal of Molecular Structure 2022, 1258 , 132627. https://doi.org/10.1016/j.molstruc.2022.132627
    43. Sreerama Rajasekhar, Soumyadip Das, Ramanathan Karuppasamy, Balamurali Musuvathi Motilal, Kaushik Chanda. Identification of novel inhibitors for Prp protein of Mycobacterium tuberculosis by structure based drug design, and molecular dynamics simulations. Journal of Computational Chemistry 2022, 43 (9) , 619-630. https://doi.org/10.1002/jcc.26823
    44. M. Reddy Gorla, M. Sarma. Synthesis of Pyrazole–Oxothiazolidine Hybrids as Potential Anticancer Agents in [Bmim]OH Ionic Liquid Medium. Russian Journal of Organic Chemistry 2022, 58 (4) , 572-579. https://doi.org/10.1134/S1070428022040157
    45. Tarek A‐Z K Gaber, Marwa Eltemamy. Ponesimod for the treatment of relapsing‐remitting multiple sclerosis. Progress in Neurology and Psychiatry 2022, 26 (2) , 18-19. https://doi.org/10.1002/pnp.745
    46. Davide Benedetto Tiz, Luana Bagnoli, Ornelio Rosati, Francesca Marini, Luca Sancineto, Claudio Santi. New Halogen-Containing Drugs Approved by FDA in 2021: An Overview on Their Syntheses and Pharmaceutical Use. Molecules 2022, 27 (5) , 1643. https://doi.org/10.3390/molecules27051643
    47. Ruby Singh, Munna Ram Saini. Regioselective Synthesis of Iminothiazolidinone Appended Novel Dispiro Indenoquinoxaline‐Pyrrolidines by 1,3‐Dipolar Cycloaddition Strategy. ChemistrySelect 2022, 7 (7) https://doi.org/10.1002/slct.202104080
    48. Yasuyuki Kihara, Deepa Jonnalagadda, Yunjiao Zhu, Manisha Ray, Tony Ngo, Carter Palmer, Richard Rivera, Jerold Chun. Ponesimod inhibits astrocyte‐mediated neuroinflammation and protects against cingulum demyelination via S1P 1 ‐selective modulation. The FASEB Journal 2022, 36 (2) https://doi.org/10.1096/fj.202101531R
    49. Lili Huang, Yeye Guo, Shujing Liu, Huaishan Wang, Jinjin Zhu, Lingling Ou, Xiaowei Xu. Targeting regulatory T cells for immunotherapy in melanoma. Molecular Biomedicine 2021, 2 (1) https://doi.org/10.1186/s43556-021-00038-z
    50. Laila H. Abdel-Rahman, Shaaban K. Mohamed, Youness El Bakri, Sajjad Ahmad, Chin-Hung Lai, Amer A. Amer, Joel T. Mague, Ehab M. Abdalla. Synthesis, crystal structural determination and in silco biological studies of 3,3′-ethane-1,2-diylbis(2-benzylidene-1,3-thiazolidin-4-one. Journal of Molecular Structure 2021, 1245 , 130997. https://doi.org/10.1016/j.molstruc.2021.130997
    51. Serhii Holota, Andrii Lozynskyi, Yulian Konechnyi, Yulia Shepeta, Roman Lesyk. 5-[4-(tert-Butyl)cyclohexylidene]-2-thioxothiazolidin-4-one. Molbank 2021, 2021 (4) , M1281. https://doi.org/10.3390/M1281
    52. Belén Valenzuela, Juan-José Pérez-Ruixo, Quentin Leirens, Sivi Ouwerkerk-Mahadevan, Italo Poggesi. Effect of Ponesimod Exposure on Total Lymphocyte Dynamics in Patients with Multiple Sclerosis. Clinical Pharmacokinetics 2021, 60 (9) , 1239-1250. https://doi.org/10.1007/s40262-021-01019-9
    53. Mattia Annatelli, Giacomo Trapasso, Claudio Salaris, Cristiano Salata, Sabrina Castellano, Fabio Aricò. Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols. European Journal of Organic Chemistry 2021, 2021 (24) , 3459-3464. https://doi.org/10.1002/ejoc.202100328
    54. William J. Pitts, Alaric J. Dyckman. Multiple Sclerosis. 2021, 1-43. https://doi.org/10.1002/0471266949.bmc203.pub2
    55. Dilep Kumar Sigalapalli, Venkatesh Pooladanda, Manasa Kadagathur, Sravanthi Devi Guggilapu, Jaya Lakshmi Uppu, Chandraiah Godugu, Nagendra Babu Bathini, Neelima D. Tangellamudi. Novel chromenyl-based 2-iminothiazolidin-4-one derivatives as tubulin polymerization inhibitors: Design, synthesis, biological evaluation and molecular modelling studies. Journal of Molecular Structure 2021, 1225 , 128847. https://doi.org/10.1016/j.molstruc.2020.128847
    56. Nienke M. de Wit, Kevin Mol, Sabela Rodríguez-Lorenzo, Helga E. de Vries, Gijs Kooij. The Role of Sphingolipids and Specialized Pro-Resolving Mediators in Alzheimer’s Disease. Frontiers in Immunology 2021, 11 https://doi.org/10.3389/fimmu.2020.620348
    57. Stanley L. Cohan, Elisabeth B. Lucassen, Kyle E. Smoot, Kiren Kresa-Reahl, Meghan Romba, Stefanie N. Linch. The impact of translational research on the development of therapeutic agents for multiple sclerosis. 2021, 203-242. https://doi.org/10.1016/B978-0-12-816475-4.00010-0
    58. Elena Campione, Terenzio Cosio, Monia Di Prete, Caterina Lanna, Annunziata Dattola, Luca Bianchi. Experimental Pharmacological Management of Psoriasis. Journal of Experimental Pharmacology 2021, Volume 13 , 725-737. https://doi.org/10.2147/JEP.S265632
    59. Elisa Baldin, Alessandra Lugaresi. Ponesimod for the treatment of relapsing multiple sclerosis. Expert Opinion on Pharmacotherapy 2020, 21 (16) , 1955-1964. https://doi.org/10.1080/14656566.2020.1799977
    60. Michio Tokuyama, Tomotaka Mabuchi. New Treatment Addressing the Pathogenesis of Psoriasis. International Journal of Molecular Sciences 2020, 21 (20) , 7488. https://doi.org/10.3390/ijms21207488
    61. Michiel Langeslag, Michaela Kress. The ceramide-S1P pathway as a druggable target to alleviate peripheral neuropathic pain. Expert Opinion on Therapeutic Targets 2020, 24 (9) , 869-884. https://doi.org/10.1080/14728222.2020.1787989
    62. Timothy M. Doyle, Kali Janes, Zhoumou Chen, Peter M. Grace, Emanuela Esposito, Salvatore Cuzzocrea, Tally M. Largent-Milnes, William L. Neumann, Linda R. Watkins, Sarah Spiegel, Todd W. Vanderah, Daniela Salvemini. Activation of sphingosine-1-phosphate receptor subtype 1 in the central nervous system contributes to morphine-induced hyperalgesia and antinociceptive tolerance in rodents. Pain 2020, 161 (9) , 2107-2118. https://doi.org/10.1097/j.pain.0000000000001888
    63. Stanley Cohan, Elisabeth Lucassen, Kyle Smoot, Justine Brink, Chiayi Chen. Sphingosine-1-Phosphate: Its Pharmacological Regulation and the Treatment of Multiple Sclerosis: A Review Article. Biomedicines 2020, 8 (7) , 227. https://doi.org/10.3390/biomedicines8070227
    64. Ruby Singh, Munna Ram Saini, Diksha Bhardwaj, Aakash Singh. An expedient synthesis of new imino-thiazolidinone grafted dispiro-pyrrolidine-oxindole/indeno hybrids via a multicomponent [3+2] cycloaddition reaction in a deep eutectic solvent. New Journal of Chemistry 2020, 44 (19) , 7923-7931. https://doi.org/10.1039/D0NJ00801J
    65. Nusrat Sahiba, Ayushi Sethiya, Jay Soni, Dinesh K. Agarwal, Shikha Agarwal. Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications. Topics in Current Chemistry 2020, 378 (2) https://doi.org/10.1007/s41061-020-0298-4
    66. Jing Jin, Nina Xue, Yuan Liu, Rong Fu, Mingjin Wang, Ming Ji, Fangfang Lai, Jinping Hu, Xiaojian Wang, Qiong Xiao, Xiaoying Zhang, Dali Yin, Liping Bai, Xiaoguang Chen, Shuan Rao. A novel S1P1 modulator IMMH002 ameliorates psoriasis in multiple animal models. Acta Pharmaceutica Sinica B 2020, 10 (2) , 276-288. https://doi.org/10.1016/j.apsb.2019.11.006
    67. Leila Zare Fekri, Hooshang Hamidian, Masoomeh Abdollahi Chekosarani. Urazolium diacetate as a new, efficient and reusable Brønsted acid ionic liquid for the synthesis of novel derivatives of thiazolidine-4-ones. RSC Advances 2020, 10 (1) , 556-564. https://doi.org/10.1039/C9RA08649H
    68. Mwadham M. Kabanda, Kgalaletso P. Otukile. A Theoretical Study of the Preferred Reaction Mechanism Between Chloroacetic Acid and Thiourea. 2020, 119-142. https://doi.org/10.1007/978-3-030-34941-7_7
    69. Edward D. Zanders. Medicinal Chemistry. 2020, 143-163. https://doi.org/10.1007/978-3-030-57814-5_7
    70. Ali Akbar Alizadeh, Behzad Jafari, Siavoush Dastmalchi. Alignment independent 3D-QSAR studies and molecular dynamics simulations for the identification of potent and selective S1P1 receptor agonists. Journal of Molecular Graphics and Modelling 2020, 94 , 107459. https://doi.org/10.1016/j.jmgm.2019.107459
    71. Victoria A. Blaho. Druggable Sphingolipid Pathways: Experimental Models and Clinical Opportunities. 2020, 101-135. https://doi.org/10.1007/978-3-030-50621-6_6
    72. Ghaneya S. Hassan, Hanan H. Georgey, Esraa Z. Mohammed, Farghaly A. Omar. Anti-hepatitis-C virus activity and QSAR study of certain thiazolidinone and thiazolotriazine derivatives as potential NS5B polymerase inhibitors. European Journal of Medicinal Chemistry 2019, 184 , 111747. https://doi.org/10.1016/j.ejmech.2019.111747
    73. Abderrahman El Bouakher, Arnaud Martel, Sébastien Comesse. α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles. Organic & Biomolecular Chemistry 2019, 17 (37) , 8467-8485. https://doi.org/10.1039/C9OB01683J
    74. Sara Grassi, Laura Mauri, Simona Prioni, Livia Cabitta, Sandro Sonnino, Alessandro Prinetti, Paola Giussani. Sphingosine 1-Phosphate Receptors and Metabolic Enzymes as Druggable Targets for Brain Diseases. Frontiers in Pharmacology 2019, 10 https://doi.org/10.3389/fphar.2019.00807
    75. RAMALINGAM KUNDENAPALLY, RAMESH DOMALA, B. SREENIVASULU. Regioselective Synthesis of Novel [N-(4-Oxo-3-(2-phenyl-1,8-naphthyridin-3-yl)-thiazolidin-2-ylidene)]acetamide/benzamides and their Biological Activity. Asian Journal of Chemistry 2019, 31 (6) , 1246-1250. https://doi.org/10.14233/ajchem.2019.21881
    76. Zhoumou Chen, Timothy M. Doyle, Livio Luongo, Tally M. Largent-Milnes, Luigino Antonio Giancotti, Grant Kolar, Silvia Squillace, Serena Boccella, John K. Walker, Alexander Pendleton, Sarah Spiegel, William L. Neumann, Todd W. Vanderah, Daniela Salvemini. Sphingosine-1-phosphate receptor 1 activation in astrocytes contributes to neuropathic pain. Proceedings of the National Academy of Sciences 2019, 116 (21) , 10557-10562. https://doi.org/10.1073/pnas.1820466116
    77. Constance D. Franklin, Peter Y. Zavalij, Courtney Diamond, Ashley J. Groth, David J. Lebron, Samuel G. Holmes, Danny R. Anderson, Dilip K. Paul, Julio C. Alvarez, Vladimir Sidorov. A Controlled Cyclization of Functionalized Thioureas and Unprecedented Termolecular Decyclization of Iminothiazolidinones. ChemistrySelect 2019, 4 (12) , 3567-3576. https://doi.org/10.1002/slct.201900832
    78. Senel Teke Tuncel, Sule Erol Gunal, Melike Ekizoglu, Nesrin Gokhan Kelekci, Safiye S. Erdem, Ece Bulak, Wolfgang Frey, Ilknur Dogan. Thioureas and their cyclized derivatives: Synthesis, conformational analysis and antimicrobial evaluation. Journal of Molecular Structure 2019, 1179 , 40-56. https://doi.org/10.1016/j.molstruc.2018.10.055
    79. Tianqi Liu, Jing Jin, Yonghui Chen, Qiumu Xi, Jinping Hu, Wenqiang Jia, Xiaoguang Chen, Yan Li, Xiaojian Wang, Dali Yin. Identification and Structure–Activity Relationship (SAR) of potent and selective oxadiazole-based agonists of sphingosine-1-phosphate receptor (S1P1). Bioorganic Chemistry 2019, 82 , 41-57. https://doi.org/10.1016/j.bioorg.2018.09.008
    80. Ludwig Rasche, Friedemann Paul. Ozanimod for the treatment of relapsing remitting multiple sclerosis. Expert Opinion on Pharmacotherapy 2018, 19 (18) , 2073-2086. https://doi.org/10.1080/14656566.2018.1540592
    81. Preeti Preeti, Krishna Nand Singh. Multicomponent reactions: a sustainable tool to 1,2- and 1,3-azoles. Organic & Biomolecular Chemistry 2018, 16 (47) , 9084-9116. https://doi.org/10.1039/C8OB01872C
    82. Sakineh Asghari, Maryam Pourshab, Mojtaba Mohseni. Synthesis, characterization, and evaluation of antioxidant and antibacterial activities of novel indole-hydrazono thiazolidinones. Monatshefte für Chemie - Chemical Monthly 2018, 149 (12) , 2327-2336. https://doi.org/10.1007/s00706-018-2292-x
    83. Alexander Marciniak, Sara M. Camp, Joe G.N. Garcia, Robin Polt. An update on sphingosine-1-phosphate receptor 1 modulators. Bioorganic & Medicinal Chemistry Letters 2018, 28 (23-24) , 3585-3591. https://doi.org/10.1016/j.bmcl.2018.10.042
    84. Rei Saito, Naohiro Uemura, Hiroki Ishikawa, Akina Magara, Yasushi Yoshida, Takashi Mino, Yoshio Kasashima, Masami Sakamoto. Umpolung cyclization reaction of N -cinnamoylthioureas in the presence of DBU. Organic & Biomolecular Chemistry 2018, 16 (42) , 7910-7919. https://doi.org/10.1039/C8OB02066C
    85. Mark Bell, David Foley, Claire Naylor, Colin Robinson, Jennifer Riley, Ola Epemolu, Paul Scullion, Yoko Shishikura, Elad Katz, W.H. Irwin McLean, Paul Wyatt, Kevin D. Read, Andrew Woodland. Discovery of super soft-drug modulators of sphingosine-1-phosphate receptor 1. Bioorganic & Medicinal Chemistry Letters 2018, 28 (19) , 3255-3259. https://doi.org/10.1016/j.bmcl.2018.07.044
    86. Katherine Stockstill, Timothy M. Doyle, Xisheng Yan, Zhoumou Chen, Kali Janes, Joshua W. Little, Kathryn Braden, Filomena Lauro, Luigino Antonio Giancotti, Caron Mitsue Harada, Ruchi Yadav, Wen Hua Xiao, Jack M. Lionberger, William L. Neumann, Gary J. Bennett, Han-Rong Weng, Sarah Spiegel, Daniela Salvemini. Dysregulation of sphingolipid metabolism contributes to bortezomib-induced neuropathic pain. Journal of Experimental Medicine 2018, 215 (5) , 1301-1313. https://doi.org/10.1084/jem.20170584
    87. Magdalena Birker-Robaczewska, Martin Bolli, Markus Rey, Ruben de Kanter, Christopher Kohl, Cyrille Lescop, Maxime Boucher, Sylvie Poirey, Beat Steiner, Oliver Nayler. S1P 1 Modulator-Induced G α i Signaling and β -Arrestin Recruitment Are Both Necessary to Induce Rapid and Efficient Reduction of Blood Lymphocyte Count In Vivo. Molecular Pharmacology 2018, 93 (2) , 109-118. https://doi.org/10.1124/mol.117.109140
    88. Himanshu Chokhawala, Shyamal C. Bir, Alireza Minagar. Existing and Emerging Therapies for Multiple Sclerosis. 2018, 247-259. https://doi.org/10.1016/B978-0-12-811709-5.00013-2
    89. Luca Piali, Magdalena Birker‐Robaczewska, Cyrille Lescop, Sylvie Froidevaux, Nicole Schmitz, Keith Morrison, Christopher Kohl, Markus Rey, Rolf Studer, Enrico Vezzali, Patrick Hess, Martine Clozel, Beat Steiner, Martin H. Bolli, Oliver Nayler. Cenerimod, a novel selective S1P 1 receptor modulator with unique signaling properties. Pharmacology Research & Perspectives 2017, 5 (6) https://doi.org/10.1002/prp2.370
    90. Danylo Kaminskyy, Anna Kryshchyshyn, Roman Lesyk. 5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry. European Journal of Medicinal Chemistry 2017, 140 , 542-594. https://doi.org/10.1016/j.ejmech.2017.09.031
    91. Gangqiang Wang, Sen Zhao, Rongxing Chen, Liangfeng Yang, Jian Wang, Haibing Guo, Minghu Wu, Justin Domena, Yalan Xing, Shaofa Sun. Synthesis of thiazolidin-4-ones via [3+2] cycloaddition of in situ generated aza-oxyallylic cations with isothiocyanates. Tetrahedron Letters 2017, 58 (45) , 4308-4311. https://doi.org/10.1016/j.tetlet.2017.10.004
    92. Anna Bielenica, Giuseppina Sanna, Silvia Madeddu, Marta Struga, Michał Jóźwiak, Anna E. Kozioł, Aleksandra Sawczenko, Ilona B. Materek, Alessandra Serra, Gabriele Giliberti. New thiourea and 1,3-thiazolidin-4-one derivatives effective on the HIV-1 virus. Chemical Biology & Drug Design 2017, 90 (5) , 883-891. https://doi.org/10.1111/cbdd.13009
    93. Shaness A. Grenald, Timothy M. Doyle, Hong Zhang, Lauren M. Slosky, Zhoumou Chen, Tally M. Largent-Milnes, Sarah Spiegel, Todd W. Vanderah, Daniela Salvemini. Targeting the S1P/S1PR1 axis mitigates cancer-induced bone pain and neuroinflammation. Pain 2017, 158 (9) , 1733-1742. https://doi.org/10.1097/j.pain.0000000000000965
    94. Hong‐Wu Zhao, Yu‐Di Zhao, Yue‐Yang Liu, Juan Du, Hai‐Liang Pang, Xiao‐Qin Chen, Xiu‐Qing Song, Ning‐Ning Feng. Base‐Promoted [3+2] Cycloaddition of In Situ Formed Azaoxyallyl Cations with Isothiocyanides. European Journal of Organic Chemistry 2017, 2017 (24) , 3466-3472. https://doi.org/10.1002/ejoc.201700278
    95. Pierre‐Eric Juif, Matthias Hoch, Andrea Vaclavkova, Andreas Krause, Jim Bush, Jasper Dingemanse. Mitigation of Initial Cardiodynamic Effects of the S1P 1 Receptor Modulator Ponesimod Using a Novel Up‐Titration Regimen. The Journal of Clinical Pharmacology 2017, 57 (3) , 401-410. https://doi.org/10.1002/jcph.820
    96. Soo-Jin Park, Dong-Soon Im. Sphingosine 1-Phosphate Receptor Modulators and Drug Discovery. Biomolecules & Therapeutics 2017, 25 (1) , 80-90. https://doi.org/10.4062/biomolther.2016.160
    97. Minhajul Arfeen, Shweta Bhagat, Rahul Patel, Shivcharan Prasad, Ipsita Roy, Asit K. Chakraborti, Prasad V. Bharatam. Design, synthesis and biological evaluation of 5-benzylidene-2-iminothiazolidin-4-ones as selective GSK-3β inhibitors. European Journal of Medicinal Chemistry 2016, 121 , 727-736. https://doi.org/10.1016/j.ejmech.2016.04.075
    98. Beya Haouas, Taieb Saied, Hanen Ayari, Youssef Arfaoui, Mohamed Lamine Benkhoud, Khaled Boujlel. Electrogenerated base-promoted synthesis and antimicrobial activity of 2-imino-1,3-thiazolidin-4-one derivatives. Journal of Sulfur Chemistry 2016, 37 (4) , 391-400. https://doi.org/10.1080/17415993.2016.1155588
    99. Martin H. Bolli, Cyrille Lescop, Magdalena Birker, Ruben de Kanter, Patrick Hess, Christopher Kohl, Oliver Nayler, Markus Rey, Patrick Sieber, Jörg Velker, Thomas Weller, Beat Steiner. Novel S1P1 receptor agonists – Part 5: From amino-to alkoxy-pyridines. European Journal of Medicinal Chemistry 2016, 115 , 326-341. https://doi.org/10.1016/j.ejmech.2016.03.020
    100. Cyrille Lescop, Claus Müller, Boris Mathys, Magdalena Birker, Ruben de Kanter, Christopher Kohl, Patrick Hess, Oliver Nayler, Markus Rey, Patrick Sieber, Beat Steiner, Thomas Weller, Martin H. Bolli. Novel S1P 1 receptor agonists – Part 4: Alkylaminomethyl substituted aryl head groups. European Journal of Medicinal Chemistry 2016, 116 , 222-238. https://doi.org/10.1016/j.ejmech.2016.03.048
    Load all citations
    Download PDF
    Go to Journal of Medicinal Chemistry
    Get e-Alerts
    Get e-Alerts

    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2010, 53, 10, 4198–4211
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm100181s
    Published May 6, 2010
    Copyright © 2010 American Chemical Society
    Request reuse permissions

    Article Views

    5477

    Altmetric

    -

    Citations

    156
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.