ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Synthesis and Structure-Activity Relationships of Novel Retinoid X Receptor-Selective Retinoids

Cite this: J. Med. Chem. 1994, 37, 18, 2930–2941
Publication Date (Print):September 1, 1994
https://doi.org/10.1021/jm00044a014
    ACS Legacy Archive

    Article Views

    2025

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    PDF (2 MB)

    Note: In lieu of an abstract, this is the article's first page.

    Free first page

    Cited By

    This article is cited by 305 publications.

    1. Meng-Fan Li, Ling-Qi Chen, Jia-Yin Wang, Man-Su Tu, Wen-Juan Hao, Bo Jiang. Lewis Acid-Catalyzed Remote Site-Selective Ring Deconstruction of Cyclobuteno[a]naphthalene-4-ones to Access Unsymmetric 1,1-Diarylated Olefins. The Journal of Organic Chemistry 2023, 88 (6) , 3615-3625. https://doi.org/10.1021/acs.joc.2c02804
    2. Yuta Takamura, Izumi Kato, Manami Fujita-Takahashi, Midori Azuma-Nishii, Masaki Watanabe, Rui Nozaki, Masaru Akehi, Takanori Sasaki, Hiroyuki Hirano, Hiroki Kakuta. Teratogenicity and Fetal-Transfer Assessment of the Retinoid X Receptor Agonist Bexarotene. ACS Pharmacology & Translational Science 2022, 5 (9) , 811-818. https://doi.org/10.1021/acsptsci.2c00126
    3. Sabine Willems, Daniel Zaienne, Daniel Merk. Targeting Nuclear Receptors in Neurodegeneration and Neuroinflammation. Journal of Medicinal Chemistry 2021, 64 (14) , 9592-9638. https://doi.org/10.1021/acs.jmedchem.1c00186
    4. Simone Schierle, Apirat Chaikuad, Felix F. Lillich, Xiaomin Ni, Stefano Woltersdorf, Espen Schallmayer, Beatrice Renelt, Riccardo Ronchetti, Stefan Knapp, Ewgenij Proschak, Daniel Merk. Oxaprozin Analogues as Selective RXR Agonists with Superior Properties and Pharmacokinetics. Journal of Medicinal Chemistry 2021, 64 (8) , 5123-5136. https://doi.org/10.1021/acs.jmedchem.1c00235
    5. Sanchita Mallick, Pamela A. Marshall, Carl E. Wagner, Michael C. Heck, Zhela L. Sabir, Marya S. Sabir, Christoper M. Dussik, Aleksandra Grozic, Ichiro Kaneko, Peter W. Jurutka. Evaluating Novel RXR Agonists That Induce ApoE and Tyrosine Hydroxylase in Cultured Human Glioblastoma Cells. ACS Chemical Neuroscience 2021, 12 (5) , 857-871. https://doi.org/10.1021/acschemneuro.0c00707
    6. Meng-Yang Chang, Yu-Lin Tsai, Hsing-Yin Chen. CuBr2-Mediated One-Pot Synthesis of Sulfonyl 9-Fluorenylidenes. The Journal of Organic Chemistry 2020, 85 (11) , 6897-6909. https://doi.org/10.1021/acs.joc.0c00035
    7. Ian R. Duffy, Neil Vasdev, Kenneth Dahl. Copper(I)-Mediated 11C-Carboxylation of (Hetero)arylstannanes. ACS Omega 2020, 5 (14) , 8242-8250. https://doi.org/10.1021/acsomega.0c00524
    8. Julius Pollinger, Leonie Gellrich, Simone Schierle, Whitney Kilu, Jurema Schmidt, Lena Kalinowsky, Julia Ohrndorf, Astrid Kaiser, Jan Heering, Ewgenij Proschak, Daniel Merk. Tuning Nuclear Receptor Selectivity of Wy14,643 towards Selective Retinoid X Receptor Modulation. Journal of Medicinal Chemistry 2019, 62 (4) , 2112-2126. https://doi.org/10.1021/acs.jmedchem.8b01848
    9. Tanaji T. Talele. Natural-Products-Inspired Use of the gem-Dimethyl Group in Medicinal Chemistry. Journal of Medicinal Chemistry 2018, 61 (6) , 2166-2210. https://doi.org/10.1021/acs.jmedchem.7b00315
    10. Osamu Shibahara, Masaki Watanabe, Shoya Yamada, Masaru Akehi, Takanori Sasaki, Akiya Akahoshi, Takahisa Hanada, Hiroyuki Hirano, Shunsuke Nakatani, Hiromi Nishioka, Yasuo Takeuchi, and Hiroki Kakuta . Synthesis of 11C-Labeled RXR Partial Agonist 1-[(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]benzotriazole-5-carboxylic Acid (CBt-PMN) by Direct [11C]Carbon Dioxide Fixation via Organolithiation of Trialkyltin Precursor and PET Imaging Thereof. Journal of Medicinal Chemistry 2017, 60 (16) , 7139-7145. https://doi.org/10.1021/acs.jmedchem.7b00817
    11. Michael C. Heck, Carl E. Wagner, Pritika H. Shahani, Mairi MacNeill, Aleksandra Grozic, Tamana Darwaiz, Micah Shimabuku, David G. Deans, Nathan M. Robinson, Samer H. Salama, Joseph W. Ziller, Ning Ma, Arjan van der Vaart, Pamela A. Marshall, and Peter W. Jurutka . Modeling, Synthesis, and Biological Evaluation of Potential Retinoid X Receptor (RXR)-Selective Agonists: Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene) and 6-(Ethyl(5,5,8,8-tetrahydronaphthalen-2-yl)amino)nicotinic Acid (NEt-TMN). Journal of Medicinal Chemistry 2016, 59 (19) , 8924-8940. https://doi.org/10.1021/acs.jmedchem.6b00812
    12. Philippe Diaz, Weize Huang, Charles M. Keyari, Brian Buttrick, Lauren Price, Nicolas Guilloteau, Sasmita Tripathy, Vanessa G. Sperandio, Frank R. Fronczek, Fanny Astruc-Diaz, and Nina Isoherranen . Development and Characterization of Novel and Selective Inhibitors of Cytochrome P450 CYP26A1, the Human Liver Retinoic Acid Hydroxylase. Journal of Medicinal Chemistry 2016, 59 (6) , 2579-2595. https://doi.org/10.1021/acs.jmedchem.5b01780
    13. Amelia H. Baker, James Watt, Cassie K. Huang, Louis C. Gerstenfeld, and Jennifer J. Schlezinger . Tributyltin Engages Multiple Nuclear Receptor Pathways and Suppresses Osteogenesis in Bone Marrow Multipotent Stromal Cells. Chemical Research in Toxicology 2015, 28 (6) , 1156-1166. https://doi.org/10.1021/tx500433r
    14. Venkatram R. Atigadda, Gang Xia, Anil Desphande, LeeAnn J. Boerma, Susan Lobo-Ruppert, Clinton J. Grubbs, Craig D. Smith, Wayne J. Brouillette, and Donald D. Muccio . Methyl Substitution of a Rexinoid Agonist Improves Potency and Reveals Site of Lipid Toxicity. Journal of Medicinal Chemistry 2014, 57 (12) , 5370-5380. https://doi.org/10.1021/jm5004792
    15. Benjamin H. Rotstein, Jacob M. Hooker, Jiyeon Woo, Thomas Lee Collier, Thomas J. Brady, Steven H. Liang, and Neil Vasdev . Synthesis of [11C]Bexarotene by Cu-Mediated [11C]Carbon Dioxide Fixation and Preliminary PET Imaging. ACS Medicinal Chemistry Letters 2014, 5 (6) , 668-672. https://doi.org/10.1021/ml500065q
    16. Krista McFarland, Tracy A. Spalding, David Hubbard, Jian-Nong Ma, Roger Olsson, and Ethan S. Burstein . Low Dose Bexarotene Treatment Rescues Dopamine Neurons and Restores Behavioral Function in Models of Parkinson’s Disease. ACS Chemical Neuroscience 2013, 4 (11) , 1430-1438. https://doi.org/10.1021/cn400100f
    17. Peter W. Jurutka, Ichiro Kaneko, Joanna Yang, Jaskaran S. Bhogal, Johnathon C. Swierski, Christa R. Tabacaru, Luis A. Montano, Chanh C. Huynh, Rabia A. Jama, Ryan D. Mahelona, Joseph T. Sarnowski, Lisa M. Marcus, Alexis Quezada, Brittney Lemming, Maria A. Tedesco, Audra J. Fischer, Said A. Mohamed, Joseph W. Ziller, Ning Ma, Geoffrey M. Gray, Arjan van der Vaart, Pamela A. Marshall, and Carl E. Wagner . Modeling, Synthesis, and Biological Evaluation of Potential Retinoid X Receptor (RXR) Selective Agonists: Novel Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene) and (E)-3-(3-(1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalen-7-yl)-4-hydroxyphenyl)acrylic Acid (CD3254). Journal of Medicinal Chemistry 2013, 56 (21) , 8432-8454. https://doi.org/10.1021/jm4008517
    18. Fuminori Ohsawa, Shoya Yamada, Nobumasa Yakushiji, Ryosuke Shinozaki, Mariko Nakayama, Kohei Kawata, Manabu Hagaya, Toshiki Kobayashi, Kazutaka Kohara, Yuuki Furusawa, Chisa Fujiwara, Yui Ohta, Makoto Makishima, Hirotaka Naitou, Akihiro Tai, Yutaka Yoshikawa, Hiroyuki Yasui, and Hiroki Kakuta . Mechanism of Retinoid X Receptor Partial Agonistic Action of 1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-1H-benzotriazole-5-carboxylic Acid and Structural Development To Increase Potency. Journal of Medicinal Chemistry 2013, 56 (5) , 1865-1877. https://doi.org/10.1021/jm400033f
    19. Maxime Roche, Abdallah Hamze, Olivier Provot, Jean-Daniel Brion, and Mouad Alami . Synthesis of Ortho/Ortho′-Substituted 1,1-Diarylethylenes through Cross-Coupling Reactions of Sterically Encumbered Hydrazones and Aryl Halides. The Journal of Organic Chemistry 2013, 78 (2) , 445-454. https://doi.org/10.1021/jo3023268
    20. Abdallah Hamze, Jean-Daniel Brion, and Mouad Alami . Synthesis of 1,1-Diarylethylenes via Efficient Iron/Copper Co-Catalyzed Coupling of 1-Arylvinyl Halides with Grignard Reagents. Organic Letters 2012, 14 (11) , 2782-2785. https://doi.org/10.1021/ol3010112
    21. Mariko Nakayama, Shoya Yamada, Fuminori Ohsawa, Yui Ohta, Kohei Kawata, Makoto Makishima, and Hiroki Kakuta . Discovery of a Potent Retinoid X Receptor Antagonist Structurally Closely Related to RXR Agonist NEt-3IB. ACS Medicinal Chemistry Letters 2011, 2 (12) , 896-900. https://doi.org/10.1021/ml200197e
    22. Zebin Xia, Lulu Farhana, Ricardo G. Correa, Jayanta K. Das, David J. Castro, Jinghua Yu, Robert G. Oshima, John C. Reed, Joseph A. Fontana, and Marcia I. Dawson . Heteroatom-Substituted Analogues of Orphan Nuclear Receptor Small Heterodimer Partner Ligand and Apoptosis Inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic Acid. Journal of Medicinal Chemistry 2011, 54 (11) , 3793-3816. https://doi.org/10.1021/jm200051z
    23. Raymond J. Patch, Lily L. Searle, Alexander J. Kim, Debyendu De, Xizhen Zhu, Hossein B. Askari, John C. O’Neill, Marta C. Abad, Dionisios Rentzeperis, Jianying Liu, Michael Kemmerer, Ling Lin, Jyotsna Kasturi, John G. Geisler, James M. Lenhard, Mark R. Player, and Micheal D. Gaul . Identification of Diaryl Ether-Based Ligands for Estrogen-Related Receptor α as Potential Antidiabetic Agents. Journal of Medicinal Chemistry 2011, 54 (3) , 788-808. https://doi.org/10.1021/jm101063h
    24. Ioannis S. Vizirianakis, Maria Chatzopoulou, Ioannis D. Bonovolias, Ioannis Nicolaou, Vassilis J. Demopoulos, and Asterios S. Tsiftsoglou . Toward the Development of Innovative Bifunctional Agents To Induce Differentiation and To Promote Apoptosis in Leukemia: Clinical Candidates and Perspectives. Journal of Medicinal Chemistry 2010, 53 (19) , 6779-6810. https://doi.org/10.1021/jm100189a
    25. Carl E. Wagner and Pamela A. Marshall . Synthesis of 2,5-Dichloro-2,5-dimethylhexane by an SN1 Reaction. Journal of Chemical Education 2010, 87 (1) , 81-83. https://doi.org/10.1021/ed8000057
    26. Carl E. Wagner, Peter W. Jurutka, Pamela A. Marshall, Thomas L. Groy, Arjan van der Vaart, Joseph W. Ziller, Julie K. Furmick, Mark E. Graeber, Erik Matro, Belinda V. Miguel, Ivy T. Tran, Jungeun Kwon, Jamie N. Tedeschi, Shahram Moosavi, Amina Danishyar, Joshua S. Philp, Reina O. Khamees, Jevon N. Jackson, Darci K. Grupe, Syed L. Badshah and Justin W. Hart . Modeling, Synthesis and Biological Evaluation of Potential Retinoid X Receptor (RXR) Selective Agonists: Novel Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene). Journal of Medicinal Chemistry 2009, 52 (19) , 5950-5966. https://doi.org/10.1021/jm900496b
    27. Abdallah Hamze, Damien Veau, Olivier Provot, Jean-Daniel Brion and Mouâd Alami. Palladium-Catalyzed Markovnikov Terminal Arylalkynes Hydrostannation: Application to the Synthesis of 1,1-Diarylethylenes. The Journal of Organic Chemistry 2009, 74 (3) , 1337-1340. https://doi.org/10.1021/jo802460z
    28. James H. Nettles,, Jeremy L. Jenkins,, Andreas Bender,, Zhan Deng,, John W. Davies, and, Meir Glick. Bridging Chemical and Biological Space:  “Target Fishing” Using 2D and 3D Molecular Descriptors. Journal of Medicinal Chemistry 2006, 49 (23) , 6802-6810. https://doi.org/10.1021/jm060902w
    29. Claudio N. Cavasotto,, Gang Liu,, Sharon Y. James,, Peter D. Hobbs,, Valerie J. Peterson,, Ananyo A. Bhattacharya,, Siva K. Kolluri,, Xiao-kun Zhang,, Mark Leid,, Ruben Abagyan,, Robert C. Liddington, and, Marcia I. Dawson. Determinants of Retinoid X Receptor Transcriptional Antagonism. Journal of Medicinal Chemistry 2004, 47 (18) , 4360-4372. https://doi.org/10.1021/jm030651g
    30. Curt D. Haffner,, James M. Lenhard,, Aaron B. Miller,, Darryl L. McDougald,, Kate Dwornik,, Olivia R. Ittoop,, Robert T. Gampe, Jr.,, H. Eric Xu,, Steve Blanchard,, Valerie G. Montana,, Tom G. Consler,, Randy K. Bledsoe,, Andrea Ayscue, and, Dallas Croom. Structure-Based Design of Potent Retinoid X Receptor α Agonists. Journal of Medicinal Chemistry 2004, 47 (8) , 2010-2029. https://doi.org/10.1021/jm030565g
    31. Pierre-Yves Michellys,, Robert J. Ardecky,, Jyun-Hung Chen,, Jennifer D'Arrigo,, Timothy A. Grese,, Donald S. Karanewsky,, Mark D. Leibowitz,, Sha Liu,, Dale A. Mais,, Christopher M. Mapes,, Chahrzad Montrose-Rafizadeh,, Katheen M. Ogilvie, Anne Reifel-Miller,, Deepa Rungta,, Anthony W. Thompson,, John S. Tyhonas, and, Marcus F. Boehm. Design, Synthesis, and Structure−Activity Relationship Studies of Novel 6,7-Locked-[7-(2-alkoxy-3,5-dialkylbenzene)-3-methylocta]-2,4,6-trienoic Acids. Journal of Medicinal Chemistry 2003, 46 (19) , 4087-4103. https://doi.org/10.1021/jm020401k
    32. P. Y. Michellys , R. J. Ardecky , J. H. Chen , D. L. Crombie , G. J. Etgen , A. L. Faulkner , M. M. Faul , T. A. Grese , R. A. Heyman , D. S. Karanewsky , K. Klausing , M. D. Leibowitz , S. Liu , D. A. Mais , C. M. Mapes , K. B. Marschke , A. Reifel-Miller , K. M. Ogilvie , D. Rungta , A. W. Thompson , J. S. Tyhonas , and M. F. Boehm . Novel (2E,4E,6Z)-7-(2-Alkoxy-3,5-dialkylbenzene)-3-methylocta-2,4,6-trienoic Acid Retinoid X Receptor Modulators Are Active in Models of Type 2 Diabetes. Journal of Medicinal Chemistry 2003, 46 (13) , 2683-2696. https://doi.org/10.1021/jm020340q
    33. Lawrence G. Hamann. An Efficient, Stereospecific Synthesis of the Dimer-Selective Retinoid X Receptor Modulator (2E,4E,6Z)-7-[5,6,7,8- Tetrahydro-5,5,8,8-tetramethyl-2- (n-propyloxy)naphthalen-3-yl]-3- methylocta-2,4,6-trienoic Acid. The Journal of Organic Chemistry 2000, 65 (10) , 3233-3235. https://doi.org/10.1021/jo991936x
    34. David Zacheis,, Arindam Dhar,, Shennan Lu,, Matora M. Madler,, Jozef Klucik,, Chad W. Brown,, Shengquan Liu,, Francis Clement,, Shankar Subramanian,, G. Mahika Weerasekare,, K. Darrell Berlin,, Michael A. Gold,, John R. Houck, Jr.,, Kenneth R. Fountain, and, Doris M. Benbrook. Heteroarotinoids Inhibit Head and Neck Cancer Cell Lines in Vitro and in Vivo Through Both RAR and RXR Retinoic Acid Receptors. Journal of Medicinal Chemistry 1999, 42 (21) , 4434-4445. https://doi.org/10.1021/jm990292i
    35. Arindam Dhar,, Shengquan Liu,, Jozef Klucik,, K. Darrell Berlin,, Matora M. Madler,, Shennan Lu,, R. Todd Ivey,, David Zacheis,, Chad W. Brown,, E. C. Nelson,, Paul J. Birckbichler, and, Doris M. Benbrook. Synthesis, Structure−Activity Relationships, and RARγ−Ligand Interactions of Nitrogen Heteroarotinoids. Journal of Medicinal Chemistry 1999, 42 (18) , 3602-3614. https://doi.org/10.1021/jm9900974
    36. Stacie S. Canan Koch,, Laura J. Dardashti,, Rosemary M. Cesario,, Glenn E. Croston,, Marcus F. Boehm,, Richard A. Heyman, and, Alex M. Nadzan. Synthesis of Retinoid X Receptor-Specific Ligands That Are Potent Inducers of Adipogenesis in 3T3-L1 Cells. Journal of Medicinal Chemistry 1999, 42 (4) , 742-750. https://doi.org/10.1021/jm980621r
    37. Shigeki Hibi,, Kouichi Kikuchi,, Hiroyuki Yoshimura,, Mitsuo Nagai,, Kenji Tai, and, Takayuki Hida. Syntheses and Structure−Activity Relationships of Novel Retinoid X Receptor Agonists. Journal of Medicinal Chemistry 1998, 41 (17) , 3245-3252. https://doi.org/10.1021/jm980058c
    38. Hiroki Umemiya,, Hiroshi Fukasawa,, Masayuki Ebisawa,, Laurence Eyrolles,, Emiko Kawachi,, Ghislaine Eisenmann,, Hinrich Gronemeyer,, Yuichi Hashimoto,, Koichi Shudo, and, Hiroyuki Kagechika. Regulation of Retinoidal Actions by Diazepinylbenzoic Acids. Retinoid Synergists Which Activate the RXR−RAR Heterodimers. Journal of Medicinal Chemistry 1997, 40 (26) , 4222-4234. https://doi.org/10.1021/jm9704309
    39. Keiko Yamamoto,, Wei Yan Sun,, Masateru Ohta,, Kazuhiro Hamada,, Hector F. DeLuca, and, Sachiko Yamada. Conformationally Restricted Analogs of 1α,25-Dihydroxyvitamin D3 and Its 20-Epimer:  Compounds for Study of the Three-Dimensional Structure of Vitamin D Responsible for Binding to the Receptor. Journal of Medicinal Chemistry 1996, 39 (14) , 2727-2737. https://doi.org/10.1021/jm9600048
    40. Lin Zhang,, Alex M. Nadzan,, Richard A. Heyman,, Deborah L. Love,, Dale E. Mais,, Glenn Croston,, William W. Lamph, and, Marcus F. Boehm. Discovery of Novel Retinoic Acid Receptor Agonists Having Potent Antiproliferative Activity in Cervical Cancer Cells. Journal of Medicinal Chemistry 1996, 39 (14) , 2659-2663. https://doi.org/10.1021/jm960285j
    41. Stacie S. Canan Koch,, Laura J. Dardashti,, Jonathan J. Hebert,, Steven K. White,, Glenn E. Croston,, Karen S. Flatten,, Richard A. Heyman, and, Alex M. Nadzan. Identification of the First Retinoid X Receptor Homodimer Antagonist. Journal of Medicinal Chemistry 1996, 39 (17) , 3229-3234. https://doi.org/10.1021/jm960311d
    42. Donald D. Muccio,, Wayne J. Brouillette,, Muzaffar Alam,, Michael F. Vaezi,, Brahma P. Sani,, Pratap Venepally,, Lakshmi Reddy,, Ellen Li,, Andrew W. Norris,, Linda Simpson-Herren, and, Donald L. Hill. Conformationally Defined 6-s-trans-Retinoic Acid Analogs. 3. Structure−Activity Relationships for Nuclear Receptor Binding, Transcriptional Activity, and Cancer Chemopreventive Activity. Journal of Medicinal Chemistry 1996, 39 (19) , 3625-3635. https://doi.org/10.1021/jm9603126
    43. Richard L. Beard,, Diana F. Colon,, Tae K. Song,, Peter J. A. Davies,, Devendra M. Kochhar, and, Roshantha A. S. Chandraratna. Synthesis and Structure−Activity Relationships of Retinoid X Receptor Selective Diaryl Sulfide Analogs of Retinoic Acid. Journal of Medicinal Chemistry 1996, 39 (18) , 3556-3563. https://doi.org/10.1021/jm960386h
    44. Alan T. Johnson,, Elliott S. Klein,, Liming Wang,, Mary E. Pino, and, Roshantha A. S. Chandraratna. Identification of Retinoic Acid Receptor β Subtype Specific Agonists. Journal of Medicinal Chemistry 1996, 39 (26) , 5027-5030. https://doi.org/10.1021/jm960687r
    45. Yuan-Yuan Guo, Jing-Yi Zhang, Jin-Feng Sun, Peng Nie, Hua Gao. Synthesis and application of small molecules approved for the treatment of lymphoma. European Journal of Medicinal Chemistry 2023, 261 , 115835. https://doi.org/10.1016/j.ejmech.2023.115835
    46. Ana S. Leal, Pei-Yu Hung, Afrin Sultana Chowdhury, Karen T. Liby. Retinoid X Receptor agonists as selective modulators of the immune system for the treatment of cancer. Pharmacology & Therapeutics 2023, 252 , 108561. https://doi.org/10.1016/j.pharmthera.2023.108561
    47. Ankedo Warda, Lech J. P. Staniszewski, Zhela Sabir, Sarah Livingston, Michael Sausedo, Sabeeha Reshi, Eyal Ron, Michael T. Applegate, Dena Haddad, Madleen Khamisi, Pamela A. Marshall, Carl E. Wagner, Peter W. Jurutka. Development of Bexarotene Analogs for Treating Cutaneous T-Cell Lymphomas. Cells 2023, 12 (21) , 2575. https://doi.org/10.3390/cells12212575
    48. Weicai Li, Lu Tan, Yijun Chen, Rui Liu, Zhongyu Qi, Shixuan Yuan, Zhanwen Huang, Siping Wei, Xi Du, Dong Yi. Metal‐Free Photocatalytic [4+2] Annulation of Acrylamides with 2‐Benzyl ‐2‐bromocarbonyls to Assemble Tetralin‐1‐carboxamides. Chinese Journal of Chemistry 2023, 252 https://doi.org/10.1002/cjoc.202300483
    49. Jie‐Lin Wang, Sheng‐Ni Hua, Hai‐Juan Bao, Jing Yuan, Yang Zhao, Shuo Chen. Pyroptosis and inflammasomes in cancer and inflammation. MedComm 2023, 4 (5) https://doi.org/10.1002/mco2.374
    50. L. V. Kovalenko, A. G. Polivanova, A. P. Ilyin, I. N. Solovieva, E. I. Gorbacheva, M. S. Oshchepkov. Medicinal Perspectives of Retinoids (Review). Drug development & registration 2023, https://doi.org/10.33380/2305-2066-2023-12-4-1521
    51. Tanpreet Kaur, Jay S. Wright, Bradford D. Henderson, Jonathan Godinez, Xia Shao, Peter J. H. Scott. Automated production of 11 C‐labeled carboxylic acids and esters via “in‐loop” 11 C‐carbonylation using GE FX synthesis modules. Journal of Labelled Compounds and Radiopharmaceuticals 2023, 9 https://doi.org/10.1002/jlcr.4058
    52. Jun Chen, Taige Zhao, Fengming He, Yijing Zhong, Susu Wang, Ziqing Tang, Yingkun Qiu, Zhen Wu, Meijuan Fang. Discovery of bipyridine amide derivatives targeting pRXRα-PLK1 interaction for anticancer therapy. European Journal of Medicinal Chemistry 2023, 254 , 115341. https://doi.org/10.1016/j.ejmech.2023.115341
    53. A. Selen Gurkan‐Alp, Arzu Z. Karabay, Asli Koc, Erdem Buyukbingol. Novel indole retinoid derivative induces apoptosis and cell cycle arrest and modulates AKT and ERK signaling in HL‐60 cells. Fundamental & Clinical Pharmacology 2023, 37 (3) , 557-565. https://doi.org/10.1111/fcp.12876
    54. Yuta Takamura, Shota Kikuzawa, Michiko Fujihara, Yukinari Sunatsuki, Kazutaka Higaki, Hiroki Kakuta. Characterization and Interconversion of Two Crystal Forms of NEt-3IB, a Retinoid X Receptor Agonist. Chemical and Pharmaceutical Bulletin 2023, 71 (4) , 282-288. https://doi.org/10.1248/cpb.c22-00817
    55. Susumu Kodama, Shuzo Matsumoto, Yuta Takamura, Michiko Fujihara, Masaki Watanabe, Atsushi Ono, Hiroki Kakuta. Structural characterization of 1,3-bis-tert-butyl monocyclic benzene derivatives with agonistic activity towards retinoid X receptor alpha. Toxicology Letters 2023, 373 , 76-83. https://doi.org/10.1016/j.toxlet.2022.11.003
    56. Tatsuya Kobayashi, Akira Mitsuhashi, Piao Hongying, Masashi Shioya, Katsushi Kojima, Kyoko Nishikimi, Kinnosuke Yahiro, Makio Shozu. Bexarotene-induced cell death in ovarian cancer cells through Caspase-4-gasdermin E mediated pyroptosis. Scientific Reports 2022, 12 (1) https://doi.org/10.1038/s41598-022-15348-7
    57. Peter W. Jurutka, Orsola di Martino, Sabeeha Reshi, Sanchita Mallick, Michael A. Sausedo, Grant A. Moen, Isaac J. Lee, Dominic J. Ivan, Tyler D. Krall, Samuel J. Peoples, Anthony Perez, Lucas Tromba, Anh Le, Iraj Khadka, Ryan Petros, Brianna M. Savage, Eleine Salama, Jakline Salama, Joseph W. Ziller, Youngbin Noh, Ming-Yue Lee, Wei Liu, John S. Welch, Pamela A. Marshall, Carl E. Wagner. An Isochroman Analog of CD3254 and Allyl-, Isochroman-Analogs of NEt-TMN Prove to Be More Potent Retinoid-X-Receptor (RXR) Selective Agonists Than Bexarotene. International Journal of Molecular Sciences 2022, 23 (24) , 16213. https://doi.org/10.3390/ijms232416213
    58. Johanna Nyffeler, Clinton Willis, Felix R. Harris, Laura W. Taylor, Richard Judson, Logan J. Everett, Joshua A. Harrill. Combining phenotypic profiling and targeted RNA-Seq reveals linkages between transcriptional perturbations and chemical effects on cell morphology: Retinoic acid as an example. Toxicology and Applied Pharmacology 2022, 444 , 116032. https://doi.org/10.1016/j.taap.2022.116032
    59. Axel Kleemann. Antineoplastic and Immunomodulating Agents (L). 2022, 1-87. https://doi.org/10.1002/14356007.a05_001.pub4
    60. Huimei Fu, Lijuan Chu, He Jiao, Longyi Lin, Youping Liu, Guoliang Chen, Libo Zou, Xin Wang, Xin Di. A highly sensitive and rapid LC-MS/MS method for quantification of bexarotene in mouse plasma and brain tissue: Application to mice pharmacokinetic study. Journal of Chromatography B 2022, 1189 , 123025. https://doi.org/10.1016/j.jchromb.2021.123025
    61. Peter W. Jurutka, Orsola di Martino, Sabeeha Reshi, Sanchita Mallick, Zhela L. Sabir, Lech J. P. Staniszewski, Ankedo Warda, Emma L. Maiorella, Ani Minasian, Jesse Davidson, Samir J. Ibrahim, San Raban, Dena Haddad, Madleen Khamisi, Stephanie L. Suban, Bradley J. Dawson, Riley Candia, Joseph W. Ziller, Ming-Yue Lee, Chang Liu, Wei Liu, Pamela A. Marshall, John S. Welch, Carl E. Wagner. Modeling, Synthesis, and Biological Evaluation of Potential Retinoid-X-Receptor (RXR) Selective Agonists: Analogs of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahyro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene) and 6-(Ethyl(4-isobutoxy-3-isopropylphenyl)amino)nicotinic Acid (NEt-4IB). International Journal of Molecular Sciences 2021, 22 (22) , 12371. https://doi.org/10.3390/ijms222212371
    62. Ana S. Leal, Jessica A. Moerland, Di Zhang, Sarah Carapellucci, Beth Lockwood, Teresa Krieger-Burke, Bilal Aleiwi, Edmund Ellsworth, Karen T. Liby. The RXR Agonist MSU42011 Is Effective for the Treatment of Preclinical HER2+ Breast Cancer and Kras-Driven Lung Cancer. Cancers 2021, 13 (19) , 5004. https://doi.org/10.3390/cancers13195004
    63. Bhawna Chopra, Ashwani Kumar Dhingra. Natural products: A lead for drug discovery and development. Phytotherapy Research 2021, 35 (9) , 4660-4702. https://doi.org/10.1002/ptr.7099
    64. Ryohtaroh Matsumoto, Daisuke Takahashi, Masaki Watanabe, Shunsuke Nakatani, Yuta Takamura, Yuji Kurosaki, Hiroki Kakuta, Koji Hase. A Retinoid X Receptor Agonist Directed to the Large Intestine Ameliorates T-Cell-Mediated Colitis in Mice. Frontiers in Pharmacology 2021, 12 https://doi.org/10.3389/fphar.2021.715752
    65. Stephanie Kim, Eric Reed, Stefano Monti, Jennifer J. Schlezinger. A Data-Driven Transcriptional Taxonomy of Adipogenic Chemicals to Identify White and Brite Adipogens. Environmental Health Perspectives 2021, 129 (7) https://doi.org/10.1289/EHP6886
    66. Erik Weis, Martin A. Hayes, Magnus J. Johansson, Belén Martín-Matute. Iridium-catalyzed C−H methylation and d3-methylation of benzoic acids with application to late-stage functionalizations. iScience 2021, 24 (5) , 102467. https://doi.org/10.1016/j.isci.2021.102467
    67. Xiao-Qiang Hu, Ye-Xing Hou, Zi-Kui Liu, Yang Gao. Ruthenium-catalysed C–H/C–N bond activation: facile access to isoindolinones. Organic Chemistry Frontiers 2021, 8 (5) , 915-921. https://doi.org/10.1039/D0QO01406K
    68. Ana S. Leal, Lyndsey A. Reich, Jessica A. Moerland, Di Zhang, Karen T. Liby. Potential therapeutic uses of rexinoids. 2021, 141-183. https://doi.org/10.1016/bs.apha.2021.01.004
    69. Xiaozheng Dou, Adam S. Duerfeldt. Small-Molecule Modulation of PPARs for the Treatment of Prevalent Vascular Retinal Diseases. International Journal of Molecular Sciences 2020, 21 (23) , 9251. https://doi.org/10.3390/ijms21239251
    70. Alexandra Lasch, Jimmy Alarcan, Alfonso Lampen, Albert Braeuning, Dajana Lichtenstein. Combinations of LXR and RXR agonists induce triglyceride accumulation in human HepaRG cells in a synergistic manner. Archives of Toxicology 2020, 94 (4) , 1303-1320. https://doi.org/10.1007/s00204-020-02685-7
    71. David R. Chisholm, Andrew Whiting. Design of synthetic retinoids. 2020, 453-491. https://doi.org/10.1016/bs.mie.2020.02.011
    72. Ana S. Leal, Kayla Zydeck, Sarah Carapellucci, Lyndsey A. Reich, Di Zhang, Jessica A. Moerland, Michael B. Sporn, Karen T. Liby. Retinoid X receptor agonist LG100268 modulates the immune microenvironment in preclinical breast cancer models. npj Breast Cancer 2019, 5 (1) https://doi.org/10.1038/s41523-019-0135-5
    73. Yasuhiro Ishihara, Hikaru Sakurai, Ami Oguro, Mayumi Tsuji, Christoph F.A. Vogel, Takeshi Yamazaki. Retinoid X receptor-mediated neuroprotection via CYP19 upregulation and subsequent increases in estradiol synthesis. The Journal of Steroid Biochemistry and Molecular Biology 2019, 193 , 105421. https://doi.org/10.1016/j.jsbmb.2019.105421
    74. Nathalia Rodrigues de Almeida, Martin Conda‐Sheridan. A review of the molecular design and biological activities of RXR agonists. Medicinal Research Reviews 2019, 39 (4) , 1372-1397. https://doi.org/10.1002/med.21578
    75. Wojciech Krężel, Ralph Rühl, Angel R. de Lera. Alternative retinoid X receptor (RXR) ligands. Molecular and Cellular Endocrinology 2019, 491 , 110436. https://doi.org/10.1016/j.mce.2019.04.016
    76. Di Zhang, Ana S. Leal, Sarah Carapellucci, Pritika H. Shahani, Jaskaran S. Bhogal, Samir Ibrahim, San Raban, Peter W. Jurutka, Pamela A. Marshall, Michael B. Sporn, Carl E. Wagner, Karen T. Liby. Testing Novel Pyrimidinyl Rexinoids: A New Paradigm for Evaluating Rexinoids for Cancer Prevention. Cancer Prevention Research 2019, 12 (4) , 211-224. https://doi.org/10.1158/1940-6207.CAPR-18-0317
    77. Yong Li, Jingjing Wang. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C 9 H 8 O 4. Zeitschrift für Kristallographie - New Crystal Structures 2019, 234 (2) , 349-350. https://doi.org/10.1515/ncrs-2018-0408
    78. Yurina Miyashita, Nobutaka Numoto, Sundaram Arulmozhiraja, Shogo Nakano, Naoya Matsuo, Kanade Shimizu, Osamu Shibahara, Michiko Fujihara, Hiroki Kakuta, Sohei Ito, Teikichi Ikura, Nobutoshi Ito, Hiroaki Tokiwa. Dual conformation of the ligand induces the partial agonistic activity of retinoid X receptor α ( RXR α). FEBS Letters 2019, 593 (2) , 242-250. https://doi.org/10.1002/1873-3468.13301
    79. Claudio Martínez, José A. Souto, Angel R. de Lera. Ligand Design for Modulation of RXR Functions. 2019, 51-72. https://doi.org/10.1007/978-1-4939-9585-1_4
    80. Peter W. Jurutka, Carl E. Wagner. Methods to Assess Activity and Potency of Rexinoids Using Rapid Luciferase-Based Assays: A Case Study with NEt-TMN. 2019, 95-108. https://doi.org/10.1007/978-1-4939-9585-1_7
    81. Carl E. Wagner, Peter W. Jurutka. Methods to Generate an Array of Novel Rexinoids by SAR on a Potent Retinoid X Receptor Agonist: A Case Study with NEt-TMN. 2019, 109-121. https://doi.org/10.1007/978-1-4939-9585-1_8
    82. Verena Hiebl, Angela Ladurner, Simone Latkolik, Verena M. Dirsch. Natural products as modulators of the nuclear receptors and metabolic sensors LXR, FXR and RXR. Biotechnology Advances 2018, 36 (6) , 1657-1698. https://doi.org/10.1016/j.biotechadv.2018.03.003
    83. Ryutaro Hayashi, Akihiro Shimizu, Jonathan A. Davies, Yu Ishizaki, Chris Willis, Jun‐ichi Yoshida. Metal‐ and Oxidant‐Free Alkenyl C−H/Aromatic C−H Cross‐Coupling Using Electrochemically Generated Iodosulfonium Ions. Angewandte Chemie 2018, 130 (39) , 13073-13077. https://doi.org/10.1002/ange.201807592
    84. Ryutaro Hayashi, Akihiro Shimizu, Jonathan A. Davies, Yu Ishizaki, Chris Willis, Jun‐ichi Yoshida. Metal‐ and Oxidant‐Free Alkenyl C−H/Aromatic C−H Cross‐Coupling Using Electrochemically Generated Iodosulfonium Ions. Angewandte Chemie International Edition 2018, 57 (39) , 12891-12895. https://doi.org/10.1002/anie.201807592
    85. Masaki Watanabe, Hiroki Kakuta. Retinoid X Receptor Antagonists. International Journal of Molecular Sciences 2018, 19 (8) , 2354. https://doi.org/10.3390/ijms19082354
    86. Bentley J. Hanish, Jennifer F. Hackney Price, Ichiro Kaneko, Ning Ma, Arjan van der Vaart, Carl E. Wagner, Peter W. Jurutka, Pamela A. Marshall. A novel gene expression analytics-based approach to structure aided design of rexinoids for development as next-generation cancer therapeutics. Steroids 2018, 135 , 36-49. https://doi.org/10.1016/j.steroids.2018.04.009
    87. Brenda J Mengeling, Michael L Goodson, J David Furlow. RXR Ligands Modulate Thyroid Hormone Signaling Competence in Young Xenopus laevis Tadpoles. Endocrinology 2018, 159 (7) , 2576-2595. https://doi.org/10.1210/en.2018-00172
    88. Daniel Merk, Lukas Friedrich, Francesca Grisoni, Gisbert Schneider. De Novo Design of Bioactive Small Molecules by Artificial Intelligence. Molecular Informatics 2018, 37 (1-2) https://doi.org/10.1002/minf.201700153
    89. Daniel Merk, Francesca Grisoni, Lukas Friedrich, Elena Gelzinyte, Gisbert Schneider. Scaffold hopping from synthetic RXR modulators by virtual screening and de novo design. MedChemComm 2018, 9 (8) , 1289-1292. https://doi.org/10.1039/C8MD00134K
    90. Timothée Naret, Olivier Provot, Mouad Alami, Abdallah Hamze. Metal‐Catalyzed Synthesis of 1,1‐Diarylethylene Scaffolds. Asian Journal of Organic Chemistry 2017, 6 (11) , 1509-1518. https://doi.org/10.1002/ajoc.201700342
    91. V. S. Masyuk, I. V. Mineeva. Synthesis of phenyl analog of retinoic acid methyl ester proceeding from 3-(bromomethyl)but-3-enal diethylacetal. Russian Journal of Organic Chemistry 2017, 53 (11) , 1642-1650. https://doi.org/10.1134/S1070428017110045
    92. Axel Kleemann. Antineoplastic and Immunomodulating Agents (L). 2017, 1-56. https://doi.org/10.1002/14356007.a05_001.pub3
    93. Geoffrey M. Gray, Ning Ma, Carl E. Wagner, Arjan van der Vaart. Molecular dynamics simulations and molecular flooding studies of the retinoid X-receptor ligand binding domain. Journal of Molecular Modeling 2017, 23 (3) https://doi.org/10.1007/s00894-017-3260-9
    94. Zongru Guo. The modification of natural products for medical use. Acta Pharmaceutica Sinica B 2017, 7 (2) , 119-136. https://doi.org/10.1016/j.apsb.2016.06.003
    95. Sarah L. Clarke, Gerard P. McGlacken. Methyl fluorosulfonyldifluoroacetate (MFSDA): An Underutilised Reagent for Trifluoromethylation. Chemistry – A European Journal 2017, 23 (6) , 1219-1230. https://doi.org/10.1002/chem.201602511
    96. Jong Bong Lee, Atheer Zgair, Tae Hwan Kim, Min Gi Kim, Sun Dong Yoo, Peter M. Fischer, Pavel Gershkovich. Simple and sensitive HPLC-UV method for determination of bexarotene in rat plasma. Journal of Chromatography B 2017, 1040 , 73-80. https://doi.org/10.1016/j.jchromb.2016.11.024
    97. Hesham Haffez, David R. Chisholm, Roy Valentine, Ehmke Pohl, Christopher Redfern, Andrew Whiting. The molecular basis of the interactions between synthetic retinoic acid analogues and the retinoic acid receptors. MedChemComm 2017, 8 (3) , 578-592. https://doi.org/10.1039/C6MD00680A
    98. Meng-Yang Chang, Yi-Hsuan Huang, Heui-Sin Wang. Synthesis of 1,1-diarylethylenes. Tetrahedron 2016, 72 (22) , 3022-3031. https://doi.org/10.1016/j.tet.2016.04.018
    99. Kaushik Ghosal, Michael Haag, Philip B. Verghese, Tim West, Tim Veenstra, Joel B. Braunstein, Randall J. Bateman, David M. Holtzman, Gary E. Landreth. A randomized controlled study to evaluate the effect of bexarotene on amyloid‐β and apolipoprotein E metabolism in healthy subjects. Alzheimer's & Dementia: Translational Research & Clinical Interventions 2016, 2 (2) , 110-120. https://doi.org/10.1016/j.trci.2016.06.001
    100. Zhenquan Liu, Bingling Luo, Xiaomin Liu, Yumim Hu, Baojian Wu, Peng Huang, Shijun Wen. Cu/Pd‐Catalyzed Cascade Reactions of Cyclic Diaryliodoniums and Alkynes – Access to Fluorenes with Conjugate Enynes/Dienes. European Journal of Organic Chemistry 2016, 2016 (6) , 1110-1118. https://doi.org/10.1002/ejoc.201501544
    Load more citations

    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