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
My Activity
CONTENT TYPES

Discovery of a Novel Series of Orally Active Non-Peptide Endothelin-A (ETA) Receptor-Selective Antagonists

Cite this: J. Med. Chem. 1995, 38, 8, 1259–1263
Publication Date (Print):April 1, 1995
https://doi.org/10.1021/jm00008a002
    ACS Legacy Archive

    Article Views

    379

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (3)»

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

    Free first page

    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. You can change your affiliated institution below.

    Supporting Information


    Terms & Conditions

    Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 98 publications.

    1. Yoshitaka Ichikawa, Takahiro Nishimura, and Tamio Hayashi . Rhodium/Chiral Diene-Catalyzed Asymmetric Cyclopolymerization of Achiral 1,8-Diynes. Organometallics 2011, 30 (8) , 2342-2348. https://doi.org/10.1021/om200088q
    2. Kristin Michel, Katrin Büther, Marilyn P. Law, Stefan Wagner, Otmar Schober, Sven Hermann, Michael Schäfers, Burkhard Riemann, Carsten Höltke, and Klaus Kopka . Development and Evaluation of Endothelin-A Receptor (Radio)Ligands for Positron Emission Tomography. Journal of Medicinal Chemistry 2011, 54 (4) , 939-948. https://doi.org/10.1021/jm101110w
    3. Carsten Höltke,, Angelika von Wallbrunn,, Klaus Kopka,, Otmar Schober,, Walter Heindel,, Michael Schäfers, and, Christoph Bremer. A Fluorescent Photoprobe for the Imaging of Endothelin Receptors. Bioconjugate Chemistry 2007, 18 (3) , 685-694. https://doi.org/10.1021/bc060264w
    4. Oliver F. Funk,, Viktor Kettmann,, Jan Drimal, and, Thierry Langer. Chemical Function Based Pharmacophore Generation of Endothelin-A Selective Receptor Antagonists. Journal of Medicinal Chemistry 2004, 47 (11) , 2750-2760. https://doi.org/10.1021/jm031041j
    5. Natsuki Ishizuka,, Ken-ichi Matsumura,, Katsunori Sakai,, Masafumi Fujimoto,, Shin-ichi Mihara, and, Teruo Yamamori. Structure−Activity Relationships of a Novel Class of Endothelin-A Receptor Antagonists and Discovery of Potent and Selective Receptor Antagonist, 2-(Benzo[1,3]dioxol-5-yl)-6-isopropyloxy-4-(4-methoxyphenyl)-2H-chromene-3- carboxylic Acid (S-1255). 1. Study on Structure−Activity Relationships and Basic Structure Crucial for ETA Antagonism. Journal of Medicinal Chemistry 2002, 45 (10) , 2041-2055. https://doi.org/10.1021/jm010382z
    6. James E. Ellis,, Edward M. Davis,, Gary J. Dozeman,, Edward A. Lenoir,, Daniel T. Belmont, and, Phillip L. Brower. Development of a Scalable Process for CI-1020, A Novel Endothelin Antagonist1. Organic Process Research & Development 2001, 5 (3) , 226-233. https://doi.org/10.1021/op010200a
    7. Peter C. Astles,, Thomas J. Brown,, Frank Halley,, Caroline M. Handscombe,, Neil V. Harris,, Tahir N. Majid,, Clive McCarthy,, Iain M. McLay,, Andrew Morley,, Barry Porter,, Alan G. Roach,, Carol Sargent,, Christopher Smith, and, Roger J. A. Walsh. Selective ETA Antagonists. 5. Discovery and Structure−Activity Relationships of Phenoxyphenylacetic Acid Derivatives. Journal of Medicinal Chemistry 2000, 43 (5) , 900-910. https://doi.org/10.1021/jm990378b
    8. Chengde Wu,, E. Radford Decker,, Natalie Blok,, Huong Bui,, Qi Chen,, B. Raju,, Andree R. Bourgoyne,, Vippra Knowles,, Ronald J. Biediger,, Robert V. Market,, Shuqun Lin,, Brian Dupré,, Timothy P. Kogan,, George W. Holland,, Tommy A. Brock, and, Richard A. F. Dixon. Endothelin Antagonists:  Substituted Mesitylcarboxamides with High Potency and Selectivity for ETA Receptors. Journal of Medicinal Chemistry 1999, 42 (22) , 4485-4499. https://doi.org/10.1021/jm9900063
    9. William C. Patt,, Xue-Min Cheng,, Joseph T. Repine,, Chet Lee,, Bill R. Reisdorph,, Mark A. Massa,, Annette M. Doherty,, Kathleen M. Welch,, John W. Bryant,, Michael A. Flynn,, Donnelle M. Walker,, Richard L. Schroeder,, Stephen J. Haleen, and, Joan A. Keiser. Butenolide Endothelin Antagonists with Improved Aqueous Solubility. Journal of Medicinal Chemistry 1999, 42 (12) , 2162-2168. https://doi.org/10.1021/jm980504w
    10. Natesan Murugesan,, Zhengxiang Gu,, Philip D. Stein,, Sharon Bisaha,, Steve Spergel,, Ravi Girotra,, Ving G. Lee,, John Lloyd,, Raj N. Misra,, Joan Schmidt,, Arvind Mathur,, Leslie Stratton,, Yolanda F. Kelly,, Eileen Bird,, Tom Waldron,, Eddie C.-K. Liu,, Rongan Zhang,, Helen Lee,, Randy Serafino,, Benoni Abboa-Offei,, Parker Mathers,, Mary Giancarli,, Andrea Ann Seymour,, Maria L. Webb,, Suzanne Moreland,, Joel C. Barrish, and, John T. Hunt. Biphenylsulfonamide Endothelin Antagonists:  Structure−Activity Relationships of a Series of Mono- and Disubstituted Analogues and Pharmacology of the Orally Active Endothelin Antagonist 2‘-Amino-N- (3,4-dimethyl-5-isoxazolyl)-4‘-(2-methylpropyl)[1,1‘-biphenyl]-2-sulfonamide (BMS-187308). Journal of Medicinal Chemistry 1998, 41 (26) , 5198-5218. https://doi.org/10.1021/jm970872k
    11. Gang Liu,, Kenneth J. Henry, Jr.,, Bruce G. Szczepankiewicz,, Martin Winn,, Natasha S. Kozmina,, Steven A. Boyd,, James Wasicak,, Thomas W. von Geldern,, Jinshyun R. Wu-Wong,, William J. Chiou,, Douglas B. Dixon,, Bach Nguyen,, Kennan C. Marsh, and, Terry J. Opgenorth. Pyrrolidine-3-carboxylic Acids as Endothelin Antagonists. 3. Discovery of a Potent, 2-Nonaryl, Highly Selective ETA Antagonist (A-216546). Journal of Medicinal Chemistry 1998, 41 (17) , 3261-3275. https://doi.org/10.1021/jm980217s
    12. Peter C. Astles,, Clive Brealey,, Thomas J. Brown,, Vincenzo Facchini,, Caroline Handscombe,, Neil V. Harris,, Clive McCarthy,, Iain M. McLay,, Barry Porter,, Alan G. Roach,, Carol Sargent,, Christopher Smith, and, Roger J. A. Walsh. Selective Endothelin A Receptor Antagonists. 3. Discovery and Structure−Activity Relationships of a Series of 4-Phenoxybutanoic Acid Derivatives. Journal of Medicinal Chemistry 1998, 41 (15) , 2732-2744. https://doi.org/10.1021/jm9707131
    13. Chengde Wu,, Ming F. Chan,, Fiona Stavros,, B. Raju,, Ilya Okun, and, Rosario S. Castillo. Structure−Activity Relationships of N 2-Aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides as Selective Endothelin Receptor-A Antagonists. Journal of Medicinal Chemistry 1997, 40 (11) , 1682-1689. https://doi.org/10.1021/jm9608366
    14. James E. Ellis,, Edward M. Davis, and, Phillip L. Brower. A Novel and Practical Method for Hydrocyanation of Chalcones. Organic Process Research & Development 1997, 1 (3) , 250-252. https://doi.org/10.1021/op960048q
    15. Robert H. Bradbury,, Colin Bath,, Roger J. Butlin,, Michael Dennis,, Christine Heys,, Sarah J. Hunt,, Roger James,, Andrew A. Mortlock,, Neil F. Sumner,, Eric K. Tang,, Berwick Telford,, Elaine Whiting, and, Campbell Wilson. New Non-Peptide Endothelin-A Receptor Antagonists:  Synthesis, Biological Properties, and Structure−Activity Relationships of 5-(Dimethylamino)-N-pyridyl-, -N-pyrimidinyl-, -N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides. Journal of Medicinal Chemistry 1997, 40 (6) , 996-1004. https://doi.org/10.1021/jm9604585
    16. William C. Patt,, Jeremy J. Edmunds,, Joseph T. Repine,, Kent A. Berryman,, Billy R. Reisdorph,, Chet Lee,, Mark S. Plummer,, Aurash Shahripour,, Stephen J. Haleen,, Joan A. Keiser,, Mike A. Flynn,, Kathleen M. Welch,, Elwood E. Reynolds,, Ron Rubin,, Brian Tobias,, Hussein Hallak, and, Annette M. Doherty. Structure−Activity Relationships in a Series of Orally Active γ-Hydroxy Butenolide Endothelin Antagonists. Journal of Medicinal Chemistry 1997, 40 (7) , 1063-1074. https://doi.org/10.1021/jm9606507
    17. Andrew S. Tasker,, Bryan K. Sorensen,, Hwan-Soo Jae,, Martin Winn,, Thomas W. von Geldern,, Douglas B. Dixon,, William J. Chiou,, Brian D. Dayton,, Samuel Calzadila,, Lisa Hernandez,, Kennan C. Marsh,, J. Ruth WuWong, and, Terry J. Opgenorth. Potent and Selective Non-Benzodioxole-Containing Endothelin-A Receptor Antagonists. Journal of Medicinal Chemistry 1997, 40 (3) , 322-330. https://doi.org/10.1021/jm960077r
    18. Maria L. Webb,, Pramathesh S. Patel,, Patricia M. Rose,, Eddie C. K. Liu,, Philip D. Stein,, Joel Barrish,, David A. Lach,, Terry Stouch,, Susan M. Fisher,, Ophelia Hadjilambris,, Helen Lee,, Stephen Skwish,, Kenneth E. J. Dickinson, and, Stanley R. Krystek, Jr.. Mutational Analysis of the Endothelin Type A Receptor (ETA):  Interactions and Model of the Selective ETA Antagonist BMS-182874 with the Putative ETA Receptor Binding Cavity. Biochemistry 1996, 35 (8) , 2548-2556. https://doi.org/10.1021/bi951836v
    19. Martin Winn,, Thomas W. von Geldern,, Terry J. Opgenorth,, Hwan-Soo Jae,, Andrew S. Tasker,, Steven A. Boyd,, Jeffrey A. Kester,, Robert A. Mantei,, Radhika Bal,, Bryan K. Sorensen,, Jinshyun R. Wu-Wong,, William J. Chiou,, Douglas B. Dixon,, Eugene I. Novosad,, Lisa Hernandez, and, Kennan C. Marsh. 2,4-Diarylpyrrolidine-3-carboxylic AcidsPotent ETA Selective Endothelin Receptor Antagonists. 1. Discovery of A-127722. Journal of Medicinal Chemistry 1996, 39 (5) , 1039-1048. https://doi.org/10.1021/jm9505369
    20. Thomas W. von Geldern,, Charles Hutchins,, Jeffrey A. Kester,, Jinshyun R. Wu-Wong,, William Chiou,, Douglas B. Dixon, and, Terry J. Opgenorth. Azole Endothelin Antagonists. 1. A Receptor Model Explains an Unusual Structure−Activity Profile. Journal of Medicinal Chemistry 1996, 39 (4) , 957-967. https://doi.org/10.1021/jm950591h
    21. Hartmut Riechers,, Hans-Peter Albrecht,, Willi Amberg,, Ernst Baumann,, Harald Bernard,, Hans-Joachim Böhm,, Dagmar Klinge,, Andreas Kling,, Stefan Müller,, Manfred Raschack,, Liliane Unger,, Nigel Walker, and, Wolfgang Wernet. Discovery and Optimization of a Novel Class of Orally Active Nonpeptidic Endothelin-A Receptor Antagonists. Journal of Medicinal Chemistry 1996, 39 (11) , 2123-2128. https://doi.org/10.1021/jm960274q
    22. Marit ten Hove, Andreas Smyris, Richell Booijink, Lydia Wachsmuth, Uwe Hansen, Lejla Alic, Cornelius Faber, Carsten Hӧltke, Ruchi Bansal. Engineered SPIONs functionalized with endothelin a receptor antagonist ameliorate liver fibrosis by inhibiting hepatic stellate cell activation. Bioactive Materials 2024, 39 , 406-426. https://doi.org/10.1016/j.bioactmat.2024.05.034
    23. Beibei Zhao, Zhen Zhang, Yu Ge, Pinhua Li, Tao Miao, Lei Wang. Photochemical synthesis of 3-hydroxyphenanthro[9,10- c ]furan-1(3 H )-ones from α-keto acids and alkynes. Organic Chemistry Frontiers 2021, 8 (5) , 975-982. https://doi.org/10.1039/D0QO01487G
    24. Lala Qu, Xiuli Zhang, Jixia Wang, Han Zhou, Tao Hou, Lai Wei, Fangfang Xu, Xinmiao Liang. Phenotypic assessment and ligand screening of ETA/ETB receptors with label-free dynamic mass redistribution assay. Naunyn-Schmiedeberg's Archives of Pharmacology 2020, 393 (6) , 937-950. https://doi.org/10.1007/s00210-019-01756-6
    25. Mathias Schacht, Djawid Mohammadi, Nina Schützenmeister. Pd‐Catalyzed Synthesis of γ‐Keto Esters as Key Intermediates for the Synthesis of γ‐Hydroxybutenolides. European Journal of Organic Chemistry 2019, 2019 (15) , 2587-2591. https://doi.org/10.1002/ejoc.201900023
    26. Xiaobao Zeng, Chulong Liu, Weiguang Yang, Xingyong Wang, Xinyan Wang, Yuefei Hu. A general two-step one-pot synthesis process of ynones from α-keto acids and 1-iodoalkynes. Chemical Communications 2018, 54 (68) , 9517-9520. https://doi.org/10.1039/C8CC05429K
    27. Wenbin Mao, Chen Zhu. Efficient synthesis of multiply substituted butenolides from keto acids and terminal alkynes promoted by combined acids. Organic Chemistry Frontiers 2017, 4 (6) , 1029-1033. https://doi.org/10.1039/C6QO00820H
    28. Hiroki Miura, Kazuki Takeuchi, Tetsuya Shishido. Intermolecular [2+2+1] Carbonylative Cycloaddition of Aldehydes with Alkynes, and Subsequent Oxidation to γ‐Hydroxybutenolides by a Supported Ruthenium Catalyst. Angewandte Chemie International Edition 2016, 55 (1) , 278-282. https://doi.org/10.1002/anie.201507814
    29. Hiroki Miura, Kazuki Takeuchi, Tetsuya Shishido. Intermolecular [2+2+1] Carbonylative Cycloaddition of Aldehydes with Alkynes, and Subsequent Oxidation to γ‐Hydroxybutenolides by a Supported Ruthenium Catalyst. Angewandte Chemie 2016, 128 (1) , 286-290. https://doi.org/10.1002/ange.201507814
    30. Wenbin Mao, Chen Zhu. Synthesis of highly substituted γ-hydroxybutenolides through the annulation of keto acids with alkynes and subsequent hydroxyl transposition. Chemical Communications 2016, 52 (30) , 5269-5272. https://doi.org/10.1039/C6CC01554A
    31. Clemens Lamberth, Edouard Godineau, Tomas Smejkal, Stephan Trah. A new Knoevenagel-type synthesis of fully substituted γ-hydroxybutenolides. Tetrahedron Letters 2012, 53 (32) , 4117-4120. https://doi.org/10.1016/j.tetlet.2012.05.125
    32. Katrin Büther, Matthijs G. Compeer, Jo G. R. De Mey, Otmar Schober, Michael Schäfers, Christoph Bremer, Burkhard Riemann, Carsten Höltke. Assessment of Endothelin-A Receptor Expression in Subcutaneous and Orthotopic Thyroid Carcinoma Xenografts in Vivo Employing Optical Imaging Methods. Endocrinology 2012, 153 (6) , 2907-2918. https://doi.org/10.1210/en.2011-2017
    33. Nan Zhang, Larry N. Agbor, Jason A. Scott, Tyler Zalobowski, Khalid M. Elased, Alicia Trujillo, Melissa Skelton Duke, Valerie Wolf, Mary T. Walsh, Jerry L. Born, Linda A. Felton, Jian Wang, Wei Wang, Nancy L. Kanagy, Mary K. Walker. An activated renin–angiotensin system maintains normal blood pressure in aryl hydrocarbon receptor heterozygous mice but not in null mice. Biochemical Pharmacology 2010, 80 (2) , 197-204. https://doi.org/10.1016/j.bcp.2010.03.023
    34. Juan J. Perez, Francesc J. Corcho, Jaime Rubio‐Martinez. Design of Peptidomimetics. 2010, 205-248. https://doi.org/10.1002/0471266949.bmc120
    35. Carsten Höltke, Marilyn P. Law, Stefan Wagner, Klaus Kopka, Andreas Faust, Hans-Jörg Breyholz, Otmar Schober, Christoph Bremer, Burkhard Riemann, Michael Schäfers. PET-compatible endothelin receptor radioligands: Synthesis and first in vitro and in vivo studies. Bioorganic & Medicinal Chemistry 2009, 17 (20) , 7197-7208. https://doi.org/10.1016/j.bmc.2009.08.058
    36. Nader M. Boshta, Martin Bomkamp, Siegfried R. Waldvogel. Synthesis of 2,2-functionalized benzo[1,3]dioxoles. Tetrahedron 2009, 65 (18) , 3773-3779. https://doi.org/10.1016/j.tet.2009.02.053
    37. Carsten Höltke, Jens Waldeck, Klaus Kopka, Walter Heindel, Otmar Schober, Michael Schäfers, Christoph Bremer. Biodistribution of a Nonpeptidic Fluorescent Endothelin a Receptor Imaging Probe. Molecular Imaging 2009, 8 (1) , 7290.2009.00003. https://doi.org/10.2310/7290.2009.00003
    38. Tamás Patonay, József Jekő, Éva Juhász‐Tóth. Synthesis of Highly Substituted 2 H ‐Azirine‐2‐carboxylates via 3‐Azido‐4‐oxobut‐2‐enoates. European Journal of Organic Chemistry 2008, 2008 (8) , 1441-1448. https://doi.org/10.1002/ejoc.200701072
    39. T.K. Sawyer. Peptidomimetic and Nonpeptide Drug Discovery: Receptor, Protease, and Signal Transduction Therapeutic Targets. 2007, 603-647. https://doi.org/10.1016/B0-08-045044-X/00052-3
    40. Shane Perrine. PD156707. 2007, 1-3. https://doi.org/10.1016/B978-008055232-3.62375-X
    41. Carsten Höltke, Marilyn P. Law, Stefan Wagner, Hans-Jörg Breyholz, Klaus Kopka, Christoph Bremer, Bodo Levkau, Otmar Schober, Michael Schäfers. Synthesis, in vitro pharmacology and biodistribution studies of new PD 156707-derived ETA receptor radioligands. Bioorganic & Medicinal Chemistry 2006, 14 (6) , 1910-1917. https://doi.org/10.1016/j.bmc.2005.10.039
    42. Rajeshwar P. Verma, Alka Kurup, Corwin Hansch. On the role of polarizability in QSAR. Bioorganic & Medicinal Chemistry 2005, 13 (1) , 237-255. https://doi.org/10.1016/j.bmc.2004.09.039
    43. Hirobumi Takahashi, Norikazu Ohtake, Toshihiro Sakamoto, Tomoharu Iino, Nobuhiko Kawanishi, Masayuki Nakamura, Takashi Yoshizumi, Kenji Niiyama, Satoshi Ozaki, Hiromasa Okada, Akiko Kano, Hiroyuki Takahashi, Yasuyuki Ishii, Megumu Okada, Michiyasu Saito, Yoshio Sawazaki, Takashi Hayama, Masaru Nishikibe. Structure–activity relationships of a novel class of endothelin receptor selective antagonists; 6-carboxy-2-isopropylamino-5,7-diarylcyclopenteno[1,2-b]pyridines. Bioorganic & Medicinal Chemistry Letters 2004, 14 (6) , 1503-1507. https://doi.org/10.1016/j.bmcl.2004.01.008
    44. Udo E.W Lange, Wilfried M Braje, Willi Amberg, Georg Kettschau. Solid-Phase synthesis of endothelin receptor antagonists. Bioorganic & Medicinal Chemistry Letters 2003, 13 (10) , 1721-1724. https://doi.org/10.1016/S0960-894X(03)00236-1
    45. Srinivas Padakanti, Venugopal Rao Veeramaneni, Vijaya Raghavan Pattabiraman, Manojit Pal, Koteswar Rao Yeleswarapu. A simple and rapid entry to 5-alkyl (aryl)-5-hydroxy-3,4-diarylfuranones and 3a-hydroxy-1-aryl-2,3a,4,5-tetrahydronaphthofuranones via a tandem esterification and oxidative cyclization process. Tetrahedron Letters 2002, 43 (48) , 8715-8719. https://doi.org/10.1016/S0040-4039(02)02144-5
    46. Kenji Niiyama, Toshiaki Mase, Hirobumi Takahashi, Akira Naya, Kasumi Katsuki, Toshio Nagase, Satoshi Ito, Takashi Hayama, Akihiro Hisaka, Satoshi Ozaki, Masaki Ihara, Mitsuo Yano, Takahiro Fukuroda, Kazuhito Noguchi, Masaru Nishikibe, Kiyofumi Ishikawa. 6-Carboxy-5,7-diarylcyclopenteno[1,2-b]pyridine derivatives. Bioorganic & Medicinal Chemistry 2002, 10 (8) , 2461-2470. https://doi.org/10.1016/S0968-0896(02)00122-0
    47. Yashu Coe, Stephen J. Haleen, Kathleen M. Welch, You-An Liu, Flavio Coceani. The Endothelin A Receptor Antagonists PD 156707 (CI-1020) and PD 180988 (CI-1034) Reverse the Hypoxic Pulmonary Vasoconstriction in the Perinatal Lamb. Journal of Pharmacology and Experimental Therapeutics 2002, 302 (2) , 672-680. https://doi.org/10.1124/jpet.302.2.672
    48. Friedrich Brunner, Gerald Wölkart, Stephen Haleen. Defective Intracellular Calcium Handling in Monocrotaline-Induced Right Ventricular Hypertrophy: Protective Effect of Long-Term Endothelin-A Receptor Blockade with 2-Benzo[1,3]dioxol-5-yl-3-benzyl-4-(4-methoxy-phenyl-)- 4-oxobut-2-enoate-sodium (PD 155080). Journal of Pharmacology and Experimental Therapeutics 2002, 300 (2) , 442-449. https://doi.org/10.1124/jpet.300.2.442
    49. Hironori Harada, Jun-ichi Kazami, Susumu Watanuki, Ryuji Tsuzuki, Katsumi Sudoh, Akira Fujimori, Masanao Sanagi, Masaya Orita, Hideaki Nakahara, Jun Shimaya, Shin-ichi Tsukamoto, Akihiro Tanaka, Isao Yanagisawa. Ethenesulfonamide and ethanesulfonamide derivatives, a novel class of orally active endothelin-A receptor antagonists. Bioorganic & Medicinal Chemistry 2001, 9 (11) , 2955-2968. https://doi.org/10.1016/S0968-0896(01)00187-0
    50. Janet J Maguire, Rhoda E Kuc, Anthony P Davenport. Vasoconstrictor activity of novel endothelin peptide, ET‐1 (1 – 31) , in human mammary and coronary arteries in vitro. British Journal of Pharmacology 2001, 134 (6) , 1360-1366. https://doi.org/10.1038/sj.bjp.0704384
    51. Paivi J. Kukkola, Natalie A. Bilci, Theodore Ikler, Paula Savage, Suraj S. Shetty, Dominick DelGrande, Arco Y. Jeng. Isoindolines: A new series of potent and selective endothelin-A receptor antagonists. Bioorganic & Medicinal Chemistry Letters 2001, 11 (13) , 1737-1740. https://doi.org/10.1016/S0960-894X(01)00273-6
    52. Yasuhiko Kanda, Yasuyuki Kawanishi, Katsuo Oda, Teruo Sakata, Shin-ichi Mihara, Kenji Asakura, Toshiyuki Kanemasa, Mitsuyoshi Ninomiya, Masafumi Fujimoto, Toshiro Konoike. Synthesis and structure–activity relationships of potent and orally active sulfonamide ETB selective antagonists. Bioorganic & Medicinal Chemistry 2001, 9 (4) , 897-907. https://doi.org/10.1016/S0968-0896(00)00305-9
    53. P. J. Henry, R. G. Goldie. Endothelin Receptors. 2001, 69-114. https://doi.org/10.1007/978-3-642-56899-2_4
    54. Hironori HARADA, Jun-ichi KAZAMI, Susumu WATANUKI, Ryuji TSUZUKI, Katsumi SUDOH, Akira FUJIMORI, Tatsuhiro TOKUNAGA, Akihiro TANAKA, Shin-ichi TSUKAMOTO, Isao YANAGISAWA. Synthesis and Structure-Activity Relationships in a Series of Ethenesulfonamide Derivatives, a Novel Class of Endothelin Receptor Antagonists.. Chemical and Pharmaceutical Bulletin 2001, 49 (12) , 1593-1603. https://doi.org/10.1248/cpb.49.1593
    55. Chengde Wu. Recent discovery and development of endothelin receptor antagonists. Expert Opinion on Therapeutic Patents 2000, 10 (11) , 1653-1668. https://doi.org/10.1517/13543776.10.11.1653
    56. Yasuhiko Kanda, Tadashi Takahashi, Yoshitaka Araki, Toshiro Konoike, Shin-ichi Mihara, Masafumi Fujimoto. Discovery and synthesis of a potent sulfonamide ETB selective antagonist. Bioorganic & Medicinal Chemistry Letters 2000, 10 (16) , 1875-1878. https://doi.org/10.1016/S0960-894X(00)00366-8
    57. Jidong Zhang, Stanislas Didierlaurent, Michel Fortin, Dominique Lefrançois, Eric Uridat, Jean Paul Vevert. Nonpeptide endothelin antagonists: from lower affinity pyrazol-5-ols to higher affinity pyrazole-5-carboxylic acids. Bioorganic & Medicinal Chemistry Letters 2000, 10 (12) , 1351-1355. https://doi.org/10.1016/S0960-894X(00)00232-8
    58. Eliot H. Ohlstein, Robert R. Ruffolo Jr, John D. Elliott. Drug Discovery in the Next Millennium. Annual Review of Pharmacology and Toxicology 2000, 40 (1) , 177-191. https://doi.org/10.1146/annurev.pharmtox.40.1.177
    59. Mitsuo Takahashi, Kuniya Sakurai, Seji Niwa, Seiji Oono. Pharmacophore Model of Endothelin Antagonists. 2000, 416-417. https://doi.org/10.1007/978-1-4615-4141-7_103
    60. F. Coceani, Y.-A. Liu, E. Seidlitz, L. Kelsey, T. Kuwaki, C. Ackerley, M. Yanagisawa. Endothelin A receptor is necessary for O 2 constriction but not closure of ductus arteriosus. American Journal of Physiology-Heart and Circulatory Physiology 1999, 277 (4) , H1521-H1531. https://doi.org/10.1152/ajpheart.1999.277.4.H1521
    61. Steven A Boyd, Robert A Mantei, Andrew S Tasker, Gang Liu, Bryan K Sorensen, Kenneth J Henry Jr, Thomas W von Geldern, Martin Winn, Jinshyun R Wu-Wong, William J Chiou, Douglas B Dixon, Charles W Hutchins, Kennan C Marsh, Bach Nguyen, Terry J Opgenorth. Discovery of a series of pyrrolidine-based endothelin receptor antagonists with enhanced ETA receptor selectivity. Bioorganic & Medicinal Chemistry 1999, 7 (6) , 991-1002. https://doi.org/10.1016/S0968-0896(99)00022-X
    62. Janet J Maguire, Anthony P Davenport. The therapeutic potential of PD156707 and related butenolide endothelin antagonists. Expert Opinion on Investigational Drugs 1999, 8 (1) , 71-78. https://doi.org/10.1517/13543784.8.1.71
    63. Janet J Maguire, Anthony P Davenport. Endothelin receptor expression and pharmacology in human saphenous vein graft. British Journal of Pharmacology 1999, 126 (2) , 443-450. https://doi.org/10.1038/sj.bjp.0702326
    64. Ming Fai Chan, Adam Kois, Erik J. Verner, Bore G. Raju, Rosario S. Castillo, Chengde Wu, Ilya Okun, Fiona D. Stavros, V.N. Balaji. The discovery and structure—activity relationships of nonpeptide, low molecular weight antagonists selective for the endothelin ETB receptor. Bioorganic & Medicinal Chemistry 1998, 6 (12) , 2301-2316. https://doi.org/10.1016/S0968-0896(98)80010-2
    65. Spencer P. Harland, Rhoda E. Kuc, John D. Pickard, Anthony P. Davenport. Expression of EndothelinA Receptors in Human Gliomas and Meningiomas, with High Affinity for the Selective Antagonist PD156707. Neurosurgery 1998, 43 (4) , 890-898. https://doi.org/10.1097/00006123-199810000-00097
    66. K.A. Berryman, J.J. Edmunds, A.M. Bunker, S. Haleen, J. Bryant, K.M. Welch, A.M. Doherty. Endothelin receptor antagonists: synthesis and structure–activity relationships of substituted benzothiazine-1,1-dioxides. Bioorganic & Medicinal Chemistry 1998, 6 (9) , 1447-1456. https://doi.org/10.1016/S0968-0896(98)00080-7
    67. Mark A. Massa, William C. Patt, Kyunghye Ahn, Andre M. Sisneros, Sarah B. Herman, Annette Doherty. Synthesis of novel substituted pyridines as inhibitors of endothelin coverting enzyme-1 (ECE-1). Bioorganic & Medicinal Chemistry Letters 1998, 8 (16) , 2117-2122. https://doi.org/10.1016/S0960-894X(98)00375-8
    68. Peter Cernacek, Luigi Franchi, Jocelyn Dupuis, Jean-Lucien Rouleau, Mortimer Levy. Radioreceptor assay of an endothelin A receptor antagonist in plasma and urine. Clinical Chemistry 1998, 44 (8) , 1666-1673. https://doi.org/10.1093/clinchem/44.8.1666
    69. Andrew C. G. Uprichard, Alan L. Metz, Hussein Hallak, Stephen J. Haleen. PD‐156707: A Selective Endothelin‐A Receptor Antagonist. Cardiovascular Drug Reviews 1998, 16 (2) , 89-104. https://doi.org/10.1111/j.1527-3466.1998.tb00347.x
    70. James E. Ellis, Steven R. Lenger. A Convenient Synthesis of 3,4-Dimethoxy-5-hydroxybenzaldehyde. Synthetic Communications 1998, 28 (9) , 1517-1524. https://doi.org/10.1080/00397919808006854
    71. Friedrich Brunner, Lionel H. Opie. Role of Endothelin-A Receptors in Ischemic Contracture and Reperfusion Injury. Circulation 1998, 97 (4) , 391-398. https://doi.org/10.1161/01.CIR.97.4.391
    72. Janet J. Maguire, Anthony P. Davenport. PD156707: A Potent Antagonist of Endothelin-1 in Human Diseased Coronary Arteries and Vein Grafts. Journal of Cardiovascular Pharmacology 1998, 31 , S239-S240. https://doi.org/10.1097/00005344-199800001-00067
    73. Anthony P Davenport, Rhoda E Kuc, Michael J Ashby, William C Patt, Annette M Doherty. Characterization of [ 125 I]‐PD164333, an ET A selective non‐peptide radiolabelled antagonist, in normal and diseased human tissues. British Journal of Pharmacology 1998, 123 (2) , 223-230. https://doi.org/10.1038/sj.bjp.0701597
    74. B. Raju, Chengde Wu, Rosario Castillo, Ilya Okun, Fiona Stavros, Ming Fai Chan. 2-Aryloxycarbonylthiophene-3-sulfonamides: Highly potent and etA selective endothelin receptor antagonists. Bioorganic & Medicinal Chemistry Letters 1997, 7 (16) , 2093-2098. https://doi.org/10.1016/S0960-894X(97)00367-3
    75. Chieko Imajo, Paul D. Walden, Ellen Shapiro, Annette M. Doherty, Herbert Lepor. Evaluation of the Effect of Endothelin-1 and Characterization of the Selective Endothelin A Receptor Antagonist PD155080 in the Prostate. Journal of Urology 1997, 158 (1) , 253-257. https://doi.org/10.1097/00005392-199707000-00081
    76. Sanjay Rajagopalan, Jørn Bech Laursen, Alain Borthayre, Sabine Kurz, Joan Keiser, Steven Haleen, Adel Giaid, David G. Harrison. \E Role for Endothelin-1 in Angiotensin II– Mediated Hypertension. Hypertension 1997, 30 (1) , 29-34. https://doi.org/10.1161/01.HYP.30.1.29
    77. PC Astles, TJ Brown, CM Handscombe, MF Harper, NV Harris, RA Lewis, PM Lockey, C McCarthy, IM McLay, B Porter, AG Roach, C Smith, RJA Walsh. Selective endothelin A receptor ligands. 1. Discovery and structure-activity of 2,4-disubstituted benzoic acid derivatives. European Journal of Medicinal Chemistry 1997, 32 (5) , 409-423. https://doi.org/10.1016/S0223-5234(97)81678-9
    78. JS Kaltenbronn, J Quin, BR Reisdorph, S Klutchko, EE Reynolds, KM Welch, MA Flynn, AM Doherty. Benzofuran derivatives as ETA-selective, non-peptide endothelin antagonists. European Journal of Medicinal Chemistry 1997, 32 (5) , 425-431. https://doi.org/10.1016/S0223-5234(97)81679-0
    79. Francis G. Spinale, Jennifer D. Walker, Rupak Mukherjee, Julie P. Iannini, Anthony T. Keever, Kim P. Gallagher. Concomitant Endothelin Receptor Subtype-A Blockade During the Progression of Pacing-Induced Congestive Heart Failure in Rabbits. Circulation 1997, 95 (7) , 1918-1929. https://doi.org/10.1161/01.CIR.95.7.1918
    80. Diane P Ignasiak, Thomas B McClanahan, Lori J Saganek, Ronald E Potoczak, Hussein Hallak, Kim P Gallagher. Effects of endothelin ETA receptor antagonism with PD 156707 on hemodynamics and renal vascular resistance in rabbits. European Journal of Pharmacology 1997, 321 (3) , 295-300. https://doi.org/10.1016/S0014-2999(96)00954-5
    81. William C. Patt, Billy R. Reisdorph, Joseph T. Repine, Annette M. Doherty, Stephen J. Haleen, Donnelle M. Walker, Kathleen M. Welch, Michael A. Flynn, Hussein Hallak, Eric L. Reyner, Barbra H. Stewart. γ-Carbamate butenolide analogues as potent ETA selective endothelin receptor antagonists and prodrugs. Bioorganic & Medicinal Chemistry Letters 1997, 7 (3) , 297-302. https://doi.org/10.1016/S0960-894X(97)00002-4
    82. Donald E. Kohan. Endothelins in the normal and diseased kidney. American Journal of Kidney Diseases 1997, 29 (1) , 2-26. https://doi.org/10.1016/S0272-6386(97)90004-4
    83. X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E.E. Reynolds, K.M. Welch, M.A. Flynn, A.M. Doherty. Synthesis and structure-activity relationships of 9-substituted acridines as endothelin-A receptor antagonists. Bioorganic & Medicinal Chemistry Letters 1996, 6 (24) , 2999-3002. https://doi.org/10.1016/S0960-894X(96)00551-3
    84. Friedrich Brunner, Annette M. Doherty. Role of ET B receptors in local clearance of endothelin‐1 in rat heart: studies with the antagonists PD 155080 and BQ‐788. FEBS Letters 1996, 396 (2-3) , 238-242. https://doi.org/10.1016/0014-5793(96)01103-9
    85. Toshal R. Patel, Samuel Galbraith, David I. Graham, Hussein Hallak, Annette M. Doherty, James McCulloch. Endothelin Receptor Antagonist Increases Cerebral Perfusion and Reduces Ischaemic Damage in Feline Focal Cerebral Ischaemia. Journal of Cerebral Blood Flow & Metabolism 1996, 16 (5) , 950-958. https://doi.org/10.1097/00004647-199609000-00019
    86. Toshal R. Patel, Samuel Galbraith, Moira A. McAuley, James McCulloch. Endothelin-Mediated Vascular Tone following Focal Cerebral Ischaemia in the Cat. Journal of Cerebral Blood Flow & Metabolism 1996, 16 (4) , 679-687. https://doi.org/10.1097/00004647-199607000-00019
    87. Toshal R. Patel, Moira A. McAuley, James McCulloch. Endothelin receptor mediated constriction and dilatation in feline cerebral resistance arterioles in vivo. European Journal of Pharmacology 1996, 307 (1) , 41-48. https://doi.org/10.1016/0014-2999(96)00188-4
    88. Amy M. Bunker, Jeremy J. Edmunds, Kent A. Berryman, Donnelle M. Walker, Michael A. Flynn, Kathy M. Welch, Annette M. Doherty. 1-benzyl-3-thioaryl-2-carboxyindoles as potent non-peptide endothelin antagonists. Bioorganic & Medicinal Chemistry Letters 1996, 6 (12) , 1367-1370. https://doi.org/10.1016/0960-894X(96)00232-6
    89. Amy M Bunker, Jeremy J Edmunds, Kent A Berryman, Donnelle M Walker, Michael A Flynn, Kathy M Welch, Annette M Doherty. 1,3-diaryl-2-carboxyindoles as potent non-peptide endothelin antagonists. Bioorganic & Medicinal Chemistry Letters 1996, 6 (9) , 1061-1066. https://doi.org/10.1016/0960-894X(96)00170-9
    90. . POSTER COMMUNICATIONS. British Journal of Pharmacology 1996https://doi.org/10.1111/j.1476-5381.1996.tb17244.x
    91. David T. Rossi, Hussein Hallak, Laura Bradford. Liquid chromatographic assay for a butenolide endothelin antagonist (PD 156707) in plasma. Journal of Chromatography B: Biomedical Sciences and Applications 1996, 677 (2) , 299-304. https://doi.org/10.1016/0378-4347(95)00456-4
    92. Mario Zuccarello, Giovanni B. Soattin, Adam I. Lewis, Volker Breu, Hussein Hallak, Robert M. Rapoport. Prevention of subarachnoid hemorrhage—induced cerebral vasospasm by oral administration of endothelin receptor antagonists. Journal of Neurosurgery 1996, 84 (3) , 503-507. https://doi.org/10.3171/jns.1996.84.3.0503
    93. Annette M. Doherty. Design and discovery of nonpeptide endothelin antagonists. Drug Discovery Today 1996, 1 (2) , 60-70. https://doi.org/10.1016/1359-6446(96)89090-8
    94. M.A. Lago, J.I. Luengo, C.E. Peishoff, J.D. Elliott. Chapter 9. Endothelin Antagonists. 1996, 81-90. https://doi.org/10.1016/S0065-7743(08)60448-0
    95. . Cardiovascular & Renal: Novel ET receptor antagonists. Expert Opinion on Therapeutic Patents 1995, 1115-1116. https://doi.org/10.1517/13543776.5.10.1115
    96. Thomas F. Walsh. Chapter 10. Progress in the Development of Endothelin Receptor Antagonists. 1995, 91-100. https://doi.org/10.1016/S0065-7743(08)60923-9
    97. Annette M. Doherty, Andrew C. G. Uprichard. Discovery and Development of an Endothelin a Receptor-Selective Antagonist PD 156707. , 81-112. https://doi.org/10.1007/0-306-47384-4_5
    98. A. P. Davenport, J. J. Maguire. Endothelin. , 295-329. https://doi.org/10.1007/3-540-32967-6_9