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Cholecystokinin dipeptoid antagonists: design, synthesis, and anxiolytic profile of some novel CCK-A and CCK-B selective and mixed CCK-A/CCK-B antagonists

Cite this: J. Med. Chem. 1993, 36, 5, 552–565
Publication Date (Print):March 1, 1993
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    This article is cited by 59 publications.

    1. Mercedes Martín-Martínez,, Natalia De la Figuera,, Miriam LaTorre,, M. Teresa García-López,, Edurne Cenarruzabeitia,, Joaquín Del Río, and, Rosario González-Muñiz. Conformationally Constrained CCK4 Analogues Incorporating IBTM and BTD β-Turn Mimetics. Journal of Medicinal Chemistry 2005, 48 (24) , 7667-7674.
    2. Dirk Weber,, Claudia Berger,, Peter Eickelmann,, Jochen Antel, and, Horst Kessler. Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3. Journal of Medicinal Chemistry 2003, 46 (10) , 1918-1930.
    3. Mercedes Martín-Martínez,, Natalia De la Figuera,, Miriam Latorre,, Rosario Herranz,, M. Teresa García-López,, Edurne Cenarruzabeitia,, Joaquín Del Río, and, Rosario González-Muñiz. β-Turned Dipeptoids as Potent and Selective CCK1 Receptor Antagonists. Journal of Medicinal Chemistry 2000, 43 (20) , 3770-3777.
    4. José M. Bartolomé-Nebreda,, Isabel Gómez-Monterrey,, M. Teresa García-López,, Rosario González-Muñiz,, Mercedes Martín-Martínez,, Santiago Ballaz,, Edurne Cenarruzabeitia,, Miriam LaTorre,, Joaquín Del Río, and, Rosario Herranz. 5-(Tryptophyl)amino-1,3-dioxoperhydropyrido[1,2-c]pyrimidine-Based Potent and Selective CCK1 Receptor Antagonists:  Structural Modifications at the Tryptophan Domain. Journal of Medicinal Chemistry 1999, 42 (22) , 4659-4668.
    5. Bharat K. Trivedi,, Janak K. Padia,, Ann Holmes,, Steven Rose,, D. Scott Wright,, Joanna P. Hinton,, Martyn C. Pritchard,, Jon M. Eden,, Clare Kneen,, Louise Webdale,, Nirmala Suman-Chauhan,, Phil Boden,, Lakhbir Singh,, Mark J. Field, and, David Hill. Second Generation “Peptoid” CCK-B Receptor Antagonists:  Identification and Development of N-(Adamantyloxycarbonyl)-α-methyl-(R)-tryptophan Derivative (CI-1015) with an Improved Pharmacokinetic Profile. Journal of Medicinal Chemistry 1998, 41 (1) , 38-45.
    6. Mercedes Martín-Martínez,, José M. Bartolomé-Nebreda,, Isabel Gómez-Monterrey,, Rosario González-Muñiz,, M. Teresa García-López,, Santiago Ballaz,, Ana Barber,, Ana Fortuño,, Joaquín Del Río, and, Rosario Herranz. Synthesis and Stereochemical Structure−Activity Relationships of 1,3-Dioxoperhydropyrido[1,2-c]pyrimidine Derivatives:  Potent and Selective Cholecystokinin-A Receptor Antagonists. Journal of Medicinal Chemistry 1997, 40 (21) , 3402-3407.
    7. Kazumi Shiosaki,, Chun Wel Lin,, Hana Kopecka,, Bruce Bianchi,, Thomas Miller,, Michael Stashko, and, David Witte. Minor Structural Differences in Boc-CCK-4 Derivatives Dictate Affinity and Selectivity for CCK-A and CCK-B Receptors. Journal of Medicinal Chemistry 1997, 40 (7) , 1169-1172.
    8. Santiago Ballaz. The unappreciated roles of the cholecystokinin receptor CCK(1) in brain functioning. Reviews in the Neurosciences 2017, 28 (6) , 573-585.
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    12. Lucia Lassiani, Michela V. Pavan, Federico Berti, George Kokotos, Theodoros Markidis, Laura Mennuni, Francesco Makovec, Antonio Varnavas. Anthranilic acid based CCK1 receptor antagonists: Blocking the receptor with the same ‘words’ of the endogenous ligand. Bioorganic & Medicinal Chemistry 2009, 17 (6) , 2336-2350.
    13. R. T. Jensen, J. F. Battey, E. R. Spindel, R. V. Benya. International Union of Pharmacology. LXVIII. Mammalian Bombesin Receptors: Nomenclature, Distribution, Pharmacology, Signaling, and Functions in Normal and Disease States. Pharmacological Reviews 2008, 60 (1) , 1-42.
    14. Hans Gerhard Vogel. Activity on the Gastrointestinal Tract. 2007, 1191-1321.
    15. Antonio Varnavas, Lucia Lassiani. Twenty years of non-peptide CCK 1 receptor antagonists: all that glitters is not gold. Expert Opinion on Therapeutic Patents 2006, 16 (9) , 1193-1213.
    16. B.F. Kania, K. Kania, K. Romanowicz, D. Tomaszewska, V. Sutiak, D. Wronska-Fortuna. Centrally administered PD 140.548 N-methyl-d-glucamine prevents the autonomic responses to duodenal pain in sheep. Research in Veterinary Science 2006, 81 (1) , 109-118.
    17. Michael Offel, Pornthip Lattmann, Harjit Singh, D. C. Billington, Yodchai Bunprakob, Jintana Sattayasai, Eric Lattmann. Synthesis of Substituted 3‐Anilino‐5‐phenyl‐1,3‐dihydro‐ 2 H ‐1,4‐benzodiazepine‐2‐ones and their Evaluation as Cholecystokinin‐Ligands. Archiv der Pharmazie 2006, 339 (4) , 163-173.
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    25. Antonio Varnavas, Valentina Valenta, Federico Berti, Lucia Lassiani. Synthesis of N-terminal substituted anthranilic acid dimer derivatives for evaluation on CCK receptors. Il Farmaco 2001, 56 (8) , 555-564.
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    29. Atul C Pande, Martha Greiner, Judith Bammert Adams, R.Bruce Lydiard, Mark W Pierce. Placebo-controlled trial of the CCK-B antagonist, CI-988, in panic disorder. Biological Psychiatry 1999, 46 (6) , 860-862.
    30. Luca Romanelli, Maria Carmela Amico, Francesca Mattioli, Luigi Antonio Morrone, Pacifico Valeri. Interactions between cholecystokinin and opioids in the isolated guinea‐pig ileum. British Journal of Pharmacology 1999, 127 (4) , 909-918.
    31. Rolf Håkanson, Xi-Qin Ding, Per Norlén, Erik Lindström. CCK2 receptor antagonists: pharmacological tools to study the gastrin–ECL cell-parietal cell axis. Regulatory Peptides 1999, 80 (1-2) , 1-12.
    32. David C. Horwell, Martyn C. Pritchard, Jenny Raphy. Design of non-peptide agonists and antagonists for neuropeptide receptors. 1999, 165-190.
    33. Michael W Bunting, Philip M Beart, Robert E Widdop. Effects of the CCKA receptor antagonists SR 27897B and PD140548 on baroreflex function in conscious rats. European Journal of Pharmacology 1997, 337 (1) , 35-39.
    34. Corinne E. Augelli-Szafran, Terri S. Purchase, Bruce D. Roth, Bradley Tait, Bharat K. Trivedi, Michael Wilson, Nirmala Suman-Chauhan, Louise Webdale. SAR study of the indole moiety of CI-988, a potent and selective CCK-B antagonist. Bioorganic & Medicinal Chemistry Letters 1997, 7 (15) , 2009-2014.
    35. Arthur Shulkes, Graham S. Baldwin. BRIEF REVIEW BIOLOGY OF GUT CHOLECYSTOKININ AND GASTRIN RECEPTORS. Clinical and Experimental Pharmacology and Physiology 1997, 24 (3-4) , 209-216.
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    37. Seiichiro Tabuchi, Harunobu Ito, Hajime Sogabe, Masako Kuno, Ikuyo Katsumi, Naoko Yamamoto, Hitoshi Mitsui, Yoshinari Satoh. Dual CCK-A and -B receptor antagonists (I) C9-methyl-1,4-benzodiazepines. Bioorganic & Medicinal Chemistry Letters 1997, 7 (2) , 169-174.
    38. David C. Horwell. Use of the chemical structure of peptides as the starting point to design nonpeptide agonists and antagonists at peptide receptors: Examples with cholecystokinin and tachykinins. Bioorganic & Medicinal Chemistry 1996, 4 (10) , 1573-1576.
    39. Corinne E. Augelli-Szafran, David C. Horwell, Clare Kneen, Daniel F. Ortwine, Martyn C. Pritchard, Terri S. Purchase, Bruce D. Roth, Bharat K. Trivedi, David Hill, Nirmala Suman-Chauhan, Louise Webdale. Cholecystokinin B antagonists. Synthesis and quantitative structure-activity relationships of a series of C-terminal analogues of CI-988. Bioorganic & Medicinal Chemistry 1996, 4 (10) , 1733-1745.
    40. J. Hughes, G.J. Dockray, D. Hill, L. Garcia, M.C. Pritchard, E. Forster, E. Toescu, G. Woodruff, D.C. Horwell. Characterization of novel peptoid agonists for the CCK-A receptor. Regulatory Peptides 1996, 65 (1) , 15-21.
    41. Lakhbir Singh, Mark J. Field, John C. Hunter, Ryszard J. Oles, Geoffrey N. Woodruff. Modulation of the in vivo actions of morphine by the mixed receptor antagonist PD 142898. European Journal of Pharmacology 1996, 307 (3) , 283-289.
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    44. Philip M. Beart, Elena Krstew, Robert E. Widdop. Electrophysiological studies of the cholecystokininA receptor antagonists SR27897B and PD140548 in the rat isolated nodose ganglion. Naunyn-Schmiedeberg's Archives of Pharmacology 1996, 353 (6) , 693-697.
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    46. Lakhbir Singh, Mark J. Field, David R. Hill, David C. Horwell, Alexander T. McKnight, Edward Roberts, Kim W. Tang, Geoffrey N. Woodruff. Peptoid CCK receptor antagonists: pharmacological evaluation of CCKA, CCKB and mixed receptor antagonists. European Journal of Pharmacology 1995, 286 (2) , 185-191.
    47. Xi-Qin Ding, Duan Chen, Rolf Håkanson. Cholecystokinin-B receptor ligands of the dipeptoid series act as agonists on rat stomach histidine decarboxylase. Gastroenterology 1995, 109 (4) , 1181-1187.
    48. Akos Heinemann, Milana Jociĉ, Ulrike Holzer‐Petsche, Gábor Pethö, Brigitta M. Peskar, David C. Horwell, Peter Holzer. Mediation by CCK B receptors of the CCK‐evoked hyperaemia in rat gastric mucosa. British Journal of Pharmacology 1995, 116 (4) , 2274-2278.
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    52. Franca Zanardi, Lucia Battistini, Gloria Rassu, Mara Cornia, Giovanni Casiraghi. γ-Substituted pyrrole-based silyl dienol ethers as α-amino acid enolate equivalents: a versatile entry to racemic α-substituted α-amino acids. J. Chem. Soc., Perkin Trans. 1 1995, 35 (19) , 2471-2475.
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    55. THOMAS HERGET, TARIQ SETHI, S. VINCENT WU, JOHN H. WALSH, ENRIQUE ROZENGURT. Cholecystokinin Stimulates Ca 2+ Mobilization and Clonal Growth in Small Cell Lung Cancer through CCK A and CCK B /Gastrin Receptors a. Annals of the New York Academy of Sciences 1994, 713 (1) , 283-297.
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    58. J.K. Padia, G.L. Bolton, D. Hill, D.C. Horell, B.D. Roth, B.K. Trivedi. Synthesis and sar study of novel CCK-B antagonists. Bioorganic & Medicinal Chemistry Letters 1993, 3 (12) , 2805-2810.
    59. M. Higginbottom, D.R. Hill, D.C. Horwell, E. Mostafai, N. Suman-Chauhan, Edward Roberts. Conformationally restricted analogues of the potent CCK-B antagonist CI-988. Bioorganic & Medicinal Chemistry 1993, 1 (3) , 209-217.

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