Design and synthesis of nonpeptide angiotensin II receptor antagonists featuring acyclic imidazole-mimicking structural units

Bioorganic and Medicinal Chemistry

Volumn 6, Issue 11, 1998, Pages 2013-2027

  Angiolini, Mauro ^a   Belvisi, Laura ^a   Poma, Davide ^b   Salimbeni, Aldo ^b   Sciammetta, Nunzio ^a   Scolastico, Carlo ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b Lusofarmaco   (Italy)

Author keywords

Antagonists; Antihypertension; Molecular modelling

Indexed keywords

ANGIOTENSIN 2 RECEPTOR ANTAGONIST; ANGIOTENSIN RECEPTOR; LOSARTAN POTASSIUM; VALSARTAN;

ARTICLE; CONFORMATION; DRUG ACTIVITY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

ANTIHYPERTENSIVE AGENTS; BIPHENYL COMPOUNDS; DRUG DESIGN; ELECTROSTATICS; HUMANS; IMIDAZOLES; KINETICS; LOSARTAN; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; RECEPTORS, ANGIOTENSIN; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAZOLES; VALINE;

EID: 0031796532     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(98)00160-6     Document Type: Article

References (24)

1. Valloton, M. B. Trends Pharmacol. Sci. 1987, 8, 69.
2. Carini, D. J.; Duncia, J. V.; Aldrich, P. E.; Chiu, A. T.; Johnson, A. L.; Pierce, M. E.; Price, W. A.; Santella III, J. B.; Wells, G. J.; Wexler, R. R.; Wong, P. C.; Yoo, S. E.; Timmermans, P. B. M. W. M. J. Med. Chem. 1991, 34, 2525.
3. Christen, Y.; Waeber, B.; Nussberger, J.; Prochet, M.; Borland, R. M.; Lee, R. J.; Maggon, K.; Shum, L.; Timmermans, P. B. M. W. M.; Brunner, M. R. Circulation 1991, 83, 1271.
4. Greenlee, W. J.; Mantlo, N. B., Eds. Bioorg. Med. Chem. Lett. 1994, 4, entire issue.
5. Salimbeni, A.; Canevotti, R.; Paleari, F.; Bonaccorsi, F.; Renzetti, A.R.; Belvisi, L.; Bravi, G.; Scolastico, C. J. Med. Chem. 1994, 37, 3928, and references cited therein.
6. Salimbeni, A.; Canevotti, R.; Paleari, F.; Poma, D.; Caliari, S.; Fici, F.; Cirillo, R.; Renzetti, A. R.; Subissi, A.; Belvisi, L.; Bravi, G.; Scolastico, C.; Giachetti, A. J. Med. Chem. 1995, 38, 4806, and references cited therein.
7. Cirillo, R.; Renzetti, A. R.; Cucchi, P.; Guelfi, M.; Salimbeni, A.; Caliari, S.; Castellucci, A.; Evangelista, S.; Subissi, A.; Giachetti, A. Br. J. Pharmacol. 1995, 114, 1117.
8. Belvisi, L.; Bravi, G.; Scolastico, C.; Vulpetti, A.; Salimbeni, A.; Todeschini, R. J. Comput.-Aided Mol. Des. 1994, 8, 211.
9. Belvisi, L.; Bonati, L.; Bravi, G.; Pitea, D.; Scolastico, C; Vulpetti, A. J. Mol. Struct. (TEOCHEM) 1993, 281, 237.
10. Bühlmayer, P.; Furet, P.; Criscione, L.; De Gasparo, M.; Whitebread, S.; Schmidlin, T.; Lattmann, R.; Wood, J. Bioorg. Med. Chem. Lett. 1994, 4, 29.
11. Belvisi, L.; Bravi, G.; Catalano, G.; Mabilia, M.; Salimbeni, A.; Scolastico, C. J. Comput.-Aided Mol. Des. 1996, 10, 567.
12. Todeschini, R.; Marengo, E. Chemom. Intell. Lab. Syst. 1992, 16, 25.
13. Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379.
14. Burkert, U.; Allinger, N. L. Molecular Mechanics; ACS Monograph 177: Washington, DC, 1982.
15. Ponder, W. J.; Richards, F. M. J. Comput. Chem. 1987, 8, 1016.
16. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
17. An 8 kcal/mol cutoff was arbitrarily chosen in our first 3-D QSAR study to ensure a large representative sampling of populated minima for the conformationally flexible antagonists under investigation. In the present work the same cutoff was adopted to be in keeping with the previous study and to properly use the geometrical activity model.
18. Frisch, M. J.; Head-Gordon, M.; Trucks, G. W.; Foresman, J. B.; Schlegel, H. B.; Raghavachari, K.; Robb, M. A.; Binkley, J. S.; Gonzalez, C.; Defrees, D. J.; Fox, D. J.; Whiteside, R. A.; Seeger, R.; Melius, C. F.; Baker, J.; Martin, R. L.; Kahn, L. R.; Stewart, J. J. P.; Topiol, S.; Pople, J. A. GAUSSIAN 90, Gaussian Inc., Pittsburgh, PA, 1990.
19. SURFER V4, Golden Software, Golden, CO.
20. Ford-Moore, A. H.; Perry, B. J. Organic Syntheses, Collect. IV, 325.
21. Wadsworth, W. S.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733.
22. Jung, M. E.; Shishido, K.; Davis, L. M. J. Org. Chem. 1982, 47, 891.
23. Feringa, B. L.; De Lange, B.; De Jong, J. C. J. Org. Chem. 1989, 54, 2471.
24. Carrié, R. Heterocycles 1980, 14, 1529.