Molecular modeling study and synthesis of quinazolinone-arylpiperazine derivatives as α 1-adrenoreceptor antagonists

European Journal of Medicinal Chemistry

Volumn 46, Issue 2, 2011, Pages 647-658

  Abou Seri, Sahar Mahmoud ^a   Abouzid, Khaled ^b   Abou El Ella, Dalal A ^b  

^a CAIRO UNIVERSITY   (Egypt)

^b African Union Organization St Abbassia   (Egypt)

Author keywords

1 Adrenoceptor antagonists; Arylpiperazine derivatives; Molecular modeling; Quinazolinones

Indexed keywords

2 [(4 PHENYLPIPERAZIN 1 YL)METHYL]QUINAZOLIN 4(3H) ONE; 2 [[4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]METHYL]QUINAZOLIN 4(3H) ONE; 2 [[4 (4 NITROPHENYL)PIPERAZIN 1 YL]METHYL]QUINAZOLIN 4(3H) ONE; ALPHA 1 ADRENORECEPTOR ANTAGONIST; ALPHA ADRENERGIC RECEPTOR BLOCKING AGENT; ETHYL 6,7 DIMETHOXY 3 {2 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL] ACETAMIDO} 4 OXO 3,4 DIHYDROQUINAZOLINE 2 CARBOXYLATE; ETHYL 6,7 DIMETHOXY 3 {2 [4 (4 NITROPHENYL)PIPERAZIN 1 YL] ACETAMIDO} 4 OXO 3,4 DIHYDROQUINAZOLINE 2 CARBOXYLATE; ETHYL 6,7 DIMETHOXY 3 {3 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL] PROPANAMIDO} 4 OXO 3,4 DIHYDROQUINAZOLINE 2 CARBOXYLATE; ETHYL 6,7 DIMETHOXY 3 {3 [4 (4 NITROPHENYL)PIPERAZIN 1 YL] PROPANAMIDO} 4 OXO 3,4 DIHYDROQUINAZOLINE 2 CARBOXYLATE; ETHYL 6,7 DIMETHOXY 4 OXO 3 [2 (4 PHENYLPIPERAZIN 1 YL)ACETAMIDO 3,4 DIHYDROQUINAZOLINE 2 CARBOXYLATE; ETHYL 6,7 DIMETHOXY 4 OXO 3 [3 (4 PHENYLPIPERAZIN 1 YL)PROPANAMIDO] 3,4 DIHYDROQUINAZOLINE 2 CARBOXYLATE; N (2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 2 (4 (2 METHOXYPHENYL) PIPERAZIN 1 YL) ACETAMIDE; N (2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 2 (4 PHENYLPIPERAZIN 1 YL) ACETAMIDE; N (2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 2 [4 (4 NITROPHENYL)PIPERAZIN 1 YL]ACETAMIDE; N (2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 3 (4 PHENYLPIPERAZIN 1 YL) PROPANAMIDE; N (2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 3 [4 (4 NITROPHENYL)PIPERAZIN 1 YL]PROPANAMIDE; N (6,7 DIMETHOXY 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 2 (4 PHENYLPIPERAZIN 1 YL)ACETAMIDE; N (6,7 DIMETHOXY 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 2 [4 (FURAN 2 CARBONYL)PIPERAZIN 1 YL]ACETAMIDE; N (6,7 DIMETHOXY 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 3 (4 PHENYLPIPERAZIN 1 YL)PROPANAMIDE; N (6,7 DIMETHOXY 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 3 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]ACETAMIDE; N (6,7 DIMETHOXY 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 3 [4 (4 NITROPHENYL)PIPERAZIN 1 YL]PROPANAMIDE; N (6,7 DIMETHOXY 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 3 [4 (FURAN 2 CARBONYL)PIPERAZIN 1 YL]PROPANAMIDE; N (6,7 DIMETHOXY 2 METHYL 4 OXOQUINAZOLIN 3(4H) YL) 3 [4(2 METHOXYPHENYL)PIPERAZIN 1 YL]PROPANAMIDE; PIPERAZINE DERIVATIVE; PRAZOSIN; QUINAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG;

ALPHA ADRENERGIC RECEPTOR BLOCKING; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; COMPUTER PROGRAM; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; HYPOTENSION; HYPOTHESIS; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR MODEL; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; THORACIC AORTIC RING; VASCULAR RING;

ADRENERGIC ALPHA-1 RECEPTOR ANTAGONISTS; ANIMALS; CATS; HUMANS; MALE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERAZINES; QUINAZOLINONES; RATS; RATS, WISTAR; RECEPTORS, ADRENERGIC, ALPHA-1; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79151477888     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.11.045     Document Type: Article

References (30)

1. A. Ferro, R. Gilbert, and H. Krum Int. J. Clin. Pract. 60 2006 577 581 American Heart Association, Statistics: (2007)
2. R. Barbaro, L. Betti, M. Botta, F. Corelli, G. Giannaccini, L. Maccari, F. Manetti, G. Strappaghetti, and F. Corsano J. Med. Chem. 44 2001 2118 2132
3. D. Bylund, D. Eikenberg, J. Heieble, S. Langer, R. Lefkowiskitz, K. Minneman, P. Molinoff, R. Rufolo, and U. Trendelenburg Pharmacol. Rev. 46 1994 121 136
4. C. Forray, J. Wetzel, T. Brancheck, J. Bard, G. Chin, E. Shapiro, R. Tang, H. Lepor, P. Hartig, R. Weinshbank, and C. Gluchowski Mol. Pharmacol. 45 1994 703 708
5. A. Michael, L. Ann, P. Theodore, S. Raymond, W. Richard, D. Jerry, and F. Carlos J. Med. Chem. 41 1998 1206 1210
6. J. Handzlik, D. Maciag, M. Kubacka, S. Mogliski, B. Filipek, K. Stadnicka, and K. Kiec-Kononowicz Bioorg. Med. Chem. 16 2008 5982 5998
7. V. Alabaster, S. Campbell, J. Danilewicz, C. Greengrass, and R.M. Plews J. Med. Chem. 30 1987 999 1003
8. H. Lepor Prostate Suppl. 3 1990 75 84
9. H. Nagano, M. Takagi, N. Kubodera, I. Matsunaga, H. Nabata, Y. Ohba, K. Sakai, S. Hata, Y. Uchida, Eur. Pat. 89065, 1983, Chugai Pharmaceutical Co., Ltd., Japan; Chem. Abstr. 100 (1983) 6547p.
10. V. Bandurco, C. Schwender, R. Falotico, A. Tobia, J. Eur. Patent 0 219 259, 1987, Ortho Pharmaceutical Corp., U.S. Route 202 P.O. Box 300, Raritan New Jersey 08869-0602(US).
11. R. Russell, J. Press, R. Rampulla, J. McNally, R. Falotico, J. Keiser, D. Bright, and A. Tobia J. Med. Chem. 31 1988 1786 1793
12. T. Elworthy, A. Ford, G. Bantle, and D. Morgans J. Med. Chem. 40 1997 2674 2687
13. D.A. Abou El Ella, and R.A. Taha Bull. Fac. Pharm. Cairo Univ. 45 2007 267 281
14. L. Betti, M. Botto, F. Corelli, M. Floridi, P. Fossa, G. Giannaccini, F. Manetti, G. Strappaghetti, and S. Corasno Bioorg. Med. Chem. Lett. 12 2002 437 440
15. M.A.H. Ismail, M.N.Y. Aboul-Enein, K.A.M. Abouzid, and R.A.T. Serya Bioorg. Med. Chem. 14 2006 898 910
16. K.I. Ozaki, Y. Yamada, and T. Oine Chem. Pharm. Bull. 31 1983 2234 2243
17. D. Tworowski, R. Matsievitch, PCT Int. Appl. 2007, 108pp. CODEN: PIXXD2 WO 2007110868 A2 20071004.
18. C.M. Gupta, A.P. Bhaduri, and N.M. Khanna J. Med. Chem. 11 1968 392 395
19. E. Schuler, N. Juanico, J. Teixido, E.L. Michelotti, and J.I. Borrell Heterocycles 67 2006 161 173
20. T. George, D.V. Mehta, and R. Tahilramani Indian J. Chem. 9 1971 755 758
21. L.A. Errede J. Org. Chem. 41 1976 1763 1767
22. S. Bueyuektimkin Pharmazie 40 1985 393 395
23. V. Alagarsamy Pharmazie 59 2004 753 755
24. J. Zou, H.Z. Xie, S.Y. Yang, J.J. Chen, J.X. Ren, and Y.Q. Wei J. Mol. Graph. Model. 27 2008 430 438
25. S. Ekins, J. Mestres, and B. Testa Br. J. Pharmacol. 152 2007 21 37
26. R. Barbaro, L. Betti, M. Botta, F. Corelli, G. Giannaccini, L. Maccari, F. Manetti, G. Strappaghetti, and F. Corsano Bioorg. Med. Chem. 10 2002 361 369
27. T. Litchfield, and A. Wilcoxon J. Pharmacol. Exp. Ther. 96 1949 99 113
28. A.S. Girgis, N. Mishriky, A.M. Forag, W.I. El-Eraky, and H. Farag Eur. J. Med. Chem. 43 2008 1818 1827
29. A.S. Girgis, A. Kalmouch, and M. Ellithey Bioorg. Med. Chem. 14 2006 8488 8494
30. G.H. Kuo, C. Prouty, W.V. Murray, V. Pulito, L. Jolliffe, P. Cheung, S. Varga, M. Evangelisto, and C. Shaw Bioorg. Med. Chem. 8 2000 2263 2275