Synthesis and β-glucuronidase inhibitory activity of 2-arylquinazolin-4(3H)-ones

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 13, 2014, Pages 3449-3454

  Khan, Khalid Mohammed ^a   Saad, Syed Muhammad ^a   Shaikh, Nimra Naveed ^a   Hussain, Shafqat ^a   Fakhri, Muhammad Imran ^a   Perveen, Shahnaz ^b   Taha, Muhammad ^d   Choudhary, Muhammad Iqbal ^a,c  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b PCSIR LABORATORIES COMPLEX   (Pakistan)

^c KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

^d UNIVERSITI TEKNOLOGI MARA   (Malaysia)

Author keywords

2 Arylquinazolin 4(3H) ones; Cytotoxicity; Structure activity relationship; Glucuronidase inhibition

Indexed keywords

2 (2' BROMO 6' HYDROXYPHENYL)QUINAZOLIN 4[3H]ONE; 2 (2' CHLOROPHENYL)QUINAZOLIN 4[3H]ONE; 2 (2' HYDROXYPHENYL)QUINAZOLIN 4[3]ONE; 2 (2' NITROPHENYL)QUINAZOLIN 4[3H]ONE; 2 (2',4' DICHLOROPHENYL)QUINAZOLIN 4[3H]ONE; 2 (2',5' DIHYDROXYPHENYL)QUINAZOLIN 4[3H]ONE; 2 (2',6' DICHLOROPHENYL)QUINAZOLIN 4[3H]ONE; 2 (3' HYDROXYPHENYL)QUINAZOLIN 4[3H]ONE; 2 (3' NITROPHENYL)QUINAZOLIN 4[3H]ONE; 2 (3',4' DIHYDROXYPHENYL)QUINAZOLIN 4[3H]ONE; 2 (4' CHLOROPHENYL)QUINAZOLIN 4[3H]ONE; 2 (4' HYDROXYPHENYL)QUINAZOLIN 4[3H]ONE; 2 (4' METHYLPHENYL)QUINAZOLIN 4[3H]ONE; 2 (4' NITROPHENYL)QUINAZOLIN 4[3H]ONE; 2 ARYLQUINAZOLIN 4[3H]ONE DERIVATIVE; 2 PHENYLQUINAZOLIN 4[3H]ONE; 2 [2' (ETHYLOXY)PHENYL]QUINAZOLIN 4[3H]ONE; 2 [2' HYDROXY 3' (METHYLOXY)PHENYL]QUINAZOLIN 4[3H]ONE; 2 [2' HYDROXY 5' (METHYLOXY)PHENYL]QUINAZOLIN 4[3H]ONE; 2 [3' (ETHYLOXY)PHENYL]QUINAZOLIN 4[3H]ONE; 2 [3' HYDROXY 4' (METHOXY)PHENYL]QUINAZOLIN 4[3H]ONE; 2 [3',4' BIS(METHYLOXY)PHENYL]QUINAZOLIN 4[3H]ONE; 2 [3',4',5' TRIS(METHOXY)PHENYL]QUINAZOLIN 4[3H]ONE; 2 [4' (DIMETHYLAMINO)PHENYL]QUINAZOLIN 4[3H]ONE; 2 [4' (METHOXY)PHENYL]QUINAZOLIN 4[3H]ONE; BETA GLUCURONIDASE; BETA GLUCURONIDASE INHIBITOR; GLYCOSIDASE INHIBITOR; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ENZYME INHIBITOR;

ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; SOLVENT EFFECT; STANDARD; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; TEMPERATURE SENSITIVITY; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; ENZYMOLOGY; ESCHERICHIA COLI; METABOLISM; SYNTHESIS;

DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; ESCHERICHIA COLI; GLUCURONIDASE; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84901927895     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.04.039     Document Type: Article

References (40)

1. B.S. Kuarm, Y.T. Reddy, J.V. Madhav, P.A. Crooks, and B. Rajitha Bioorg. Med. Chem. Lett. 21 2011 524
2. V. Alagarsamy, M. Rupeshkumar, K. Kavitha, S. Meena, D. Shankar, A.A. Siddiqui, and R. Rajesh Eur. J. Med. Chem. 43 2008 2331
3. C. Ryu, Y.H. Kim, H.A. Im, J.Y. Kim, J.H. Yoon, and A. Kim Bioorg. Med. Chem. Lett. 22 2012 500
4. V.M. Sharma, K.V.A. Seshu, V.C. Sekhar, S. Madan, B. Vishnu, P.A. Babu, C.V. Krishna, J. Sreenu, V.R. Krishna, A. Venkateswarlu, S. Rajagopal, R. Ajaykumarb, and T.S. Kumarb Bioorg. Med. Chem. Lett. 14 2004 67
5. A. Kumar, and C.S. Rajput Eur. J. Med. Chem. 44 2009 83
6. R. Anderskewitz, R. Bauer, G. Bodenbach, D. Gester, B. Gramlich, G. Morschhauser, and F.W. Birke Bioorg. Med. Chem. Lett. 15 2005 669
7. V. Alagarsamy, D. Shankar, and S. Murugesan Biomed. Pharmacother. 62 2008 173
8. M.T.H. Khan, R. Khan, Y. Wuxiuer, M. Arfan, M. Ahmed, and I. Sylte Bioorg. Med. Chem. 18 2010 4317
9. J. Lin, W. Shen, J. Xue, J. Sun, X. Zhang, and C. Zhang Eur. J. Med. Chem. 55 2012 39
10. F.A.M. Al-Omary, G.S. Hassan, S.M. El-Messery, M.N. Nagi, E.E. Habib, and H.I. El-Subbagh Eur. J. Med. Chem. 63 2013 33
11. G.G. Belz, H.C. Stern, and R.J. Butzer Cardiovasc. Pharmacol. 7 1985 86
12. C.M. Cheng, Y.J. Lee, W.T. Wang, C.T. Hsu, J.S. Tsai, C.M. Wu, K.L. Ou, and T.S. Yang Biochem. Biophys. Res. Commun. 404 2011 297
13. E. Cohen, E. Klarberg, and R.J. Vaughan J. Am. Chem. Soc. 82 1960 2731
14. D. Denis, and D. Riendeau Eur. J. Pharmacol. 367 1999 343
15. R. Eigenmann, M. Gerold, and M.J. Holck Cardiovasc. Pharmacol. 6 1984 511
16. M.T. Osinski, and K. Schrör Biochem. Pharmacol. 60 2000 381
17. V.R. Rivera, M.A. Poli, and G.S. Bignami Toxicon 33 1995 1231
18. V.K. Archana, R. Srivastava, A. Chandra, and Kumar Eur. J. Med. Chem. 37 2002 873
19. G. Daidone, B. Maggio, D. Raffa, S. Plescia, M.L. Bajardi, A. Caruso, V.M.C. Cutuli, and M.A. Roxas Eur. J. Med. Chem. 29 1994 707
20. P.M. Chandrika, A.R.R. Rao, B. Narasaiah, and M.B. Raju Int. J. Chem. Sci. 6 2008 1119
21. V.J. Ram, U.K. Singha, and P.Y. Guru Eur. J. Med. Chem. 25 1990 533
22. K. Yasuhisa, I. Yasuhide, T. Kazuhiko, N. Shizuo, N. Kazushi, Y. Hiroki, and T.J. Yoshihiko Med. Chem. 39 1996 1433
23. B. Sperker, J.T. Backman, and K. Kromer Clin. Pharmacokinet. 33 1997 18
24. M. Wakabayashi W.H. Fishman, Metabolic Conjugation and Metabolic Hydrolysis 1970 Academic Press New-York 519 602
25. K. Paigen Prog. Nucleic Acid Res. Mol. Biol. 37 1989 155
26. C.M. Plum Enzymol. Biol. Clin. 8 1967 97
27. H.C. Gonick, H.J. Kramer, and A.E. Schapiro Arch. Intern. Med. 132 1973 63
28. N. Bank, and S.H. Bailine N. Engl. J. Med. 272 1965 70
29. A.P. Roberts, J. Frampton, S.M.M. Karim, and R.W. Beard N. Engl. J. Med. 276 1967 1468
30. A.R. Ronald, F. Silverblatt, H. Clark, R.E. Cutler, and M. Turck Appl. Microbiol. 21 1971 990
31. H.A. Kallet, and L. Lapco J. Urol. 97 1967 352
32. A. Schapiro, W. Paul, and H. Gonick J. Urol. 100 1968 146
33. E. Hradec, R. Petrík, and J. Pezlarová J. Urol. 94 1965 430
34. E. Boyland, J.E. Gasson, and D.C. Williams Br. J. Cancer 11 1957 120
35. J.C. Caygill, and D.A. Pitkeathly Ann. Rheum. Dis. 25 1966 137
36. G. Weissmann, R.B. Zurier, P.J. Spieler, and I.M. Goldstein J. Exp. Med. 134 1971 149
37. B.R. Goldin, and S.L. Gorbach J. Natl Cancer Inst. 57 1976 371
38. K.M. Khan, M. Khan, N. Ambreen, F. Rahim, S. Naureen, S. Perveen, M.I. Choudhary, and W. Voelter Med. Chem. 8 2012 421
39. R.A. Collins, T.B. Ng, W.P. Fong, C.C. Wan, and H.W. Yeung Biochem. Mol. Biol. Int. 42 1997 1163
40. T.J. Mosmann Immunol. Methods 65 1983 55