Design, synthesis and antiviral activity of novel quinazolinones

European Journal of Medicinal Chemistry

Volumn 53, Issue , 2012, Pages 275-282

  Wang, Ziwen ^a   Wang, Mingxiao ^a   Yao, Xue ^a   Li, Yue ^a   Tan, Juan ^a   Wang, Lizhong ^a   Qiao, Wentao ^a   Geng, Yunqi ^a   Liu, Yuxiu ^a   Wang, Qingmin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Anti HIV activity; Anti TMV activity; Multi functional antiviral agents; Quinazolinones; Synthesis

Indexed keywords

2 BUTYL N (4 FLUOROBENZYL) 5 HYDROXY 3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; 2 BUTYL N (4 FLUOROBENZYL) 5 METHOXY 3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; 2 BUTYLN (4 FLUOROBENZYL) 5 METHOXY 3 METHYL 4 OXO 1,2,3,4 TETRAHYDROQUINAZOLINE 6 CARBOXAMIDE; 5 HYDROXY QUINAZOLINONE; ANTIVIRUS AGENT; N (4 FLUOROBENZYL) 2 (4 FLUOROPHENYL) 5 HYDROXY 3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 2 (4 FLUOROPHENYL) 5 METHOXY 3 METHYL 4 OXO 1,2,3,4 TETRAHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 2 (4 FLUOROPHENYL) 5 METHOXY 3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 2 (FURAN 2 YL) 5 HYDROXY 3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 2 (FURAN 2 YL) 5 METHOXY 3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 2 (FURAN 2 YL) 5 METHOXY 3 METHYL 4 XO 1,2,3,4 TETRAHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 5 HYDROXY 3 METHYL 2 (4 NITROBENZYL) 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 5 HYDROXY 3 METHYL 2 (4 NITROPHENYL) 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 5 HYDROXY 3 METHYL 4 OXO 2 (PYRIDIN 2 YL) 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 5 HYDROXY 3 METHYL 4 OXO 2 (THIOPHEN 2 YL) 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 5 METHOXY 3 METHYL 2 (4 NITROBENZYL) 4 OXO 1,2,3,4 TETRAHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 5 METHOXY 3 METHYL 2 (4 NITROBENZYL) 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 5 METHOXY 3 METHYL 2 (4 NITROPHENYL) 4 OXO 1,2,3,4 TETRAHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 5 METHOXY 3 METHYL 2 (4 NITROPHENYL) 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 5 METHOXY 3 METHYL 4 OXO 2 (PYRIDIN 2 YL) 1,2,3,4 TETRAHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 5 METHOXY 3 METHYL 4 OXO 2 (THIOPHEN 2 YL) 1,2,3,4 TETRAHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4 FLUOROBENZYL) 5 METHOXY 3 METHYL 4 OXO 2 (THIOPHEN 2 YL) 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N (4- FLUOROBENZYL) 5 METHOXY 3 METHYL 4 OXO 2 (PYRIDIN 2 YL) 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N,2 BIS(4 FLUOROBENZYL) 5 HYDROXY 3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; N,2 BIS(4 FLUOROBENZYL) 5 METHOXY 3 METHYL 4 OXO 1,2,3,4 TETRAHYDROQUINAZOLINE 6 CARBOXAMIDE; N,2 BIS(4 FLUOROBENZYL) 5 METHOXY 3 METHYL 4 OXO 3,4 DIHYDROQUINAZOLINE 6 CARBOXAMIDE; QUINAZOLINONE DERIVATIVE; RALTEGRAVIR; RIBAVIRIN; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; BIOASSAY; CONTROLLED STUDY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1;

ANTIVIRAL AGENTS; CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG DESIGN; HIV; QUINAZOLINONES; TOBACCO MOSAIC VIRUS;

EID: 84861602512     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.04.010     Document Type: Article

References (36)

1. GLOBAL HIV/AIDS RESPONSE - Epidemic Update and Health Sector Progress Towards Universal Access - Progress Report 2011.
2. Y. Mehellou, and E. De Clercq Twenty-six years of anti-HIV drug discovery: where do we stand and where do we go? J. Med. Chem. 53 2010 521 538
3. M. Sechi, G. Rizzi, A. Bacchi, M. Carcelli, D. Rogolino, N. Pala, T.W. Sanchez, L. Taheri, R. Dayam, and N. Neamati Design and synthesis of novel dihydroquinoline-3-carboxylic acids as HIV-1 integrase inhibitors Bioorg. Med. Chem. 17 2009 2925 2935
4. Y. Pommier, A.A. Johnson, and C. Marchand HIV-1 integrase inhibitors: update and perspectives Nat. Rev. Drug Discov. 4 2005 236 248
5. N. Neamati Structure-based HIV-1 integrase inhibitor design: a future perspective Expert Opin. Investig. Drugs 10 2001 281 296
6. V. Nair, and G. Chi HIV integrase inhibitors as therapeutic agents in AIDS Rev. Med. Virol. 17 2007 277 295
7. V. Summa, A. Petrocchi, F. Bonelli, B. Crescenzi, M. Donghi, M. Ferrara, F. Fiore, C. Gardelli, O. Gonzalez Paz, J.D. Hazuda, P. Jones, O. Kinzel, R. Laufer, E. Monteagudo, E. Muraglia, E. Nizi, F. Orvieto, P. Pace, G. Pescatore, R. Scarpelli, K. Stillmock, V.M. Witmer, and M. Rowley Discovery of raltegravir, a potent, selective orally bioavailable HIV-integrase inhibitor for the treatment of HIV-AIDS infection J. Med. Chem. 51 2008 5843 5855
8. M. Sato, H. Kawakami, T. Motomura, H. Aramaki, T. Matsuda, M. Yamashita, Y. Ito, Y. Matsuzaki, K. Yamataka, S. Ikeda, and H. Shinkai Quinolone carboxylic acids as a novel monoketo acid class of human immunodeficiency virus type 1 integrase inhibitors J. Med. Chem. 52 2009 4869 4882
9. B.A. Johns, J.G. Weatherhead, Tricyclic heterocyclic compounds as antiviral agents and their preparation and use in the treatment of HIV infection, WO 2010011819 A1, 2010; CAN 152:192166.
10. M. Rowley The discovery of raltegravir, an integrase inhibitor for the treatment of HIV infection Prog. Med. Chem. 46 2008 1 28
11. D.J. Hazuda, P. Felock, M. Witmer, A. Wolfe, K. Stillmock, J.A. Grobler, A. Espeseth, L. Gabryelski, W. Schleif, C. Blau, and M.D. Miller Inhibitors of strand transfer that prevent integration and inhibit HIV-1 replication in cells Science 287 2000 646 650
12. A.S. Espeseth, P. Felock, A. Wolfe, M. Witmer, J. Grobler, N. Anthony, M. Egbertson, J.Y. Melamed, S. Young, T. Hamill, J.L. Cole, and D.J. Hazuda HIV-1 integrase inhibitors that compete with the target DNA substrate define a unique strand transfer conformation for integrase Proc. Natl. Acad. Sci. U.S.A. 97 2000 11244 11249
13. A. Bacchi, M. Biemmi, M. Carcelli, F. Carta, C. Compari, E. Fisicaro, D. Rogolino, M. Sechi, M. Sippel, C.A. Sotriffer, T.W. Sanchez, and N. Neamati From ligand to complexes. Part 2. Remarks on human immunodeficiency virus type 1 integrase inhibition by β-diketo acid metal complexes J. Med. Chem. 51 2008 7253 7264
14. S. Hare, S.S. Gupta, E. Valkov, A. Engelman, and P. Cherepanov Retroviral intasome assembly and inhibition of DNA strand transfer Nature 464 2010 232 236
15. S. Hare, A.M. Vos, R.F. Clayton, J.W. Thuring, M.D. Cummings, and P. Cherepanov Molecular mechanisms of retroviral integrase inhibition and the evolution of viral resistance Proc. Natl. Acad. Sci. U.S.A. 107 2010 20057 20062
16. J. Bartroli, E. Turmo, M. Alguero, E. Boncompte, M.L. Vericant, J. Conte Ramis, M. Merlos, and J.F. Gracia-Rafanell New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones J. Med. Chem. 48 1998 1869 1882
17. I.M.Sh. El-Sharief, Y.A. Ammar, M.A. Zahran, A.H. Ali, and M.S.A. El-Gaby Aminoacids in the synthesis of heterocyclic systems: the synthesis of triazinoquinazolinones, triazepinoquinazolinones and triazocinoquinazolinones of potential biological interest Molecules 6 2001 267 278
18. D.M. Purohit, V.R. Bhuva, and V.H. Shah Synthesis of 5-arylaminosulpho-N- acetylanthranilic acid, 6-arylaminosulpho-2-methyl-3-amino/3-N-chloroacetamido/ 3-N-arylaminoacetamido-4-(3H)-quinazolones as potential anti-HIV, anticancer and antimicrobial agents Chemistry: An Indian Journal 1 2003 233 245
19. K.M. Murav'eva, N.V. Arkhangel'skaya, M.N. Shchukina, T.N. Zykova, and G.N. Pershin Synthesis and tuberculostatic activity of aminoquinazolines Khim.-Farm. Zh. 5 1971 25 27
20. S.G. Abdel-Hamid Synthesis of some new heterocyclic systems bearing 2-phenyl-6-iodo-4(3H)-quinazolinon-3-yl moiety as antibacterial agents J. Indian Chem. Soc. 74 1997 613 618
21. A.J. Barker, Quinazoline derivatives and their use as anti-cancer agents, Eur Pat 635498, 1995 [Chem. Abstr. 122 (1995) 214099].
22. M.A. Aziza, M.K. Ibrahim, and A.G. El-Helpy Part II. Synthesis of novel-2-styryl-3-benzylidenimino-4(3H)-quinazolone derivatives of expected anticonvulsant activity Al-Azhar J. Pharm. Sci. 14 1994 193 201
23. N. Ergenc, S. Buyuktimkin, G. Capan, G. Baktir, and S. Rollas Quinazolinones. 19. Communication [1]: synthesis and evaluation of some CNS depressant properties of 3-{2-[(5-aryl-1,3,4-oxadiazol-2-yl)amino]acetamido}-2- methyl-4(3H)-quinazolinones Pharmazie 46 1991 290 291
24. A.A. Bekhit, and M.A. Khalil Synthesis benzopyrazolyl derivatives of quinazolinones Pharmazie 53 1998 539 544
25. E. Hamel, C.M. Lin, J. Plowman, H.K. Wang, K.H. Lee, and K.D. Paull Antitumor 2,3-dihydro-2-aryl-4(1H)-quinazolinone derivatives. Interactions with tubulin Biochem. Pharmacol. 51 1996 53 59
26. K. Terashima, H. Shimamura, A. Kawase, Y. Tanaka, T. Tanimura, T. Kamisaki, Y. Ishizuka, and M. Sato Studies on antiulcer agents. IV: antiulcer effects of 2-benzylthio-5,6,7,8-tetrahydro-4(3H)-quinazolinones and related compounds Chem. Pharm. Bull. 43 1995 2021 2023
27. A. Gursoy, and N. Karali Synthesis and anticonvulsant activity of new acylthiosemicarbazides and thiazolidones Farmaco 50 1995 857 866
28. D.J. Baek, Y.K. Park, H.I. Heo, M.H. Lee, Z.Y. Yang, and M.H. Chio Synthesis of 5-substituted quinazolinone derivatives and their inhibitory activity in vitro Bioorg. Med. Chem. Lett. 8 1998 3287 3290
29. R.J. Griffin, S. Srinivasan, K. Bowman, A.H. Calvert, N.J. Curtin, D.R. Neweli, L.C. Pemberton, and B.T. Golding Resistance-modifying agents. 5. Synthesis and biological properties of quinazolinone inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase (PARP) J. Med. Chem. 41 1998 5247 5256
30. B. Sumegi, K. Hideg, T. Kalai, Quinazolinone-derivatives and their use for preparation of pharmaceutical compositions having parp enzyme inhibitory effect [P], US Pat. Appl. 20070042935, 2007.
31. M. Uehara, T. Shimizu, S. Fujioka, M. Kimura, K. Tsubata, and A. Seo Synthesis and insecticidal activity of 3-amino-quinazolinone derivatives Pestic. Sci. 55 1999 359 362
32. G.P. Ouyang, P.Q. Zhang, G.F. Xu, B.A. Song, S. Yang, L.H. Jin, W. Xue, D.Y. Hu, P. Lu, and Z. Chen Synthesis and antifungal bioactivities of 3-alkylquinazolin-4-one derivatives Molecules 11 2006 383 392
33. X. Liu, R.Q. Huang, H.Y. Li, and Z. Yang Synthesis and bioactivity of O-(4-quinazolinyl)hydroximic thioesters (amides) Chin. J. Appl. Chem. 16 1999 23 26
34. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63
35. Z.W. Wang, M.X. Wang, X. Yao, Y. Li, W.T. Qiao, Y.Q. Geng, Y.X. Liu, and Q.M. Wang Hydroxyl may not be indispensable for raltegravir: design, synthesis and SAR studies of raltegravir derivatives as HIV-1 inhibitors Eur. J. Med. Chem. 50 2012 361 369
36. K.L. Wang, B. Su, Z.W. Wang, M. Wu, Z. Li, Y.N. Hu, Z.J. Fan, N. Mi, and Q.M. Wang Synthesis and antiviral activities of phenanthroindolizidine alkaloids and their derivatives J. Agric. Food. Chem. 58 2010 2703 2709