Novel 1,3,4-heterodiazole analogues: Synthesis and in-vitro antitumor activity

European Journal of Medicinal Chemistry

Volumn 47, Issue 1, 2012, Pages 445-451

  Taher, Azza T ^a   Georgey, Hanan H ^a   El Subbagh, Hussein I ^b  

^a CAIRO UNIVERSITY   (Egypt)

^b FUTURE UNIVERSITY IN EGYPT   (Egypt)

Author keywords

1,3,4 Oxadiazole; Antitumor activity; Heterodiazole; Thiadiazole, 3,2 a pyimidine

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 1,3,4 THIADIAZOLE DERIVATIVE; 2 (4 CHLOROPHENYL) 8 AH[1,3,4]OXADIAZOLO[3,2 A]PYRIMIDINE 5,7 DIAMINE; 2 (4 CHLOROPHENYL) 8 AH[1,3,4]THIADIAZOLO[3,2 A]PYRIMIDINE 5,7 DIAMINE; 2 (4 CHLOROPHENYL)IMIDAZO 2,1 B][1,3,4]THIADIAZOL 5,6 DIONE; 2 (4 CHLOROPHENYL)IMIDAZO[2,1 B][1,3,4]OXADIAZOL 5,6 DIONE; 2 (4 CHLOROPHENYL)IMIDAZO[2,1 B][1,3,4]OXADIAZOL 6 (5H)ONE; 2 (4 CHLOROPHENYL)IMIDAZO[2,1 B][1,3,4]THIADIAZOL 6 (5H)ONE; 2 PHENYL 8AH[1,3,4]OXADIAZOLO[3,2 A]PYRIMIDINE 5,7 DIAMINE; 2 PHENYL 8AH[1,3,4]THIADIAZOLO[3,2 A]PYRIMIDINE 5,7 DIAMINE; 2 PHENYLIMIDAZO[2,1 B][1,3,4]OXADIAZOL 5,6 DIONE; 2 PHENYLIMIDAZO[2,1 B][1,3,4]OXADIAZOL 6 (5H)ONE; 2 PHENYLIMIDAZO[2,1 B][1,3,4]THIADIAZOL 6 (5H)ONE; 2 PHENYLIMIDAZO[2,1 B][1,3,4]THIADIAZOLE 5,6 DIONE; ANTINEOPLASTIC AGENT; FLUOROURACIL; N (5 (4 CHLOROPHENYL) 1,3,4 OXADIAZOL 2 YL) 3 (PIPERIDIN 1 YL)PROPAMIDE; N (5 (4 CHLOROPHENYL) 1,3,4 THIADIAZOL 2 YL) 3 (PIPERIDIN 1 YL)PROPAMIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CENTRAL NERVOUS SYSTEM TUMOR; COLON CANCER; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA CELL; LUNG NON SMALL CELL CANCER; MELANOMA CELL;

ANTINEOPLASTIC AGENTS; AZOLES; BIOLOGICAL AVAILABILITY; CELL LINE, TUMOR; CELL PROLIFERATION; HUMANS;

EID: 84855758520     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.11.013     Document Type: Article

References (32)

1. A.A.M. Abdel-Aziz Novel and versatile methodology for synthesis of cyclic imides and evaluation of their cytotoxic, DNA binding, apoptotic inducing activities and molecular modeling study Eur. J. Med. Chem. 42 2007 614 626
2. H.Y.P. Choo, M. Kim, S.K. Lee, S.W. Kim, and S.W. Chung Synthesis and biological evaluation of novel 9-functional heterocyclic coupled 7-deoxy-9-Dihydropaclitaxel analogue Bioorg. Med. Chem. 10 2002 517 523
3. S.T. Al-Rashood, I.A. Aboldahab, M.N. Nagi, L.A. Abouzeid, A.A.M. Abdel-Aziz, S.G. Abdel-Hamide, K.M. Youssef, A.M. Al-Obaid, and H.I. El-Subbagh Synthesis, dihydrofolate reductase inhibition, antitumor testing, and molecular modeling study of some new 4(3H)-quinazolinone analogs Bioorg. Med.Chem. 14 2006 8608 8621
4. A.M. Al-Obaid, S.G. Abdel-Hamide, H.A. El-Kashef, A.A.M. Abdel-Aziz, A.S. El-Azab, and H.A.H.I. Al-Khamees El-Subbagh Substituted quinazolines, part 3. Synthesis, in vitro antitumor activity and molecular modeling study of certain 2-thieno-4(3H)-quinazolinone analogs Eur. J.Med. Chem. 44 2009 2379 2391
5. F.A.M. Al-Omary, L.A. Abouzeid, M.N. Nagi, E.E. Habib, A.A.M. Abdel-Aziz, A.S. El-Azab, S.G. Abdel-Hamide, M.A. Al-Omar, A.M. Al-Obaid, and H.I. El-Subbagh Non-classical antifolates. Part 2: synthesis, biological evaluation, and molecular modeling study of some new 2,6-substituted-quinazolin-4-ones Bioorg. Med. Chem. 18 2010 2849 2863
6. C.J. Chen, B.A. Song, S. Yang, G.F. Xu, P.S. Bhadury, L.H. Jin, D.Y. Hu, Q.Z. Li, F. Liu, W. Xue, P. Lu, and Z. Chen Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives Bioorg. Med. Chem. 15 2007 3981 3989
7. A. Zarghi, S.A. Tabatabai, M. Faizi, A. Ahadian, P. Navabi, V. Zanganeh, and A. Shafiee Synthesis and anticonvulsant activity of new 2-substituted-5-(2- benzyloxyphenyl)-1,3,4-oxadiazoles Bioorg. Med. Chem. Lett. 15 2005 1863 1865
8. Y.P. Luo, and G.F. Yang Discovery of a new insecticide lead by optimizing a target-diverse scaffold: tetrazolinone derivatives Bioorg. Med. Chem. 15 2007 1716 1724
9. M.T. Khan, M.I. Choudhary, K.M. Khan, M. Rani, and A.U. Rahman Structure-activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues Bioorg. Med.Chem. 13 2005 3385 3388
10. J.T. Palmer, B.L. Hirschbein, H. Cheung, J. McCarter, J.W. Janc, W.Z. Yu, and G. Wesolowski Keto-1,3,4-oxadiazoles as cathepsin K inhibitors Bioorg. Med. Chem. Lett. 16 2006 2909 2914
11. M. Wu, Q. Sun, C. Yang, D. Chen, J. Ding, Y. Chen, L. Lin, and Y. Xie Synthesis and activity of Combretastatin A-4 analogues: 1,2,3-thiadiazoles as potent antitumor agents Bioorg. Med.Chem. Lett. 17 2007 869 873
12. L. Shen, Y. Zhang, A. Wang, E. Sieber-McMaster, X. Chen, P. Pelton, J.Z. Xu, M. Yang, P. Zhu, L. Zhou, M. Reuman, Z. Hu, R. Russell, A.C. Gibbs, H. Ross, K. Demarest, W.V. Murray, and G.-H. Kuo J. Med. Chem. 50 2007 3954 3963
13. S. Schenone, C. Brullo, O. Bruno, F. Bondavalli, A. Ranise, W. Filippelli, B. Rinaldi, A. Capuano, and G. Falcone New 1,3,4-thiadiazole derivatives endowed with analgesic and anti-inflammatory activities Bioorg. Med. Chem. 14 2006 1698 1705
14. A.A. Kadi, N.R. El-Brollosy, O.A. Al-Deeb, E.E. Habib, T.M. Ibrahim, and A.A. El- Emam Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)- 5-substituted-1,3,4-thiadiazoles Eur. J. Med. Chem. 42 2007 235 242
15. A. Foroumadi, S. Mansouri, Z. Kiani, and A. Rahmani Synthesis and in vitro antibacterial evaluation of N-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2- yl] piperazinyl quinolones Eur. J. Med. Chem. 38 2003 851 854
16. F. Poorrajab, S.K. Ardestani, S. Emami, M. Behrouzi-Fardmoghadam, A. Shafiee, and A. Foroumadi Nitroimidazolyl-1,3,4-thiadiazole-based anti-leishmanial agents: synthesis and in vitro biological evaluation Eur. J. Med. Chem. 44 2009 1758 1762
17. Q. Zhang, J. Pan, R.L. Zheng, and Q. Wang Redifferentiation of human hepatoma cell induced by 6-(p-chlorophenyl)-3-[1-(p-chlorophenyl)-5-methyl-1H-1, 2,3-triazol-4-yl]-s-triazolo[3,4-b]-1,3,4-thiadiazole Pharmazie 60 2005 378 382
18. C. Loetchutinat, F. Chau, and S. Mankhetkorn Synthesis and evaluation of 5-aryl-3-(4-hydroxyphenyl)-1,3,4-oxadiazole-2-(3H)-thiones as P-glycoprotein inhibitors Chem. Pharm. Bull. 51 2003 728 730
19. D. Kumar, G. Pate, E.O. Johnson, and K. Shah Synthesis and anticancer activities of novel 3,5-disubstituted-1,2,4-oxadiazoles Bioorg. Med. Chem. Lett. 19 2009 2739 2741
20. J. Matysik Evaluation of antiproliferative Effect in vitro of some 2-Amino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole derivatives Chem. Pharm. Bull. 54 2006 988 991
21. W.A. Remrs, A. Wilson, and B. Gisvolds Text Book of Organic, Medicinal and Phamaceuticals Chemistry 1982 Lippincott Company Philadeplphia
22. A. Andreani, D. Bonazzi, and M. Rambaldi Arch. Pharm. 315 1982 451 456
23. S.S. Karki, K. Panjamurthy, S. Kumar, M. Nambiar, S.A. Ramareddy, K.K. Chiruvella, and S.C. Raghavan Synthesis and biological evaluation of novel 2-aralkyl-5-substituted-6-(40-fluorophenyl)-imidazo[2,1-b][1,3,4]thiadiazole derivatives as potent anticancer agents Eur. J. Med. Chem. 46 6 2011 2109 2116
24. V. Gupta, S.K. Kashaw, and V. Jatav Synthesis and antimicrobial activity of some new 3-[5-(4-substituted)phenyl-1,3,4-oxadiazole-yl]-2-styrylquinazoline- 4(3H)-ones Med. Chem. Res. 17 2008 205
25. V. Jatav, P. Mishra, S. Kashaw, and J.P. Stables Synthesis and CNS depressant activity of some novel 3-[5-substituted-1,3,4-thiadiazole-yl]-2- styrylquinazoline-4(3H)-ones Eur. J. Med. Chem. 43 2008 135 141
26. A.M. Polozov, G. Hategan, H. Cao, A.S. Kiselyov, W. Zeller, and J. Singh A general approach to indole-7-yl derivatives of isoxazole, oxadiazole, thiadiazole and pyrazole Tetrahed. Lett. 51 4 2010 575 578
27. W. Ried, and S. Aboul-Fetouh Synthesis of new substituted pyrazolo[1,5-a]-pyrimidines and pyrazolo[1,5-a]1,3,5-triazines Tetrahed 44 1988 7155
28. A. Taher, and M. Raafat Imidazo[1,2-b]pyrazole-2,6-dione;Synthesis and preliminary evaluation of anti-inflammatory and analgesic activity Bull. Fac. Pharm. Cairo Univ. 43 2005 43 55
29. M.R. Grever, S.A. Schepartz, and B.A. Chabner The National Cancer Institute: cancer drug discovery and development program Semin. Oncol. 19 1992 622 638
30. A. Monks, D. Scudiero, and P. Skehan Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines J. Natl. Cancer Inst. 83 1991 757 766
31. M.R. Boyd, and K.D. Paull Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen Drug Dev. Res. 34 1995 91 109
32. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.R. Warren, H. Bokesch, S. Kenney, and M.R. Boyd New colorimetric cytotoxic assay for anticancer drug screening J. Natl. Cancer Inst. 82 1990 1107 1112