Synthesis, quantitative structure-activity relationship and biological evaluation of 1*3*4-oxadiazole derivatives possessing diphenylamine moiety as potential anticancer agents

Chemical and Pharmaceutical Bulletin

Volumn 61, Issue 2, 2013, Pages 151-159

  Rahman, Doaa Ezzat Abdel ^a  

^a CAIRO UNIVERSITY   (Egypt)

Author keywords

1,3,4 oxadiazole; Anticancer; HT29 cell line; Mannich base; MCF7 cell line; Quantitative structure activity relationship study

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 2 BENZYLTHIO 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE; 2 ETHYLTHIO 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE; 2[2 (PHENYLAMINO) PHENYL] 5 PHENYL 1,3,4 OXADIAZOLE; 3 (PHENYLAMINOMETHYL) 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 3 [(BENZO [D] THIAZOL 2 YL) AMINOMETHYL] 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 3 [(DIETHYLAMINO) METHYL] 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 3 [(MORPHOLIN4 YL) METHYL] 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 3[(4 ACETYLPHENYL) AMINOMETHYL] 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 3[(4 BROMOPHENYL) AMINOMETHYL] 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 3[(4 CHLOROPHENYL) AMINOMETHYL] 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 3[(4 FLUOROPHENYL) AMINOMETHYL] 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 3[(4 METHOXYPHENYL) AMINOMETHYL] 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 3[(4 METHYLPHENYL) AMINOMETHYL] 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 3[(4 METHYLPIPERAZIN 1 YL) METHYL] 5[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 4[(5(2 (PHENYLAMINO) PHENYL) 2 THIOXO 1,3,4 OXADIAZOL 3(2H) YL) METHYLAMINO] BENZENESULFONAMIDE; 5(4 CHLOROPHENYL) 2[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE; 5(4 METHOXYPHENYL) 2[2 (PHENYLAMINO) PHENYL] 1,3,4 OXADIAZOLE; 5[2 (PHENYLAMINO) PHENYL] 3 [(PIPERIDIN 1 YL) METHYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; DOXORUBICIN; SULFORHODAMINE B; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; PHYSICAL CHEMISTRY; PROTEIN LOCALIZATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; DIPHENYLAMINE; DRUG SCREENING ASSAYS, ANTITUMOR; HT29 CELLS; HUMANS; MCF-7 CELLS; OXADIAZOLES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84873592655     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.c12-00637     Document Type: Article

References (50)

1. American Cancer Society 2012: Cancer Facts & Figures. http://www.cancer.org/acs/groups/content/@epidemiologysurveilance/documents/ document/acspc-031941.pdf, cited 29 March, 2012.
2. World Health Organization (WHO). "Factsheets, Cancer 2012.": http://www.who.int/mediacentre/factsheets/fs297/en/, cited 30 March, 2012.
3. American Cancer Society, "Breast Cancer: Statistics on Incidence, Survival, and Screening.": http://www.imaginis.com/breast-health/breast- cancer-statistic, cited 27March, 2012.
4. Smith R. A., Cokkinides V., Brawley O. W., CA Cancer J. Clin., 59, 27-41 (2009).
5. Holla B. S., Gonsalves R., Shenoy S., Eur. J. Med. Chem., 35, 267-271 (2000).
6. Naveena C. S., Boja P., Kumari N. S., Eur. J. Med. Chem., 45, 4708-4719 (2010).
7. Mamolo M. G., Zampieri D., Vio L., Fermeglia M., Ferrone M., Pricl S., Scialino G., Banfi E., Bioorg. Med. Chem., 13, 3797-3809 (2005).
8. Akhter M., Husain A., Azad B., Ajmal M., Eur. J. Med. Chem., 44, 2372-2378 (2009).
9. Jayashankar B., Lokanath Rai K. M., Baskaran N., Sathish H. S., Eur. J. Med. Chem., 44, 3898-3902 (2009).
10. Palaska E., Sahin G., Kelicen P., Durlu N. T., Altinok G., Farmaco, 57, 101-107 (2002).
11. Farghaly A. A., Bekhit A. A., Park J. Y., Arch. Pharm. (Weinheim), 333, 53-57 (2000).
12. Omar F. A., Mahfouz N. M., Rahman M. A., Eur. J. Med. Chem., 31, 819-825 (1996).
13. Zarghi A., Tabatabai S. A., Faizi M., Ahadian A., Navabi P., Zanganeh V., Shafiee A., Bioorg. Med. Chem. Lett., 15, 1863-1865 (2005).
14. Rajak H., Agarawal A., Parmar P., Thakur B. S., Veerasamy R., Sharma P. C., Kharya M. D., Bioorg. Med. Chem. Lett., 21, 5735-5738 (2011).
15. Kumar D., Sundaree S., Johnson E. O., Shah K., Bioorg. Med. Chem. Lett., 19, 4492-4494 (2009).
16. Cai Z.-W., Wei D., Borzilleri R. M., Qian L., Kamath A., Mortillo S., Wautlet B., Henley B. J., Jeyaseelan R. Sr., Tokarski J., Hunt J. T., Bhide R. S., Fargnoli J., Lombardo L. J., Bioorg. Med. Chem. Lett., 18, 1354-1358 (2008).
17. Ruel R., Thibeault C., L'Heureux A., Martel A., Cai Z.-W., Wei D., Qian L., Barrish J. C., Mathur A., D'Arienzo C., Hunt J. T., Kamath A., Marathe P., Zhang Y., Derbin G., Wautlet B., Mortillo S., Jeyaseelan R. Sr., Henley B., Tejwani R., Bhide R. S., Trainor G. L., Fargnoli J., Lombardo L. J., Bioorg. Med. Chem. Lett., 18, 2985-2989 (2008).
18. Abadi A. H., Eissa A. A., Hassan G. S., Chem. Pharm. Bull., 51, 838-844 (2003).
19. El-Emam A. A., Al-Deeb O. A., Al-Omar M., Lehmann J., Bioorg. Med. Chem., 12, 5107-5113 (2004).
20. Macaev F., Rusu G., Pogrebnoi S., Gudima A., Stingaci E., Vlad L., Shvets N., Kandemirli F., Dimoglo A., Reynolds R., Bioorg. Med. Chem., 13, 4842-4850 (2005).
21. Bettarini F., Caouzzi L., La Porta P., Massimini S., Caprioli V., Eur. Patent 533276 (1993)
22. [Chem. Abstr., 119, 49400v (1993)].
23. Eckhardt W., Berigar E., Zondler H., Eur. Patent 371925 (1990)
24. [Chem. Abstr., 113, 191385p (1990)].
25. Yamamoto S., Jpn. Patent 05124948 (1993)
26. [Chem. Abstr., 119, 146370t (1993)].
27. Zhang X.-M., Qiu M., Sun J., Zhang Y.-B., Yang Y.-S., Wang X.-L., Tang J.-F., Zhu H.-L., Bioorg. Med. Chem., 19, 6518-6524 (2011).
28. Gudipati R., Anreddy R. N. R., Man S., Saudi Pharm. J., 19, 153-158 (2011).
29. Abou-Seri S. M., Eur. J. Med. Chem., 45, 4113-4121 (2010).
30. Loetchutinat C., Chau F., Mankhetkorn S., Chem. Pharm. Bull., 51, 728-730 (2003).
31. Küçükgüzel S. G., Rollas S., Erdeniz H., Kiraz M., Eur. J. Med. Chem., 34, 153-160 (1999).
32. Manjunatha K., Poojary B., Lobo P. L., Fernandes J., Kumari N. S., Eur. J. Med. Chem., 45, 5225-5233 (2010).
33. Aboraia A. S., Abdel-Rahman H. M., Mahfouz N. M., El-Gendy M.A., Bioorg. Med. Chem., 14, 1236-1246 (2006).
34. Shimizu T., Fujiwara Y., Osawa T., Sakai T., Kubo K., Kubo K., Nishitoba T., Kimura K., Senga T., Murooka H., Iwai A., Fukushima K., Yoshino T., Miwa A., Bioorg. Med. Chem. Lett., 14, 875-879 (2004).
35. Sebolt-Leopold J. S., Dudley D. T., Herrera R., Van Becelaere K., Wiland A., Gowan R. C., Tecle H., Barrett S. D., Bridges A. J., Przybranowski S., Leopold W. R., Saltiel A. R., Nat. Med., 5, 810-816 (1999).
36. Barrett S. D., Bridges A. J., Dudley D. T., Saltiel A. R., Fergus J. H., Flamme C. M., Delaney A. M., Kaufman M., LePage S., Leopold W. R., Przybranowski S. A., Sebolt-Leopold J., Van Becelaere K., Doherty A. M., Kennedy R. M., Marston D., Howard W. A. Jr., Smith Y., Warmus J. S., Tecle H., Bioorg. Med. Chem. Lett., 18, 6501-6504 (2008).
37. Ohren J. F., Chen H., Pavlovsky A., Whitehead C., Zhang E., Kuffa P., Yan C., McConnell P., Spessard C., Banotai C., Mueller W. T., Delaney A., Omer C., Sebolt-Leopold J., Dudley D. T., Leung I. K., Flamme C., Warmus J., Kaufman M., Barrett S., Tecle H., Hasemann C. A., Nat. Struct. Mol. Biol., 11, 1192-1197 (2004).
38. Berner N. H., Varma R. S., Boykin D. W. Jr., J. Med. Chem., 13, 552-554 (1970).
39. Allen C. F. H., McKee G. H. W., Org. Synth., 19, 6-8 (1936).
40. Von Koenig A., Kabbe H. J., Ger. Offen. 1930263 (1971)
41. [Chem. Abstr., 74, 105695m (1971)].
42. Pospieszny T., Małecka I., Paryzek Z., Tetrahedron Lett., 51, 4166-4169 (2010).
43. Pospieszny T., Wyrzykiewicz E., Tetrahedron Lett., 49, 5319-5321 (2008).
44. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J. T., Bokesch H., Kenney S., Boyd M. R., J. Natl. Cancer Inst., 82, 1107-1112 (1990).
45. Al-Abd A. M., Lee J. H., Kim S. Y., Kun N., Kuh H. J., Cancer Sci., 99, 423-431 (2008).
46. MOE. Chemical Computing Group, Inc., Montréal: http://www.chemcomp.com.
47. Jamloki A., Karthikeyan C., Hari Narayana Moorthy N. S., Trivedi P., Bioorg. Med. Chem. Lett., 16, 3847-3854 (2006).
48. Verma R. P., Hansch C., Eur. J. Med. Chem., 45, 1470-1477 (2010).
49. Golbraikh A., Tropsha A., J. Mol. Graph. Model., 20, 269-276 (2002).
50. Ghose A. K., Pritchett A., Crippen G. M., J. Comput. Chem., 9, 80-90 (1988).