In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2-thione derivatives

Acta Pharmaceutica

Volumn 58, Issue 2, 2008, Pages 135-149

  Akhtar, Tashfeen ^a   Hameed, Shahid ^a   Al Masoudi, Najim A ^b   Loddo, Roberta ^c   Colla, Paolo La ^c  

^a QUAID I AZAM UNIVERSITY   (Pakistan)

^b UNIVERSITY OF KONSTANZ   (Germany)

^c UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

1,3,4 oxathiazoles; Antitumor activity; Antiviral activity; Substituted benzothiazoles

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; DOUBLE STRANDED RNA; PHENOL; SINGLE STRANDED RNA;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; FLAVIVIRUS; IN VITRO STUDY; LEUKEMIA CELL LINE; NONHUMAN; RNA VIRUS; VIRUS GENOME;

EID: 44649091552     PISSN: 13300075     EISSN: None     Source Type: Journal    
DOI: 10.2478/v10007-008-0007-2     Document Type: Article

References (21)

1. D. Shi, T. D. Bradshaw, S. Wrigley, C. J. McCall, P. Lelieveld, I. Fichtner and M. F. G. Stevens, Antitumor benzothiazoles. 3. Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo, J. Med. Chem. 39 (1996) 3375-3384; DOI:10.1021/jm9600959.
2. T. D. Bradshaw, S. Wrigley, R. J. Schultz, K. D. Paull and M. F. G. Stevens, 2-(4-Aminophenyl) benzothiazoles: novel agents with selective profiles of in vitro antitumor activity, Br. J. Cancer 77 (1998) 745-752.
3. A. Rana, N. Siddiqui and S. A. Khan, Benzothiazoles: a new profile of biological activities, Indian J. Pharm Sci. 69 (2007) 10-17.
4. G. Trapani, M. Franco, A. Latrofa, A. Reho and G. Liso, Synthesis, in vitro and in vivo cytotoxicity, and prediction of the intestinal absorption of substituted 2-ethoxycarbonyl-imidazo[2,1-b] benzothiazoles, Eur. J. Pharm. Sci. 14 (2001) 209-216; DOI: 10.1016/S0928- 0987(01)00173-7.
5. K. J. Watson, D. R. Anderson and S. T. Nguyen, Toward polymeric anticancer drug cocktails from ring-opening metathesis polymerization, Macromolecules 34 (2001) 3507-3509; DOI:10.1016/S0928-0987(01) 00173-7.
6. I. Caleta, M. Grdisa, D. Mrvos-Sermek, M. Cetina, V. K. Tralić-Kulenović, G. Pavelić and G. Karminski-Zamola, Synthesis, crystal structure and antiproliferative evaluation of some new substituted benzothiazoles and styrylbenzothiazoles, Farmaco 59 (2004) 297-305; DOI: 10.1016/j.farmac.2004.01.008.
7. A. I. Loaiza-Pérez, V. Trapni, V. Patel, C. Hose, S. S. Singh, J. B. Trepel, M. F. G. Stevens, T. D. Bradshaw and E. A. Sauville, The aryl hydrocarbons receptor mediates sensitivity of MCF-7 breast cancer cells to the antitumor agent 2-(4-amino-3-methylphenyl) benzothiazole, Mol. Pharmacol. 61 (2002) 13-19.
8. V. Trapani, V. Patel, C.-O. Leong, H. P. Ciolino, G. C. Yeh, C. Hose, J. B. Trepel, M. F. G. Stevens, E. A. Sausville and A. I. Loaiza-Pérez, DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5- fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells, Br. J. Cancer 88 (2003) 599-605; DOI:10.1038/sj.bjc.6600722
9. G. Mortimer, G. Wells, J.-P. Grochard, E. L. Stone, T. D. Bradshaw, M. F. G. Stevens and A. D. Westwell, Antitumor benzothiazoles. 26. 2-(3,4-dimethoxyphenyl)-5-fluoro benzothiazole (GW 610, NSC 721648), a simple fluorinated 2-arylbenzothiazole, shows potents and selective inhibitory activity against lung, colon, and breast cancer cell lines, J. Med. Chem. 49 (2006) 179-185; DOI: 10.1021/jm050942k.
10. G. Wells, J. M. Berry, T. D. Bradshaw, A. M. Burger, A. Seaton, B. Wang, A. D. Westwell and M. F. G. Stevens, Substituted -4-hydroxycyclohexa-2,5-dien-1- ones with selective activities against colon and renal cancer cell lines, J. Med. Chem. 46 (2003) 532-541; DOI:10.1021/jm020984y.
11. T. D. Bradshaw and A. D. Westwell, The development of the antitumor benzothiazole prodrug, Phortress, as a clinical candidate, Curr. Med. Chem. 11 (2004) 1009-1021.
12. M. Yoshida, I. Hayakawa, N. Hayashi, T. Agatsuma, Y. Oda, F. Tanzawa, S. Iwasaki, K. Koyama, H. Furukawa, S. Kurakata and Y. Sugano, Synthesis and biological evaluation of benzothiazole derivatives as potent antitumor agents, Bioorg. Med. Chem. Lett. 15 (2005) 3328-3333; DOI:10.1016/j.bmcl. 2005.05.077.
13. I. Hutchinson, T. D. Bradshaw, C. S. Matthews, M. F. G. Stevens and A. D. Westwell, Antitumour benzothiazoles. Part 20: 3′-cyano and 3′-alkynyl-substituted 2-(4′-aminophenyl)benzothiazoles as new potent and selective analogues, Bioorg. Med. Chem. Lett. 13 (2003) 471-474; DOI: 10.1016/S0960-894X(02)00930-7.
14. T. Akhtar, M. K. Rauf, M. Ebihara and S. Hameed, 2-(3,4-Dichlorophenoxy) propionic acid. Acta Cryst. E63 (2007) 2590-2592; DOI: 10.1107/S1600536807014249.
15. 2-amino acids involving the reformatsky reaction and mannich-type imminium electrophile, J. Org. Chem. 71 (2006) 3332-3334; DOI: 10.1021/jo060316a.
16. M. C. Alley, D. A. Scudiero, A. Monks, M. L. Hursey, M. J. Czerwinski, D. L. Fine, B. J. Abbott, L. G. Mayo, R. H. Schoemaker and M. R. Boyd, Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay, Cancer Res. 48 (1988) 589-601.
17. G. Yang, L. Xu, and A. Lu, Synthesis and bioactivity of novel triazolo [1,5-a]pyrimidine derivatives, Heteroatom Chem. 12 (2001) 491-498; DOI: 10.1002/hc.1075.
18. S. D. Young, S. F. Britcher, L. O. Tran, L. S. Payne, W. C. Lumma, T. A. Lyle, J. R. Huff, P. S. Anderson, D. B. Olsen, S. S. Carroll, D. J. Pettibone, J. A. Obrien, R. G. Ball, S. K. Balani, J. H. Lin, I. W. Chen, W. A. Schleif, V. V. Sardana, W. J. Long, V. W. Byrnes and E. A. Emini, Novel, highly potent non-nucleoside inhibitor of the human immunodeficiency-virus type-1 reverse transcriptase, Antimicrob. Agents Chemother. 39 (1995) 2602-2605.
19. E. De Clercq, Clinical potential of the acyclic nucleoside phosphonates cidofovir, adefovir, and tenofovir in treatment of DNA virus and retrovirus infections, Clin. Microbiol. Rev. 16 (2003) 569-596; DOI: 10.1128/CMR.16.4.
20. R. B. Weiss, The anthracyclines: will we never find a better docorubicin, 19 (1992) 670-686.
21. C. D. Hose, M. Hollingshead, E. A. Sauville and A. Monks, Induction of CYP1A1 in tumor cells by the antitumor agent 2-[4-amino-3-methylphenyl]-5- fluoro-benzothizole: A potential surrogate marker for patient sensitivity, Mol. Cancer Ther. 2 (2003) 1265-1272.