Synthesis, cytotoxic and phytotoxic effects of some new N-4aryl substituted isatin-3-thiosemicarbazones

Letters in Drug Design and Discovery

Volumn 8, Issue 5, 2011, Pages 452-458

  Pervez, Humayun ^a   Ramzan, Muhammad ^a   Yaqub, Muhammad ^a   Khan, Khalid Mohammed ^b  

^a BAHAUDDIN ZAKARIYA UNIVERSITY   (Pakistan)

^b UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

Cytotoxicity; Isatin; Isatin Derivatives; Isatin 3 thiosemicarbazones; Phytotoxicity; Thiosemicarbazones

Indexed keywords

ACETIC ACID; ISATIN; ISATIN DERIVATIVE; N (2 ETHYLPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (2 IODOPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (2,3 DICHLOROPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (2,4 DICHLOROPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (2,4 DIMETHOXYPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (2,5 DICHLOROPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (2,5 DIMETHOXYPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (3 CYANOPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (3 IODOPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (3,5 DICHLOROPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (4 CYANOPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (4 ETHYLPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; N (4 IODOPHENYL) 2 (2 OXO 1,2 DIHYDRO 3H INDOL 3 YLIDENE) 1 HYDRAZINECARBOTHIOAMIDE; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; LD 50; NONHUMAN; PHYTOTOXICITY; PRIORITY JOURNAL;

EID: 79955772657     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018011795514159     Document Type: Article

References (32)

1. Pandeya, S. N.; Smitha, S.; Jyoti, M.; Sridhar, S. K. Biological activities of isatin and its derivatives. Acta Pharm., 2005, 55, 27-46 and references therein. (Pubitemid 40562617)
2. Da Silva, J. F. M.; Garden, S. J.; Pinto, A.C. The chemistry of isatins: A review from 1975 to 1999. J. Braz. Chem. Soc., 2001, 273-324 and references therein.
3. Chiyanzu, I.; Clarkson, C.; Smith, P. J.; Lehman, J.; Gut, J.; Rosenthal, P. J.; Chibale, K. Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives. Bioorg. Med. Chem., 2005, 13, 3249-3261. (Pubitemid 40462126)
4. Chen, Li-Rung; Wang, Yu-Chin; Lin, Y. W.; Chou, Shan-Yen; Chen, Shyh-Fong; Liu, L. T.; Wu, Ying-Ta; Kuo, Chih-Jung; Chen, T. Shieh-Shung; Juang, Shin-Hun. Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors. Bioorg. Med. Chem. Lett., 2005, 15, 3058-3062.
5. Beauchard, A.; Ferandin, Y.; Frere, S.; Lozach, O.; Blairvacq, M.; Meijer, L.; Thiery, V.; Besson, T. Synthesis of novel 5-substituted indirubins as protein kinases inhibitors. Bioorg. Med. Chem., 2006, 14, 6434-6443.
6. Hyatt, J. L.; Moak, T.; Hatfield, M. -J.; Tsurkan, L.; Edwards, C. C.; Wierdl, M.; Danks, M. K.; Wadkins, R. M.; Potter, P. M. Selective inhibition of carboxylesterases by isatins,indole-2,3- diones. J. Med. Chem., 2007, 50, 1876-1885. (Pubitemid 46626597)
7. Ravichandran, V.; Mohan, S.; Kumar, K. S. Synthesis and antimicrobial activity of Mannich bases of isatin and its derivatives with 2-[(2,6-dichlorophenyl)amino]phenylacetic acid. Arkivoc, 2007, XIV, 51-57.
8. Aboul-Fadi, T.; Bin-Jubair, F. A. S. Anti-tubercular activity of isatin derivatives. Int. J. Res. Pharm. Sci., 2010, 1, 113-126 and references therein.
9. Singh, U. K.; Pandeya, S. N.; Singh, A.; Srivastava, B. K.; Pandey, M. Synthesis and antimicrobial activity of Schiff's and N-Mannich bases of isatin and its derivatives with 4-amino-N-carbamimidoyl benzene sulfonamide. Int. J. Pharm. Sci. Drug Res., 2010, 2, 151-154.
10. Karali, N. Synthesis and primary cytotoxicity evaluation of new 5- nitroindole-2, 3-dione derivatives. Eur. J. Med. Chem., 2002, 37, 909-918. (Pubitemid 35356427)
11. Chiyanzu, I.; Hansell, E.; Gut, J.; Rosenthal, P. J.; McKerrow, J. H.; Chibale, K. Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain falcipain-2 and rhodesain. Bioorg. Med. Chem. Lett., 2003, 13, 3527-3530. (Pubitemid 37141422)
12. Bal, T. R.; Anand, B.; Yogeeswari, P.; Sriram, D. Synthesis and evaluation of anti-HIV activity of isatin -thiosemicarbazone derivatives. Bioorg. Med. Chem. Lett., 2005, 15, 4451-4455. (Pubitemid 41253873)
13. Terzioglu, N.; Karali, N.; Gursoy, A.; Pannecouque, C.; Leysen, P.; Paeshuyse, J.; Neyts, J.; De Clercq, E. Synthesis and primary antiviral activity evaluation of 3-hydrazono-5-nitro-2-indolinone derivatives. Arkivoc, 2006, 109-118. (Pubitemid 41586738)
14. Quenelle, D. C.; Keith, K. A.; Kern, E. R. In vitro and in vivo evaluation of isatin -thiosemicarbazone and marboran against vaccinia and cowpox virus infections. Antiviral Res., 2006, 71, 24-30.
15. Karali, N.; Gursoy A.; Kandemirli, F.; Shvets, N.; Kaynak, F. B.; Ozbey, S.; Kovalishyn, V.; Dimoglo, A. Synthesis and structureantituberculosis activity relationship of 1H-indole-2,3-dione derivatives. Bioorg. Med. Chem., 2007, 15, 5888-5904. (Pubitemid 47043467)
16. Guzel, O.; Karali, N.; Salman, A. Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives. Bioorg. Med. Chem., 2008, 16, 8976-8987.
17. Pervez, H.; Iqbal, M.S.; Tahir, M. Y.; Choudhary, M. I.; Khan, K. M. Synthesis of some N4-substituted isatin-3-thiosemicarbazones. Nat. Prod. Res., 2007, 21, 1178-1186.
18. Pervez, H.; Iqbal, M. S.; Tahir, M. Y.; Nasim, F. H.; Choudhary, M. I.; Khan, K. M. In vitro cytotoxic, antibacterial, antifungal and urease inhibitory activities of some N4-substituted isatin-3- thiosemicarbazones. J. Enz. Inhib. Med. Chem., 2008, 23, 848-854.
19. Pervez, H.; Chohan, Z. H.; Ramzan, M.; Nasim, F. H.; Khan, K. M. Synthesis and biological evaluation of some new N4-substituted isatin-3-thiosemicarbazones. J. Enz. Inhib. Med. Chem., 2009, 24, 437-446.
20. Pervez, H.; Manzoor, N.; Yaqub, M.; Khan, A.; Khan, K. M.; Nasim, F. H.; Choudhary, M. I. Synthesis and urease inhibitory properties of some new N4-substituted 5-nitroisatin-3-thiosemicarbazones. Lett. Drug. Des. Discov., 2010, 7, 102-108.
21. Omar, A. M. E.; Eshba, N. H.; Salama, H. M. Synthesis of some substituted isatin-thiosemicarbazones and isatin-α-hydrazonothiazoline derivatives as potential antiviral and antimicrobial agents. Arch. Pharm., 1984, 317, 701-709.
22. Petrov, I.; Grupce, O.; Stafilov, T. The nitrogen-hydrogen stretching region of some imides and thioimides. J. Mol. Struct., 1986, 142, 275-278
23. Naumov, P.; Anastasova, F. Experimental and theoretical vibrational study of isatin, its 5-(NO2, F, Cl, Br, I, CH3) analogues and the isatinato anion. Spectrochim. Acta, 2001, 57A, 469-481.
24. Nizamuddin, Khan, M. H.; Alauddin, S.; Haque, R. Synthesis and fungicidal activity of some 2-arylamino-1,3,4-thiadiazino[6,5-b] indoles and 2-aryl-1 ,3,4-oxadiazolo-[2,3-c]-1 ,2,4-triazino[5,6-b] indoles. Indian J. Chem., 1999, 38B, 501-504.
25. Laatsch, H.; Thomson, R. H.; Cox, P. J. Spectroscopic properties of violacein and related compounds: Crystal structure of tetramethyl violacein. J. Chem. Soc. Perkin Trans 2, 1984, 1331-1339.
26. Baron, M. L.; Martin, L. L.; Rae, I. D.; Simmonds, P. M.; Woolcock, M. L. Relaxation processes in aromatic methyl groups. II. Methyl-methyl nuclear overhauser enhancements. Aust. J. Chem., 1990, 43, 741-747.
27. Eshba, N. H.; Salama, H. M.; Labouta, I. M.; Omar, A. M. E. Synthesis of some substituted 1,2,4- triazino [5,6-b] indole derivatives as potential antiviral anticancer agents. Pharmazie, 1987, 42, 664-666. (Pubitemid 18054008)
28. Pervez, H.; Yaqub, M.; Ramzan, M.; Tahir, M. N.; Iqbal, M. S. 4- (2-Ethylphenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazides. Acta Cryst., 2010, E66, o1609.
29. Pervez, H.; Yaqub, M.; Ramzan, M.; Tahir, M. N. 4-(3- Iodophenyl)-1-(2-oxoindolin-3-ylidene) thiosemicarbazides. Acta Cryst., 2010, E66, o1629.
30. McLaughlin, J. L.; Chang, C. J.; Smith, D. L. In: Atta-ur-Rahman, editor. Studies in natural products chemistry; Bench top bioassays for the discovery of bioactive products: Structure and chemistry (part B). Amsterdam: Elsevier; 1991; p. 383.
31. Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobsen, L. B.; Nicholas, D. E.; McLaughlin, J. L. Brine shrimp: a convenient general bioassay for active plant constituents. Planta Medica, 1982, 45, 31-34. (Pubitemid 12063501)
32. Finney, D. J. Probit Analysis. 3rd ed. London: Cambridge University Press; 1971.