Synthesis, antituberculosis activity and QSAR study of some novel 2-(nitroaryl)-5-(nitrobenzylsulfinyl and sulfonyl)-1,3,4-thiadiazole derivatives

Daru

Volumn 15, Issue 4, 2007, Pages 218-226

  Foroumadi, A ^a,b   Sakhteman, A ^a   Sharifzadeh, Z ^b   Mohammadhosseini, N ^a   Hemmateenejad, B ^c   Moshafi, M H ^b   Vosooghi, M ^a   Amini, M ^a   Shafiee, A ^a  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b KERMAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c SHIRAZ UNIVERSITY   (Iran)

Author keywords

1,3,4 thiadiazoles; Antituberculosis activity; QSAR study; Synthesis

Indexed keywords

1,3,4 THIADIAZOLE DERIVATIVE; 2 (2 NITROBENZYLSULFINYL) 5 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 1,3,4 THIADIAZOLE; 2 (2 NITROBENZYLSULFINYL) 5 (5 NITROFURAN 2 YL) 1,3,4 THIADIAZOLE; 2 (2 NITROBENZYLSULFONYL) 5 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 1,3,4 THIADIAZOLE; 2 (2 NITROBENZYLSULFONYL) 5 (NITROFURAN 2 YL) 1,3,4 THIADIAZOLE; 2 (3 NITROBENZYLSULFINYL) 5 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 1,3,4 THIADIAZOLE; 2 (3 NITROBENZYLSULFINYL) 5 (5 NITROFURAN 2 YL) 1,3,4 THIADIAZOLE; 2 (3 NITROBENZYLSULFONYL) 5 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 1,3,4 THIADIAZOLE; 2 (3 NITROBENZYLSULFONYL) 5 (NITROFURAN 2 YL) 1,3,4 THIADIAZOLE; 2 (4 NITROBENZYLSULFINYL) 5 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 1,3,4 THIADIAZOLE; 2 (4 NITROBENZYLSULFINYL) 5 (5 NITROFURAN 2 YL) 1,3,4 THIADIAZOLE; 2 (4 NITROBENZYLSULFONYL) 5 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 1,3,4 THIADIAZOLE; 2 (4 NITROBENZYLSULFONYL) 5 (NITROFURAN 2 YL) 1,3,4 THIADIAZOLE; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; BROTH DILUTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 40749117261     PISSN: 15608115     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. Gupta P, Hameed S, Jain R. Ring-substituted imidazoles as a new class of anti-tuberculosis agents. Eur. J. Med. Chem 2004; 39: 805-814.
2. Tripathi R, Tewari N, Dwivedi N, Tiwari VK. Fighting tuberculosis: an old disease with new challenges. Med Res Rev 2005; 25: 93-131.
3. Gadad AK, Noolvi MN, Karpoormath RV. Synthesis and anti-tubercular activity of a series of 2-sulfonamido/trifluoromethyl-6-substituted imidazo(2,1-b)-1,3,4-thiadiazole derivatives Bioorg Med Chem 2005; 12: 5651-5659.
4. Shindikar AV, Viswanathan CL. Novel fluoroquinolones: design, synthesis, and in vivo activity in mice against Mycobacterium tuberculosis H37Rv. Bioorg. Med Chem Lett 2005:15:1803-1806.
5. Stover CK, Warrener P, Vandervanter DR, Sherman DR, Arain TM, Langhorne MH, Anderosn SW, Towell JA, Yuan Y, McMurray DM, Kreiswirth BN, Barry CA, Baker WR. A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis Nature 2000; 405: 962-966.
6. Foroumadi A, Kiani Z, Soltani F. Antituberculosis agents VIII. Synthesis and in vitro antimycobacterial activity of alkyl alpha-[5-(5-nitro-2-thienyl)-1, 3,4-thiadiazole-2-ylthio]acetates. Il Farmco 2003; 58: 1073-1076.
7. Tangallapally RP, Lee RE, Yendapally R, Hevener K, Jones VC, Lenaerts AJM, McNeil MR, Wang Y, Lee RE, Synthesis and evaluation of nitrofuranylamides as novel antituberculosis agents. J Med Chem. 2004; 47: 5276-5283.
8. Tangallapally RP, Yendapally R, Lee RE, Lenaerts AJM. Synthesis and evaluation of cyclic secondary amine substituted phenyl and benzyl nitrofuranyl amides as novel antituberculosis agents. J Med Chem 2005; 48: 8261-8269.
9. Foroumadi A, Kargar Z, Sakhteman A, Sharifzadeh Z, Feyzmohammadi R, Kazemi M, Shafiee A, Synthesis and antimycobacterial activity of some alkyl [5-(nitroaryl)-1,3,4-thiadiazol-2-ylthio]propionates. Bioorg Med Chem Lett 2006; 16: 1164-1167.
10. Foroumadi A, Mirzaei M, Shafiee A, Antituberculosis agents II. Evaluation of in vitro antituberculosis activity and cytotoxicity of some 2-(1-methyl-5-nitro-2-imidazolyl)-1,3,4-thiadiazole derivatives. Il Farmaco. 2001; 56: 621-623.
11. Hemateenajad B, Miri R, Jafarpour M, Tabarzad M, Foroumadi A. Multiple Linear Regression and Principal Component Analysis-Based Prediction of the Anti-Tuberculosis Activity of Some 2-aryl-1,3,4-Thiadiazole Derivatives. J. QSAR Comb Sci. 2006; 1: 56-66.
12. Foroumadi A, Mirzaei M, Shafiee A. Antituberculosis agents, I: Synthesis and antituberculosis activity of 2-aryl-1,3,4-thiadiazole derivatives. Pharmazie 2001; 56: 610-612.
13. Foroumadi A, Soltani F, Moallemzadeh-Haghighi H , Shafiee A. Synthesis, in vitro-antimycobacterial activity and cytotoxicity of some alkyl alpha-(5-aryl-1, 3, 4-thiadiazole-2-ylthio)acetates. Arch Pharm Chem Life Sci 2005; 338: 112-116.
14. Foroumadi A, Soltani F, Jabini R, Moshafi MH, Rasnani F, FAntituberculosis agents X. Synthesis and evaluation of in vitro antituberculosis activity of 2-(5-nitro-2-furyl)- and 2-(1-methyl-5-nitro-1H- imidazol-2-yl)-1,3,4-thiadiazole derivatives. Arch. Pharm. Res. 2004; 27: 502-506.
15. Collins L, Franzblau SG, Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents. Chemother. 1997;41: 1004-1009.
16. Hemmateenejad B., Miri R., Safarpour M. A., Khoshneviszadeh M,. Edraki N (2005) Conformational analysis of some new derivatives of 4-nitroimidazolyl-1,4- dihydropyridine based calcium channel blockers. J Mol Struct (Theochem) ; 717 : 139-152.
17. R. Todeschini, Milano Chemometrics and QSAR Research Group, http://www.disat.unimib.it/chm/.
18. Sharama P, Rane N, Gurram VK. Synthesis and QSAR studies of pyrimido[4,5- d]pyrimidine-2,5-dione derivatives as potential antimicrobial agents. Bioorg Med Chem Lett.2004; 14: 4185-4190.
19. Khalafi-Nezhad A, Soltani Rad MN, Mohabatkar H, Asrari Z, Hemateenejad B. Design, synthesis, antibacterial and QSAR studies of benzimidazole and imidazole chloroaryloxyalkyl derivatives. Bioorg Med Chem 2005; 13: 1931-1938.
20. Kuramochi T, Kakefuda A, Sato I, Tsukamoto I, Taguchi T, Sakamoto S, Synthesis and structure-activity relationships of 6-{4-[(3-fluorobenzyl)oxy] phenoxy}nicotinamide derivatives as a novel class of NCX inhibitors: a QSAR study. Bioorg. Med. Chem 2005; 13: 717-724.
21. Osten DWJ. Selection of optimal regression models via cross-validation J Chemometrics. 1998; 2: 39-48.
22. Lindgren F, Hansen B, Karcher W, Sjöström M, Eriksson L. Model validation by permutation tests: Applications to variable selection J Chemometrics. 1996; 10: 521-532