Synthesis and pharmacological evaluation of some novel 4-isopropyl thiazole-based sulfonyl derivatives as potent antimicrobial and antitubercular agents

被引:19
作者
Kumar, G. V. Suresh [1 ]
Prasad, Y. Rajendra [2 ]
Chandrashekar, S. M. [3 ]
机构
[1] St Johns Pharm Coll, Dept Med Chem, Bangalore 560040, Karnataka, India
[2] Andhra Univ, AU Coll Pharmaceut Sci, Visakhapatnam 530003, Andhra Pradesh, India
[3] Poornaprajna Inst Sci Res PPISR, Bangalore 562110, Karnataka, India
关键词
4-Isopropylthiazole; Cytotoxicity; Antibacterial; Antifungal; Antitubercular activity; INHIBITORS;
D O I
10.1007/s00044-012-0431-1
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of novel sulfonyl derivatives 3-(substituted benzylsulfonyl)-5-(4-isopropylthiazol-2-yl)-4-phenyl-4H-1,2,4-triazoles 4a-4e, isopropyl thiazole-derived schiff bases 8a-8l, and 2-(substituted benzylsulfonyl)-5-(4-isopropylthiazol-2-yl)-1,3,4-oxadiazoles 11a-11e were synthesized and characterized by IR, H-1 NMR, C-13 NMR, elemental, and mass spectral analysis. All the compounds exhibited moderate to significant antibacterial and antifungal activities. Results of the antitubercular screening against Mycobacterium tuberculosis H37Rv ascertain compounds 4e, 8b, and 8f as excellent antitubercular molecules, when compared with first line drug isoniazid (0.25 mu g/mL).
引用
收藏
页码:4239 / 4252
页数:14
相关论文
共 25 条
[1]   Novel inhibitors of an emerging target in Mycobacterium tuberculosis;: Substituted thiazolidinones as inhibitors of dTDP-rhamnose synthesis [J].
Babaoglu, K ;
Page, MA ;
Jones, VC ;
McNeil, MR ;
Dong, CJ ;
Naismith, JH ;
Lee, RE .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (19) :3227-3230
[2]   New small-molecule synthetic antimycobacterials [J].
Ballell, L ;
Field, RA ;
Duncan, K ;
Young, RJ .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2005, 49 (06) :2153-2163
[3]   RELATIONSHIPS AMONG ANTIBACTERIAL ACTIVITY, INHIBITION OF DNA GYRASE, AND INTRACELLULAR ACCUMULATION OF 11-FLUOROQUINOLONES [J].
BAZILE, S ;
MOREAU, N ;
BOUZARD, D ;
ESSIZ, M .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (12) :2622-2627
[4]   Validation of a biophysical drug absorption model by the PATQSAR system [J].
Bermejo, M ;
Merino, V ;
Garrigues, TM ;
Delfina, JMP ;
Mulet, A ;
Vizet, P ;
Trouiller, G ;
Mercier, C .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1999, 88 (04) :398-405
[5]   The global tuberculosis situation - Progress and problems in the 20th century, prospects for the 21st century [J].
Cegielski, JP ;
Chin, DP ;
Espinal, MA ;
Frieden, TR ;
Cruz, RR ;
Talbot, EA ;
Weil, DEC ;
Zaleskis, R ;
Raviglione, MC .
INFECTIOUS DISEASE CLINICS OF NORTH AMERICA, 2002, 16 (01) :1-+
[6]   SYNTHESIS OF HETEROCYCLES .6. SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME 4-AMINO-5-ARYL-1,2,4-TRIAZOLE-3-THIONES AND THEIR DERIVATIVES [J].
EWEISS, NF ;
BAHAJAJ, AA ;
ELSHERBINI, EA .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (05) :1451-1458
[7]  
Goto S, 1981, JAP J CHEMOTHER, V29, P76
[8]  
Goulding Celia W., 2002, Current Drug Targets - Infectious Disorders, V2, P121, DOI 10.2174/1568005023342551
[9]  
HASSAN E, 1983, PHARMAZIE, V38, P833
[10]   5-ARYL-3-(ALKYLTHIO)-4H-1,2,4-TRIAZOLES AS SELECTIVE ANTAGONISTS OF STRYCHNINE-INDUCED CONVULSIONS AND POTENTIAL ANTISPASTIC AGENTS [J].
KANE, JM ;
STAEGER, MA ;
DALTON, CR ;
MILLER, FP ;
DUDLEY, MW ;
OGDEN, AML ;
KEHNE, JH ;
KETTELER, HJ ;
MCCLOSKEY, TC ;
SENYAH, Y ;
CHMIELEWSKI, PA ;
MILLER, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (01) :125-132