Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis

被引：112

作者：

Shanmugavelan, Poovan ^{[1
]}

Nagarajan, Sangaraiah ^{[1
]}

Sathishkumar, Murugan ^{[1
]}

Ponnuswamy, Alagusundaram ^{[1
]}

Yogeeswari, Perumal ^{[2
]}

Sriram, Dharmarajan ^{[2
]}

机构：

[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India

[2] Birla Inst Technol & Sci, Pharm Grp, Med Chem & Antimycobacterial Res Lab, Hyderabad 500078, Andhra Pradesh, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 24期

关键词：

1,2,3-Triazoles; 1,3-Dipolar cycloaddition; Antituberculosis; 1,3-DIPOLAR CYCLOADDITIONS; AGENTS; ANALOGS; DERIVATIVES; TRIAZOLES; RESISTANT; TARGETS; ALKYNES; AZIDES; BM212;

D O I：

10.1016/j.bmcl.2011.10.048

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Efficient and rapid synthesis of 1,2,3-triazole derivatives has been achieved via Huisgen's 1,3-dipolar cycloaddition between alkyl/arylazides and diethyl/dimethyl acetylenedicarboxylate in excellent yields under solvent-free conditions. The environmentally friendly solvent-free protocol overcomes the limitations associated with the prevailing time-consuming solution phase protocols and affords the triazoles just in 1-3 min. In vitro antitubercular activity of these triazoles was screened against Mycobacterium tuberculosis H(37)Rv strain. Four of the compounds showed MIC in the range of 1.56-3.13 mu g/mL proving their potential activity. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：7273 / 7276

页数：4

共 42 条

[1]

Abdou N. A., 1991, B FACPHARM, V28, P29

[2] DIPOLAR CYCLO-ADDITION REACTIONS OF ORGANIC AZIDES WITH SOME ACETYLENIC-COMPOUNDS [J].

ABUORABI, ST ;

ATFAH, MA ;

JIBRIL, I ;

MARII, FM ;

ALI, AAS .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (05) :1461-1468

[3] 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].

ALVAREZ, R ;

VELAZQUEZ, S ;

SANFELIX, A ;

AQUARO, S ;

DECLERCQ, E ;

PERNO, CF ;

KARLSSON, A ;

BALZARINI, J ;

CAMARASA, MJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194

[4]

[Anonymous], 2003, INT EL C SYNTH ORG C, P1

[5]

[Anonymous], 2004, INT EL C SYNTH ORG C, P914

[6]

[Anonymous], 2002, INT EL C SYNTH ORG C, P1

[7] New pyrrole derivatives as antimycobacterial agents analogs of BM212 [J].

Biava, M ;

Fioravanti, R ;

Porretta, GC ;

Deidda, D ;

Maullu, C ;

Pompei, R .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (20) :2983-2988

[8] Freeze-frame inhibitor captures acetylcholinesterase in a unique conformation [J].

Bourne, Y ;

Kolb, HC ;

Radic, Z ;

Sharpless, KB ;

Taylor, P ;

Marchot, P .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (06) :1449-1454

[9] Synthesis of ruthenium triazolato and tetrazolato complexes by 1,3-dipolar cycloadditions of ruthenium azido complex with alkynes and alkenes and regiospecific alkylation of triazolates [J].

Chang, CW ;

Lee, GH .

ORGANOMETALLICS, 2003, 22 (15) :3107-3116

[10] Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives [J].

Costa, Marilia S. ;

Boechat, Nubia ;

Rangel, Erica A. ;

Da Silva, Fernando de C. ;

de Souza, Alessandra M. T. ;

Rodrigues, Carlos R. ;

Castro, Helena C. ;

Junior, Ivan N. ;

Lourenco, Maria Cristina S. ;

Wardell, Solange M. S. V. ;

Ferreira, Vitor F. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (24) :8644-8653

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