Synthesis, characterization, and in vitro antimicrobial evaluation of new 5-chloro-8-bromo-3-aryl-1,2,4-triazolo[4,3-c]pyrimidines

被引:4
作者
Kumara, Basavapatna N. Prasanna [1 ]
Mohana, Kikkeri N. [1 ]
Mallesha, Lingappa [2 ]
机构
[1] Univ Mysore, Dept Studies Chem, Mysore 570006, Karnataka, India
[2] JSS Coll Arts Commerce & Sci, PG Dept Chem, Mysore 570025, Karnataka, India
关键词
8-Bromo-2,4-dichloropyrimidine; Triazolopyrimidines; Iodobenzene diacetate; Antimicrobial activity; Oxidative cyclization; ANTIBACTERIAL; REAGENTS; IODINE;
D O I
10.1007/s00044-013-0656-7
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of new 5-chloro-8-bromo-3-aryl-1,2,4-triazolo[4,3-c]pyrimidines (4a-j) have been accomplished in excellent yields by the oxidative cyclization of pyrimidinylhydrazines (3a-j) of various aryl aldehydes with one equivalents of iodobenzene diacetate in methanol. The chemical structures of the synthesized compounds were confirmed by elemental analyses, FT-IR, H-1 NMR, C-13 NMR, and mass spectral studies. Ten new compounds (4a-j) were tested in vitro for their antimicrobial activity against clinically isolated strains. Variable and modest activities were observed against the investigated strains of bacteria and fungi. Compounds 4f, 4i, and 4j demonstrated good antimicrobial activity against all the tested microbial strains.
引用
收藏
页码:445 / 453
页数:9
相关论文
共 19 条
[1]   BSAC standardized disc susceptibility testing method [J].
Andrews, JM .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2001, 48 :43-57
[2]  
Bansal S., 2013, INT J PHARM PHARM SC, V5, P346
[3]   Antimicrobial and antitumor activity of N-heteroimmine-1,2,3-dithiazoles and their transformation in triazolo-, imidazo-, and pyrazolopirimidines [J].
Baraldi, PG ;
Pavani, MG ;
Nuñez, MD ;
Brigidi, P ;
Vitali, B ;
Gambari, R ;
Romagnoli, R .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (02) :449-456
[4]  
Bukhari MH, 2011, J CHEM SOC PAKISTAN, V33, P720
[5]  
Cieplik J, 2011, ACTA POL PHARM, V68, P57
[6]   Synthesis, antifolate, and antitumor activities of classical and nonclassical 2-amino-4-oxo-5-substituted-pyrrolo[2,3-d]pyrimidines [J].
Gangjee, A ;
Vidwans, A ;
Elzein, E ;
McGuire, JJ ;
Queener, SF ;
Kisliuk, RL .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (12) :1993-2003
[7]   Synthesis pharmacological evaluation and docking studies of pyrimidine derivatives [J].
Giles, D. ;
Roopa, Karki ;
Sheeba, F. R. ;
Gurubasavarajaswamy, P. M. ;
Divakar, Goli ;
Vidhya, Thomas .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 58 :478-484
[8]   Synthesis and in vitro activity of novel 1,2,4-triazolo[4,3-a]pyrimidine oxazolidinone antibacterial agents [J].
Khera, Manoj K. ;
Cliffe, Ian A. ;
Mathur, Tarun ;
Prakash, Om .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (10) :2887-2889
[9]   Syntheses of novel antimycobacterial combinatorial libraries of structurally diverse substituted pyrimidines by three-component solid-phase reactions [J].
Kumar, A ;
Sinha, S ;
Chauhan, PMS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (04) :667-669
[10]  
Kumar N, 2001, HETEROATOM CHEM, V12, P52, DOI 10.1002/1098-1071(2001)12:1<52::AID-HC11>3.0.CO