Synthesis, evaluation of antimicrobial activity, and molecular modeling of novel 2-((4-(2H-benzo[d] [1,2,3] triazol-2-yl)piperidin-1-yl)methyl)-5-substituted phenyl-1,3,4-oxadiazoles

被引：0
作者：
Srinivas Rao Vankadari
Devender Mandala
Jalapathi Pochampalli
Parthasarathy Tigulla
Anil Valeru
Rajakomuraiah Thampu
机构：
[1] University College of Science,Department of Chemistry
[2] Osmania University,Department of Microbiology
[3] Allied Fabrichem Pvt. Ltd,undefined
[4] Kakatiya University,undefined
来源：
Medicinal Chemistry Research | 2013年 / 22卷
关键词：
Benzotriazole; Antibacterial; Antifungal; Oxidoreductase (1XDQ, 3QLS) proteins;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A new series of 2-((4-(2H-benzo[d][1,2,3]triazol-2-yl)piperidin-1-yl)methyl)-5-substituted-1-yl)-acetic acid hydrazide (3) with various substituted aromatic carboxylic acids phenyl-1,3,4-oxadiazoles (4a–j) were synthesized by cyclization of 4-benzotriazol-2-yl-piperidin in the presence of POCl3. The structures were characterized by spectral data. The representative examples were screened invitro antibacterial activity and antifungal activity. The compounds showed significant antibacterial activity and showed moderate antifungal activity as that of standards, respectively. The data were further compared with structure-based investigations using docking studies with the crystal structure of oxidoreductase (1XDQ) protein organism: Escherichia coli for antibacterial activity and oxidoreductase (3QLS) protein, organism: Candida albicans for antifungal activity. The score values estimated by genetic algorithm were found to have a good correlation with the experimental inhibitory potencies.
引用
收藏
页码：5912 / 5919
页数：7
相关论文
共 133 条
[1]  
Aboraia AS(2006)Novel 5-(2-hydroxyphenyl)-3-substituted-2, 3-dihydro-1, 3, 4-oxadiazole-2-thione derivatives: promising anticancer agents Bioorg Med Chem 14 1236-1246
[2]  
Hamdy MAR(2003)Synthesis and properties of new substituted 1,2,4-triazoles: potential antitumor agents Bioorg Med Chem 11 1701-1708
[3]  
Nadia MM(1998)Synthesis and anti-inflammatory of naphthylmethyl oxadiazoles, thiadiazoles and triazoles Ind J Heterocycl Chem 8 107-110
[4]  
Mahmoud AEG(1975)Synthesis and structure-activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores Chem Abstr 62 156324-286
[5]  
Al-Soud YA(2001)Synthesis and antibacterial studies of a new series of 1,2-bis(1,3,4-oxadiazol-2-yl)ethanes and 1,2-bis(4-amino-1,2,4-triazol-3-yl)ethanes Eur J Med Chem 36 265-23
[6]  
Al-Masoudi NA(1976)An efficient synthesis, characterization and antimicrobial screening of N-substituted 2-(piperidin-4-yl)- Agric Biol Chem 40 17-271
[7]  
Ferwanah AS(2000)-benzo [d][l, 2, 3] triazoles Eur J Med Chem 35 267-478
[8]  
Amir M(2012)1,3,4-Oxadiazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 2: SAR of the C5 position Lett Drug Des Discovery 9 471-1810
[9]  
Shahani S(2009)Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation Bioorg Med Chem Lett 19 1807-548
[10]  
Baqet G(1995)Properties and synthetic utility of N-substituted benzotriazoles J mol biol 43 245-116
12345678910