Design, synthesis and in vitro anti-tuberculosis activity of benzo [6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole derivatives

被引：39

作者：

Sajja, Yasodakrishna ^{[1
]}

Vanguru, Sowmya ^{[1
]}

Vulupala, Hanmanth Reddy ^{[1
]}

Bantu, Rajashaker ^{[1
]}

Yogeswari, Perumal ^{[2
]}

Sriram, Dharmarajan ^{[2
]}

Nagarapu, Lingaiah ^{[1
]}

机构：

[1] Indian Inst Chem Technol, CSIR, CPC Div, Organ Chem Div 2, Hyderabad 500007, Telangana, India

[2] Birla Inst Technol & Sci Pilani, Pharm Grp, Med Chem & Antimycobacterial Res Lab, Hyderabad Campus, Hyderabad 500078, Telangana, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2017年 / 27卷 / 23期

关键词：

Triazole; Click reaction; Benzo[6,7]cyclohepta[1,2-b]pyridine; Mycobacterium tuberculosis; POTENTIAL ANTICANCER AGENTS; ANTIMICROBIAL ACTIVITY; MYCOBACTERIUM-TUBERCULOSIS; ANTIINFLAMMATORY ACTIVITY; PYRIDINE-DERIVATIVES; MEDICINAL CHEMISTRY; CLICK CHEMISTRY; DRUGS; 1,2,3-TRIAZOLES; DESLORATADINE;

D O I：

10.1016/j.bmcl.2017.10.071

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of novel benzo[6,7] cyclohepta[1,2-b] pyridine-1,2,3-triazole hybrids (7a-j & 8a-j) have been designed and synthesized in excellent yields by Huisgen's [3+2] cyclo addition reaction of 3-(azidomethyl)-2-methyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine (5) with various alkynes 6 in presence of copper sulphate and sodium ascorbate and their structures were confirmed by IR, H-1 NMR, C-13 NMR and HRMS. The newly synthesized compounds 7a-j & 8a-j were evaluated for their in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC 27294). Among the compounds tested, the compounds 7i and 8g displayed most potent activity with MIC value of 1.56 mu g/mL with low cytotoxicity. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：5119 / 5121

页数：3

共 48 条

[1] Anti-inflammatory properties of desloratadine [J].

Agrawal, DK .

CLINICAL AND EXPERIMENTAL ALLERGY, 2004, 34 (09) :1342-1348

[2]

[Anonymous], 2017, TUBERCULOSIS

[3] Rational design, synthesis and anti-proliferative evaluation of novel 1,4-benzoxazine-[1,2,3]triazole hybrids [J].

Bollu, Rajitha ;

Palem, Jyothsna Devi ;

Bantu, Rajashaker ;

Guguloth, Vijayacharan ;

Nagarapu, Lingaiah ;

Polepalli, Sowjanya ;

Jain, Nishant .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 89 :138-146

[4] Checkpoint kinase 1-mediated phosphorylation of Cdc25C and bad proteins are involved in antitumor effects of loratadine-induced G2/M phase cell-cycle arrest and apoptosis [J].

Chen, Jinn-Shiun ;

Lin, Shyr-Yi ;

Tso, Wei-Ling ;

Yeh, Geng-Chang ;

Lee, Wen-Sen ;

Tseng, How ;

Chen, Li-Ching ;

Ho, Yuan-Soon .

MOLECULAR CARCINOGENESIS, 2006, 45 (07) :461-478

[5] 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

[6] Prospects for new antitubercular drugs [J].

Duncan, K ;

Barry, CE .

CURRENT OPINION IN MICROBIOLOGY, 2004, 7 (05) :460-465

[7] WHO guidelines for the programmatic management of drug-resistant tuberculosis: 2011 update [J].

Falzon, D. ;

Jaramillo, E. ;

Schuenemann, H. J. ;

Arentz, M. ;

Bauer, M. ;

Bayona, J. ;

Blanc, L. ;

Caminero, J. A. ;

Daley, C. L. ;

Duncombe, C. ;

Fitzpatrick, C. ;

Gebhard, A. ;

Getahun, H. ;

Henkens, M. ;

Holtz, T. H. ;

Keravec, J. ;

Keshavjee, S. ;

Khan, A. J. ;

Kulier, R. ;

Leimane, V. ;

Lienhardt, C. ;

Lu, C. ;

Mariandyshev, A. ;

Migliori, G. B. ;

Mirzayev, F. ;

Mitnick, C. D. ;

Nunn, P. ;

Nwagboniwe, G. ;

Oxlade, O. ;

Palmero, D. ;

Pavlinac, P. ;

Quelapio, M. I. ;

Raviglione, M. C. ;

Rich, M. L. ;

Royce, S. ;

Ruesch-Gerdes, S. ;

Salakaia, A. ;

Sarin, R. ;

Sculier, D. ;

Varaine, F. ;

Vitoria, M. ;

Walson, J. L. ;

Wares, F. ;

Weyer, K. ;

White, R. A. ;

Zignol, M. .

EUROPEAN RESPIRATORY JOURNAL, 2011, 38 (03) :516-528

[8] Synthesis and evaluation of 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives as antimycobacterial agent [J].

Gallardo, Hugo ;

Conte, Gilmar ;

Bryk, Fernando ;

Lourenco, Maria Cristina S. ;

Costa, Marilia S. ;

Ferreira, Vitor F. .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2007, 18 (06) :1285-1291

[9] Anti-inflammatory activity of H1-receptor antagonists:: review of recent experimental research [J].

Gelfand, EW ;

Appajosyula, S ;

Meeves, S .

CURRENT MEDICAL RESEARCH AND OPINION, 2004, 20 (01) :73-81

[10] Clubbed [1,2,3] triazoles by fluorine benzimidazole: A novel approach to H37Rv inhibitors as a potential treatment for tuberculosis [J].

Gill, Charansingh ;

Jadhav, Ganesh ;

Shaikh, Mohammad ;

Kale, Rajesh ;

Ghawalkar, Anant ;

Nagargoje, Deepak ;

Shiradkar, Mahendra .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (23) :6244-6247

← 1 2 3 4 5 →