Potential antimicrobial agents from triazole-functionalized 2H-benzo[b] [1,4]oxazin-3(4H)-ones

被引：23

作者：

Bollu, Rajitha ^{[1
]}

Banu, Saleha ^{[1
]}

Bantu, Rajashaker ^{[1
]}

Reddy, A. Gopi ^{[1
]}

Nagarapu, Lingaiah ^{[1
]}

Sirisha, K. ^{[2
]}

Kumar, C. Ganesh ^{[2
]}

Gunda, Shravan Kumar ^{[3
]}

Shaik, Kamal ^{[3
]}

机构：

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

[2] Indian Inst Chem Technol, CSIR, Med Chem & Biotechnol Div MCB, Hyderabad 500007, Andhra Prades, India

[3] Osmania Univ, Dept Bot, Bioinformat Wing, Mycol & Plant Pathol Lab, Hyderabad 500007, Andhra Prades, India

来源：

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

关键词：

1,4-Benzoxazine; 1,2,3 Triazoles; Antimicrobial activity; Molecular docking; Dehydrosqualene synthase; STAPHYLOCOCCUS-AUREUS; BACTERIAL-RESISTANCE; BENZOXAZOLINONE; 1,2,3-TRIAZOLES; TUBERCULOSIS; DESTRUCTION; DERIVATIVES; MECHANISMS; INHIBITORS; DISCOVERY;

D O I：

10.1016/j.bmcl.2017.10.061

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of substituted triazole functionalized 2H-benzo[b][1,4] oxazin-3(4H)-ones were synthesized by employing click chemistry and further characterized based on H-1 NMR, C-13 NMR, IR and mass spectral studies. All the synthesized derivatives were screened for their in vitro antimicrobial activities. Further, molecular docking studies were accomplished to explore the binding interactions between 1,2,3-triazol-4-yl-2H-benzo[b][1,4] oxazin-3(4H)-one and the active site of Staphylococcus aureus (CrtM) dehydrosqualene synthase (PDB ID: 2ZCS). These docking studies revealed that the synthesized derivatives showed high binding energies and strong H-bond interactions with the dehydrosqualene synthase validating the observed antimicrobial activity data. Based on antimicrobial activity and docking studies, the compounds 9c, 9d and 9e were identified as promising antimicrobial leads. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：5158 / 5162

页数：5

共 41 条

[1] Synthesis and antifungal activity of 1,2,3-triazole containing fluconazole analogues [J].

Aher, Nilkanth G. ;

Pore, Vandana S. ;

Mishra, Nripendra N. ;

Kumar, Awanit ;

Shukla, Praveen K. ;

Sharma, Aanchal ;

Bhat, Manoj K. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (03) :759-763

[2] Mechanisms and consequences of bacterial resistance to antimicrobial peptides [J].

Andersson, D. I. ;

Hughes, D. ;

Kubicek-Sutherland, J. Z. .

DRUG RESISTANCE UPDATES, 2016, 26 :43-57

[3] Antibiotic resistance and its cost: is it possible to reverse resistance? [J].

Andersson, Dan I. ;

Hughes, Diarmaid .

NATURE REVIEWS MICROBIOLOGY, 2010, 8 (04) :260-271

[4] STUDIES ON V-TRIAZOLES .7. ANTI-ALLERGIC 9-OXO-1H,9H-BENZOPYRANO[2,3-D]-V-TRIAZOLES [J].

BUCKLE, DR ;

OUTRED, DJ ;

ROCKELL, CJM ;

SMITH, H ;

SPICER, BA .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (02) :251-254

[5] Vancomycin serum trough concentration vs. clinical outcome in patients with gram-positive infection: a retrospective analysis [J].

Cao, G. ;

Liang, X. ;

Zhang, J. ;

Zhou, Y. ;

Wu, J. ;

Zhang, Y. ;

Chen, Y. ;

Huang, J. ;

Liu, X. ;

Yu, J. .

JOURNAL OF CLINICAL PHARMACY AND THERAPEUTICS, 2015, 40 (06) :640-644

[6] Staphyloxanthin plays a role in the fitness of Staphylococcus aureus and its ability to cope with oxidative stress [J].

Clauditz, Alexandra ;

Resch, Alexandra ;

Wieland, Karsten-Peter ;

Peschel, Andreas ;

Goetz, Friedrich .

INFECTION AND IMMUNITY, 2006, 74 (08) :4950-4953

[7] The future challenges facing the development of new antimicrobial drugs [J].

Coates, A ;

Hu, YM ;

Bax, R ;

Page, C .

NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (11) :895-910

[8] 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

[9] Biotransformation reactions of five-membered aromatic heterocyclic rings [J].

Dalvie, DK ;

Kalgutkar, AS ;

Khojasteh-Bakht, SC ;

Obach, RS ;

O'Donnell, JP .

CHEMICAL RESEARCH IN TOXICOLOGY, 2002, 15 (03) :269-299

[10] Structure-Based Discovery of Inhibitors of Microsomal Prostaglandin E2 Synthase-1, 5-Lipoxygenase and 5-Lipoxygenase-Activating Protein: Promising Hits for the Development of New Anti-inflammatory Agents [J].

De Simone, Rosa ;

Chini, Maria Giovanna ;

Bruno, Ines ;

Riccio, Raffaele ;

Mueller, Daniela ;

Werz, Oliver ;

Bifulco, Giuseppe .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (06) :1565-1575

← 1 2 3 4 5 →