Synthesis of novel 1,2,3-triazole based benzoxazolinones: Their TNF-α based molecular docking with in-vivo anti-inflammatory, antinociceptive activities and ulcerogenic risk evaluation

被引：64

作者：

Haider, Saqlain ^{[1
]}

Alam, M. Sarwar ^{[1
]}

Hamid, Hinna ^{[1
]}

Shafi, Syed ^{[1
]}

Nargotra, Amit ^{[3
]}

Mahajan, Priya ^{[3
]}

Nazreen, Syed ^{[1
]}

Kalle, Arunasree M. ^{[4
]}

Kharbanda, Chetna ^{[1
]}

Ali, Yakub ^{[1
]}

Alam, Aftab ^{[2
]}

Panda, Amulya K. ^{[2
]}

机构：

[1] Jamia Hamdard, Fac Sci, Dept Chem, New Delhi 110062, India

[2] Natl Inst Immunol, New Delhi 110067, India

[3] Indian Inst Integrat Med, Jammu 180001, India

[4] Univ Hyderabad, Dept Anim Sci, Hyderabad 500046, Andhra Pradesh, India

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 70卷

关键词：

1,2,3-Triazole; Click chemistry; Molecular docking; Benzoxazolinone; Carrageenan cyclooxygenase; ANTIBACTERIAL ACTIVITY; INHIBITION; DERIVATIVES; MECHANISM; EFFICIENT; SYNTHASE; EXTRACT; RAT; PAW;

D O I：

10.1016/j.ejmech.2013.10.032

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A library of novel bis-heterocycles containing benzoxazolinone based 1,2,3-triazoles has been synthesized using click chemistry approach. The compound 3f exhibited potent selective COX-2 inhibition of 59.48% in comparison to standard drug celecoxib (6636% inhibition). The compound 31 showed significant (p < 0.001, 50.95%), TNF-alpha inhibitory activity as compared to indomethacin (p <0.001, 64.01%). The results of the carrageenan induced hind paw oedema showed that compounds 3a, 3f, 3i, 30, and 3e exhibited potent anti-inflammatory activity in comparison to Indomethacin. The molecular docking studies revealed that 3i exhibits strong inhibitory effect due to the extra stability of the complex because of an extra pi-pi bond. The histopathology report showed that none of the compounds caused gastric ulceration. (C) 2013 Elsevier Masson SAS. All rights reserved.

引用

页码：579 / 588

页数：10

共 52 条

[41] GROWTH-INHIBITION AND INDUCTION OF CELLULAR-DIFFERENTIATION OF HUMAN MYELOID-LEUKEMIA CELLS IN CULTURE BY CARBAMOYL CONGENERS OF RIBAVIRIN [J].

SANGHVI, YS ;

BHATTACHARYA, BK ;

KINI, GD ;

MATSUMOTO, SS ;

LARSON, SB ;

JOLLEY, WB ;

ROBINS, RK ;

REVANKAR, GR .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :336-344

[42]

Schrodinger, 2011, MAESTR VERS 9 2

[43]

Schrodinger, 2011, CONFGEN VERS 2 3

[44] Inhibition of nitric oxide synthase by benzoxazolones [J].

Shankaran, K ;

Donnelly, KL ;

Shah, SK ;

Humes, JL ;

Pacholok, SG ;

Grant, SK ;

Green, BG ;

MacCoss, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (22) :2887-2892

[45] Synthesis of 4-aryl-5-nitro-1,2,3-triazoles [J].

Sheremet, EA ;

Tomanov, RI ;

Trukhin, EV ;

Berestovitskaya, VM .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (04) :594-595

[46]

VACCHER MP, 1986, FARMACO-ED SCI, V41, P257

[47] SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF CERTAIN 3-SUBSTITUTED BENZOXAZOLINONES [J].

VARMA, RS ;

NOBLES, WL .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1968, 57 (01) :39-&

[48]

VARMA RS, 1979, INDIAN J CHEM B, V18, P200

[49]

Wamhoff H., 1984, COMPREHENSIVE HETERO, V5, P669

[50] ConfGen: A Conformational Search Method for Efficient Generation of Bioactive Conformers [J].

Watts, K. Shawn ;

Dalal, Pranav ;

Murphy, Robert B. ;

Sherman, Woody ;

Friesner, Rich A. ;

Shelley, John C. .

JOURNAL OF CHEMICAL INFORMATION AND MODELING, 2010, 50 (04) :534-546

← 1 2 3 4 5 6 →