Synthesis, biological evaluation, and docking studies of 3-(substituted)-aryl-5-(9-methyl-3-carbazole)-1H-2-pyrazolines as potent anti-inflammatory and antioxidant agents

被引：142

作者：

Bandgar, Babasaheb P. ^{[1
]}

Adsul, Laxman K. ^{[1
]}

Chavan, Hemant V. ^{[1
]}

Jalde, Shivkumar S. ^{[1
]}

Shringare, Sadanand N. ^{[1
]}

Shaikh, Rafique ^{[2
]}

Meshram, Rohan J. ^{[2
]}

Gacche, Rajesh N. ^{[2
]}

Masand, Vijay ^{[3
]}

机构：

[1] Solapur Univ, Sch Chem Sci, Med Chem Res Lab, Solapur 413255, Maharashtra, India

[2] SRTM Univ, Sch Life Sci, Biochem Res Lab, Nanded 431606, Maharashtra, India

[3] Vidyabharati Mahavidyalaya, Dept Chem, Amravati 444602, Maharashtra, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 18期

关键词：

Carbazole; Pyrazoline; Anti-inflammatory activity; Antioxidant; Molecular docking; OXIDATIVE STRESS; INHIBITORS; PYRAZOLINES; RADICALS; DRUGS;

D O I：

10.1016/j.bmcl.2012.07.080

中图分类号：

R914 [药物化学];

学科分类号：

100705 [微生物与生化药学];

摘要：

A novel series of 3-(substituted)-aryl-5-(9-methyl-3-carbazole)-1H-2-pyrazolines (5a-o) has been synthesized and the structures of newly synthesized compounds were characterized by IR, H-1 NMR and mass spectral analysis. All the synthesized compounds were evaluated for their in vitro and in vivo anti-inflammatory activity, and also for their antioxidant activity. Compounds 5b, 5c, 5d and 5n were found to be selective COX-2 inhibitors. Compound 5c was found to potent inhibitor of the carrageenin induced paw edema in rats. Most of the compounds exhibited good DPPH and superoxide radical scavenging activity, while compounds 5c, 5d, 5i and 5k exhibited good hydroxyl radical scavenging activity. Molecular docking result, along with the biological assay data, suggested that compound 5c was a potential anti-inflammatory agent. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5839 / 5844

页数：6

共 36 条

[1]

Adsul L.K., 2012, J ENZYME INHIB MED C

[2]

DIETARY CARCINOGENS AND ANTICARCINOGENS - OXYGEN RADICALS AND DEGENERATIVE DISEASES [J].

AMES, BN .

SCIENCE, 1983, 221 (4617) :1256-1264

[3]

Synthesis and antioxidant, cytotoxicity and antimicrobial activities of novel curcumin mimics [J].

Bandgar, Babasaheb P. ;

Jalde, Shivkumar S. ;

Korbad, Balaji L. ;

Patil, Sachin A. ;

Chavan, Hemant V. ;

Kinkar, Santosh N. ;

Adsul, Laxman K. ;

Shringare, Sadanand N. ;

Nile, Shivraj H. .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2012, 27 (02) :267-274

[4]

Synthesis and Biological Evaluation of Orally Active Prodrugs of Indomethacin [J].

Bandgar, Babasaheb P. ;

Sarangdhar, Rajendra Janardan ;

Viswakarma, Santosh ;

Ahamed, Fakrudeen Ali .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (05) :1191-1201

[5]

Synthesis and anti-inflammatory activity of 1-acetyl-5-substitute daryl-3-(β-aminonapthyl)-2-pyrazolines and β-(substituted aminoethyl) amidonaphthalenes [J].

Bansal, E ;

Srivastava, VK ;

Kumar, A .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (01) :81-92

[6]

The role of oxidized lipoproteins in atherogenesis [J].

Berliner, JA ;

Heinecke, JW .

FREE RADICAL BIOLOGY AND MEDICINE, 1996, 20 (05) :707-727

[7]

ANTIOXIDANT DETERMINATIONS BY THE USE OF A STABLE FREE RADICAL [J].

BLOIS, MS .

NATURE, 1958, 181 (4617) :1199-1200

[8]

Synthesis and in vitro antitumor activity of new 4,5-dihydropyrazole derivatives [J].

Congiu, Cenzo ;

Onnis, Valentina ;

Vesci, Loredana ;

Castorina, Massimo ;

Pisano, Claudio .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (17) :6238-6248

[9]

Cyclooxygenase inhibitors - current status and future prospects [J].

Dannhardt, G ;

Kiefer, W .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (02) :109-126

[10]

Davies KJA, 1995, BIOCHEM SOC SYMP, P1, DOI 10.1042/bss0610001

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