An efficient green synthesis of 2-arylbenzothiazole analogues as potent antibacterial and anticancer agents

被引：41

作者：

Chhabra, Mohit ^{[1
]}

Sinha, Sohini ^{[1
]}

Banerjee, Swagata ^{[1
]}

Paira, Priyankar ^{[1
]}

机构：

[1] VIT Univ, Pharmaceut Chem Div, Sch Adv Sci, Vellore 632014, Tamil Nadu, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2016年 / 26卷 / 01期

关键词：

2-Arylbenzothiazole; Green chemistry; Amberlite IR-120; Antibacterial agents; Anticancer agents; SOLVENT-FREE SYNTHESIS; METAL-FREE SYNTHESIS; BENZOTHIAZOLES; CONDENSATION; 2-ARYL; BENZIMIDAZOLES; DERIVATIVES;

D O I：

10.1016/j.bmcl.2015.10.087

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

We have demonstrated a novel and green approach for the synthesis of 2-substituted benzothiazole analogues. A number of 2-aryl and heteroaryl benzothiazole scaffolds were synthesized using Amberlite IR-120 resin under microwave irradiation. The catalytic role and reusability of the resin was well established here. 2-Substituted benzothiazole analogues (3a-l) were also tested against several bacterial strains (Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Salmonella) and cancer cell lines (MCF-7 and HeLa). The stability of compound 2-phenyl benzothiazole (3a) and 2-pyridin-2-yl-benzothiazole (3k) in GSH (0.01 mM dissolved in DMSO) was measured by UV-Vis spectroscopy. Compound 3k also shows remarkable fluorescence in MeOH. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：213 / 217

页数：5

共 48 条

[1] Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648) [J].

Aiello, Stefania ;

Wells, Geoffrey ;

Stone, Erica L. ;

Kadri, Hachemi ;

Bazzi, Rana ;

Bell, David R. ;

Stevens, Malcolm F. G. ;

Matthews, Charles S. ;

Bradshaw, Tracey D. ;

Westwell, Andrew D. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (16) :5135-5139

[2]

Amsterdam D., 1996, ANTIBIOTICS LAB MED, V4th, P52

[3] Elucidation of thioredoxin as a molecular target for antitumor quinols [J].

Bradshaw, TD ;

Matthews, CS ;

Cookson, J ;

Chew, EH ;

Shah, M ;

Bailey, K ;

Monks, A ;

Harris, E ;

Westwell, AD ;

Wells, G ;

Laughton, CA ;

Stevens, MFG .

CANCER RESEARCH, 2005, 65 (09) :3911-3919

[4] ANTIMALARIALS .3. BENZOTHIAZOLE AMINO ALCOHOLS [J].

BURGER, A ;

SAWHNEY, SN .

JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (02) :270-&

[5] Aerobic Visible-Light Photoredox Radical C-H Functionalization: Catalytic Synthesis of 2-Substituted Benzothiazoles [J].

Cheng, Yannan ;

Yang, Jun ;

Qu, Yue ;

Li, Pixu .

ORGANIC LETTERS, 2012, 14 (01) :98-101

[6] Benzothiazole Aniline Tetra(ethylene glycol) and 3-Amino-1,2,4-triazole Inhibit Neuroprotection against Amyloid Peptides by Catalase Overexpression in Vitro [J].

Chilumuri, Amrutha ;

Odell, Mark ;

Milton, Nathaniel G. N. .

ACS CHEMICAL NEUROSCIENCE, 2013, 4 (11) :1501-1512

[7]

Cuenca J. L., 2009, LIFE SCI, V84, P125

[8] Metal-Free Synthesis of 2-Substituted (N, O, C) Benzothiazoles via an Intramolecular C-S Bond Formation [J].

Feng, Enguang ;

Huang, He ;

Zhou, Yu ;

Ye, Deju ;

Jiang, Hualiang ;

Liu, Hong .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (04) :422-429

[9]

Gupta S., 2010, INT J PHARM PHARM SC, V2, P57

[10] Iodine-catalyzed, one-pot, solid-phase synthesis of benzothiazole derivatives [J].

Gupta, Sayan Dutta ;

Singh, Hemendra Pratap ;

Moorthy, N. S. H. N. .

SYNTHETIC COMMUNICATIONS, 2007, 37 (22-24) :4327-4329

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