Synthesis of novel 1-substituted triazole linked 1,2-benzothiazine 1,1-dioxido propenone derivatives as potent anti-inflammatory agents and inhibitors of monocyte-to-macrophage differentiation

Malla Reddy Gannarapu; Sathish Babu Vasamsetti; Nagender Punna; Srigiridhar Kotamraju; Narsaiah Banda

doi:10.1039/C5MD00171D

Synthesis of novel 1-substituted triazole linked 1,2-benzothiazine 1,1-dioxido propenone derivatives as potent anti-inflammatory agents and inhibitors of monocyte-to-macrophage differentiation

Malla Reddy Gannarapu,^a^b Sathish Babu Vasamsetti,^a^c Nagender Punna,^a^b Srigiridhar Kotamraju*^a^c and Narsaiah Banda*^a^b

Author affiliations

* Corresponding authors

^a Academy of Scientific and Innovative Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500607, India
E-mail: giridhar@iict.res.in, narsaiah@iict.res.in

^b Fluoroorganic Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500607, India

^c Centre for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500607, India

Abstract

A series of novel 1-substituted-triazole linked 1,2-benzothiazine 1,1-dioxido propenone derivatives 8a–s & 12a–l were prepared from 1-substituted 1,2,3-triazol-4-aldehydes 6 & 11 with N-methyl-3-acetyl-4-hydroxybenzothiazine-1,1-dioxide 7 by condensation. Final compounds 8 and 12 were evaluated for their anti-inflammatory activity and ability to inhibit monocyte-to-macrophage transformation, a process pivotal during the development and progression of atherosclerosis. Among all the compounds, 12e, 12g, 12i, 12j, 12k and 12l showed impressive anti-inflammatory activity against TNF-α, IL-1β and MCP-1 cytokines released in a dose-dependent manner. The most promising compounds 12g, 12i and 12l further significantly inhibited phorbol 12-myristate 13-acetate (PMA)-induced MMP-9 activity and PMA-induced monocyte-to-macrophage differentiation.

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The article was received on 22 Apr 2015, accepted on 11 Jun 2015 and first published on 12 Jun 2015

Article type: Concise Article

DOI: 10.1039/C5MD00171D

Author version available: Download Author version (PDF)

Citation: Med. Chem. Commun., 2015,6, 1494-1500

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Synthesis of novel 1-substituted triazole linked 1,2-benzothiazine 1,1-dioxido propenone derivatives as potent anti-inflammatory agents and inhibitors of monocyte-to-macrophage differentiation

M. R. Gannarapu, S. B. Vasamsetti, N. Punna, S. Kotamraju and N. Banda, Med. Chem. Commun., 2015, 6, 1494
DOI: 10.1039/C5MD00171D
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Synthesis of novel 1-substituted triazole linked 1,2-benzothiazine 1,1-dioxido propenone derivatives as potent anti-inflammatory agents and inhibitors of monocyte-to-macrophage differentiation

Abstract

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Synthesis of novel 1-substituted triazole linked 1,2-benzothiazine 1,1-dioxido propenone derivatives as potent anti-inflammatory agents and inhibitors of monocyte-to-macrophage differentiation

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