Synthesis of 2-ethoxycarbonylthieno[2,3-b]quinolines in biomass-derived solvent γ-valerolactone and their biological evaluation against protein tyrosine phosphatase 1B

Xu-Yang Mu; Zhi-Jia Wang; Bo Feng; Lei Xu; Li-Xin Gao; Rajendran Satheeshkumar; Jia Li; Yu-Bo Zhou; Wen-Long Wang

doi:10.1039/D0RA09247A

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Synthesis of 2-ethoxycarbonylthieno[2,3-b]quinolines in biomass-derived solvent γ-valerolactone and their biological evaluation against protein tyrosine phosphatase 1B†

Xu-Yang Mu,‡^a Zhi-Jia Wang,‡^a Bo Feng,‡^a Lei Xu,^b Li-Xin Gao,^b Rajendran Satheeshkumar,

^ac Jia Li,^b Yu-Bo Zhou*^b and Wen-Long Wang

*^a

Author affiliations

* Corresponding authors

^a School of Pharmaceutical Sciences, Jiangnan University, Wuxi, China
E-mail: wwenlong2011@163.com

^b State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China
E-mail: ybzhou@simm.ac.cn

^c Departamento de Química Orgánica, Facultad de Química y de Farmacia, Pontificia Universidad Católica de Chile, Santiago de Chile, Chile

Abstract

A series of 2-ethoxycarbonylthieno[2,3-b]quinolines were synthesized in the bio-derived “green” solvent γ-valerolactone (GVL) and evaluated for their inhibitory activities against PTP1B, the representative compound 6a displayed an IC₅₀ value of 8.04 ± 0.71 μM with 4.34-fold preference over TCPTP. These results provided novel lead compounds for the design of inhibitors of PTP1B as well as other PTPs.

This article is part of the themed collection: Editors' Collection: Greener synthetic approaches towards quinoline derivatives

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DOI: https://doi.org/10.1039/D0RA09247A
Article type: Paper
Submitted: 30 Oct 2020
Accepted: 24 Dec 2020
First published: 14 Jan 2021
This article is Open Access

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RSC Adv., 2021,11, 3216-3220

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Synthesis of 2-ethoxycarbonylthieno[2,3-b]quinolines in biomass-derived solvent γ-valerolactone and their biological evaluation against protein tyrosine phosphatase 1B

X. Mu, Z. Wang, B. Feng, L. Xu, L. Gao, R. Satheeshkumar, J. Li, Y. Zhou and W. Wang, RSC Adv., 2021, 11, 3216 DOI: 10.1039/D0RA09247A

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Synthesis of 2-ethoxycarbonylthieno[2,3-b]quinolines in biomass-derived solvent γ-valerolactone and their biological evaluation against protein tyrosine phosphatase 1B†

Abstract

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Synthesis of 2-ethoxycarbonylthieno[2,3-b]quinolines in biomass-derived solvent γ-valerolactone and their biological evaluation against protein tyrosine phosphatase 1B

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