Synthesis of pyridazine and thiazole analogs as SGLT2 inhibitors

Bioorganic & Medicinal Chemistry
Suk Youn KangJinhwa Lee

Abstract

With anticipation of the improvement in biological aspects in our SGLT2 program, novel pyridazinyl and thiazolyl analogs were designed and efficiently synthesized. The installation of the pyridazine ring at the anomeric carbon of d-glucopyranose was carried out in a stereoselective fashion. On the other hand, a series of thiazolyl analogs was also synthesized through a coupling reaction between perbenzyl gluconolactone 9 and 2-lithiothiazole. Biological activities of the compounds thus prepared were evaluated by the in vitro SGLT2 inhibition assay. Considering assay results, the novel benzylpyridazinyl and benzylthiazolyl analogs, disclosed in this article, could be a quick reference to prospective SGLT2 inhibitors useful for pharmacotherapy.

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Citations

Nov 29, 2011·Journal of Molecular Modeling·Chunlei TangWenlong Huang
Nov 5, 2016·The Journal of Organic Chemistry·Raffaele ColomboPeter Wipf
Apr 15, 2016·Journal of Computational Chemistry·Leighton Jones, Benjamin J Whitaker
Nov 20, 2014·Organic & Biomolecular Chemistry·Xin HuangShengming Ma
May 12, 2018·Future Medicinal Chemistry·Yajing ZhangDayong Zhang
Jan 12, 2013·SAR and QSAR in Environmental Research·V K VyasM Ghate
Jun 6, 2019·Topics in Current Chemistry·Aleksandra PałaszBartłomiej Bazan
Oct 31, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Michaël BoscoChristine Gravier-Pelletier
Feb 10, 2011·ACS Medicinal Chemistry Letters·Kwang-Seop SongJinhwa Lee
Aug 17, 2021·Tetrahedron Letters·Ernest G NolenDanielle M LaPaglia
Oct 30, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Indrapal Singh Aidhen, Naveenkumar Thoti

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