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. 2010 Dec 13;2(2):182-7.
doi: 10.1021/ml100256c. eCollection 2011 Feb 10.

Synthesis and SAR of Thiazolylmethylphenyl Glucoside as Novel C-Aryl Glucoside SGLT2 Inhibitors

Kwang-Seop Song  1 , Suk Ho Lee  1 , Min Ju Kim  1 , Hee Jeong Seo  1 , Junwon Lee  1 , Sung-Han Lee  1 , Myung Eun Jung  1 , Eun-Jung Son  1 , MinWoo Lee  1 , Jeongmin Kim  1 , Jinhwa Lee  1
Affiliations

Synthesis and SAR of Thiazolylmethylphenyl Glucoside as Novel C-Aryl Glucoside SGLT2 Inhibitors

Kwang-Seop Song et al. ACS Med Chem Lett. .

Abstract

Novel C-aryl glucoside SGLT2 inhibitors containing the thiazole motif were designed and synthesized for biological evaluation. Among the compounds assayed, thiazole containing furanyl moiety 14v and thiophenyl moiety 14y demonstrated the best in vitro inhibitory activity against SGLT2 in this series to date (IC50 = 0.720 nM for 14v and IC50 = 0.772 nM for 14y). Both of these compounds have been further evaluated on a urinary glucose excretion test and the urine volumes excreted.

Keywords: SAR; SGLT2; Thiazole; diabetes; glucoside.

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Figures

Figure 1
Figure 1
Exploration of C-glucoside bearing thiazole at the distal ring.
Scheme 1
Scheme 1
Figure 2
Figure 2
Effects of dapagliflozin, compound 14y and 14v on urine glucose excretion and urine volume in normal Spraue−Dawley rats. All results are expressed as means ± SEM. The statistical analysis was performed by one-way ANOVA followed by Dunnett’s posthoc test. *P < 0.05 vs vehicle. **P < 0.01 vs vehicle.
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