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Design and synthesis of sulfonamide derivatives of pyrrolidine and piperidine as anti-diabetic agents.

Design and synthesis of sulfonamide derivatives of pyrrolidine and piperidine as anti-diabetic agents.

European journal of medicinal chemistry (2014-12-02)

Radhika Sharma, Shubhangi S Soman

ABSTRACT

Type 2 diabetes (T2D) is a lifestyle disease affecting millions of people worldwide. Various therapies are available for the management of T2D and dipeptidyl peptidase-IV (DPP-IV) inhibition has emerged as a promising therapy for the treatment of type 2 diabetes (T2D). Here we report design, synthesis and in vitro efficacy of sulfonamide derivatives of pyrrolidine and piperidine as anti-diabetic agents. Amongst all the compounds synthesized in this series, 9a, is the most potent (IC50 = 41.17 nM).

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Sodium sulfate, puriss., meets analytical specification of Ph. Eur., BP, USP, anhydrous, 99.0-100.5% (calc. to the dried substance)

Sigma-Aldrich

Potassium bromide, ReagentPlus^®, ≥99.0%

Sigma-Aldrich

Sodium sulfate, ReagentPlus^®, ≥99.0%

Supelco

Methanol, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

1,3-Propylene sulfite, 99%

Sigma-Aldrich

Methanol, LR, ≥99%

Sigma-Aldrich

Methanol, suitable for HPLC, ≥99.9%

Sigma-Aldrich

Methanol, suitable for NMR (reference standard)

Sigma-Aldrich

Dimethyl sulfoxide-d₆, 99.9 atom % D, contains 0.03 % (v/v) TMS

Sigma-Aldrich

Sodium sulfate, ≥99.99% trace metals basis

Sigma-Aldrich

Dimethyl sulfoxide-d₆, 99.9 atom % D, contains 1 % (v/v) TMS

Sigma-Aldrich

Dimethyl sulfoxide-d₆, "100%", 99.96 atom % D

Sigma-Aldrich

Dimethyl sulfoxide-d₆, anhydrous, 99.9 atom % D

Sigma-Aldrich

Sodium sulfate, BioXtra, ≥99.0%

Sigma-Aldrich

Sodium sulfate, ≥99.0%, suitable for plant cell culture

Sigma-Aldrich

Potassium bromide, BioXtra, ≥99.0%

Sigma-Aldrich

Methanol, low water for titration

Sigma-Aldrich

Dimethyl sulfoxide-d₆, "Special HOH", ≥99.9 atom % D

Sigma-Aldrich

Dimethyl sulfoxide-d₆, 99.9 atom % D

Sigma-Aldrich

Potassium bromide, anhydrous, powder, 99.95% trace metals basis

Sigma-Aldrich

Potassium bromide, anhydrous, powder, 99.999% trace metals basis

Sigma-Aldrich

Dimethyl sulfoxide-d₆, "100%", 99.96 atom % D

Sigma-Aldrich

Dimethyl sulfoxide-d₆, "100%", 99.96 atom % D

Sigma-Aldrich

Potassium bromide, BioUltra, ≥99.5% (AT)

Supelco

Methanol, analytical standard

Sigma-Aldrich

Dimethyl sulfoxide-d₆, 99.5 atom % D

Sigma-Aldrich

Dimethyl sulfoxide-d₆, 99.9 atom % D

Sigma-Aldrich

Sodium sulfate, tested according to Ph. Eur., anhydrous

Sigma-Aldrich

Sodium sulfate, BioUltra, anhydrous, ≥99.0% (T)

Sigma-Aldrich

Dimethyl sulfoxide-d₆, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS