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

PHR1481

Supelco

Ethyl Acetate, Pharmaceutical Secondary Standard; Certified Reference Material

L092004

Sigma-Aldrich

Ethyl acetate

L092003

Sigma-Aldrich

Ethyl acetate

PHR1557

Supelco

Methylene Chloride, Pharmaceutical Secondary Standard; Certified Reference Material

1424109

USP

Methyl alcohol, United States Pharmacopeia (USP) Reference Standard

34856

Sigma-Aldrich

Dichloromethane, suitable for HPLC, ≥99.8%, contains amylene as stabilizer

650463

Sigma-Aldrich

Dichloromethane, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%, contains 50-150 ppm amylene as stabilizer

34858

Sigma-Aldrich

Ethyl acetate, suitable for HPLC, ≥99.7%

650528

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Ethyl acetate, HPLC Plus, for HPLC, GC, and residue analysis, 99.9%

439169

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Ethyl acetate, suitable for HPLC, ≥99.8%

676853

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

676810

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Ethyl acetate, ACS reagent, ≥99.5%

D65100

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Dichloromethane, contains 40-150 ppm amylene as stabilizer, ACS reagent, ≥99.5%

494453

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Dichloromethane, biotech. grade, 99.9%, contains 40-150 ppm amylene as stabilizer

494518

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Ethyl acetate, biotech. grade, ≥99.8%

319902

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Ethyl acetate, ACS reagent, ≥99.5%

320269

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Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

W241407

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Ethyl acetate, ≥99%, FCC, FG

W241415

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Ethyl acetate, natural, ≥99%, FCC, FG

431788

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Ethylenediaminetetraacetic acid, 99.995% trace metals basis

439223

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Dichloromethane, suitable for HPLC, ≥99.9%, contains 40-150 ppm amylene as stabilizer

03690

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Ethylenediaminetetraacetic acid disodium salt solution, BioUltra, pH 8.0, ~0.5 M in H₂O

03609

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Ethylenediaminetetraacetic acid, BioUltra, ≥99.0% (KT)

03620

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Ethylenediaminetetraacetic acid, ≥98.0% (KT)

02575

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Dichloromethane, analytical standard

66742

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Dichloromethane, Selectophore^™, ≥99.5%

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Ethylenediaminetetraacetic acid, BioUltra, anhydrous, ≥99% (titration)

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