Synthesis and biological evaluation of thiophene-C-glucosides as sodium-dependent glucose cotransporter 2 inhibitors.

Sakamaki, Shigeki; Kawanishi, Eiji; Koga, Yuichi; Yamamoto, Yasuo; Kuriyama, Chiaki; Matsushita, Yasuaki; Ueta, Kiichiro; Nomura, Sumihiro

Sakamaki, Shigeki; Kawanishi, Eiji; Koga, Yuichi; Yamamoto, Yasuo; Kuriyama, Chiaki; Matsushita, Yasuaki; Ueta, Kiichiro; Nomura, Sumihiro.

Affiliation

Sakamaki S; Medicinal Chemistry Research Laboratories, Mitsubishi Tanabe Pharma Corporation.

Chem Pharm Bull (Tokyo) ; 61(10): 1037-43, 2013.

Article in En | MEDLINE | ID: mdl-24088695

ABSTRACT

ABSTRACT

The synthesis and structure-activity relationship (SAR) of thiophene-C-glucosides have been explored, and the human sodium-dependent glucose cotransporter 2 (hSGLT2) inhibitory activities and rat urinary glucose excretion (UGE) effects of 3a-f were evaluated. As a result, they showed good hSGLT2 inhibitory activities and rat UGE effects. In particular, the chlorothiophene derivative 3f showed remarkable inhibitory activity against hSGLT2.

Subject(s)

Glucose/metabolism; Glucosides/chemistry; Hypoglycemic Agents/chemical synthesis; Sodium-Glucose Transporter 2 Inhibitors; Sorbitol/analogs & derivatives; Thiophenes/chemistry; Animals; Body Weight/drug effects; CHO Cells; Cricetinae; Cricetulus; Glucosides/chemical synthesis; Glucosides/pharmacology; Humans; Hypoglycemic Agents/chemistry; Hypoglycemic Agents/pharmacology; Male; Rats; Rats, Sprague-Dawley; Sodium-Glucose Transporter 2/metabolism; Sorbitol/chemical synthesis; Sorbitol/chemistry; Sorbitol/pharmacology; Structure-Activity Relationship

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Collection: 01-internacional Database: MEDLINE Main subject: Sorbitol / Thiophenes / Sodium-Glucose Transporter 2 Inhibitors / Glucose / Glucosides / Hypoglycemic Agents Limits: Animals / Humans / Male Language: En Journal: Chem Pharm Bull (Tokyo) Year: 2013 Document type: Article

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