Structure-activity relationship studies of 4-benzyl-1H-pyrazol-3-yl β-d-glucopyranoside derivatives as potent and selective sodium glucose co-transporter 1 (SGLT1) inhibitors with therapeutic activity on postprandial hyperglycemia

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 22, 2012, Pages 6598-6612

  Fushimi, Nobuhiko ^a   Fujikura, Hideki ^a   Shiohara, Hiroaki ^a   Teranishi, Hirotaka ^a   Shimizu, Kazuo ^a   Yonekubo, Shigeru ^a   Ohno, Kohsuke ^a   Miyagi, Takashi ^a   Itoh, Fumiaki ^a   Shibazaki, Toshihide ^a   Tomae, Masaki ^a   Ishikawa Takemura, Yukiko ^a   Nakabayashi, Takeshi ^a   Kamada, Noboru ^a   Ozawa, Tomonaga ^a   Kobayashi, Susumu ^b   Isaji, Masayuki ^a  

^a KISSEI PHARMACEUTICAL CO LTD   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Diabetes; Postprandial hyperglycemia; SGLT1; SGLT1 inhibitor

Indexed keywords

4 (2 BENZYLOXYPHENYLMETHYL) 5 CYCLOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 BENZYLOXYPHENYLMETHYL) 5 ETHYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 BENZYLOXYPHENYLMETHYL) 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 BENZYLOXYPHENYLMETHYL) 5 METHYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 BENZYLOXYPHENYLMETHYL) 5 TERT BUTYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 BENZYLOXYPHENYLMETHYL) 5 TRIFLUOROMETHYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 CYANOPHENYLMETHYL) 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 ETHYLPHENYLMETHYL) 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 FLUOROPHENYLMETHYL) 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 METHOXYPHENYLMETHYL) 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 METHYLPHENYLMETHYL) 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 TRIFLUOROMETHYLPHENYLMETHYL) 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (2,4 DIMETHYLPHENYLMETHYL) 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (3 BENZYLOXYPHENYLMETHYL) 5 TRIFLUOROMETHYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (4 BENZYLOXYPHENYLMETHYL) 5 TRIFLUOROMETHYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (4 FLUOROPHENYLMETHYL) 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (4 HYDROXY 2 METHYLPHENYLMETHYL) 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 (4 METHYLPHENYLMETHYL) 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 BENZYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE DERIVATIVE; 4 BENZYL 5 ISOPROPYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 4 BENZYL 5 TRIFLUOROMETHYL 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 5 TRIFLUOROMETHYL 4 (2 HYDROXYPHENYLMETHYL) 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 5 TRIFLUOROMETHYL 4 (3 HYDROXYPHENYLMETHYL) 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; 5 TRIFLUOROMETHYL 4 (4 HYDROXYPHENYLMETHYL) 1H PYRAZOL 3 YL BETA DEXTRO GLUCOPYRANOSIDE; ANTIDIABETIC AGENT; GLUCOSE; PHENYL GROUP; PYRAZOLE DERIVATIVE; SODIUM GLUCOSE COTRANSPORTER 1 INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIDIABETIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DIABETES MELLITUS; DOSE RESPONSE; DRUG SYNTHESIS; GLUCOSE BLOOD LEVEL; HYPERGLYCEMIA; NONHUMAN; ORAL GLUCOSE TOLERANCE TEST; POSTPRANDIAL HYPERGLYCEMIA; RAT; STREPTOZOCIN DIABETES; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANIMALS; BLOOD GLUCOSE; CRYSTALLOGRAPHY, X-RAY; DIABETES MELLITUS, EXPERIMENTAL; GLUCOSIDES; HUMANS; HYPERGLYCEMIA; HYPOGLYCEMIC AGENTS; MOLECULAR CONFORMATION; RATS; SODIUM-GLUCOSE TRANSPORTER 1; SODIUM-GLUCOSE TRANSPORTER 2; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 84867847742     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.09.037     Document Type: Article

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