Synthesis and antidiabetic activity of 3,6,7-trisubstituted-2-(1H-imidazol-2-ylsulfanyl)quinoxalines and quinoxalin-2-yl isothioureas.
Two series of 3,6,7-trisubstituted-2-(1H-imidazol-2-ylsulfanyl)-quinoxalines 2a-l and 2-(quinoxalin-2-yl)-isothioureas 3a-l were prepared. All the test compounds 2a-l and 3a-l were screened in vitro, in a RIN5F cell-based assay for glucose-dependent insulinotropic activity. A significant concentration and glucose-dependent insulin secretion effect was seen with compounds 2a-l and the insulinotropic activity of compound 2l was found to be identical to that of the standard compound (6,7-dichloro-2-trifluromethyl-3-(5-methyl-1,3,4-thiadiazo-2-ylsulfanyl)-quinoxaline (1)).
Bahekar
Rajesh H
RH
Zydus Research Centre, Cadila Healthcare Ltd., Moraiya, Ahmedabad, India. rajeshbahekar@zyduscadila.com
Jain
Mukul R
MR
Gupta
Arun A
AA
Goel
Ashish
A
Jadav
Pradip A
PA
Patel
Dipam N
DN
Prajapati
Vijay M
VM
Patel
Pankaj R
PR
D000818:Animals; D045744:Cell Line, Tumor; D004305:Dose-Response Relationship, Drug; D007004:Hypoglycemic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007328:Insulin / Q000378:metabolism*; D000078790:Insulin Secretion; D050417:Insulin-Secreting Cells / Q000187:drug effects / Q000378:metabolism; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013890:Thiourea / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D007004:Hypoglycemic Agents; D007093:Imidazoles; D007328:Insulin; D011810:Quinoxalines; D013450:Sulfones; D013890:Thiourea