[Synthesis and alpha-glucosidase inhibitory activity of N-(1,5-diaryl-3-pentone-1-yl)-4-aminobenzoic acid].
In order to find highly active antidiabetic lead compound, sixteen 4-aminobenzoic acid derivatives were designed and synthesized directly through Mannich reaction in the solution of ethanol at 15-35 degrees C with facile method, mild reaction condition and high yield (45%-90%). Fifteen of them are new compounds. Their structures were confirmed by 1H NMR, 13C NMR, IR, ESI-MS and HR-MS. Alpha-glucosidase inhibitory activity of these compounds indicated that most of these compounds possess the activity with the order: 2c > 2b > 2h > 1a > 1f. The structure-activity relationship of these 4-aminobenzoic acid derivatives was also discussed.
School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
Jin
J
Xu
Ju-fang
JF
Yan
Li
L
Fan
Xiao-li
XL
Song
Xue-mei
XM
Tang
Da-cheng
DC
Yang
D010129:4-Aminobenzoic Acid / Q000138:chemical synthesis* / Q000494:pharmacology; D015195:Drug Design; D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D008352:Mannich Bases / Q000737:chemistry; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D000520:alpha-Glucosidases / Q000378:metabolism*; D062366:para-Aminobenzoates
D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents; D008352:Mannich Bases; D062366:para-Aminobenzoates; D000520:alpha-Glucosidases; D010129:4-Aminobenzoic Acid