Synthesis and bioevaluation of glycosyl ureas as alpha-glucosidase inhibitors and their effect on mycobacterium.
Glycosyl amino esters (2-13) on reaction with different isocyanates resulted in quantitative conversion to glycosyl ureas (14--32). Few of the selected ureas (15-20, 22-28, 30 and 32) on cyclative amidation with DBU/TBAB/4 A MS gave respective dihydropyrimidinones in fair to good yields (33-47). The compounds were screened for alpha-glucosidase inhibitory activity and two (19 and 23) of them showed strong inhibition against rat intestinal alpha-glucosidase. The compounds were also screened against Mycobacterium aurum, however, only one (19) of them exhibited marginal antitubercular activity.
Tewari
Neetu
N
Division of Medicinal Chemistry, Central Drug Research Institute, Lucknow-226001, India.
Tiwari
V K
VK
Mishra
R C
RC
Tripathi
R P
RP
Srivastava
A K
AK
Ahmad
R
R
Srivastava
R
R
Srivastava
B S
BS
D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D065089:Glycoside Hydrolase Inhibitors; D006031:Glycosylation; D007422:Intestines / Q000201:enzymology; D009161:Mycobacterium / Q000187:drug effects*; D018583:Pliability; D011744:Pyrimidinones / Q000138:chemical synthesis / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D000995:Antitubercular Agents; D065089:Glycoside Hydrolase Inhibitors; D011744:Pyrimidinones; D014508:Urea