Syntheses and biological activities of chalcone and 1,5-benzothiazepine derivatives: promising new free-radical scavengers, and esterase, urease, and alpha-glucosidase inhibitors.
A series of 2,4-diaryl-2,3,4,5-tetrahydro- (36-40) and 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines (25-35) have been synthesized from the corresponding chalcones 1-24. Both the benzothiazepines and chalcones were evaluated as DPPH free-radical scavengers and as inhibitors of cholinesterases, urease, and alpha-glucosidase. Compounds 2, 5, 6, 7, 10, 13, 18, 21, 36a, 37a, 37b, and 39a showed significant cholinesterase inhibiting activities. Among the 15 dihydro-1,5-benzothiazepines, 26, 32, and 35 exhibited significant radical-scavenging activities; and six tetrahydro-1,5-benzothiazepines (35, 36a, 36b, 37a, 37b, and 39a) were found to be inhibitors of AChE and BChE. Compounds 22, 25, 26, 33, 35, 36a, 37b, and 39a inhibited urease, and 25 and 27-31 were found to be potent inhibitors of alpha-glucosidase.
Ansari
Farzana L
FL
Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan. fla_qau@yahoo.com
Umbreen
Sumaira
S
Hussain
Latif
L
Makhmoor
Talat
T
Nawaz
Sarfraz A
SA
Lodhi
Muhammad A
MA
Khan
Shamsun N
SN
Shaheen
Farzana
F
Choudhary
Muhammad I
MI
D002091:Butyrylcholinesterase / Q000378:metabolism; D047188:Chalcones / Q000737:chemistry* / Q000494:pharmacology; D002800:Cholinesterase Inhibitors / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry*; D065089:Glycoside Hydrolase Inhibitors; D015394:Molecular Structure; D013841:Thiazepines / Q000737:chemistry* / Q000494:pharmacology; D014510:Urease / Q000037:antagonists & inhibitors*
C106746:1,5-benzothiazepine; D047188:Chalcones; D002800:Cholinesterase Inhibitors; D016166:Free Radical Scavengers; D065089:Glycoside Hydrolase Inhibitors; D013841:Thiazepines; D002091:Butyrylcholinesterase; D014510:Urease