title: New convenient approach for the synthesis of benzyl 2H-chromenones and their α-amylase Inhibitory, ABTS.+ scavenging activities.
abstract: Series of new benzyl 2H-chromenones 6a-n was synthesized by Pechmann condensation of substituted benzyl resorcinols 2a-c and 3a with various β-ketoesters such as ethyl 3-oxobutanoate, ethyl 3-oxo-3-phenylpropanoate, ethyl 4- chloro-3-oxobutanoate, ethyl 4,4,4-trifluoro-3-oxobutanoate and ethyl 2-chloro-3-oxobutanoate 5a-e in very good yields. Synthesized compounds 6a-n were screened for their α-amylase inhibitory, and ABTS.+ scavenging activities. In the present series of compounds, compound 8-benzyl-7-hydroxy-4-phenyl-2H-chromen-2-one 6c and 8-benzyl-7-hydroxy-4- methyl-2H-chromen-2-one 6a were most potent ABTS.+ radical scavenging and α-amylase inhibitor. Although compound 6,8-dibenzyl-7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one 6h displayed potent ABTS.+ free radical scavenging potential, it was found poor in inhibiting pancreatic α-amylase.
authors.affiliation: Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India.
authors.forename: Jaladi Ashok
authors.initials: JA
authors.lastname: Kumar
authors.forename: Ashok Kumar
authors.initials: AK
authors.lastname: Tiwari
authors.forename: Gannerla
authors.initials: G
authors.lastname: Saidachary
authors.forename: Domati Anand
authors.initials: DA
authors.lastname: Kumar
authors.forename: Zehra
authors.initials: Z
authors.lastname: Ali
authors.forename: Balasubramanian
authors.initials: B
authors.lastname: Sridhar
authors.forename: Bhimapaka China
authors.initials: BC
authors.lastname: Raju
mesh_terms: D052160:Benzothiazoles / Q000737:chemistry*; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D010179:Pancreas / Q000187:drug effects / Q000201:enzymology; D013451:Sulfonic Acids / Q000737:chemistry*; D000516:alpha-Amylases / Q000037:antagonists & inhibitors* / Q000737:chemistry
chemical_list: C587036:8-benzyl-7-hydroxy-4-methyl-2H-chromen-2-one; C587035:8-benzyl-7-hydroxy-4-phenyl-2H-chromen-2-one; D052160:Benzothiazoles; D003374:Coumarins; D016166:Free Radical Scavengers; D013451:Sulfonic Acids; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C030123:coumarin; D000516:alpha-Amylases