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New Convenient Approach for the Synthesis of Benzyl 2H-Chromenones and their α-Amylase Inhibitory, ABTS.+ Scavenging Activities

[ Vol. 9 , Issue. 6 ]

Author(s):

Jaladi Ashok Kumar, Ashok Kumar Tiwari, Gannerla Saidachary, Domati Anand Kumar, Zehra Ali, Balasubramanian Sridhar and Bhimapaka China Raju   Pages 806 - 811 ( 6 )

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.

Keywords:

2H-Chromenones, Pechmann condensation, α-Amylase inhibition, ABTS.+ scavenging activity.

Affiliation:

Natural Products Chemistry Division, Medicinal Chemistry & Pharmacology Division, X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India.



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