Synthesis and biological evaluation of some stilbene-based analogues

The phytoalexin 3,5,4′-trihydroxy- trans -stilbene (resveratrol) has attracted considerable attention from biologists and chemists due to its diverse biological properties. Owing to the biological importance of this compound, we have synthesized new stilbene-based analogues by using substituted benz...

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Bibliographic Details
Published in:Medicinal chemistry research 2011-11, Vol.20 (8), p.1158-1163
Main Authors: Karki, Subhas S., Bhutle, Santosh R., Pedgaonkar, Ganesh S., Zubaidha, P. K., Shaikh, Rizwan M., Rajput, Chitra G., Shendarkar, Girish S.
Format: Article
Language:English
Subjects:
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Original Research
Pharmacology/Toxicology
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Summary:The phytoalexin 3,5,4′-trihydroxy- trans -stilbene (resveratrol) has attracted considerable attention from biologists and chemists due to its diverse biological properties. Owing to the biological importance of this compound, we have synthesized new stilbene-based analogues by using substituted benzyl chlorides and substituted aldehydes in a two-step reaction and evaluated their in vitro antioxidant, antibacterial and antifungal potential. Most of the compounds displayed moderate to significant radical scavenging activity. ( E )-1-(3,4-difluorophenyl)-2-(4-fluorophenyl)ethene ( 4c ) showed nearer equipotent antibacterial activity against Staphylococcus aureus. ( E )-1,2-bis(4-fluorophenyl)ethene ( 4a ), ( E )-1-(3-fluorophenyl)-2-(4-fluorophenyl)ethene ( 4b ), ( E )-1-(2,4-dichlorophenyl)-2-(3,4-dichlorophenyl)ethene ( 4f ), ( E )-1-(2,4-dichlorophenyl)-2-(3-chlorophenyl)ethene ( 4g ), ( E )-1-(2,4-dichlorophenyl)-2-(4-fluorophenyl)ethene ( 4j ) ( E )-1-(4-fluorophenyl)-2-(3-chlorophenyl)ethene ( 4l ) and ( E )-1-(4-chlorophenyl)-2-(4-fluorophenyl)ethene ( 4n ) inhibited the growth of Penicillium chrysogenum.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-010-9450-y