Synthesis of (+/-)Abyssinone I and related compounds: Their anti-oxidant and cytotoxic activities.
An efficient and facile synthesis of naturally occurring prenylated flavonoids and their analogs have been described. Abyssinone I (9a) was prepared by condensing 2,2-dimethyl chrom-3-en-6-carboxaldehyde (5a) with protected resacetophenone under phase transfer conditions followed by deprotection and cyclization. The influence of prenyl group on anti-oxidant and cytotoxic activities was studied. The presence of 3'-prenyl group as in 8c enhanced radical scavenging activity but decreased reducing power activity when compared to non-prenylated analog 8f. In vitro testing in MCF-7 cell line revealed that prenylated chalcones and flavanones showed better inhibitory activity than their non-prenylated counterparts. Abyssinone I and its chalcone though exhibited negligible anti-oxidant activity their cytotoxic activities were comparable with other prenylated analogs.
Rao
Gudapati Venkateswara
GV
Vittal Mallya Scientific Research Foundation, P.B. No. 406, K.R. Road, Bangalore 560004, India.
Swamy
Badrappa Narayana
BN
Chandregowda
Venkateshappa
V
Reddy
G Chandrasekara
GC
D000098:Acetophenones / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D047188:Chalcones; D005419:Flavonoids / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D054876:Prenylation; D012118:Resorcinols / Q000737:chemistry; D013329:Structure-Activity Relationship
D000098:Acetophenones; D000447:Aldehydes; D000970:Antineoplastic Agents; D000975:Antioxidants; D047188:Chalcones; D005419:Flavonoids; D012118:Resorcinols; C541239:abyssinone I; C412963:resacetophenone