title: Synthesis of (+/-)Abyssinone I and related compounds: Their anti-oxidant and cytotoxic activities.
abstract: 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.
authors.affiliation: Vittal Mallya Scientific Research Foundation, P.B. No. 406, K.R. Road, Bangalore 560004, India.
authors.forename: Gudapati Venkateswara
authors.initials: GV
authors.lastname: Rao
authors.forename: Badrappa Narayana
authors.initials: BN
authors.lastname: Swamy
authors.forename: Venkateshappa
authors.initials: V
authors.lastname: Chandregowda
authors.forename: G Chandrasekara
authors.initials: GC
authors.lastname: Reddy
mesh_terms: 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
chemical_list: D000098:Acetophenones; D000447:Aldehydes; D000970:Antineoplastic Agents; D000975:Antioxidants; D047188:Chalcones; D005419:Flavonoids; D012118:Resorcinols; C541239:abyssinone I; C412963:resacetophenone