title: Tandem allylic oxidation-condensation/esterification catalyzed by silica gel: an expeditious approach towards antimalarial diaryldienones and enones from natural methoxylated phenylpropenes.
abstract: A new one-pot strategy has been developed, wherein abundantly available methoxylated phenylpropenes are directly transformed into corresponding dienones (1,5-diarylpenta-2,4-dien-1-ones) and enones (chalcones and cinnamic esters) via allylic oxidation-condensation or allylic oxidation-esterification sequences. Preliminary antimalarial activity studies of the above synthesized diaryldienones and enones against Plasmodium falciparum (Pf3D7) have shown them to be promising lead candidates for developing newer and economical antimalarial agents. In particular, two enones (12b and 13b) were found to possess comparatively better activity (IC(50) = 4.0 and 3.4 μM, respectively) than licochalcone (IC(50) = 4.1 μM), a well known natural antimalarial compound.
authors.affiliation: Natural Plant Products Division, Institute of Himalayan Bioresource Technology, Council of Scientific and Industrial Research (C.S.I.R), Palampur (H.P.)-176061, India.
authors.forename: Abhishek
authors.initials: A
authors.lastname: Sharma
authors.forename: Naina
authors.initials: N
authors.lastname: Sharma
authors.forename: Amit
authors.initials: A
authors.lastname: Shard
authors.forename: Rakesh
authors.initials: R
authors.lastname: Kumar
authors.forename: Dinesh
authors.initials: D
authors.lastname: Mohanakrishnan
authors.lastname: Saima
authors.forename: Arun K
authors.initials: AK
authors.lastname: Sinha
authors.forename: Dinkar
authors.initials: D
authors.lastname: Sahal
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry; D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001685:Biological Factors / Q000737:chemistry*; D002384:Catalysis; D005782:Gels / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D021261:Parasitic Sensitivity Tests; D010963:Plasmodium falciparum / Q000187:drug effects*; D012822:Silicon Dioxide / Q000737:chemistry*; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D000962:Antimalarials; D001685:Biological Factors; D005782:Gels; D007659:Ketones; D013343:Styrenes; D012822:Silicon Dioxide; C505958:1-phenylpropene