title: Stereoselective synthesis of alpinoid-C and its analogues and study of their cytotoxic activity against cancer cell lines.
abstract: A simple, highly efficient and stereoselective synthetic route has been developed for synthesis of alpinoid-C (1) and its analogues (2, 3 and 4) from commercially available starting materials by using Wittig olefination, Sharpless asymmetric epoxidation, Grubbs cross metathesis as key steps. All the compounds showed moderate anti-proliferative activity against human leukemia/carcinoma (U-937, THP-1, COLO-205 and HepG2) and mouse melanoma (B16-F10) cancer cell lines. Compounds 3 and 4 are found to be most potent with an IC(50) of 7.53 μM and 32.26 μM on THP-1, 11.12 μM and 7.21 μM on COLO-205 cell lines, respectively.
authors.affiliation: Division of Natural Products Chemistry, IICT, Hyderabad 500 007, India.
authors.forename: S
authors.initials: S
authors.lastname: Purushotham Reddy
authors.forename: B
authors.initials: B
authors.lastname: Chinnababu
authors.forename: V
authors.initials: V
authors.lastname: Shekhar
authors.forename: D
authors.initials: D
authors.lastname: Kumar Reddy
authors.forename: G V S
authors.initials: GV
authors.lastname: Bhanuprakash
authors.forename: L R
authors.initials: LR
authors.lastname: Velatoor
authors.forename: J
authors.initials: J
authors.lastname: Venkateswara Rao
authors.forename: Y
authors.initials: Y
authors.lastname: Venkateswarlu
mesh_terms: D032429:Alpinia / Q000737:chemistry*; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D036381:Diarylheptanoids / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D051379:Mice; D010980:Platelet Membrane Glycoproteins / Q000037:antagonists & inhibitors*; D043562:Receptors, G-Protein-Coupled / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D036381:Diarylheptanoids; D010980:Platelet Membrane Glycoproteins; D043562:Receptors, G-Protein-Coupled; C575107:alpinoid-C; C039351:platelet activating factor receptor