ABSTRACT
Chemical investigation on Caesalpinia crista afforded two new diterpenoids, 6beta-cinnamoyloxy-7beta-acetoxyvouacapen-5alpha-ol and 6beta,7beta-dibenzoyloxyvouacapen-5alpha-ol and on Caesalpiniapulcherrima another new diterpenoid, 12-demethyl neocaesalpin F along with several known constituents. The structures of the new compounds were settled from their 1D and 2D NMR spectral data. The cytotoxicity of these compounds was measured on two different cancer cell lines.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Caesalpinia/chemistry , Diterpenes/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/toxicity , Diterpenes/isolation & purification , Diterpenes/pharmacology , Diterpenes/toxicity , HL-60 Cells , HeLa Cells , Humans , Magnetic Resonance Spectroscopy , Molecular ConformationABSTRACT
A practical stereoselective synthesis of (6S)-5,6,dihydro-6-[(2R)-2-hydroxy-6-phenyl hexyl]-2H-pyran-2-one, a potent natural antifungal compound, is described. The sequence involves diastereoselective iodine-induced electrophilic cyclization, epoxide ring opening with a vinyl Grignard reagent and ring closing metathesis (RCM) as the key steps.
Subject(s)
Antifungal Agents/chemical synthesis , Epoxy Compounds/chemical synthesis , Structure-Activity Relationship , Antifungal Agents/pharmacology , Candidiasis/drug therapy , Catalysis , Cyclization , Drug Design , Epoxy Compounds/chemistry , Epoxy Compounds/pharmacology , Kinetics , Molecular Structure , Stereoisomerism , Tubulin Modulators/chemical synthesis , Tubulin Modulators/chemistryABSTRACT
Chemical investigation on the stems of Jatropha multifida resulted in the isolation of two new macrocyclic diterpenoids whose structures were established by extensive studies of their 1D and 2D-NMR spectra. The occurrence of ten other known compounds in this species is reported here for the first time.
Subject(s)
Diterpenes/chemistry , Jatropha/chemistry , Magnetic Resonance Spectroscopy , Plant Stems/chemistryABSTRACT
Silica supported phosphomolybdic acid, an eco-friendly heterogeneous catalyst, has been found to be highly efficient for Friedlander synthesis of quinolines in excellent yields. A variety of ketones afford the quinolines smoothly. The catalyst can be easily recovered and reused.
