ABSTRACT
A series of dibenzyl-γ-butyrolactones bearing a hydroxyl group at the benzylic position of 3-benzyl group were synthesized as hydrated analogue of isochaihulactone and evaluated against breast cancer human cell lines (MDA-M231, MCF-7 and T47D). The target compounds were synthesized in 7 steps from known lactone; (S)-(+)-γ-benzyloxymethyl-γ-butyrolactone. The key step was the aldol condensation between (+)-(R)-ß-(benzo[d][1,3]dioxol-5-ylmethyl)-γ-butyrolactone and substituted benzaldehydes which afforded corresponding α-hydroxybenzyl butyrolactone analogues. The cytotoxic study of the synthesized compounds against breast cancer human cell lines showed that some of them inhibit breast cancer human cell proliferation with percentage inhibitions over 50% at concentrations less than 50 µg/mL.
Subject(s)
4-Butyrolactone/analogs & derivatives , Antitubercular Agents/pharmacology , Benzodioxoles/pharmacology , 4-Butyrolactone/chemical synthesis , 4-Butyrolactone/chemistry , 4-Butyrolactone/pharmacology , Antitubercular Agents/chemical synthesis , Antitubercular Agents/chemistry , Benzodioxoles/chemical synthesis , Benzodioxoles/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Stereoisomerism , Structure-Activity RelationshipABSTRACT
In the present paper, twelve chromenes were synthesized by coupling of 2,2,8,8-tetramethyl-8H-pyrano[2,3-f]chroman-4-one 1 with various aryl and benzylmagnesium chlorides. The synthetic compounds were examined for in-vitro activity against Leishmania major, and some of them displayed efficient anti-leishmanial activity. Among the compounds tested, compounds 9 (4-(2-chloro-benzylidene)-2,2,8,8-tetramethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromene 9a and 4-(2-chloro-benzyl)-2,2,8,8-tetramethyl-2H,8H-pyrano[2,3-f]chromene 9b) were the most active with an inhibitory activity of 73.4%.
Subject(s)
Antiprotozoal Agents/chemical synthesis , Benzopyrans/chemical synthesis , Leishmania/drug effects , Animals , Antiprotozoal Agents/pharmacology , Benzopyrans/pharmacology , Drug Screening Assays, Antitumor , Structure-Activity RelationshipABSTRACT
The racemate of (Z)-exo-alpha-bergamotenal, a sex pheromone component of the white-spotted spined bug, was synthesized from racemic exo-alpha-bergamotene by a five-step sequence involving regioselective epoxidation and (Z)-selective Wittig olefination reactions. The 1H- and 13C-NMR spectra of the synthetic sample were identical with those of the natural material.
Subject(s)
Insecta/chemistry , Pentanols/chemical synthesis , Sesquiterpenes/chemical synthesis , Sex Attractants/chemical synthesis , Animals , Magnetic Resonance Spectroscopy , Molecular Structure , Pentanols/chemistry , Sesquiterpenes/chemistry , Sex Attractants/chemistry , Spectrophotometry, InfraredABSTRACT
A series of N-substituted aryl and alkyl carbamates (RNHCOOR'; R: aryl, alkyl; R': aryl, alkyl) was prepared and screened for inhibitory activity toward the germination of oat seeds. The activity of each compound was compared with that of chlorpropham (isopropyl 3-chlorocarbanilate). Some of the synthetic carbamates possessing the N-(phenylthio)methyl group, PhSCH2NHCOOR', showed inhibitory activity close or comparable to that of chlorpropham.
