Twelve compounds with a 1,5-diaryl-1-penten-3-one structure were synthesized and their cytotoxic activities were evaluated. The 1,5-diaryl-1-penten-3-one compounds were obtained via in situ enaminations of 4-phenyl-2-butanone and 4-(4-hydroxyphenyl)-2-butanone in the presence of pyrrolidine-AcOH, followed by condensation with six different benzaldehydes. The synthesized compounds were tested for their cytotoxic activity against human glioblastoma (U87-MG), breast (MCF-7), and prostate (PC-3) cancer cell lines.
View Article and Find Full Text PDFBackground: Oleanolic acid (OA) is a known natural compound with many important biological activities. Thirteen oleanolic acid derivatives linked at C-3 and C-28 were synthesized and their structures were confirmed by 1H- and 13C NMR and mass spectral analyses. Among them, compounds 4, 6, 8-10, 12, 13 were synthesized for the first time.
View Article and Find Full Text PDFFour multicaulin and miltirone-like phenanthrene derivatives were synthesised and evaluated as antituberculosis agents. The crucial step of the synthesis was Pschorr coupling of 4-(3-isopropyl-4-methoxyphenyl)-2-(2-aminophenyl)ethane (13) to give 2-isopropyl-3-methoxy-9,10-dihydrophenanthrene (9) and 4-isopropyl-3-methoxy-9,10-dihydrophenanthrene (9a). Compound 9 was converted to multicaulin and miltirone-like phenanthrene derivatives by further reactions.
View Article and Find Full Text PDFVicia sativa (common vetch), which contains β-cyanoalanine (BCA) and γ-glutamyl β-cyanoalanine (γGBCA) is used for adulteration of lentil and have neuro toxic effects on people and animals. Therefore the determination of BCA and γGBCA analytes in accurate and reliable manner has high importance for human and animal health. LC-IDMS/MS method has been developed and validated for quantitative analyses of β-cyanoalanine and C labeled BCA is used as an internal standard in γGBCA analysis.
View Article and Find Full Text PDFThe Wittig reaction of 3-isopropyl-4-methoxybenzaldehyde and 2,3-dimethylbenzylphosphonium bromide afforded the corresponding stilbene mixture 16. Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6-methoxy-1,2-dimethylphenanthrene, multicaulin (1). The O-demethylation of 1 with BBr3 afforded the 7-isopropyl-1,2-dimethylphenanthren-6-ol, O-demethylmulticaulin (2).
View Article and Find Full Text PDFPhotooxygenation of azidoalkyl furans has revealed both a novel triazole formation method and a unique endoperoxide rearrangement. The key step of this method is a 3 + 2 cycloaddion of the azide to the endoperoxide intermediate. The reduction of the peroxide bond and two subsequent C-C bond cleavages provide a triazole having a newly formed carboxylic acid functionality.
View Article and Find Full Text PDFSonchus erzincanicus (Asteraceae) is an endemic species in Turkey, where six Sonchus species grow. In this study, a phytochemical study was performed on the aerial parts of the plant. The study describes the isolation and structure elucidation of five flavonoids and two a-ionone glycosides from S.
View Article and Find Full Text PDFA new series of mono Mannich bases of 4'-hydroxychalcones 2a-e carrying a variety of aryl groups was synthesized and the in vitro cytotoxic activities of the new compounds were screened against PC-3 cell lines. Bioactivities of 2a-e, which are reported for the first time in this study, were compared against their precursor 4'-hydroxychalcones 1a-e. Compound 2b was found to be the most potent (IC(50 )= 3.
View Article and Find Full Text PDFPhotooxygenation of 1,4-cyclohexadiene afforded hydroperoxy endoperoxides 3 and 4 in a ratio of 88:12. Reduction of 3 with LiAlH(4) or thiourea followed by acetylation of the hydroxyl group and KMnO(4) oxidation of the double bond gave proto-quercitol 10b. Application of the same reaction sequences to 4 resulted in the formation of gala-quercitol 14.
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