Synthesis and antifungal activity of a series of novel 1,2-disubstituted propenones

Abstract

To find an antifungal agent other than those of the imidazole and triazole series, a new class of 1,2-disubstituted propenones I and II was prepared and tested for antifungal activity. Comparison of the structure-activity relationships showed that the conjugated structure of carbonyl and exomethylene groups in I and II plays an important role in potent antifungal activity. However, it is noteworthy that compounds 53, 54, and 56, which have a hydroxymethyl or methoxymethyl group instead of an exo-methylene group in I, also showed potent activity. Although many compounds exhibited strong antifungal activity in vitro, none showed activity in vivo of oral efficacy against subacute systemic candidiasis in mice.

Synthesis and biological evaluation of 2-amino-1-thiazolyl imidazoles as orally active anticancer agents

“…2-Bromoacetophenone and amidinothiourea mixed in ethanol were condensed to provide benzyl guanidine 1 in 87% yield [25]. 2-Bromo-1-(thiophen-2-yl) ethanone was synthesized from the bromination of 1-(thiophen-2-yl)ethanone according to the previously reported procedure [26]. Subsequently, cyclization reaction of benzyl guanidine 1 and 2-bromo-1-(thiophen-2-yl)ethanone was conducted by refluxing the reaction mixtures at 80°C to afford 2-amino-1-thiazolyl imidazole 2 in 62% yield [27].…”

QSAR and Docking Studies on Propenone Derivatives as Dual COX and 5- LOX Inhibitors

“…This attempt has been made by several researchers [7][8][9]. Earlier studies have reported the use of propenone compounds such as 1-furan-2-yl-3-pyridin-2-yl-propenone (FPP-3) for inflammatory disorders [10], and 1, 2-disubstituted propanones as antifungal agents [11]. The wide range of biological activities of 1,3-diphenyl-2-propen-1-one derivatives has been studied by other researchers [12].…”

New heterocycles with cycloamidine substructure and their ringtransformation reactions with acetylene dicarboxylic ester

“…The intermediate adduct 9 extruded nitrogen to form the 2-pyridone 10. These types of pyridones are difficult to obtain by other methods and are of interest for their biological activity [6].…”