115846-97-4Relevant articles and documents
Alkylation of 6-C(O)R-7-aryl-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidines
Kolosov, Maksim A.,Shvets, Elena H.,Kulyk, Olesia G.,Orlov, Valeriy D.
, p. 1052 - 1056 (2015)
Alkylation of 6-C(O)R-7-aryl-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidines with methyl iodide or ethyl bromide in either saturated aqueous KOH–MeCN or NaH–DMF led to the formation of N4-alkyl derivatives in good yields (60–98%). Reactivity of the acetyl group of N4-alkyl derivatives towards aromatic aldehydes under the conditions of the Claisen–Schmidt reaction was significantly higher than in 4-unsubstituted compounds. The starting 6-C(O)R-7-aryl-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidines were synthesized via a three-component condensation of an aromatic aldehyde, 3-amino-1,2,4-triazole, and a dicarbonyl compound (2,4-pentanedione or ethyl acetoacetate) in DMF.
Antibacterials and antimycotics: Part 1: Synthesis and activity of 2- pyrazoline derivatives
Nauduri, Dhananjaya,Reddy, Gopu Bala Show
, p. 1254 - 1260 (1998)
A series of 3-styryl-1,5-diphenyl and 5-styryl-1,3-diphenyl 2- pyrazolines of different substitutions has been synthesized by condensation of substituted α,β-unsaturated ketones with phenylhydrazine hydrochloride in presence of catalytic amount of concentrated HCl. Compounds in the 3- styryl series had OMe, NMe2, NO2, OH and isopropyl substituents and those in the 5-styryl series had OMe, NMe2 and NO(s). The 3-styryl-1,5-diphenyl compounds showed little variation in antibacterial activity towards gram- positive and gram-negative bacteria in terms of geometric mean minimum inhibitory concentrations (MIC). The 4',4-NMe2, 4',4-NO2 and 4',4-OMe compounds were found to possess the highest activity in the series. The 5- styryl-1,3-diphenyl series showed lower activities than the 3-styryl series. The in vitro antimycotic activity of the 4',4-OH and 2',2-OH substituted compounds showed good activity than the other molecules in the two series.
Gram-scale preparation of dialkylideneacetones through Ca(OH)2-catalyzed Claisen-Schmidt condensation in dilute aqueous EtOH
Zhang, Hao,Han, Mengting,Yang, Chenggen,Yu, Lei,Xu, Qing
, (2018/02/06)
A synthetic method of dialkylideneacetones has been developed. Compared with known protocols, the method employed catalytic Ca(OH)2 as the cheap, mild base catalyst and dilute aqueous EtOH (20%, v/v) as the green and safe solvent. The procedure was easily operated: In most cases, the product could be isolated by a simple filtration, and purified by washing with water. This paper provided experimental details of the reactions, which could be applied in gram-scale synthesis and should be a very reliable and practical protocol to prepare these useful compounds in laboratory and at the industrial level.
Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids
Roman, Bart I.,De Ryck, Tine,Verhasselt, Sigrid,Bracke, Marc E.,Stevens, Christian V.
, p. 1027 - 1031 (2015/02/19)
In our ongoing search for new anti-invasive chemotypes, we have made an excursion from previously reported potent 1,3-diarylpropenones (chalcones) to congeners bearing longer linkers between the aromatic moieties. Nine 1,ω-diarylalkenones, including curcumin and bisdemethoxycurcumin, were evaluated in the chick heart invasion assay. Unfortunately, these compounds proved less potent and more toxic than earlier evaluated chemotypes. In the 1,3-diarylpenta-2,4-dien-1-one series, fluoro and/or trimethoxy substitution caused an increase in potency. This agrees with observations made earlier for the chalcone class.
