Synthesis and bioactivity studies of 1-aryl-3-(2-hydroxyethylthio)-1-propanones

A series of Mannich bases having piperidine moiety were reacted with 2-mercaptoethanol, leading to 1-aryl-3-piperidine-4-yl-1-propanone hydrochlorides. The cytotoxicity and carbonic anhydrase inhibitory activities of these new compounds were evaluated. Among the compounds, only one derivative, nitro substituent bearing EU9, showed an effective cytotoxicity, although weak tumor specificity against human oral malignant versus nonmalignant cells. The compound induced apoptosis in HSC-2 oral squamous cell carcinoma cells, but not in human gingival fibroblast. Chemical modifications of this lead are thus necessary to further investigate it as a drug candidate and to obtain compounds with a better activity profile

Synthesis of 1-Aryl-3-phenethylamino-1-propanone Hydrochlorides as Possible Potent Cytotoxic Agents

1-Aryl-3-phenethylamino-1-propanone hydrochlorides 1-10, which are potentialpotent cytotoxic agents, were synthesized via Mannich reactions using paraformaldehyde,phenethylamine hydrochloride as the amine component and acetophenone, 4’-methyl-, 4’-methoxy-, 4’-chloro-, 4’-fluoro-, 4’-bromo-, 2’,4’-dichloro-, 4’-nitro-, 4’-hydroxyacetophenone or 2-acetylthiophene as the ketone component. Yields were in the87-98 % range. Of the compounds synthesized, compounds 2, 6-8 and 10 were new. Theoptimum reaction conditions were investigated by changing the mol ratios of the reactants,the solvents and the acidity levels using 1 and 10 as representative targets. It was observedthat the best mol ratio of the ketone, paraformaldehyde and phenethylamine hydrochloridewas 1:1.2:1 (compared with a 2:2.1 ratio), and the most suitable reaction medium wasethanol containing concentrated hydrochloric acid (compared with only ethanol or nosolvent). This study may serve as a guide for the conditions of the reactions to synthesizecompounds having similar chemical structures

Studies on the Synthesis and Reactivity of Novel Benzofuran-2-yl-[3-Methyl-3-Phenylcyclobutyl] Methanones and their Antimicrobial Activity

Preparation in excellent yields of cyclobutyl benzofuran-2-yl- and naphthofuran- 2-yl-ketones, the corresponding ketoximes and thiosemicarbazones, ether derivatives of the ketoximes and thiazoles derived from the thiosemicarbazones are described. Two of the synthesized compounds have been tested against eight different microorganisms and found to be active against some of the species studied

Some Bioactivities of Isolated Apigenin-7-O-glucoside and Luteolin-7-O-glucoside

In this study, we aimed to isolate compounds from Stachys lavandulifolia (Lamiaceae) by chromatographic methods and perform tyrosinase, acetylcholinesterase, butyrylcholinesterase enzyme-inhibition and antimicrobial activity studies of these compounds by in vitro methods. In addition, a molecular docking study was planned for the molecule with the highest effect. Two flavone glycosides, apigenin-7-O-glucoside and luteolin-7-O-glucoside, were isolated from S. lavandulifolia. Both compounds were observed to be effective against Enterococcus faecalis, Klebsiella pneumoniae, and Staphylococcus aureus. The compounds showed weak tyrosinase and butyrylcholine esterase inhibition, while only luteolin-7-O-glucoside showed a more significant inhibitory effect against acetylcholinesterase (65 ± 2%). Therefore, molecular interactions between acetylcholinesterase and luteolin-7-O-glucoside were evaluated. In the docking study, it was observed that the molecule was bound to the enzyme with a low amount of free binding energy (Glide score: −8.31). As a result, the antibacterial effect of apigenin-7-O-glucoside and both antibacterial and acetylcholinesterase-inhibitory effects of luteolin-7-O-glucoside were determined

Synthesis, Reactivity and Biological Activity of Novel Bisbenzofuran-2-yl-Methanone Derivatives

Preparation of bisbenzofuran-2-yl-methanone (1), the corresponding ketoxime 4, semicarbazone and thiosemicarbazone 3a and 3b, ether derivatives of the ketoximes 5a-j and the alcohol 2 are described. These substances have been prepared in excellent yields. All the synthesized compounds except 5i have been tested against five different microorganisms and some of them were found to be active against some of the species studied

Phenylpropanoids, Sesquiterpenoids And Flavonoids From Pimpinella Tragium Vill. Subsp Lithophila (Schischkin) Tutin

A new sesquiterpenoid named germacradiene-6-O-(6'-O-acetyl)-beta-D-glucoside (1) and a new flavonol glycoside named rhamnetin-3-O-(2 ''-O-beta-D-glucopyranosyl)-beta-D-galactopyranoside (2), along with three known sesquiterpenoids dictamnol (3), radicol (4), germacradiene glucoside (5); three phenylpropanoids 4-methoxy-2-(3-methyloxiranyl)-phenyl 2-methylbutanoate (6), 4-methoxy-2-(3-methyloxiranyl)-phenyl angelate (7), thellungianin E (8); and a flavonol glycoside platanoside (9) were isolated from the aerial parts of Pimpinella tragium Vill. subsp. lithophila (Schischkin) Tutin. Their structures were elucidated by detailed analyses of 1D and 2D NMR, UV, IR and HR-ESI-MS data.Wo