Original Recyclization of S-Phenacyl Derivatives of 4-Acylamino-2-mercapto-1,3-oxazoles and Their Analogues.

ChemInform ◽  
2007 ◽  
Vol 38 (37) ◽  
Author(s):  
Andrei G. Balia ◽  
Aleksandr G. Belyuga ◽  
Vladimir S. Brovarets ◽  
Aleksandr N. Vasylenko ◽  
Aleksandr V. Turov ◽  
...  
Keyword(s):  
Phenacyl Derivatives ◽  
Derivatives Of

scholarly journals In Vitro Anti-Candida Activity and Action Mode of Benzoxazole Derivatives

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 5008
Author(s):  
Monika Staniszewska ◽  
Łukasz Kuryk ◽  
Aleksander Gryciuk ◽  
Joanna Kawalec ◽  
Marta Rogalska ◽  
...  
Keyword(s):  
Transport Process ◽  
Cross Resistance ◽  
Action Mechanism ◽  
Action Mode ◽  
Pleiotropic Action ◽  
Ergosterol Synthesis ◽  
Comparable Activity ◽  
Phenacyl Derivatives ◽  
Derivatives Of

A newly synthetized series of N-phenacyl derivatives of 2-mercaptobenzoxazole, including analogues of 5-bromo- and 5,7-dibromobenzoxazole, were screened against Candida strains and the action mechanism was evaluated. 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(4-bromophenyl)ethanone (5d), 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(2,3,4-trichloro-phenyl)ethanone (5i), 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(2,4,6-trichlorophenyl)ethanone (5k) and 2-[(5-bromo-1,3-benzoxazol-2-yl)sulfanyl]-1-phenylethanone (6a) showed anti-C. albicans SC5314 activity, where 5d displayed MICT = 16 µg/mL (%R = 100) and a weak anti-proliferative activity against the clinical strains: C. albicans resistant to azoles (Itr and Flu) and C. glabrata. Derivatives 5k and 6a displayed MICP = 16 µg/mL and %R = 64.2 ± 10.6, %R = 88.0 ± 9.7, respectively, against the C. albicans isolate. Derivative 5i was the most active against C. glabrata (%R = 53.0 ± 3.5 at 16 µg/mL). Benzoxazoles displayed no MIC against C. glabrata. Benzoxazoles showed a pleiotropic action mode: (1) the total sterols content was perturbed; (2) 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(3,4-dichlorophenyl)ethanol and 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(2,3,4-trichlorophenyl)ethanol (8h–i) at the lowest fungistatic conc. inhibited the efflux of the Rho123 tracker during the membrane transport process; (3) mitochondrial respiration was affected/inhibited by the benzoxazoles: 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(4-chlorophenyl)ethanol and 2-(1,3-benzoxazol-2-ylsulfanyl)-1-(4-bromophenyl)ethanol 8c–d and 8i. Benzoxazoles showed comparable activity to commercially available azoles due to (1) the interaction with exogenous ergosterol, (2) endogenous ergosterol synthesis blocking as well as (3) membrane permeabilizing properties typical of AmB. Benzoxazoles display a broad spectrum of anti-Candida activity and action mode towards the membrane without cross-resistance with AmB; furthermore, they are safe to mammals.

scholarly journals Phenacylation of 6-Methyl-Beta-Nitropyridin-2-Ones and Further Heterocyclization of Products

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1682
Author(s):  
Eugene V. Babaev ◽  
Victor B. Rybakov
Keyword(s):  
Pyridinium Salt ◽  
Phenacyl Bromides ◽  
Acidic Conditions ◽  
Phenacyl Derivatives ◽  
Derivatives Of

Reaction between the derivatives of 6-methyl-beta-nitropyridin-2-one and phenacyl bromides was studied, and the yields observed were extremely low. The pyridones were converted via chloropyridines to methoxyderivatives, which were N-phenacylated. N-Phenacyl derivatives of 4,6-dimethyl-5-nitropyridin-2-one under the action of base gave 5-hydroxy-8-nitroindolizine and under acidic conditions gave 5-methyl-6-nitrooxazole[3,2-a]pyridinium salt, which underwent recycization with MeONa to 5-methoxy-8-nitroindolizine.

Potential antidepressants: N-phenacyl derivatives of (E)-N-methyl-3-(6,11-dihydrodibenzo[b,e]thiepin-11-ylidene)propylamine

1988 ◽  
Vol 53 (4) ◽  
pp. 884-888 ◽  
Author(s):  
Zdeněk Polívka ◽  
Jiřina Metyšová ◽  
Martin Valchář ◽  
Miroslav Protiva
Keyword(s):  
Acute Toxicity ◽  
Potassium Carbonate ◽  
Induced Hypothermia ◽  
Activity Inhibition ◽  
The Common ◽  
Phenacyl Derivatives ◽  
Derivatives Of ◽  
Animal Tests

Reactions of (E)-N-methyl-3-(6,11-dihydrodibenzo[b,e]thiepin-11-ylidene)propylamine (V) with phenacyl chloride and 4-chlorophenacyl bromide in chloroform in the presence of sodium or potassium carbonate afforded the title compounds VI and VII. Their hydrochlorides showed very low acute toxicity in mice but in comparison with prothiadene (IV), they were less effective in the common animal tests used for assessing the thymoleptic activity (inhibition of reserpine-induced hypothermia and ptosis in mice, potentiation of yohimbine toxicity in mice, anticataleptic action in rats). These activity relations are in disagreement with those published for the analogous pair of 10,11-dihydrodibenz[b,f]azepine derivatives imipramine (I) and lofepramine (III).

One pot synthesis and conformation of N-t-butyloxycarbonyl, O-Phenacyl derivatives of proline and other secondary amino acids

Tetrahedron ◽  
1990 ◽  
Vol 46 (2) ◽  
pp. 565-576 ◽  
Author(s):  
John Hondrelis ◽  
Greg Lonergan ◽  
Stavros Voliotis ◽  
John Matsoukas
Keyword(s):  
Amino Acids ◽  
One Pot ◽  
One Pot Synthesis ◽  
Secondary Amino ◽  
Phenacyl Derivatives ◽  
Derivatives Of

scholarly journals Synthesis of substituted pyrrolo[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines in the one-pot condensation of 2-thio-6-aminouracil, arylglyoxals and CH-acids

2019 ◽  
Keyword(s):  
Acetoacetic Ester ◽  
Phenacyl Bromide ◽  
Unsaturated Ketone ◽  
Activity Profile ◽  
One Pot ◽  
Ch Acids ◽  
One Pot Condensation ◽  
The One ◽  
Phenacyl Derivatives ◽  
Derivatives Of

We have developed some available and effective methods for the synthesis of substituted pyrrolo[2,3-d]pyrimidines and 5,8-dihydropyrido[2,3-d]pyrimidines based on the three-component condensation of 6-amino-2-thiouracil with arylglyoxal hydrates and N,N-dimethylbarbituric acid or acyclic β-dicarbonyl compounds: acetylacetone (acetoacetic ester). It was shown that the optimal product yields were obtained by boiling the reagents in acetic acid. Thus, the synthesis of pyrrolo[2,3-d]pyrimidines took 15-20 minutes, while the precipitation of 5,8‑dihydropyrido[2,3-d]pyrimidines formed only after 2 hours. We proposed possible mechanisms for the formation of anelated pyrrole and pyridine rings. In both cases, the reaction includes the formation of an intermediate of α,β-unsaturated ketone with the participation of arylglyoxal and CH-acid (N,N-dimethylbarbituric or acetylacetone (acetoacetic ester)), nucleophilic addition of 6-aminothiouracil via an activated double bond, condensation of carbonyl and amino groups. The formation of the cycle takes place exclusively with the participation of the acetyl moiety, while the pyrrol one forms during the condensation of the aroyl moiety and the 6-amino group of thiouracil. A series of synthesized pyrrolo[2,3-d]pyrimidines was modified by alkylation. As it was expected, alkylation proceeds at the sulfur atom, that allowed a significant increase in the solubility of the obtained products. The reaction was carried out in DMF by stirring the initial reagents at 60ºC (reaction with methyl iodide) or boiling them (alkylation with phenacyl bromide), whereby S-methyl and S-phenacyl derivatives of pyrrolo[2,3-d]pyrimidines were obtained. The spectral data of 1H NMR showed that S-methylation products form solvates with DMF as 1:1. The synthesized compounds can become the basis to create small libraries of anelated pyrimidines with improved antiviral activity profile.

Original recyclization of S-phenacyl derivatives of 4-acylamino-2-mercapto-1,3-oxazoles and their analogues

2007 ◽  
Vol 18 (4) ◽  
pp. 432-437 ◽  
Author(s):  
Andrei G. Balia ◽  
Aleksandr G. Belyuga ◽  
Vladimir S. Brovarets ◽  
Aleksandr N. Vasylenko ◽  
Aleksandr V. Turov ◽  
...  
Keyword(s):  
Phenacyl Derivatives ◽  
Derivatives Of
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