N-heterocyclic derivatives of 2,4-dihydroxybenzcarbothioamide as antimycotic agents
J Matysiak1, E Krajewska-Kułak, J Karczewski
1Department of Chemistry, University of Agriculture, Akademicka 15, 20-950 Lublin, Poland. jmaty@agros.ar.lublin.pl
Abstract:
N-heterocyclic derivatives of 2,4-dihydroxybenzcarbothioamide were synthesized from sulfinylbis(2,4-dihydroxybenzenethioyl) and commercially available heterocyclic amines. The composition and chemical structures were confirmed by IR, (1)H NMR, EI-MS, and elemental analysis. For the estimation of potential activity in vitro the MIC values against 15 strains of dermatophytes, yeasts, and molds were determined. The strongest fungistatic potency was found for N-5'-(3'-oxobenzfurylidyne)-2,4-dihydroxybenzcarbothioamide in relation to all tested dermatophyte strains with MIC = 0.48-0.98 microg/mL. On the basis of the spectroscopic data the influence of N-heterocyclic substitution on antimycotic activity is discussed.
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Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

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