Synthesis and In Vitro Antimicrobial Evaluation of 4-alkyl/aryl-1-(3-phenoxypropionyl)-thiosemicarbazides

Author(s): Monika Wujec, Agata Siwek, Edyta Kusmierz, Joanna Stefanska.

Journal Name: Letters in Drug Design & Discovery

Volume 7 , Issue 10 , 2010

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Abstract:

Eight new 4-alkyl/aryl-1-(3-phenoxypropionyl)-thiosemicarbazides were synthesized by condensation of 3- phenoxypropionic acid hydrazide with related isothiocyanates. All compounds were tested in vitro for their antibacterial and antifungal activity. One compound, 4-(4-chlorophenyl)-1-(3-phenoxypropionyl)-thiosemicarbazide, showed high level of activity against Gram-positive species, MICs range 12.5-50 μg/mL. Semiempirical calculations of geometries, energies, and QSAR parameters have been determined in hope to get insight into different biological activity of closely related isomers.

Keywords: 4-alkyl/aryl-1-(3-phenoxypropionyl)-thiosemicarbazides, 4-(4-chlorophenyl)-1-(3-phenoxypropionyl)-thiosemicarbazide, Antibacterial activity, Antifungal activity, QSAR parameters, Thiosemicarbazides, Bacillus cereus, Micro-cocus roseus, penicillin G, Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Ampicillin, Enterococcus fae-calis, Candida albicans, Candida parapsilosis, Tricho-phyton mentagrophytes var. erinacei, Saccharomyces cerevisiae, Cryp-tococcus neoformans, Aspergillus fumigates, QSAR, growth inhi-bition zones, GIZ, MICs, CYP51, Specord IR-75 spectro- photometer, H NMR spectra, thin layer chromatogra-phy, TLC, ethyl-1-(3-phenoxypropionyl)-thiosemicarbazide, benzyl-1-(3-phenoxypropionyl)-thiosemicarbazide, phenyl-1-(3-phenoxypropionyl)-thiosemicarbazide, (4-bromophenyl)-1-(3-phenoxypropionyl)-thiosemicarbazide, 4-methoxyphenyl-1-(3-phenoxypropionyl)-thiosemicarba-zide, 4-(4-fluorophenyl)-1-(3-phenoxypropionyl)-thiosemicar-bazide, 4-(2-fluorophenyl)-1-(3-phenoxypropionyl)-thiosemicarb-azide, Ciprofloxacin, Fluconazole, M. luteus

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Article Details

VOLUME: 7
ISSUE: 10
Year: 2010
Page: [737 - 742]
Pages: 6
DOI: 10.2174/1570180811007010737
Price: $65

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