title: Synthesis, structure elucidation and antitumour activity of N-substituted amides of 3-(3-ethylthio-1,2,4-triazol-5-yl)propenoic acid.
abstract: New N-substituted amides of 3-(3-ethylthio-1,2,4-triazol-5-yl)propenoic acid (2-12) were designed and prepared by the condensation reaction of exo-S-ethyl-7-oxabicyclo-[2.2.1]-hept-5-ene-2,3-dicarbonyl isothiosemicarbazide (1) with primary amines. The chemical structure of all compounds was confirmed by IR, (1)H NMR, (13)C NMR spectra, the X-ray crystallography (for compounds 8, 11, 12) and elemental analysis. Moreover, compounds 9-11 were screened for their anticancer activity. Compounds 9 (in concentrations of 0.32 mM and 0.16 mM), 10 (in concentrations of 0.28 mM and 0.14 mM), and 11 (in concentrations of 0.35 mM and 0.17 mM) were found to be evidently effective in vitro against lung cell line (IC50). The distinctly marked antiproliferative effect of compounds 9 and 10 in breast carcinoma cells in vitro was ascertained. Moreover, the lowest cytotoxicity of compound 9 in concentrations of 0.16 mM and 0.03 mM against the normal skin fibroblast cell line and breast carcinoma cell in vitro after 24- and 48-h periods of incubation was noticed in this study.
authors.affiliation: Department of Organic Chemistry, Faculty of Pharmacy, Medical University, 6 Staszica Street, 20-081 Lublin, Poland. anna.pachuta@am.lublin.pl
authors.forename: Anna
authors.initials: A
authors.lastname: Pachuta-Stec
authors.forename: Jolanta
authors.initials: J
authors.lastname: Rzymowska
authors.forename: Liliana
authors.initials: L
authors.lastname: Mazur
authors.forename: Ewaryst
authors.initials: E
authors.lastname: Mendyk
authors.forename: Monika
authors.initials: M
authors.lastname: Pitucha
authors.forename: Zofia
authors.initials: Z
authors.lastname: Rzaczyńska
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000188:drug therapy; D002277:Carcinoma / Q000188:drug therapy; D002460:Cell Line; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D005260:Female; D005347:Fibroblasts / Q000166:cytology; D006801:Humans; D008175:Lung Neoplasms / Q000188:drug therapy; D012867:Skin / Q000166:cytology; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000577:Amides; D000970:Antineoplastic Agents; D014230:Triazoles; C045575:1,2,4-triazole