Synthesis and Antimicrobial Evaluation of Novel Derivatives of Semicarbazide and 1,2,4‐triazole

Abstract

Reaction of phenoxyacetic acid hydrazide with isocyanate was used to the synthesis of new semicarbazide derivatives. Cyclization of these compounds in a 2% aqueous solution of sodium hydroxide led to formation of 1,2,4‐triazole‐3‐one. The chemical structure of synthesized compounds was confirmed by elemental analysis and spectroscopic methods (1H and 13C NMR). On the basis of the NMR, spectra were found that cyclic compounds 1,2,4‐triazole exist in the ‐one form. Moreover, all derivatives were examined for their in vitro activity against some species of bacteria. New compounds presented mild or moderate antimicrobial activity only against reference Gram‐positive bacteria. Two derivatives (one semicarbazide and one triazole) showed bactericidal or bacteriostatic activity.

New Norcantharidin Analogs: Synthesis and Anticancer Activity

“…The synthetic route for the synthesis of N-substituted amides of 3-(3-ethylthio-1,2,4-triazol-5-yl)-7-oxabicyclo-[2.2.1]heptane-2-carboxylic acid (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) is presented in Scheme 1. S-Ethyl-N-(7-oxabicyclo-[2.2.1]heptane-2,3-dicarbonyl)isothiosemicarbazide (1) used as the starting material was obtained by condensation reaction of exo-7-oxabicyclo-[2.2.1]heptane-2,3-dicarboxylic acid anhydride with S-ethyl isothiosemicarbazide hydrobromide in boiling glacial acetic acid [39,40]. Next, the initial, cyclic isothiosemicarbazide was heated with selected primary aliphatic and aromatic amines in the boiling glacial acetic acid.…”

“…Three of them were found to be evidently effective in vitro against lung cell line. Moreover, N-(2-chlorophenyl) amide of 3-(3-ethylthio-1,2,4-triazol-5-yl)propenoic acid displayed the lowest cytotoxicity in concentrations of 0.16 and 0.03 mM against the normal skin fibroblast line and breast carcinoma cell in vitro after 24 and 48 h periods of incubation [39].…”

“…On the other hand, vorozole, letrozole, and anastrozole are antineoplastic, non-steroidal aromatase inhibitors which are approved for preventing breast cancer [36][37][38]. In view of the literature and in continuation of our search for novel improved and less toxic anticancer agents [39], it seemed promising to design and synthesize new hybrid molecules consisting of analogs of norcantharidin and 1,2,4-triazole. Our previous studies concerned 1,2,4-triazoles obtained from exo-S-ethyl-7-oxabicyclo-[2.2.1]hept-5-ene-2,3-dicarbonyl isothiosemicarbazide with primary amines by condensation reaction.…”

Synthesis and antibacterial activity of chalcone derivatives containing thioether triazole

“…Bioactivity analysis indicated that the compounds have good inhibitory effects on the tested bacteria . Several studies have shown that triazole derivatives have biological activities such as anti‐inflammatory, antibacterial, antifungal, antiviral, anticancer, and antituberculosis . For example, Singh et al developed a series of substituted aryl azide compounds containing o ‐phenylenediamines, which exhibited antifungal activities .…”

Absorption, fluorescence, Raman spectroscopic and density functional theoretical studies on the singlet and triplet excited state decay of 3-amino-5-mercapto-1,2,4-triazole

“…Thus, apart from the biological signicance, 4 1,2,4-triazoles are also applied to the protection of metals and alloys, such as corrosion inhibition. [5][6][7] Important structured features, such as the planarity (p) and lone pair of electrons on the hetero-atom, are attributed to their strong coordination on the metal surface. [8][9][10][11][12][13] In particular, 3amino-5-mercapto-1,2,4-triazole (AMT) can be considered as one pull-push electronic structure due to both electron donor (-NH 2 ) and acceptor (-S]C or -SH) groups bridged by one aromatic 1,2,4-triazole ring.…”