Adamantane-Isothiourea Hybrid Derivatives: Synthesis, Characterization, In Vitro Antimicrobial, and In Vivo Hypoglycemic Activities

Abstract

A new series of adamantane-isothiourea hybrid derivatives, namely 4-arylmethyl (Z)-N′-(adamantan-1-yl)-morpholine-4-carbothioimidates 7a–e and 4-arylmethyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidates 8a–e were prepared via the reaction of N-(adamantan-1-yl)morpholine-4-carbothioamide 5 and N-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioamide 6 with benzyl or substituted benzyl bromides, in acetone, in the presence of anhydrous potassium carbonate. The structures of the synthesized compounds were confirmed by 1H-NMR, 13C-NMR, electrospray ionization mass spectral (ESI-MS) data, and X-ray crystallographic data. The in vitro antimicrobial activity of the new compounds was determined against certain standard strains of pathogenic bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 7b, 7d and 7e displayed potent broad-spectrum antibacterial activity, while compounds 7a, 7c, 8b, 8d and 8e were active against the tested Gram-positive bacteria. The in vivo oral hypoglycemic activity of the new compounds was carried on streptozotocin (STZ)-induced diabetic rats. Compounds 7a, 8ab, and 8b produced potent dose-independent reduction of serum glucose levels, compared to the potent hypoglycemic drug gliclazide.

Synthesis and Structure Insights of Two Novel Broad-Spectrum Antibacterial Candidates Based on (E)-N′-[(Heteroaryl)methylene]adamantane-1-carbohydrazides

“…In view of the above-mentioned observations and continuing with recent studies on the chemical and pharmacological properties of adamantane-based derivatives [26][27][28][29], we report herein the synthesis of two novel N -[(heteroaryl)methylene]adamantane-1-carbohydrazides that display potent antibacterial activity. Both compounds were chemically and structurally characterized using a wide range of experimental and computational techniques, including 1 H-NMR, 13 C-NMR, infrared and UV-vis spectroscopies, single crystal X-ray diffraction, and density functional theory calculations (DFT) calculations.…”

Mechanistic insight into the formation of colloidal WS2 nanoflakes in hot alkylamine media

“…Therefore, we hypothesized a tautomerization process leading to the formation of a SH group (7.76 ppm) and a quaternary imine carbon (155.9 ppm). [36][37][38][39] The above results made easier the identication of reaction products in the mixtures containing the amine excess with respect to CS 2 and the metal, as precisely adopted for nanocrystal synthesis in this work ( Fig. 3e and f) and reported more in detail in Fig.…”

Synthesis and Bioactivity of Thiosemicarbazones Containing Adamantane Skeletons

“…Since the first adamantane derivative, amantadine, was found to have antiviral [21][22][23] activity, the synthesis and biological activities of adamantane derivatives, which became an interesting topic, were pursued by a lot of researchers. Therefore, many adamantane derivatives were discovered with various biological activities, i.e., antiviral [24][25][26][27][28][29], antimicrobial [27,[29][30][31][32][33][34][35][36][37][38][39], anticancer [32,36,[40][41][42][43][44] activities.…”