Methyl-2-arylidene hydrazinecarbodithioates: synthesis and biological activity

Abstract

Methyl-2-arylidene hydrazine-carbodithioate has not been of particular interest to researchers even though its metal complexes are extensively reported on due to their biological activity. This study examined the cytostatic and antiviral activity of twelve methyl-2-arylidene hydrazinecarbodithioates reported by many researchers as intermediates for the synthesis of thiosemicarbazides and the preparation of their metal complexes. Compounds IIc, IIi, and IIl with tridentate ligand features were found to have the lowest IC50 value (6.5 μM, ≈ 1 μM, and 0.8 μM, respectively) against HL60 human promyelocytic leukemia cells. They were also most inhibitory to human embryonic lung (HEL) fibroblast proliferation (5.3 μM, 17 μM, and 2.6 μM). Compound IIc and IIl show antiviral activity against wild-type herpes simplex virus (HSV), varicella zoster virus (VZV), and acyclovirresistant HSV; however, these activities were observed at concentrations at which the compounds also markedly inhibit HL60 and HEL cell proliferation.

One Pot Single Step Synthesis and Biological Evaluation of Some Novel Bis(1,3,4-thiadiazole) Derivatives as Potential Cytotoxic Agents

“…A mixture of bis -hydrazonoyl chloride 1 [24] and the appropriate methyl arylidene dithiocarbamate 2 [25,26,27,28] was stirred at room temperature for 30 min to afford the corresponding bis (1,3,4-thiadiazole) derivative 5 (Scheme 1). These reactions were assumed to start in each case, via S -alkylation with the elimination of two hydrochloric molecules, to afford the non-isolable bis -alkylated intermediate 3 , which underwent intramolecular Michael-type addition to give intermediate 4 .…”

“…The biological evaluation of the products was carried out at the Regional Center for Mycology and Biotechnology at Al-Azhar University, Cairo, Egypt. Bis -hydrazonoyl chloride 1 [24] and the methyl arylidene dithiocarbamate 2 , 6 , 8 [25,26,27,28] were prepared as described in the literature.…”

Synthesis, Characterization, Crystal Structure, and Stability of 2‐(5, 5‐dimethyl‐3‐oxocyclohex‐1‐en‐1‐yl) Hydrazinecarbothioamide: A Combined Experimental and Theoretical Study

“…Thiosemicarbazide is very useful reagent in organic chemistry for the synthesis of heterocycles and is of considerable interest because of their chemistry and potential biological activities, such as antibacterial, antiviral, antifungal, Anti‐inflammatory, antituber, anticonvulsant activities . The reactions of thiosemicarbazide and its derivatives with compounds containing carbonyl (C=O) and imine (C=N) groups is an elegant method for the preparation of biologically active compounds like triazoles, thiazoles pyrazoles, and thiadiazines .…”