A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents

Abstract

BackgroundMany heterocyclic compounds containing thiazole or 1,3,4-thiadiazole ring in their skeletons have been reported to possess various pharmacological activities especially anticancer activities.Results4-Methyl-2-phenylthiazole-5-carbohydrazide (2) was used as a synthon to prepare 2-(4-methyl-2-phenylthiazole-5-carbonyl)-N-phenylhydrazinecarbothioamide (3) and 2-(2-(4-methyl-2-phenylthiazole-5-carbonyl)hydrazono)-N′-phenylpropane hydrazonoyl chlorides 5a–c. In addition, thioamide 3 was used as starting material for preparation of a new series of thiadiazole derivatives via its reaction with hydrazonoyl chlorides 5a–c in dioxane using triethylamines as catalyst. In addition, a series of thiazole derivatives was synthesized by reaction of thioamide 3 with a number of α-halo compounds, namely, 3-chloropentane-2,4-dione (8) or 2-chloro-3-oxo-N-phenyl butanamide (10) phenacyl bromide 12 ethyl chloroacetate (14) in EtOH in the presence of triethylamine. The structures assigned for all the new products were elucidated based on both elemental analyses and spectral data and the mechanisms of their formation was also discussed. Moreover, the new products was evaluated in vitro by MTT assays for their anticancer activity against cell lines of Hepatocellular carcinoma cell line (HepG-2). The best result observed for compounds 7b (IC50 = 1.61 ± 1.92 (μg/mL)) and 11 (IC50 = 1.98 ± 1.22 (μg/mL)). The structure–activity relationships have been suggested based on their anticancer results.ConclusionsA novel series of new pharmacophores containing thiazole moiety have been synthesized using a facile and convenient methods and evaluated as potent anticancer agents.

Clean Grinding Technique: A Facile Synthesis and In Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (Mpro)

“…To verify the assigned structure of the products 3a – c , we have synthesized these compounds by alternative methods. Thus, treatment of aminothiouracil ( 4 ) with 2-[2-(4-methyl-2- phenylthiazole-5-carbonyl) hydrazono]- N -arylpropanehydrazonoyl chlorides ( 5a – c ) [ 37 ] in dioxane, in the presence of a catalytic amount of triethylamine, under thermal conditions, gave the authentic products identical in all respects (mp, mixed mp, IR) with the isolated products 3a – c via Smiles rearrangement [ 38 ] and elimination of H 2 S ( Scheme 2 ).…”

Synthesis and Biological Evaluation of Some Novel Thiazole-Based Heterocycles as Potential Anticancer and Antimicrobial Agents

“…Heating a mixture of hydrazonoyl halides 8a or 8b [23] and the appropriate arylidine malononitriles 9a – c [33] in ethanol containing piperidine under irradiation by MW led to the formation of the thiazolyl pyrazoles 11a – f (Scheme 2). The structure of the latter products was established based on their elemental analysis and spectral data (cf.…”

“…The reactions were carried out in a closed Teflon vessel which was placed at the center of the oven for irradiation. 5-Acetyl-4-methyl-2-phenyl-thiazole ( 1 ) [26], 2-cyanoacetohydrazide ( 2 ) [27], hydrazonoyl halides 4a [28,29], 4b – d [30], 4e – g [31], 4h [32], 8a, b [23] and arylidine malononitriles 9a – c [31] were prepared as described in the literature.…”

“…In view of these precedents and together with our research concerns of developing new convenient approaches for the synthesis of different heterocyclic systems with auspicious pharmacological activities [20,21,22,23,24,25], we present in this report an efficient synthesis of some new series of novel thiazole derivatives using chitosan-grafted-poly(vinyl pyridine) as an eco-friendly biopolymeric basic catalyst. Additionally, we have assessed a variety of biological activities for the newly synthesized compounds that demonstrated their potential antitumor, antimicrobial and hepatoprotective effectiveness.…”

Efficient Synthesis of New Benzofuran‐based Thiazoles and Investigation of their Cytotoxic Activity Against Human Breast Carcinoma Cell Lines

“…). Thiazole derivatives are reported to exhibit diverse biological activities as antimicrobial, antioxidant, antitubercular, and anticonvulsant, anticonvulsant, anticancer, and anti‐inflammatory agents . Many reports indicated that 1,3‐thiazole derivatives exhibited potential anticancer activity against various cancer types ( V – VIII ) (Fig.…”