A facile synthesis and anticancer activity of some novel thiazoles carrying 1,3,4-thiadiazole moiety

Abstract

BackgroundThiazoles and 1,3,4-thiadiazoles have been reported to possess various pharmacological activities.ResultsA novel series of thiazoles carrying 1,3,4-thiadiazole core were designed and prepared via the reaction of the 2-(4-methyl-2-phenylthiazole-5-carbonyl)-N-phenylhydrazinecarbo-thioamide with the appropriate hydrazonoyl chlorides. The structures of the newly synthesized compounds were confirmed based on elemental and spectral analysis as well as their alternative syntheses. The cytotoxic potency of the newly synthesized thiadiazoles was evaluated by their growth inhibitory potency in liver HepG2 cancer cell line. Also, the structure activity relationship was studied.ConclusionsAll the newly synthesized compounds were evaluated for their anticancer activity against liver carcinoma cell line (HepG2) using MTT assay. The results revealed that the compounds 12d, 12c, 6g, 18b, 6c, and 6f (IC50 = 0.82, 0.91, 1.06, 1.25, 1.29 and 1.88 µM, respectively) had good antitumor activity against liver carcinoma cell line (HepG2) when compared with the standard drug Doxorubicin (IC50 = 0.72 µM).Graphical abstractA facile synthesis and anticancer activity of some novel thiazoles carrying 1,3,4-thiadiazole moiety. Electronic supplementary materialThe online version of this article (doi:10.1186/s13065-017-0255-7) contains supplementary material, which is available to authorized users.

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

“…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.…”

New 1,3,4‐Thiadiazole Derivatives: Synthesis, Characterization, and Antimicrobial Activity

“…Thiadiazoles have a wide range of pharmaceutical activities including anti‐inflammatory , antifungal , antibacterial , analgesic , antitubercular , and antileishmanicidal agents . Moreover, 1,3,4‐thiadiazoles are also important classes of azoles which have significant biological properties as antiviral and anticancer . Several studies have shown that two or three heterogeneous atoms such as nitrogen and sulfur are expected to have antimicrobial activities .…”

Eco-Friendly Synthesis, Characterization and Biological Evaluation of Some Novel Pyrazolines Containing Thiazole Moiety as Potential Anticancer and Antimicrobial Agents

“…Pyrazolines have been found to possess diverse biological activities such as anticancer [ 2 , 3 , 4 ], antitumor [ 5 ], antioxidant [ 6 ], antimicrobial [ 7 , 8 ], antitubercular [ 9 ], antimalarial [ 10 ], anti-amoebic [ 11 ], DPPH radical scavenging, anti-diabetic [ 12 ], antiviral [ 13 ] and amine oxidase [ 14 ]. Also, thiazoles are known to have anticonvulsant [ 15 ], antimicrobial [ 16 ], anti-inflammatory [ 17 ], anticancer [ 18 , 19 , 20 ], antidiabetic [ 21 ], anti-HIV [ 22 ], anti-Alzheimer [ 23 ], antihypertensive [ 24 ], antifungal [ 25 ], and antioxidant [ 26 ] activities. In view of the above mentioned findings and as a part of our research interest towards developing new ways to synthesize a variety of heterocyclic systems with promising biological and pharmacological activities [ 27 , 28 , 29 , 30 ], we present in this research an efficient synthesis of a series of pyrazolines attached to thiazole moiety using N -thiocarbamoylpyrazoline [ 31 ] and the appropriate hydrazonoyl halides [ 32 , 33 , 34 ] or α-haloketones in the presence of DABCO under the solvent-drop grinding method [ 35 ].…”