Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5-b]pyridines and thiazolo[5′,4′:5,6]pyrano[2,3-d]pyrimidine derivatives and incorporating isoindoline-1,3-dione group

Abstract

Background Thiazole is a core structural motif presents in a wide range of natural products. Thiazole derivatives also have a wide range of medicinal and biological properties. Results The reaction of hydrazonoyl halides with 2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinecarbothioamidein ethanol and triethylamine yielded 2-(4-(1-(2-(4-(2-Arylhydrazono)-5-s-4,5-dihydrothiazol-2-yl)hydrazono)-ethyl)phenyl)isoindoline-1,3-dione and 2-(4-(1-(2-(5-(2-Arylhydrazono)-4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)-phenyl)isoindoline-1,3-dione.The reaction of 2-(4-(1-(2-(4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)phenyl)isoindoline-1,3-dione with arylidenemalononitrile also yielded 5-amino-2-(2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinyl)-7-substituted-7 H -pyrano[2,3- d ]thiazole-6-carbonitrile. The structures of the newly synthesized compound were elucidated whenever possible on the basis of elemental analysis, spectral data, and alternative synthetic routes. Three of them were evaluated against a breast cancer cell line for their antitumor activity. Conclusions Compound (1) has been shown to be useful in the synthesis of a new series of 1,3-thiazole, pyrano[2,3- d ]thiazole and 4,5-dihydrothiazolo[4,5- b ]pyridine derivatives using hydrazonoyl halides as precursors. The anticancer efficacy of compounds (9b) , (9e) , and (9f) against MCF-7, a breast cancer cell line, was also compared to the standard anticancer drug doxorubicin. Electronic supplementary material The online version of this article (10.1186/s13065-019-0559-x) contains supplementary material, which is available to authorized users.

Synthesis, Biological Evaluation, and Molecular Docking of Novel Azolylhydrazonothiazoles as Potential Anticancer Agents

“…The distinctive features in the structure of isolated products were elucidated by spectroscopic tools and elemental analyses. 1 H NMR spectra of products 9a–f showed in each case a singlet signal at δ = 7.40–7.48 ppm corresponding to H-5 of thiazole ring . In IR, the bands of (CO) group of compounds 11a and 11b were revealed at 1700 and 1695 cm –1 , respectively.…”

Effect of pH and concentration on the chemical stability and reaction kinetics of thiamine mononitrate and thiamine chloride hydrochloride in solution

“…Fractional order reactions are common when degradation products participate in subsequent chemical chain reactions, which is probable in the case of thiamine degradation [ 30 , 37 ]. In weakly acidic to neutral solutions (e.g., pH 6), thiamine is susceptible to hydrolysis in which the methylene bridge is broken, resulting in intact pyrimidine and thiazole moieties [ 18 , 34 , 38 , 39 ]. The resulting intact rings are then likely to undergo subsequent reactions.…”

Advances in the Synthesis of Heterocycles with Two and Three Heteroatoms using Hydrazonoyl Halides

“…The anticancer efficacy of compounds 251 (R=Me, Ar=4‐MeC 6 H 4 ; R=Ph, Ar=2‐thiophenyl or 2‐naphthyl) against the MCF‐7 breast cancer cell line was compared with that of the standard anticancer drug doxorubicin . It turned out that to obtain cytotoxicity indicators similar to doxorubicin , it is necessary that the concentration of the obtained compounds 251 be 3–4 times higher than the concentration of the reference standard [141] …”

“…It turned out that to obtain cytotoxicity indicators similar to doxorubicin, it is necessary that the concentration of the obtained compounds 251 be 3 -4 times higher than the concentration of the reference standard. [141] Noteworthy is the regiolocalization of the double bond and the proton of the NH group at the formed thiazole ring (Schemes 76 -81). If you compare their location in these schemes, they are different.…”