Stereoselective synthesis of 2-(2,4-dinitrophenyl)hydrazono- and (2-tosylhydrazono)-4-oxo-thiazolidine derivatives and screening of their anticancer activity

Abstract

Stereoselective synthesis of (Z)-methyl 2-[(Z)-3-substituted-2-(2-(2,4-dinitrophenyl)hydrazono)-4-oxothiazolidine-5-ylidine)]acetates and (Z)-methyl 2-[(Z)-3-substituted-2-(2-(tosylhydrazono)-4-oxothiazolidine-5ylidine)]acetates via the cyclization of N-substituted-2-arylhydrazinocarbothioamides with dialkyl acetylenedicarboxylates in absolute ethanol is reported. The structures were confirmed by spectroscopic data as well as single crystal X-ray analyses. The mechanism of nucleophilic addition and the role of electronic factors were discussed. The anticancer activity of the newly synthesized compounds was evaluated against a panel of 60 cell lines derived from nine different types of cancers including, leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers and the results revealed that the cyclohexyl derivative has a significant broad anticancer activity especially against different leukemia and colon cancer cell lines . MCCM_Template_Vers 4

Acetylenic Esters in Organic Synthesis

“…The structures of the products were verified by X-ray crystallographic analysis. 19 In 2015, Sabbaghan and Yousefi reported a strategy to synthesize furan-2,3,4-tricarboxylates or 2-acetylfuran-3,4-dicarboxylates in high yields via the DABCO-catalyzed reactions of dialkyl acetylenedicarboxylates and ethyl bromopyruvate or -chlorocarbonyl compounds in the presence of K 2 CO 3 (1.5 mmol) and biphasic H 2 O-Et 2 O (1:1) as the solvent system at room temperature (Scheme 15). Ethyl bromopyruvate or the -chlorocarbonyl compound were used in three-fold excess with respect to the acetylenic ester and the reactions were complete in 1 hour.…”

Convenient synthesis and X-ray determination of 2-amino-6H-1,3,4-thiadiazin-3-ium bromides endowed with antiproliferative activity

“…32 Also, thiosemicarbazides are a vital class of organic compounds that operate as the backbone of a range of heterocyclic compounds of considerable interest in medical and industrial uses. 33,34 Additionally, interactions with phenacyl bromides revealed that thiosemicarbazides have several active centers. 35 Busby and Domincy were the rst to investigate the behavior of 4substituted thiosemicarbazides toward haloketones, obtaining 2-amino-1,3,4-thiadiazines.…”