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

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Hassan , A A , Aly , A A , Ramadan , M , Mohamed , N K , Tawfeek , H N , Bräse , S & Nieger , M 2020 , ' Stereoselective synthesis of 2-(2,4-dinitrophenyl)hydrazono- and (2-tosylhydrazono)-4-oxo-thiazolidine derivatives and screening of their anticancer activity ' , Monatshefte für Chemie , vol. 151 , no. 9 , pp. 1453-1466 . https://doi.org/10.1007/s00706-020-02671-w

Title: Stereoselective synthesis of 2-(2,4-dinitrophenyl)hydrazono- and (2-tosylhydrazono)-4-oxo-thiazolidine derivatives and screening of their anticancer activity
Author: Hassan, Alaa A.; Aly, Ashraf A.; Ramadan, Mohamed; Mohamed, Nasr K.; Tawfeek, Hendawy N.; Bräse, Stefan; Nieger, Martin
Contributor: University of Helsinki, Department of Chemistry
Date: 2020-09-09
Language: eng
Number of pages: 14
Belongs to series: Monatshefte für Chemie
ISSN: 0026-9247
URI: http://hdl.handle.net/10138/334164
Abstract: Stereoselective synthesis of (Z)-methyl 2-[(Z)-3-substituted 2-[2-(2,4-dinitrophenyl)hydrazono]-4-oxothiazolidine-5-ylidene]acetates and (Z)-methyl 2-[(Z)-3-substituted 2-[2-(tosylhydrazono)-4-oxothiazolidine-5-ylidene]acetates via the cyclization ofN-substituted 2-arylhydrazino-carbothioamides 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 9 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. [GRAPHICS] .
Subject: Anticancer activity
Heterocycles
NMR spectroscopy
Nucleophilic additions
Solvent effect
Spectroscopy
Crystal structure
EFFICIENT SYNTHESIS
FACILE
DESIGN
116 Chemical sciences
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