Stereoselective synthesis of 2-(2,4-dinitrophenyl)hydrazono- and (2-tosylhydrazono)-4-oxo-thiazolidine derivatives and s
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RIGINAL PAPER
Stereoselective synthesis of 2‑(2,4‑dinitrophenyl)hydrazono‑ and (2‑tosylhydrazono)‑4‑oxo‑thiazolidine derivatives and screening of their anticancer activity Alaa A. Hassan1 · Ashraf A. Aly1 · Mohamed Ramadan2 · Nasr K. Mohamed1 · Hendawy N. Tawfeek1 · Stefan Bräse3,4 · Martin Nieger5 Received: 25 May 2020 / Accepted: 10 August 2020 / Published online: 9 September 2020 © Springer-Verlag GmbH Austria, part of Springer Nature 2020
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 of N-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. Graphic abstract
Keywords Anticancer activity · Heterocycles · NMR spectroscopy · Nucleophilic additions · Solvent effect · Spectroscopy · Crystal structure
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00706-020-02671-w) contains supplementary material, which is available to authorized users. * Alaa A. Hassan [email protected] 1
Chemistry Department, Faculty of Science, Minia University, El Minia 61519, Egypt
2
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Assiut 71524, Egypt
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Institute of Organic Chemistry, Karlsruhe Institute of Technology, 76131 Karlsruhe, Germany
4
Institute of Biological and Chemical Systems (IBCS-FMS), Karlsruhe Institute of Technology, Eggenstein‑Leopoldshafen, Germany
5
Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio I), 00014 University of Helsinki Helsinki, Finland
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Vol.:(0123456789)
1454
Introduction Thiazolidinone is one of the most frequent heterocyclic nuclei as it exhibits many types of biological activities [1]. It has been reported that thiazolidin-4-ones are explored as anti-inflammatory [2–5], antiviral [6, 7], anticonvulsant [8–10], antidiabetic [11], anticancer [12], and anti-HIV [13–15] activities. Also, the thiazolidin-4-one ring occurs in nature, for example, actithiazic acid [(−)-2-(5-carboxyphenyl)thiazolidin-4-one] was isolated from Streptomyces [16]. Different methods for the synthesis of 1,3-thiazolidin4-ones were reported from thiosemicarbazides [16–20], thiocarbohydrazides [21, 22], hydrazinocarbothioam
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