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. 2020 Jan 18;25(2):399.
doi: 10.3390/molecules25020399.

Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues

Ebtesam A Basiony  1 , Allam A Hassan  2   3 , Zahra M Al-Amshany  4 , Ahmed A Abd-Rabou  5   6 , Adel A-H Abdel-Rahman  1 , Nasser A Hassan  7   8 , Wael A El-Sayed  8   9
Affiliations

Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues

Ebtesam A Basiony et al. Molecules. .

Abstract

New thienyl- or chlorophenyl-substituted thiazolopyrimidine derivatives and their derived sugar hydrazones incorporating acyclic d-galactosyl or d-xylosyl sugar moieties in addition to their per-O-acetylated derivatives were synthesized. Heterocyclization of the formed sugar hydrazones afforded the derived acyclic nucleoside analogues possessing the 1,3,4-oxadiazoline as modified nucleobase via acetylation followed by the cyclization process. The cytotoxic activity of the synthesized compounds was studied against human breast cancer MCF7 and MDA-MB-231 cell lines as well as human colorectal cancer HCT 116 and Caco-2 cell lines. High activities were revealed by compounds 1, 8, 10, 11, and 13 against Caco-2 and MCF7 cells in addition to moderate activities exhibited by other compounds against HCT116 or MDA-MB-231 cells.

Keywords: 1,3,4-oxadiazole; acyclic nucleosides; anticancer; sugar hydrazones; thiazolopyrimidine.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Anticancer thiazolopyrimidine, pyrinidinyl-sugar, and pyrimidinyl-oxadiazole compounds.
Scheme 1
Scheme 1
Synthesis of aryl- or heteroaryl-substituted thiazolopyrimidine derivatives.
Scheme 2
Scheme 2
Synthesis of thiazolopyrimidine sugar hydrazones and their oxadiazolyl sugar derivatives.
Figure 2
Figure 2
Anti-proliferative activities of compounds against human colorectal cancer HCT 116 cells. The MTT assay was performed three independent times (n = 3) using different concentrations of the mentioned compounds.
Figure 3
Figure 3
Anti-proliferative activities of compounds against human colorectal cancer Caco-2 cells. The MTT assay was performed three independent times (n = 3) using different concentrations of the mentioned compounds.
Figure 4
Figure 4
Anti-proliferative activities of compounds against human breast cancer MDA-MB-231 cells. The MTT assay was performed three independent times (n = 3) using different concentrations of the mentioned compounds.
Figure 5
Figure 5
Anti-proliferative activities of compounds against human breast cancer MCF7 cells. The MTT assay was performed three independent times (n = 3) using different concentrations of the mentioned compounds.
See this image and copyright information in PMC

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