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

Ebtesam A Basiony; Allam A Hassan; Zahra M Al-Amshany; Ahmed A Abd-Rabou; Adel A-H Abdel-Rahman; Nasser A Hassan; Wael A El-Sayed

doi:10.3390/molecules25020399

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

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

Authors

Ebtesam A Basiony¹, Allam A Hassan^{2

3}, Zahra M Al-Amshany⁴, Ahmed A Abd-Rabou^{5

6}, Adel A-H Abdel-Rahman¹, Nasser A Hassan^{7

8}, Wael A El-Sayed^{8

9}

Affiliations

¹ Faculty of Science, Chemistry Department, Menoufia University, Shibin EL-Kom 32511, Egypt.
² Faculty of Science, Chemistry Department, Suez University, Suez 43511, Egypt.
³ Applied Medical Science, Medical Laboratories Department, Shaqra University, Shaqra 11961, Saudi Arabia.
⁴ Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21551, Saudi Arabia.
⁵ Hormones Department, Medical Research Division, National Research Centre, Giza 12511, Egypt.
⁶ Stem Cells Lab, Center of Excellence for Advanced Sciences, National Research Centre, Giza 12511, Egypt.
⁷ Pharmaceutical Science Department, College of Pharmacy, Shaqra University, Shaqra 11961, Saudi Arabia.
⁸ Photochemistry Department, National Research Centre, Giza 12511, Egypt.
⁹ Department of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi Arabia.

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.

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
Chemistry Techniques, Synthetic
Humans
Hydrazones / chemical synthesis*
Hydrazones / pharmacology*
Molecular Structure
Nucleosides / analogs & derivatives
Nucleosides / chemical synthesis*
Nucleosides / pharmacology*

Substances

Antineoplastic Agents
Hydrazones
Nucleosides

Grants and funding

D1441-222-247/King Abdulaziz University