Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues
New thienyl- or chlorophenyl-substituted thiazolopyrimidine derivatives and their derived sugar hydrazones incorporating acyclic <span style="font-variant: small-caps;">d</span>-galactosyl or <span style="font-variant: small-caps;">d</span>-xylosyl sugar m...
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MDPI AG
2020-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/2/399 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Ebtesam A. Basiony |
| collection | DOAJ |
| description | New thienyl- or chlorophenyl-substituted thiazolopyrimidine derivatives and their derived sugar hydrazones incorporating acyclic <span style="font-variant: small-caps;">d</span>-galactosyl or <span style="font-variant: small-caps;">d</span>-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 <b>1</b>, <b>8</b>, <b>10</b>, <b>11</b>, and <b>13</b> against Caco-2 and MCF7 cells in addition to moderate activities exhibited by other compounds against HCT116 or MDA-MB-231 cells. |
| first_indexed | 2024-12-13T01:03:24Z |
| format | Article |
| id | doaj.art-f587609419b94c7793c2835083f31719 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-13T01:03:24Z |
| publishDate | 2020-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f587609419b94c7793c2835083f317192022-12-22T00:04:38ZengMDPI AGMolecules1420-30492020-01-0125239910.3390/molecules25020399molecules25020399Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside AnaloguesEbtesam A. Basiony0Allam A. Hassan1Zahra M. Al-Amshany2Ahmed A. Abd-Rabou3Adel A.-H. Abdel-Rahman4Nasser A. Hassan5Wael A. El-Sayed6Faculty of Science, Chemistry Department, Menoufia University, Shibin EL-Kom 32511, EgyptFaculty of Science, Chemistry Department, Suez University, Suez 43511, EgyptDepartment of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21551, Saudi ArabiaHormones Department, Medical Research Division, National Research Centre, Giza 12511, EgyptFaculty of Science, Chemistry Department, Menoufia University, Shibin EL-Kom 32511, EgyptPharmaceutical Science Department, College of Pharmacy, Shaqra University, Shaqra 11961, Saudi ArabiaPhotochemistry Department, National Research Centre, Giza 12511, EgyptNew thienyl- or chlorophenyl-substituted thiazolopyrimidine derivatives and their derived sugar hydrazones incorporating acyclic <span style="font-variant: small-caps;">d</span>-galactosyl or <span style="font-variant: small-caps;">d</span>-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 <b>1</b>, <b>8</b>, <b>10</b>, <b>11</b>, and <b>13</b> against Caco-2 and MCF7 cells in addition to moderate activities exhibited by other compounds against HCT116 or MDA-MB-231 cells.https://www.mdpi.com/1420-3049/25/2/399thiazolopyrimidine1,3,4-oxadiazolesugar hydrazonesanticanceracyclic nucleosides |
| spellingShingle | 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 Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues Molecules thiazolopyrimidine 1,3,4-oxadiazole sugar hydrazones anticancer acyclic nucleosides |
| title | Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues |
| title_full | Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues |
| title_fullStr | Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues |
| title_full_unstemmed | Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues |
| title_short | Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues |
| title_sort | synthesis and cytotoxic activity of new thiazolopyrimidine sugar hydrazones and their derived acyclic nucleoside analogues |
| topic | thiazolopyrimidine 1,3,4-oxadiazole sugar hydrazones anticancer acyclic nucleosides |
| url | https://www.mdpi.com/1420-3049/25/2/399 |
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