期刊
JOURNAL OF MOLECULAR STRUCTURE
卷 1250, 期 -, 页码 -出版社
ELSEVIER
DOI: 10.1016/j.molstruc.2021.131751
关键词
Lupane; Betulin; Click chemistry; Triazole; 5-Thiotetrazole; Cytotoxicity; SAR
资金
- National Science Centre, Poland [2016/21/B/ST5/02141]
- Czech Science Foundation [20-25308S]
New cytotoxic derivatives based on the lupane scaffold were synthesized and tested for their activity against cancer cell lines and normal fibroblasts. Some derivatives showed cytotoxic activity against cancer cells but were also toxic to normal cells. One compound exhibited selectivity towards tumor cells without affecting the growth of normal cells.
In search of new cytotoxic derivatives based on the lupane scaffold, the s eco -lupane azides were coupled with a number of alkynes under the 1,3-dipolar cycloaddition (CuAAC) conditions to afford 1,2,3-triazoles. Phenylalkynes having different substituents at the para position were used as starting materials. Similarly, coupling of the seco -lupane thiocyanate with sodium azide gave 5-thiotetrazole. The cytotoxicity of thirteen derivatives were investigated, as well as the effect of substituents in the phenyl ring on the activity of 1,2,3-triazoles. Limited activity was observed for some of these products. Most of the studied compounds were inactive in cancer cell lines and healthy fibroblasts. Triazole 46 exhibited cytotoxic activity against CEM and MCF-7 cancer cell lines, however, it was also toxic to normal human BJ fibroblasts. Two other derivatives - triazole 45 and tetrazole 49 - exhibited low cytotoxicity. Compound 49 showed good selectivity towards tumor cell lines compared to normal fibroblasts. This compound did not affect the growth of normal human fibroblasts and therefore has a wide therapeutic window. (c) 2021 The Author(s). Published by Elsevier B.V. This is an open access article under the CC BY license ( http://creativecommons.org/licenses/by/4.0/ )
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