4.4 Article

Selective synthesis of A-ring E-arylidene derivatives from β-sitosterol and their activity

期刊

NATURAL PRODUCT RESEARCH
卷 -, 期 -, 页码 -

出版社

TAYLOR & FRANCIS LTD
DOI: 10.1080/14786419.2022.2103555

关键词

Steroids; beta-sitosterol; Claisen-Schmidt reaction; arylidene; cytotoxicity; alpha-glucosidase; ADMET

资金

  1. RFBR [20-53-54004]
  2. VAST [20-53-54004]
  3. Russian Foundation for Basic Research [QTRU01.05/20-21]
  4. Federal program [1021062311386-8-1.4.1]
  5. Vietnam Academy of Science and Technology [QTRU01.05/20-21]

向作者/读者索取更多资源

In this study, a series of 24-ethylcholest-4-ene-3,6-dione 2E-arylidene derivatives were synthesized from a natural phytosterol beta-sitosterol by Claisen-Schmidt reaction. The obtained compounds were characterized by NMR spectroscopy and evaluated for their cytotoxicity and alpha-glucosidase inhibitory activity. Compound 3 showed selective cytotoxic effect against U251 cancer cell line, while compounds with pyridin-4ylmethylene and furan-2-ylmethylene-5 fragments exhibited the most potent alpha-glucosidase inhibitory activity.
A series of 24-ethylcholest-4-ene-3,6-dione 2E-arylidene-derivatives has been synthesized by a Claisen-Schmidt reaction from a natural phytosterol beta-sitosterol with yields of 80-85%. The structure of the obtained compounds was confirmed by NMR spectroscopy, including two-dimensional correlation experiments. The synthesized compounds were evaluated for their in vitro cytotoxicity and alpha-glucosidase inhibitory activity. It was established that compound 3 with pyridin-3-ylmethylene moiety exhibited a selective cytotoxic effect against the U251 cancer cell line with 99.31% inhibition of cancer cell growth. Compounds with pyridin-4ylmethylene 4 -and furan-2-ylmethylene-5 fragments were the most active inhibitors of alpha-glucosidase with IC50 64.00 and 38.95 mu M, being 3- and 5-times more active than acarbose. Binding mode to alpha-glucosidase and ADMET characteristics for the lead molecule 5 were proposed computationally. To sum up, an efficient approach to the derivatives with promising antidiabetic activity based on available natural product beta-sitosterol is suggested. [GRAPHICS] .

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