Structure-based design, synthesis, and biological evaluation of novel piperine-resveratrol hybrids as antiproliferative agents targeting SIRT-2 was written by Tantawy, Ahmed H.;Meng, Xiang-Gao;Marzouk, Adel A.;Fouad, Ali;Abdelazeem, Ahmed H.;Youssif, Bahaa G. M.;Jiang, Hong;Wang, Man-Qun. And the article was included in RSC Advances in 2021.Application In Synthesis of (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol This article mentions the following:
A series of novel piperine-resveratrol hybrids 5a-h was designed, synthesized, and structurally elucidated by IR, and 1H, 13C, and 19F NMR. Antiproliferative activities of 5a-h were evaluated by NCI against sixty cancer cell lines. Compound 5b, possessing resveratrol pharmacophoric phenolic moieties, showed a complete cell death against leukemia HL-60 (TB) and Breast cancer MDA-MB-468 with growth inhibition percentage of -0.49 and -2.83, resp. In addition, 5b recorded significant activity against the other cancer cell lines with growth inhibition percentage between 80 to 95. New 5a-h hybrids were evaluated for their inhibitory activities against Sirt-1 and Sirt-2 as mol. targets for their antiproliferative action. Results showed that compounds 5a-h were more potent inhibitors of Sirt-2 than Sirt-1 at 5 μm and 50 μm. Compound 5b showed the strongest inhibition of Sirt-2 (78 ± 3% and 26 ± 3% inhibition at 50 μM and 5 μM, resp.). Investigation of intermol. interaction via Hirschfeld surface anal. indicates that these close contacts are mainly ascribed to the O-H ···O hydrogen bonding. To get insights into the Sirt-2 inhibitory mechanism, a docking study was performed where 5b was found to fit nicely inside both extended C-pocket and selectivity pocket and could compete with the substrate acyl-Lys. Another possible binding pattern showed that 5b could act by partial occlusion of the NAD+ C-pocket. Collectively, these findings would contribute significantly to better understanding the Sirt-2 inhibitory mechanism in order to develop a new generation of refined and selective Sirt-2 inhibitors. In the experiment, the researchers used many compounds, for example, (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6Application In Synthesis of (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol).
(E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Application In Synthesis of (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts