128294-46-2Relevant academic research and scientific papers
An unusual, mild and convenient one-pot two-step access to (E)-stilbenes from hydroxy-substituted benzaldehydes and phenylacetic acids under microwave activation: a new facet of the classical Perkin reaction
Sinha, Arun K.,Kumar, Vinod,Sharma, Abhishek,Sharma, Anuj,Kumar, Rakesh
, p. 11070 - 11077 (2007)
A mild and convenient one-pot two-step synthesis of hydroxystilbenes with trans selectivity has been developed through a modified Perkin reaction between benzaldehydes and phenylacetic acids bearing 4- or 2-hydroxy substitution at the aromatic ring, in the presence of piperidine-methylimidazole and polyethylene glycol under microwave irradiation. The observation of a simultaneous condensation-decarboxylation leading to the unusual formation of hydroxystilbenes in lieu of α-phenylcinnamic acid reveals an interesting facet to the classical Perkin reaction. The developed protocol provides a green alternative to the prevalent methods employing a toxic decarboxylating agent in the form of quinoline/Cu salt, and the requirement for harsh protection-deprotection steps for the synthesis of hydroxylated stilbenes.
Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes
Martí-Centelles, Rosa,Falomir, Eva,Murga, Juan,Carda, Miguel,Marco, J. Alberto
supporting information, p. 488 - 496 (2015/10/05)
A group of thirty-nine stilbene derivatives, prepared by means of Heck coupling reactions, has been investigated for their cytotoxicity, as well as for their ability to inhibit the production of the vascular endothelial growth factor (VEGF) and the activation of telomerase. The ability of these compounds to inhibit proliferation of two tumoral cell lines (HT-29 and MCF-7) and one non tumoral cell line (HEK-293) was first determined. Subsequently, we determined the capacity of the compounds to inhibit the secretion of VEGF in the aforementioned cell lines and to downregulate the expression of the VEGF, hTERT and c-Myc genes, the two latter involved in the control of the activation of telomerase. One of the synthetic stilbenes, (E)-4-(4-methoxystyryl)aniline, showed strong cytotoxicity and proved able to cause a marked decrease both in the secretion of VEGF and in the expression of the hTERT and c-Myc genes, in all cases at concentrations in the low nanomolar range.
Aerobic oxidative coupling of resveratrol and its analogues by visible light using mesoporous graphitic carbon nitride (mpg-C3N4) as a bioinspired catalyst
Song, Tao,Zhou, Bo,Peng, Guang-Wei,Zhang, Qing-Bao,Wu, Li-Zhu,Liu, Qiang,Wang, Yong
supporting information, p. 678 - 682 (2014/01/23)
The first aerobic oxidative coupling of resveratrol and its analogues by mesoporous graphitic carbon nitride as a bioinspired catalyst with visible light has been developed. With this method, δ-viniferin and its analogues were synthesized in moderate to high yield. The metal-free conditions, visible-light irradiation, and the ideal oxidant, molecular oxygen, make this coupling reaction environmental friendly and practical. Copyright
Synthesis, antitumor evaluation, and apoptosis-inducing activity of hydroxylated (E)-stilbenes
Lion, Cedric J.,Matthews, Charles S.,Stevens, Malcolm F. G.,Westwell, Andrew D.
, p. 1292 - 1295 (2007/10/03)
The parallel solution-phase synthesis of a series of 30 monohydroxylated (E)-stilbene analogues is described. In vitro screening revealed low micromolar activity (GI50) against the MDA MB 468 breast cancer cell line. Activity in MDA MB 468 cells correlated with the ability to induce apoptosis following drug treatment by the most potent agents in the series, e.g., 5dy and 5jy, an observation further reinforced by Annexin V-FITC analysis and fluorescence microscopy.
