14064-58-5Relevant academic research and scientific papers
Discovery of efficient stimulators for adult hippocampal neurogenesis based on scaffolds in dragon's blood
Liang, Jian-Hua,Yang, Liang,Wu, Si,Liu, Si-Si,Cushman, Mark,Tian, Jing,Li, Nuo-Min,Yang, Qing-Hu,Zhang, He-Ao,Qiu, Yun-Jie,Xiang, Lin,Ma, Cong-Xuan,Li, Xue-Meng,Qing, Hong
supporting information, p. 382 - 392 (2017/05/19)
Reduction of hippocampal neurogenesis caused by aging and neurological disorders would impair neural circuits and result in memory loss. A new lead compound (N-trans-3′,4'-methylenedioxystilben-4-yl acetamide 27) has been discovered to efficiently stimulate adult rats' neurogenesis. In-depth structure-activity relationship studies proved the necessity of a stilbene scaffold that is absent in highly cytotoxic analogs such as chalcones and heteroaryl rings and inactive analogs such as diphenyl acetylene and diphenyl ethane, and validated the importance of an NH in the carboxamide and a methylenedioxy substituent on the benzene ring. Immunohistochemical staining and biochemical analysis indicate, in contrast to previously reported neuroprotective chemicals, N-stilbenyl carboxamides have extra capacity for neuroproliferation-type neurogenesis, thereby providing a foundation for improving the plasticity of the adult mammalian brain.
Design, synthesis, and biological evaluation of benzoselenazole-stilbene hybrids as multi-target-directed anti-cancer agents
Yan, Jun,Guo, Yueyan,Wang, Yali,Mao, Fei,Huang, Ling,Li, Xingshu
, p. 220 - 229 (2015/03/31)
To identify novel multi-target-directed drug candidates for the treatment of cancer, a series of benzoselenazole-stilbene hybrids were synthesised by combining the pharmacophores of resveratrol and ebselen. The biological assay indicated that all of the h
Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: A protecting-group economic synthesis of phenolic stilbenes
Schmidt, Bernd,Elizarov, Nelli,Berger, René,H?lter, Frank
, p. 3674 - 3691 (2013/06/27)
4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4′-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior. The Royal Society of Chemistry 2013.
Mechanically activated synthesis of (E)-stilbene derivatives by high-speed ball milling
Zhu, Xingyi,Liu, Jun,Chen, Tao,Su, Weike
experimental part, p. 145 - 147 (2012/05/05)
An efficient mechanically activated solvent-free synthesis of (E)-stilbene derivatives by high-speed ball milling is described. This method has notable advantages in terms of good yield, short reaction time and high selectivity. Copyright
Separation of α-glucosidase-inhibitory and liver X receptor-antagonistic activities of phenethylphenyl phthalimide analogs and generation of LXRα-selective antagonists
Motoshima, Kazunori,Noguchi-Yachide, Tomomi,Sugita, Kazuyuki,Hashimoto, Yuichi,Ishikawa, Minoru
experimental part, p. 5001 - 5014 (2009/12/24)
Liver X receptor (LXR) α/β dual agonists are candidate medicaments for the treatment of metabolic syndrome, because their biological actions include increasing cholesterol efflux mediated by LXRβ. However, their clinical application is currently limited by their enhancing effect on triglyceride (TG) synthesis mediated by LXRα. Combination of an LXRα-selective antagonist with an LXRα/β dual agonist may overcome this disadvantage. In the present work, structural development studies of phenethylphenyl phthalimide 9, which possesses LXRα/β dual-antagonistic activity and α-glucosidase-inhibitory activity, led to the LXRα-selective antagonist 23f. Specific α-glucosidase inhibitors were also obtained.
Substituent effects on the genotoxicity of 4-nitrostilbene derivatives
Hooberman,Brezzell,Das,You,Sinsheimer
, p. 57 - 69 (2007/10/03)
4-Nitrostilbene and twelve of its derivatives (eleven E-stilbenes and two Z-stilbenes) were examined for possible quantitative structure-activity relationships of their in vitro and in vivo genotoxicity. Relative mutagenicity was studied with and without S9 activation in Salmonella strains TA98 and TA100, as well as in the nitroreductase deficient strains TA98/NR and TA100/NR. Chromosomal aberrations in the bone-marrow cells of mice following intraperitoneal administration of the nitrostilbenes were observed as an indicator of in vivo genotoxicity. All of the compounds were active in TA98 and TA100 without S9 activation, with the exception of 4-amino-4'-nitrostilbene in TA100. Mutagenic activity was greatly reduced or eliminated in the NR strains, which is consistent with metabolic activation of the compounds by bacterial reductase. The presence of S9 lowered the activity of most of the nitrostilbenes presumedly by enzymatic detoxication. Hammet values of substituents, partition coefficients and frontier orbital energies (E(LUMO) and E(HOMO)) were studied for correlations with mutagenicity of the eleven E-stilbenes. Correlations could be established between mutagenicity in TA98 without S9 activation and the Hammet values. The same mutagenicity could also be correlated to E(LUMO). Rationales for these correlations include the concept that electron-withdrawing groups which lower E(LUMO) should facilitate the reduction of the nitro group, leading to the proximate mutagen hydroxylamine. The correlations are also explained by the concept that electron-withdrawing groups should help stabilize the hydroxylamine intermediate and make the ultimate mutagenic species, the nitrenium ions, more reactive toward DNA. The relationship between mutagenicity and electronic effects of substituent groups found in vitro could not be extended to the in vivo results. However, except for the dinitrostilbenes, where insolubility prevented their testing, all the nitrostilbenes produced a statistically significant increase in chromosomal aberrations compared to the negative solvent control.
