880354-47-2Relevant articles and documents
Tandem pericyclic reactions in a new FeCl3-promoted synthesis of catechol analogues of restrytisol C
Thomas,Lee,Paraidathathu, Thomas,Weber,Awang,Rondeau,Richomme
, p. 7201 - 7206 (2002)
The uncommon stilbene, 3,4-dimethoxy-12-acetoxy stilbene, has been synthesised by Heck coupling methodology in three steps. Treatment of this stilbene with ferric chloride in dichloromethane (room temperature) gave the unnatural stilbenoid dimers; 8,8′-(12,12′-bisacetoxyphenyl)-7′-(3′,4′- dimethoxyphenyl)-3,4-dimethoxy-7′,8′-dihydro-naphthalene and 8-(12-acetoxyphenyl)-8′-(12′-hydroxyphenyl)-7′-(3′, 4′-dimethoxyphenyl)-3,4-dimethoxy-7′,8′-dihydro- naphthalene. The structures of both stilbene dimers were unambiguously confirmed by 1D (1H, 13C) and 2D NMR experiments (COSY, HMQC, HMBC and NOESY). This is the first report of a FeCl3-promoted sequential pericyclic pathway leading to a highly oxygenated oligostilbenoid dimer (incorporating two asymmetric centres). The NMR spectroscopic evidence and a mechanistic interpretation consistent with these structures are discussed.
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.
Heck arylation of styrenes with arenediazonium salts: short, efficient, and stereoselective synthesis of resveratrol, DMU-212, and analogues
Moro, Angélica Venturini,Cardoso, Flávio Sega P.,Correia, Carlos Roque D.
, p. 5668 - 5671 (2008/12/22)
Short, efficient, and stereoselective synthesis of the trans-stilbenes resveratrol, DMU-212, and analogues of both compounds are described. The synthesis of these important anti-cancer agents feature the palladium catalyzed Heck-Matsuda arylation of styre
