56041-27-1Relevant 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.
Hydrogen-bonding-promoted oxidative addition and regioselective arylation of olefins with aryl chlorides
Ruan, Jiwu,Iggo, Jonathan A.,Berry, Neil G.,Xiao, Jianliang
supporting information; experimental part, p. 16689 - 16699 (2011/02/23)
The first, general, and highly efficient catalytic system that allows a wide range of activated and unactivated aryl chlorides to couple regioselectively with olefins has been developed. The Heck arylation reaction is likely to be controlled by the oxidative addition of ArCl to Pd(0). Hence, an electron-rich diphosphine, 4-MeO-dppp, was introduced to facilitate the catalysis. Solvent choice is critical, however; only sluggish arylation is observed in DMF or DMSO, whereas the reaction proceeds well in ethylene glycol at 0.1-1 mol % catalyst loadings, displaying excellent regioselectivity. Mechanistic evidence supports that the arylation is turnover-limited by the oxidative addition step and, most importantly, that the oxidative addition is accelerated by ethylene glycol, most likely via hydrogen bonding to the chloride at the transition state as shown by DFT calculations. Ethylene glycol thus plays a double role in the arylation, facilitating oxidative addition and promoting the subsequent dissociation of chloride from Pd(II) to give a cationic Pd(II)-olefin species, which is key to the regioselectivity observed.
Palladium-catalyzed cross-coupling reactions in one-pot multicatalytic processes
Lebel, Helene,Ladjel, Chehla,Brethous, Lise
, p. 13321 - 13326 (2008/09/17)
Palladium-catalyzed cross-coupling reactions have been investigated in multicatalytic processes to synthesize disubstituted alkenes and alkanes from carbonyl derivatives. The use of copper-catalyzed methylenation reactions is the key starting reaction to produce terminal alkenes which are not isolated, but submitted to further structure elongation. Not only is the isolation of the alkene intermediate unnecessary, but also the copper catalyst is a beneficial cocatalyst in the palladium-catalyzed cross-coupling reactions. The desired products are thus typically obtained in higher yields using this one-pot approach. We have used these processes to synthesize hydroxylated (E)-stilbenoids, which are known chemopreventive and chemotherapeutic agents, odorant-substituted indanes, and non-natural amino acids, such as homophenylalanine.
Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues
Aslam, Shazia N.,Stevenson, Philip C.,Phythian, Sara J.,Veitch, Nigel C.,Hall, David R.
, p. 4214 - 4226 (2007/10/03)
Routes were investigated for the synthesis of cicerfuran, a hydroxylated benzofuran from wild chickpea implicated in resistance to Fusarium wilt, and some of its analogues. A novel method is described for the synthesis of oxygenated benzofurans by epoxidation and cyclisation of 2′-hydroxystilbenes. The stilbene intermediates required could be synthesised by palladium-catalysed coupling of styrenes with mono-oxygenated aryl halides but not with di-oxygenated aryl halides. Stilbenes corresponding to the latter were synthesised by Wittig reactions.
A sulfoxide version of the Julia-Lythgoe olefination: A new method for the synthesis of olefins from carbonyl compounds and sulfoxides with carbon-carbon coupling
Satoh, Tsuyoshi,Hanaki, Noriko,Yamada, Noriko,Asano, Tohru
, p. 6223 - 6234 (2007/10/03)
Reaction of β-mesyloxy (or acetoxy) sulfoxides, derived from alkyl (or arylmethyl) phenyl sulfoxides and carbonyl compounds in two steps, with alkylmetals (n-BuLi, t-BuLi, or EtMgBr) at low temperature gave olefins in good to excellent yields. When the β-hydroxy sulfoxides derived from arylaldehydes were treated with mesyl chloride in the presence of triethylamine, the sulfoxides directly gave E-olefins in good yields. These reactions offer a sulfoxide version of the Julia-Lythgoe olefination. The reductive vicinal elimination was found to take place through the direct sulfoxide-metal exchange. The stereochemistry of the elimination was investigated and found to be stereospecific; however, the stereospecificity was found to be dependent on the substrates. (C) 2000 Elsevier Science Ltd.
STILBENES OF GNETUM ULA
Prakash, Satya,Khan, Mushtaq A.,Khan, Khaliquz Zaman,Zaman, Asif
, p. 622 - 624 (2007/10/02)
Key Word Index - Gnetum ula; Gnetaceae; stilbenes; structure; synthesis; structure revision. - Gnetin, a new stilbene isolated from Gnetum ula is assigned the structure 3,4-methylenedioxy-4'methoxy-trans-stilbene, 3 on the basis of spectroscopic data and synthesis.The structure 3,3',4-trihydroxy-2-methoxy-trans-stilbene, 1a earlier assigned to a trihydroxymonomethoxy stilbene is now revised to 3,4,5'-trihydroxy-3'-methoxy-trans-stilbene, 1b.
