5779-96-4Relevant academic research and scientific papers
Total Synthesis of Talatisamine
Kamakura, Daiki,Todoroki, Hidenori,Urabe, Daisuke,Hagiwara, Koichi,Inoue, Masayuki
, p. 479 - 486 (2020)
Talatisamine (1) is a member of the C19-diterpenoid alkaloid family, and exhibits K+ channel inhibitory and antiarrhythmic activities. The formidable synthetic challenge that 1 presents is due to its highly oxidized and intricately fused hexacyclic 6/7/5/6/6/5-membered-ring structure (ABCDEF-ring) with 12 contiguous stereocenters. Here we report an efficient synthetic route to 1 by the assembly of two structurally simple fragments, chiral 6/6-membered AE-ring 7 and aromatic 6-membered D-ring 6. AE-ring 7 was constructed from 2-cyclohexenone (8) through fusing an N-ethylpiperidine ring by a double Mannich reaction. After coupling 6 with 7, an oxidative dearomatization/Diels–Alder reaction sequence generated fused pentacycle 4 b. The newly formed 6/6-membered ring system was then stereospecifically reorganized into the 7/5-membered BC-ring of 3 via a Wagner–Meerwein rearrangement. Finally, Hg(OAc)2 induced an oxidative aza-Prins cyclization of 2, thereby forging the remaining 5-membered F-ring. The total synthesis of 1 was thus accomplished by optimizing and orchestrating 33 transformations from 8.
Facile Synthesis of 2-Fluorobenzofurans: 5-endo-trig Cyclization of β,β-Difluoro-o-hydroxystyrenes
Morioka, Ryutaro,Fujita, Takeshi,Ichikawa, Junji
, (2020/10/22)
Efficient synthetic methods were established for obtaining 2-fluorobenzofurans involving various substituents. Upon being treated with 1,8-diazabicyclo[5.4.0]undec-7-ene under microwave irradiation, the α-unsubstituted β,β-difluoro-o-hydroxystyrenes under
Design, synthesis, and evaluation of orally available clioquinol-moracin M hybrids as multitarget-directed ligands for cognitive improvement in a rat model of neurodegeneration in Alzheimer's disease
Wang, Zhiren,Wang, Yali,Wang, Bo,Li, Wenrui,Huang, Ling,Li, Xingshu
, p. 8616 - 8637 (2015/11/25)
A novel series of clioquinol-moracin hybrids were designed and synthesized by fusing the pharmacophores of clioquinol and moracin M, and their activities as multitarget-directed ligands against Alzheimer's disease were evaluated. Biological activity results demonstrated that these hybrids possessed significant inhibitory activities against phosphodiesterase 4D (PDE4D) and Aβ aggregation as well as remarkable antioxidant effects and excellent blood-brain barrier permeability. The optimal compound, 18d (WBQ5187), exhibited excellent PDE4D inhibitory potency (IC50 = 0.32 μM), significant antioxidant effects, appropriate biometal chelating functions, and interesting properties that modulated self- and metal-induced Aβ aggregation. Two-dimensional NMR studies revealed that 18d had significant interactions with Aβ1-42 at the R5, H6, H14, Q15, and F20 residues. Furthermore, this typical hybrid possessed preeminent neuroprotective effects against inflammation in microglial cells. Most importantly, oral administration of 18d·HCl demonstrated marked improvements in cognitive and spatial memory in a rat model of Alzheimer's disease and protected hippocampal neurons from necrosis.
Asymmetric synthesis of bioactive hydrodibenzofuran alkaloids: (-)-lycoramine, (-)-galanthamine, and (+)-lunarine
Chen, Peng,Bao, Xu,Zhang, Le-Fen,Ding, Ming,Han, Xiao-Jie,Li, Jing,Zhang, Guo-Biao,Tu, Yong-Qiang,Fan, Chun-An
supporting information; experimental part, p. 8161 - 8166 (2011/10/18)
Divergent route: A direct C-C bond-forming approach to the key aryl-substituted all-carbon quaternary stereogenic center present in bioactive hydrodibenzofuran alkaloids has been discovered. This approach involves an unprecedented organocatalytic enantioselective Michael addition of α-cyanoketones with acrylates (see scheme) and was used in a novel and divergent synthetic strategy for the title compounds in asymmetric fashion.
NOVEL CURCUMIN DERIVATIVE
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Page/Page column 51, (2009/12/07)
The present invention provides a novel compound that is structurally similar to curcumin and has a suppressive effect on Aβ aggregation, a degradative effect on Aβ aggregates, an inhibitory effect on β-secretase, and a protective effect on neurons. The novel compound is a compound represented by the following general formula (Ia) or a salt thereof: wherein R1 represents a 4-hydroxy-3-methoxyphenyl group or the like, and R2 represents a 1H-indol-6-yl group or the like.
Synthesis of two naturally occurring 3-methyl-2,5-dihydro-1-benzoxepin carboxylic acids
Yamaguchi, Seiji,Tsuchida, Nao,Miyazawa, Masahiro,Hirai, Yoshiro
, p. 7505 - 7511 (2007/10/03)
Two naturally occurring 3-methyl-2,5-dihydro-1-benzoxepin carboxylic acids, 6-hydroxy-3-methyl-8-(phenylethyl)-2,5-dihydro-1-benzoxepin-9-carboxylic acid (radulanin E) (1) and 9-hydroxy-3-methyl-2,5-dihydro-1-benzoxepin-7-carboxylic acid (2), were synthes
Synthesis of (+/-)-cassumunins A and B, new curcuminoid antioxidants having protective activity of the living cell against oxidative damage.
Masuda,Matsumura,Oyama,Takeda,Jitoe,Kida,Hidaka
, p. 609 - 613 (2007/10/03)
A chemical synthesis of cassumunins A (1) and B (2), natural curcuminoid antioxidants, was developed. The synthesis was started from o-vanillin and after nine reaction steps resulted in 20% and 26% overall yields of 1 and 2, respectively. The synthetic ca
Synthesis of lignin models of β-5 type
Li, Shiming,Lundquist, Knut
, p. 1224 - 1228 (2007/10/03)
A β-5 lignin model of the phenylcoumaran type, trans-2-(3,4-dimethoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydrobenzo[b] furan, was prepared by acid-catalysed cyclization of 1-(3,4-dimethoxyphenyl)-2-(2-hydroxy-3-methoxyphenyl)-1,3-propanediol. The cycl
Synthesis and hydrolysis kinetics of 4-cyano-4-phenylpiperidine derivatives: A route to morphine analogs
Gervais,Anker,Chareire,Pacheco
, p. 241 - 248 (2007/10/05)
A description is given of a high-yield synthesis leading to various hydroxy-2 phenylacetonitriles and to various benzodihydro-2,3 furannones-2. The intermediary 12 benzylic mesylates give quantitatively the corresponding 11 chlorides by the action of hydrochlorate of triethylamine; this procedure constitutes a very rewarding and easy method for chlorinating the benzylic alcohols in two stages without isolating the intermediary. A proximate effect has been shown which makes possible the hydrolysis of certain phenylacetonitriles by dilute acetic acid. This hydrolysis becomes very rapid when these nitriles are distributed; the increase of the speed of the hydrolysis illustrates the gem dialkyle effect.
