7630-74-2Relevant academic research and scientific papers
THREE BIS-DEHYDROAPORPHINES FROM OXANDRA CF. MAJOR
Arango, Gabriel,Cortes, Diego,Cave, Andre
, p. 1227 - 1229 (1987)
The structures of urabaine, N-methylurabaine and N,N'-dimethylurabaine, three new 7,7'-bis-dehydroaporphine alkaloids from Oxandra cf. major, have been elucidated by spectroscopic analysis and synthesis. - Key Word Index: Oxandra cf. major; Annonaceae; 7,7'-bisdehydroaporphine alkaloids; urabaine.
Total Syntheses of Aporphine Alkaloids via Benzyne Chemistry: An Approach to the Formation of Aporphine Cores
Rossini, Allan F. C.,Muraca, Ana Carolina A.,Casagrande, Gleison A.,Raminelli, Cristiano
, p. 10033 - 10040 (2015/11/03)
Total syntheses of lysicamine, (±)-nuciferine, (±)-nornuciferine, (±)-zanthoxyphylline iodide, (±)-O-methylisothebaine, and (±)-trimethoxynoraporphine were accomplished by an approach that involves the formation of aporphine cores through reactions betwee
Synthesis and structure-Activity relationship of nuciferine derivatives as potential acetylcholinesterase inhibitors
Yang, Zhongduo,Song, Zhuwen,Xue, Weiwei,Sheng, Jie,Shu, Zongmei,Shi, Yin,Liang, Jibei,Yao, Xiaojun
, p. 3178 - 3186 (2014/05/06)
Acetylcholinesterase inhibitors (AChEIs) are currently the best available pharmacotherapy for Alzheimer patients, but because of bioavailability issues, there is still great interest in discovering better AChEIs. The aporphine alkaloid is an important class of natural products, which shows diverse biological activity, such as acetylcholinesterase inhibitory activity. To find new lead AChEIs compounds, eight aporphine alkaloids were synthesized by O-dealkylation, N-dealkylation, and ring aromatization reactions using nuciferine as raw material. The anti-Acetylcholinesterase activity of synthesized compounds was measured using modified Ellman's method. The results showed that some synthesized compounds exhibited higher affinity to AChE than the parent compound nuciferine. Among these compounds, 1,2-dihydroxyaporphine (2) and dehydronuciferine (5) were the most active compounds (IC50 = 28 and 25 μg/mL, respectively). Preliminary analysis of structure-Activity relationships suggested that aromatization of the C ring, the presence of the alkoxyl group at C1 and the hydroxy group at C2 position as well as the alkyl substituent at the N atom were favorable to the acetylcholinesterase inhibition. Molecular docking was also applied to predict the binding modes of compounds 1, 2, and 9 into the huperzine A binding site of AChE.
The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids
Suau,Rico,Nájera,Ortiz-López,López-Romero,Moreno-Ma?as,Roglans
, p. 5725 - 5735 (2007/10/03)
We report a flexible approach to the total synthesis of 4,5-dioxoaporphines based on the palladium(0) catalyzed Suzuki cross-coupling of phenylboronic acids with sterically hindered 2-bromo phenyl acetates or bromo phenyl acetamides, followed by sequential bicyclization of biarylacetamides promoted by oxalyl chloride/Lewis acid. The reduction of 4,5-dioxoaporphines provides a chemoselective entry to aporphines, dehydroaporphines and 4-hydroxy- dehydroaporphines. A three-steps total synthesis for (±)-O,O′- dimethylapomorphine from readily accessible precursors is also reported.
