- Synthesis of Aporphine Analogues via Palladium-Catalyzed Intramolecular Aryl-Aryl Dehydrogenative Coupling
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Reported herein is an intramolecular dehydrogenative coupling of two inert aryl C-H bonds for the synthesis of aporphine analogues. The process represents a novel tool for the preparation of aporphines via palladiun-catalyzed C-H bond activation. The present reaction is compatible with various functional groups, and the coupling products have been further applied for the synthesis of natural products aporphine and zenkerine.
- Su, Chen,Xu, Wen-Hua,Guo, Rui-Li,Zhang, Xing-Long,Zhu, Xue-Qing,Gao, Ya-Ru,Wang, Yong-Qiang
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p. 13618 - 13630
(2021/09/28)
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- A convenient formation of aporphine core via benzyne chemistry: Conformational analysis and synthesis of (R)-aporphine
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Total synthesis of (R)-aporphine has been accomplished by an approach that employs in the key step a sequence of transformations involving a [4+2] cycloaddition reaction followed by a hydrogen migration, leading to aporphine core in good yield, which was subjected to a 1D gradient NOE experiment, conformational analysis, and simple transformations, including a small scale resolution process, to afford enantiomerically enriched aporphine alkaloid.
- Perecim, Givago P.,Rodrigues, Alessandro,Raminelli, Cristiano
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p. 6848 - 6851
(2015/11/27)
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- Phenanthrene derivatives for use as medicaments
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Phenanthrene derivatives of formula I for use as medicaments. The present invention refers to phenanthrene derivatives for use as medicaments, mainly in the prevention and/or treatment of DM1, HDL2, SCA8, DM2, SCA3, FXTAS, FTD/ALS, and SCA31. In a preferred embodiment, phenanthrene derivatives of the invention are also used as antimyotonic agents.
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Page/Page column
(2014/07/07)
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- Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells
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Methanolic extracts from the flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) were found to show inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extracts, a new alkaloid, N-methylasimilobine N-oxide, was isolated together with eleven benzylisoquinoline alkaloids. The absolute stereostructure of the new alkaloid was determined from chemical and physicochemical evidence. Among the constituents isolated, nuciferine, N-methylasimilobine, (-)-lirinidine, and 2-hydroxy-1-methoxy-6a,7-dehydroaporphine showed potent inhibition of melanogenesis. Comparison of the inhibitory activities of synthetic related alkaloids facilitated characterization of the structure-activity relationships of aporphine- and benzylisoquinoline-type alkaloids. In addition, 3-30 μM nuciferine and N-methylasimilobine inhibited the expression of tyrosinase mRNA, 3-30 μM N-methylasimilobine inhibited the expression of TRP-1 mRNA, and 10-30 μM nuciferine inhibited the expression of TRP-2 mRNA.
- Nakamura, Seikou,Nakashima, Souichi,Tanabe, Genzo,Oda, Yoshimi,Yokota, Nami,Fujimoto, Katsuyoshi,Matsumoto, Takahiro,Sakuma, Rika,Ohta, Tomoe,Ogawa, Keiko,Nishida, Shino,Miki, Hisako,Matsuda, Hisashi,Muraoka, Osamu,Yoshikawa, Masayuki
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p. 779 - 787
(2013/02/25)
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- Synthesis of (±)-aporphine utilizing Pictet-Spengler and intramolecular phenol ortho-arylation reactions
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A synthesis of the alkaloid (±)-aporphine is reported. The initial key step of the synthesis involves a Pictet-Spengler cyclization of N-tosyl tyramine with 2-bromophenylacetaldehyde in trifluoroacetic acid. This step was followed by the second strategic
- Cuny, Gregory D.
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p. 5167 - 5170
(2007/10/03)
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- Preparation and Pharmacological Evaluation of Enantiomers of Certain Nonoxygenated Aporphines: (+)- and (-)-Aporphine and (+)- and (-)-10-Methylaporphine
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The subject compounds were prepared as a part of a continuing structure-activity study of the contrasting actions (agonism-antagonism) of (+)- and (-)-11-hydroxy-10-methylaporphine at serotonin (5-HT1A) receptors. None of the targeted nonoxygen
- Cannon, Joseph G.,Raghupathi, Revathi,Moe, Scott T.,Johnson, Alan K.,Long, John Paul
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p. 1316 - 1318
(2007/10/02)
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