- Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions
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Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivatives. Using a differential protecting group strategy, products could be further derivatised. Synthesis of isoquinoline starting materials using several different methods is also described.
- Pearson, Stuart E.,Fillery, Shaun M.,Goldberg, Kristin,Demeritt, Julie E.,Eden, Jonathan,Finlayson, Jonathan,Patel, Anil
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p. 4963 - 4981
(2018/12/13)
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- SMALL MOLECULE ACTIVATORS OF NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE (NAMPT) AND USES THEREOF
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Provided herein are small molecule activators of Nicotinamide Phosphoribosyltransferase (NAMPT), compositions comprising the compounds, and methods of using the compounds and compositions.
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Paragraph 00556
(2018/08/03)
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- Synthesis and radioligand binding studies of C-5- and C-8-substituted 1-(3,4-dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums as SK channel blockers related to N-methyl-laudanosine and N-methyl-noscapine
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The synthesis and the 125I-apamin binding studies of original C-5- and C-8-substituted 1-(3,4-dimethoxy-benzyl)-2,2-dimethyl-1,2,3,4- tetrahydroisoquinoliniums and 1-(3,4-dimethoxy-benzyl)-6,6-dimethyl-4,5,6,7- tetrahydrothieno[2,3-c]pyridiniums were performed in order to find a reversible and selective SK channel blocker structurally related to N-methyl-laudanosine and N-methyl-noscapine. A bulky alkyl substituent in the C-8 position of the tetrahydroisoquinoline produces a clear increase in the affinity for the apamin sensitive binding sites. The presence of an electron-withdrawing group in the C-5 and C-8 positions is not a suitable substitution for the affinity of drugs structurally related to N-methyl-laudanosine. Thiophenic analogues and 8-methoxy derivatives possess a poor affinity for the apamin sensitive binding sites. Electrophysiological studies performed with the most effective compound showed a blockade of the apamin sensitive afterhyperpolarization in rat dopaminergic neurons.
- Graulich, Amaury,Scuvée-Moreau, Jacqueline,Seutin, Vincent,Liégeois, Jean-Fran?ois
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p. 4972 - 4982
(2007/10/03)
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- 8,8′-Dialkyl-1,1′-biisoquinolines: Preparation, absolute configuration and unexpected racemization behaviour
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A series of 8,8′-dialkyl-1,1′-biisoquinolines, in which methyl, ethyl and isopropyl groups are introduced for enhancing the transannular steric hindrance, are synthesized. The atropisomeric biisoquinolines are separated into both enantiomers, of which the absolute configurations and the optical stabilities are determined. Contrary to prior expectations, the racemization behaviour is inversely proportional to the steric size of the alkyl groups. The Royal Society of Chemistry 1999.
- Tsue, Hirohito,Fujinami, Hideyuki,Itakura, Takeshi,Tsuchiya, Ryuta,Kobayashi, Kimiko,Takahashi, Hiroki,Hirao, Ken-Ichi
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p. 3677 - 3683
(2007/10/03)
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- Synthesis and resolution of 1,1-bi-8-methylisoquinoline: Formation of an optically active complex with high chiral recognition
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The synthesis and resolution of 1,1-bi-8-methylisoquinoline (±)-5 is reported. An optically active palladium complex with high chiral recognition was formed during the complexation between a chiral palladium complex and the two enantiomers of (±)-5. The free energy barrier ΔGF(≠) for interconversion of enantiomers was estimated to be 97,2 KJ/mol at 40°C.
- Chelucci, Giorgio,Cabras, M. Antonietta,Saba, Antonio,Sechi, Alessandra
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p. 1027 - 1032
(2007/10/03)
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- Preparation of optically active 8,8′-disubstituted 1,1′-biisoquinoline
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Synthesis of 1,1′-biisoquinolines having substituents in the 8,8′-positions and their resolution by hplc on a chiral column on a preparative scale are described.
- Hirao, Ken-Ichi,Tsuchiya, Ryuta,Yano, Yasuhiro,Tsue, Hirohito
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p. 415 - 422
(2007/10/02)
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- Synthesis of Isoquinolines from Indenes
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A general procedure for the synthesis of isoquinolines from appropriately substituted indenes is described.Ozonolysis of the indenes followed by reductive workup gives intermediate homophthalaldehydes which are treated with ammonium hydroxide to give the isoquinolines.This "one-pot", three-step reaction sequence was applied to the formation of all of the mono-C-methyl-substituted isoquinolines in a regiospecific manner.The procedure is applicable to both electron-withdrawing and electron-donating substituents on the indene system.In this manner the 6- and 7-nitro-,-bromo-, and -iodoisoquinolines were prepared.
- Miller, R. Bryan,Frincke, James M.
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p. 5312 - 5315
(2007/10/02)
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