111492-84-3Relevant academic research and scientific papers
Design, synthesis, and biological evaluation of novel (1-thioxo-1,2,3,4- tetrahydro-β-carbolin-9-yl)acetic acids as selective inhibitors for AKR1B1
Minehira, Daisuke,Takeda, Daisuke,Urata, Hirokazu,Kato, Atsushi,Adachi, Isao,Wang, Xu,Matsuya, Yuji,Sugimoto, Kenji,Takemura, Mayuko,Endo, Satoshi,Matsunaga, Toshiyuki,Hara, Akira,Koseki, Jun,Narukawa, Kayo,Hirono, Shuichi,Toyooka, Naoki
, p. 356 - 367 (2012/03/09)
New substituted (1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acids were designed as the inhibitor of AKR1B1 based upon the structure of rhetsinine, a minor alkaloidal component of Evodia rutaecarpa, and twenty derivatives were synthesized and evaluated. The most active compound of the series was (2-benzyl-6-methoxy-1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl) acetic acid (7m), which showed comparable inhibitory activity for AKR1B1 (IC50 = 0.15 μM) with clinically used epalrestat (IC50 = 0.1 μM). In the view of activity and selectivity, the most potent compound was (2-benzyl-6-carboxy-1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acid (7t), which showed strong inhibitory effect (IC50 = 0.17 μM) and very high selectivity for AKR1B1 against AKR1A1 (311:1) and AKR1B10 (253:1) compared with epalrestat.
FUSED TRICYCLIC COMPOUND HAVING ALDOSE REDUCTASE INHIBITORY ACTIVITY
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Page/Page column 15-16, (2010/05/13)
A fused tricyclic compound having aldose reductase inhibitory activity and shown by the following formula, wherein R1 independently represents 1 to 3 atoms or substituents selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl, cycloalkyl, alkylene, or alkoxy group, and a protected or unprotected hydroxyl or carboxyl group, R2 represents a protected or unprotected carboxyl group, R3 independently represents 1 or 2 atoms or substituents selected from a hydrogen atom, a halogen atom, an oxo group, a substituted or unsubstituted alkyl or alkoxy group, and a protected or unprotected carboxyl group, A represents an alkylene group, and B represents an oxygen atom, a sulfur atom, or a group shown by the following formula, wherein R4 represents an alkyl or aryl group substituted with an aryl, cycloalkyl, or heterocyclic group, and X represents an oxygen atom or a sulfur atom.
Indoles X: Synthesis, structure and D2-affinity of the β-carboline-analogue of flutroline
Lehmann,Knoch,Jiang
, p. 947 - 951 (2007/10/02)
10 is a β-carboline analogue of the neuroleptic flutroline(2a,b)) with significant lower affinity at the dopamine D2 binding site. Various synthetic routes to 10 and the solid state structure of 8 are described, structure activity relations, in particular the importance of the 'S-shape' and the rigid dopamine conformation are discussed.
Synthesis and Serotonin-Receptor Activity of Substituted 1-Oxo-1,2,3,4-tetrahydro-&β-carbolines
Herdeis, Claus,Bissinger, Gerhard
, p. 785 - 790 (2007/10/02)
2,3-Dihydroxypyridine is used as a starting material for the synthesis of donor and acceptor substituted 1-oxo-1,2,3,4-tetrahydro-β-carbolines via Fisher indole cyclisation.An alkaloid from Alstonia venenata is prepared.All compounds inclusive strychnocarpine show low affinity to the serotonine receptor. - Key words: 3-Hydroxy-2-pyridone, Strychnocarpine Derivatives, 5-Hydroxytryptamine Receptor Stimulators
