Syntheses of tetrahydroisoquinoline derivatives that inhibit NO production in activated BV-2 microglial cells
作者:Jai Woong Seo、Ekaruth Srisook、Hyo Jin Son、Onyou Hwang、Young-Nam Cha、Dae Yoon Chi
DOI:10.1016/j.ejmech.2007.09.009
日期:2008.6
Seventeen tetrahydroisoquinolinederivatives were designed, synthesized and evaluated for inhibition of NO production in lipopolysaccharide-stimulated BV-2 microglial cells. Compounds 5a, 9c and 11a potently attenuated NO production by >60%, and 5a and 11a inhibited BH4 production by >48% at 100 microM. In particular, N-ethylcarbonyl-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline (11a) reduced
1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES HAVING EFFECTS OF PREVENTING AND TREATING DEGENERATIVE AND INFLAMMATORY DISEASES
申请人:Hwang On-You
公开号:US20100217003A1
公开(公告)日:2010-08-26
Provided are 7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline derivatives and synthesis methods thereof. The compounds significantly inhibit the production of nitrogen monoxide (NO) and superoxide in an activated microglial cell and expressions of TNF-α, IL-1β inducive NO synthase and cyclooxygenase-2 genes. They also prevent NF-kB shift to a nucleus, decrease reactive oxygen species (ROS), inhibit expression of GTP cyclohydrolase I gene and over-production of tetrahydrobiopterin (BH
4
), and protect dopaminergic neurons from injury due to activated microglial cells. Consequently, the compounds are effective in treating inflammatory and neurodegenerative diseases.
Syntheses of Aporphine and Homoaporphine Alkaloids by Intramolecular <i>ortho</i>-Arylation of Phenols with Aryl Halides via S<sub>RN</sub>1 Reactions in Liquid Ammonia
作者:Silvia M. Barolo、Xin Teng、Gregory D. Cuny、Roberto A. Rossi
DOI:10.1021/jo061478+
日期:2006.10.1
The photostimulated intramolecular ortho-arylation reactions of bromoarenes linked with pendant phenoxy containing N-substituted tetrahydroisoquinolines in liquidammonia afforded aporphine (54−82% yield) alkaloid derivatives via SRN1reactions. This strategy was extended for the first time to the synthesis of a homoaporphine derivative (40% yield). Tetrahydroisoquinoline precursors that contained
[EN] 1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES HAVING EFFECTS OF PREVENTING AND TREATING DEGENERATIVE AND INFLAMMATORY DISEASES<br/>[FR] DÉRIVÉS DE 1,2,3,4-TÉTRAHYDROISOQUINOLINE POSSÉDANT DES EFFETS DE PRÉVENTION ET DE TRAITEMENT DE MALADIE DÉGÉNÉRATIVES OU INFLAMMATOIRES
申请人:UNIV ULSAN FOUND FOR IND COOP
公开号:WO2008069632A1
公开(公告)日:2008-06-12
[EN] Provided are 7-hydroxy-6-methoxy-l,2,3,4-tetrahydroisoquinoline derivatives and synthesis methods thereof. The compounds significantly inhibit the production of nitrogen monoxide (NO) and superoxide in an activated microglial cell and expressions of TNF-a, IL- lß inducive NO synthase and cyclooxygenase-2 genes. They also prevent NF-kB shift to a nucleus, decrease reactive oxygen species (ROS), inhibit expression of GTP cyclohydrolase I gene and over-production of tetrahydrobiopterin (BH 4 ), and protect dopaminergic neurons from injury due to activated microglial cells. Consequently, the compounds are effective in treating inflammatory and neurodegenerative diseases. [FR] L'invention concerne des dérivés de 1,2,3,4-tétrahydroisoquinoline et des procédés de leur synthèse. Les composés inhibent sensiblement la production de monoxyde d'azote (NO) et de superoxyde dans une cellule microgliale et les expressions de gènes TNF-a, NO synthase inductrice d'IL- lß et cyclooxygenase-2. Ils empêchent également le décalage de NF-kB vers un noyau, réduisent les espèces d'oxygène réactives (ERO), inhibent l'expression du gène de GTP cyclohydrolase et la surproduction de tétrahydrobioptérine (BH 4 ). Ils protènes les neurones dopaminergiques contre les lésions grâce aux cellules microgliales activées. Par conséquent, les composés sont efficaces pour traiter des maldies inflammatoires ou neurogénératives.