3-(Benzo[d][1,3]dioxol-5-yl)-6,7-dimethoxy-1,2-dimethylisoquinolinium chloride | 1099739-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-(Benzo[d][1,3]dioxol-5-yl)-6,7-dimethoxy-1,2-dimethylisoquinolinium chloride
• 英文别名: 3-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-1,2-dimethylisoquinolin-2-ium;chloride
• CAS: 1099739-04-4
• 化学式: C₂₀H₂₀NO₄*Cl
• 分子量: 373.836
• InChiKey: PNQDYEVBMUVODV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(Benzo[d][1,3]dioxol-5-yl)-6,7-dimethoxy-1,2-dimethylisoquinolinium chloride 在 三溴化硼 、 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 3-(3,4-Dihydroxyphenyl)-1,2-dimethylisoquinolin-2-ium-6,7-diol;chloride
  参考文献：
  名称：

  Structure–activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding

  摘要：

  The synthesis of a series of berberine, phenantridine and isoquinoline derivatives was realized to explore their Rho GTPase nucleotide inhibitory activity. The compounds were evaluated in a nucleotide binding competition assay against Rac1, Rac1b, Cdc42 and in a cellular Rac GTPase activation assay. The insertion of 19 AA in the splice variant Rac1b is shown to be sufficient to introduce a conformational difference that allows compounds 4, 21, 22, and 26 to exhibit selective inhibition of Rac 1b over Rac1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.037
• 作为产物：
  描述：

  3-(1,3-Benzodioxol-5-yl)-6,7-dimethoxy-1-methylisoquinoline;hydrochloride 、 碘甲烷 在 Amberlite Cl 作用下， 以 乙腈 为溶剂， 生成 3-(Benzo[d][1,3]dioxol-5-yl)-6,7-dimethoxy-1,2-dimethylisoquinolinium chloride
  参考文献：
  名称：

  Structure–activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding

  摘要：

  The synthesis of a series of berberine, phenantridine and isoquinoline derivatives was realized to explore their Rho GTPase nucleotide inhibitory activity. The compounds were evaluated in a nucleotide binding competition assay against Rac1, Rac1b, Cdc42 and in a cellular Rac GTPase activation assay. The insertion of 19 AA in the splice variant Rac1b is shown to be sufficient to introduce a conformational difference that allows compounds 4, 21, 22, and 26 to exhibit selective inhibition of Rac 1b over Rac1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.037

文献信息

• COMPOUNDS AND METHODS FOR MODULATING RHO GTPASES
  申请人：Leblond Bertrand

  公开号：US20100120810A1

  公开（公告）日：2010-05-13

  The present invention relates to methods and compositions that affect the GTP-binding activity of members of the Rho family GTPases, preferably Rac GTPases (Rac1, Rac1b, Rac2 and/or Rac3).

  本发明涉及影响Rho家族GTP酶成员的GTP结合活性的方法和组合物，优选是Rac GTP酶（Rac1，Rac1b，Rac2和/或Rac3）。
• [EN] COMPOUNDS AND METHODS FOR MODULATING RHO GTPASES<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR MODULER LES GTPASES RHO
  申请人：EXONHIT THERAPEUTICS SA

  公开号：WO2009007457A2

  公开（公告）日：2009-01-15

  The present invention relates to methods and compositions that affect the GTP-binding activity of members of the Rho family GTPases, preferably Rac GTPases (Rac1, Rac1b, Rac2 and/or Rac3).
• Structure–activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding
  作者：Eric Beausoleil、Cédric Chauvignac、Thierry Taverne、Sandrine Lacombe、Laure Pognante、Bertrand Leblond、Diego Pallares、Catherine De Oliveira、Florence Bachelot、Rachel Carton、Hélène Peillon、Séverine Coutadeur、Virginie Picard、Nathalie Lambeng、Laurent Désiré、Fabien Schweighoffer

  DOI：10.1016/j.bmcl.2009.08.037

  日期：2009.10

  The synthesis of a series of berberine, phenantridine and isoquinoline derivatives was realized to explore their Rho GTPase nucleotide inhibitory activity. The compounds were evaluated in a nucleotide binding competition assay against Rac1, Rac1b, Cdc42 and in a cellular Rac GTPase activation assay. The insertion of 19 AA in the splice variant Rac1b is shown to be sufficient to introduce a conformational difference that allows compounds 4, 21, 22, and 26 to exhibit selective inhibition of Rac 1b over Rac1. (C) 2009 Elsevier Ltd. All rights reserved.