3-(1,3-Benzodioxol-5-yl)-6,7-dimethoxy-1-methylisoquinoline;hydrochloride | 1099739-01-1

• 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-(1,3-Benzodioxol-5-yl)-6,7-dimethoxy-1-methylisoquinoline;hydrochloride
• CAS: 1099739-01-1
• 化学式: C₁₉H₁₇NO₄*ClH
• 分子量: 359.809
• InChiKey: BSCSESXCGATPJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(1,3-Benzodioxol-5-yl)-6,7-dimethoxy-1-methylisoquinoline;hydrochloride 在 三氯化硼 、 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 4-(6,7-Dimethoxy-1-methylisoquinolin-3-yl)benzene-1,2-diol hydrochloride
  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：

  6,7-dimethoxy-1-methylisoquinolin-3-yl trifluoromethanesulfonate 、 3.4-(亚甲基二氧基)苯硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 生成 3-(1,3-Benzodioxol-5-yl)-6,7-dimethoxy-1-methylisoquinoline;hydrochloride
  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）。
• 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.