1-benzyl-2-hydroxymethyl-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole | 438624-01-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-benzyl-2-hydroxymethyl-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole
• 英文别名: (1-Benzyl-4-methoxy-6,7,8,9-tetrahydrobenzo[g]indol-2-yl)methanol
• CAS: 438624-01-2
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: JASPBLYKYNSJJA-UHFFFAOYSA-N

物化性质

• 熔点：
  115-125 °C(Solvent: Dichloromethane; Hexane)
• 沸点：
  560.1±50.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-2-hydroxymethyl-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole 在 sodium hydride 、 二硫化碳 、 碘甲烷 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 23.25h， 以79%的产率得到1-benzyl-2-methyl-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole
  参考文献：
  名称：

  Carbocyclic[g]indole Inhibitors of Human Nonpancreatic s-PLA₂

  摘要：

  A vinyl azide cyclization method was used to synthesize three different carbocyclic[g]indole scaffolds as inhibitors of human nonpancreatic secretory phospholipase A(2). Each scaffold demonstrated potent enzyme activity in a chromogenic assay system, with select examples also demonstrating potent activity in a secondary DOC/PC assay. Compound 11, representative of the cyclopent[g]indole series, gave an IC50 of 10 nM for the inhibition of hnps-PLA(2) in the chromogenic assay.

  DOI：

  10.1021/jm0401309
• 作为产物：
  描述：

  2-carboethoxy-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.0h， 生成 1-benzyl-2-hydroxymethyl-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole
  参考文献：
  名称：

  Carbocyclic[g]indole Inhibitors of Human Nonpancreatic s-PLA₂

  摘要：

  A vinyl azide cyclization method was used to synthesize three different carbocyclic[g]indole scaffolds as inhibitors of human nonpancreatic secretory phospholipase A(2). Each scaffold demonstrated potent enzyme activity in a chromogenic assay system, with select examples also demonstrating potent activity in a secondary DOC/PC assay. Compound 11, representative of the cyclopent[g]indole series, gave an IC50 of 10 nM for the inhibition of hnps-PLA(2) in the chromogenic assay.

  DOI：

  10.1021/jm0401309

文献信息

• Novel spla2 inhibitors
  申请人：——

  公开号：US20040077704A1

  公开（公告）日：2004-04-22

  A novel class of cycloalkyl fused indole compounds is disclosed together with the use of such compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of Inflammatory Diseases such as septic shock.

  揭示了一类新型的环烷基融合吲哚化合物，以及利用这些化合物抑制sPLA2介导的脂肪酸释放，用于治疗炎症性疾病，如感染性休克。
• US6974831B2
  申请人：——

  公开号：US6974831B2

  公开（公告）日：2005-12-13
• Carbocyclic[<i>g</i>]indole Inhibitors of Human Nonpancreatic s-PLA₂
  作者：J. Scott Sawyer、Douglas W. Beight、Edward C. R. Smith、David W. Snyder、Marcia K. Chastain、Richard L. Tielking、Lawrence W. Hartley、Donald G. Carlson

  DOI：10.1021/jm0401309

  日期：2005.2.1

  A vinyl azide cyclization method was used to synthesize three different carbocyclic[g]indole scaffolds as inhibitors of human nonpancreatic secretory phospholipase A(2). Each scaffold demonstrated potent enzyme activity in a chromogenic assay system, with select examples also demonstrating potent activity in a secondary DOC/PC assay. Compound 11, representative of the cyclopent[g]indole series, gave an IC50 of 10 nM for the inhibition of hnps-PLA(2) in the chromogenic assay.