methyl 1-(cyanomethyl)-5-methoxy-1H-indole-2-carboxylate | 1134113-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 1-(cyanomethyl)-5-methoxy-1H-indole-2-carboxylate
• 英文别名: Methyl 1-(cyanomethyl)-5-methoxyindole-2-carboxylate
• CAS: 1134113-07-7
• 化学式: C₁₃H₁₂N₂O₃
• 分子量: 244.25
• InChiKey: XPANZIOKGASOBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-(cyanomethyl)-5-methoxy-1H-indole-2-carboxylate 在 sodium tetrahydroborate 、 cobalt(II) chloride 、 盐酸 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 以60%的产率得到8-methoxy-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 1,2,3,4-tetrahydropyrazino[1,2-a]indole and 2-[(phenylmethylamino)methyl]-1H-indole analogues as novel melatoninergic ligands

  摘要：

  Two novel series of melatonin-derived compounds have been synthesized and pharmacologically evaluated at the MT1 and MT2 subtypes of melatonin receptors. Compounds 12b-c are non-selective high-affinity MT1 and MT2 receptor ligands (K-i = 7-11 nM). Compound 12b had little intrinsic activity at the MT1 receptor and no intrinsic activity at the MT2 receptor. Compound 20d displayed the highest MT2 binding affinity (K-i = 2 nM) and moderate selectivity toward the MT2 subtype (K-i MT1/MT2 ratio = 8) behaving as MT2 antagonist and MT1 agonist (IC50 = 112 pM). The findings help define SARs around the positions 1 and 2 of melatonin with respect to binding affinity, MT2 selectivity, and intrinsic activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.068
• 作为产物：
  描述：

  5-甲氧基吲哚-2-羧酸甲酯 、 氯乙腈 在 potassium tert-butylate 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 、 水 、 乙酸乙酯 为溶剂， 反应 0.67h， 以83%的产率得到methyl 1-(cyanomethyl)-5-methoxy-1H-indole-2-carboxylate
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 1,2,3,4-tetrahydropyrazino[1,2-a]indole and 2-[(phenylmethylamino)methyl]-1H-indole analogues as novel melatoninergic ligands

  摘要：

  Two novel series of melatonin-derived compounds have been synthesized and pharmacologically evaluated at the MT1 and MT2 subtypes of melatonin receptors. Compounds 12b-c are non-selective high-affinity MT1 and MT2 receptor ligands (K-i = 7-11 nM). Compound 12b had little intrinsic activity at the MT1 receptor and no intrinsic activity at the MT2 receptor. Compound 20d displayed the highest MT2 binding affinity (K-i = 2 nM) and moderate selectivity toward the MT2 subtype (K-i MT1/MT2 ratio = 8) behaving as MT2 antagonist and MT1 agonist (IC50 = 112 pM). The findings help define SARs around the positions 1 and 2 of melatonin with respect to binding affinity, MT2 selectivity, and intrinsic activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.068

文献信息

• COMPOUNDS AND COMPOSITIONS AS MODULATORS OF GPR119 ACTIVITY
  申请人：Alper Phillip B.

  公开号：US20090270409A1

  公开（公告）日：2009-10-29

  The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of GPR119.

  本发明提供了化合物、包含此类化合物的药物组合物以及使用此类化合物治疗或预防与GPR119活性相关的疾病或疾病的方法。
• US8153635B2
  申请人：——

  公开号：US8153635B2

  公开（公告）日：2012-04-10
• US8258156B2
  申请人：——

  公开号：US8258156B2

  公开（公告）日：2012-09-04
• Synthesis and pharmacological evaluation of 1,2,3,4-tetrahydropyrazino[1,2-a]indole and 2-[(phenylmethylamino)methyl]-1H-indole analogues as novel melatoninergic ligands
  作者：Christian Markl、Mohamed I. Attia、Justin Julius、Shalini Sethi、Paula A. Witt-Enderby、Darius P. Zlotos

  DOI：10.1016/j.bmc.2009.04.068

  日期：2009.7

  Two novel series of melatonin-derived compounds have been synthesized and pharmacologically evaluated at the MT1 and MT2 subtypes of melatonin receptors. Compounds 12b-c are non-selective high-affinity MT1 and MT2 receptor ligands (K-i = 7-11 nM). Compound 12b had little intrinsic activity at the MT1 receptor and no intrinsic activity at the MT2 receptor. Compound 20d displayed the highest MT2 binding affinity (K-i = 2 nM) and moderate selectivity toward the MT2 subtype (K-i MT1/MT2 ratio = 8) behaving as MT2 antagonist and MT1 agonist (IC50 = 112 pM). The findings help define SARs around the positions 1 and 2 of melatonin with respect to binding affinity, MT2 selectivity, and intrinsic activity. (C) 2009 Elsevier Ltd. All rights reserved.