methyl 1-(cyanomethyl)-1H-indole-2-carboxylate | 1174914-87-4

• 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)-1H-indole-2-carboxylate
• 英文别名: Methyl 1-(cyanomethyl)indole-2-carboxylate
• CAS: 1174914-87-4
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: UBPOJAAWJZMIPB-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C(Solv: methanol (67-56-1))
• 沸点：
  401.0±25.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-(cyanomethyl)-1H-indole-2-carboxylate 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 氨 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、2.5 kPa 条件下， 反应 25.33h， 以76%的产率得到3,4-二氢吡嗪并[1,2-a]吲哚-1(2h)-酮
  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：

  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85%的产率得到methyl 1-(cyanomethyl)-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

• PYRAZINO(AZA)INDOLE DERIVATIVES
  申请人：VERNALIS RESEARCH LIMITED

  公开号：EP1147110A1

  公开（公告）日：2001-10-24
• [EN] PIRAZINO(AZA)INDOLE DERIVATIVES<br/>[FR] DERIVES DE PIRAZINO(AZA)INDOLE
  申请人：VERNALIS RESEARCH LIMITED

  公开号：WO2000044753A1

  公开（公告）日：2000-08-03

  A chemical compound of formula (I) wherein: R1 to R3 are independently selected from hydrogen and lower alkyl; X1 is selected from N and C-R4; X2 is selected from N and C-R5; X3 is selected from N and C-R6; X4 is selected from N and C-R7; R4, R5 and R7 are independently selected from hydrogen, halogen, hydroxy, alkyl, aryl, alkoxy, aryloxy, alkoyl, aryloyl, arylthio, alkylthio, arylthio, alkylsulfoxyl, arylsulfoxyl, alkylsulfonyl, arylsulfonyl, amino, alkylamino, dialkylamino, nitro, cyano, carboalkoxy, carboaryloxy and carboxy; and R6 is selected from hydrogen, halogen, alkyl, aryl, aryloxy, alkylthio, arylthio, alkylsulfoxyl, arylsulfoxyl, alkylsulfonyl, arylsulfonyl, amino, alkylamino, dialkylamino and cyano; with the proviso that R4 to R7 are not all selected as hydrogen, and pharmaceutically acceptable salts and addition compounds and prodrugs thereof; use thereof in therapy, particularly for the treatment of disorders of the central nervous system; damage to the central nervous system; cardiovascular disorders; gastrointestinal disorders; diabetes inspidus, and sleep apnea, and especially for the treatment of therapy.
• 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.