1-n-propylpyrrole-3-carboxaldehyde | 128600-69-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-n-propylpyrrole-3-carboxaldehyde
• 英文别名: 1-propyl-1H-pyrrole-3-carbaldehyde；1-propylpyrrole-3-carbaldehyde
• CAS: 128600-69-1
• 化学式: C₈H₁₁NO
• mdl: MFCD21766311
• 分子量: 137.181
• InChiKey: LZILQGJJPDKITG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-n-propylpyrrole-3-carboxaldehyde 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (+/-)-1-(1-n-propylpyrrol-3-yl)-2-aminopropane
  参考文献：
  名称：

  Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region

  摘要：

  Taking advantage of a proposed hydrophobic region on 5-HT2 receptors previously identified by radioligand-binding studies utilizing various phenylisopropylamine derivatives, we prepared and evaluated several N1 - and/or C7-alkyl-substituted derivatives of alpha-methyltryptamine in order to improve its affinity and selectivity. It was determined that substitution of an n-propyl or amyl group has similar effect on affinity regardless of location (i.e., N1 or C7). The low affinity of several N1-alkylpyrroleethylamines suggests that the benzene portion of the alpha-methyltryptamines is necessary for significant affinity. Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-alpha-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki greater than 10,000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.

  DOI：

  10.1021/jm00172a016
• 作为产物：
  描述：

  正丙胺 、 2,5-二甲氧基-3-四氢呋喃缩醛 在 溶剂黄146 作用下， 反应 2.5h， 以59%的产率得到1-n-propylpyrrole-3-carboxaldehyde
  参考文献：
  名称：

  Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region

  摘要：

  Taking advantage of a proposed hydrophobic region on 5-HT2 receptors previously identified by radioligand-binding studies utilizing various phenylisopropylamine derivatives, we prepared and evaluated several N1 - and/or C7-alkyl-substituted derivatives of alpha-methyltryptamine in order to improve its affinity and selectivity. It was determined that substitution of an n-propyl or amyl group has similar effect on affinity regardless of location (i.e., N1 or C7). The low affinity of several N1-alkylpyrroleethylamines suggests that the benzene portion of the alpha-methyltryptamines is necessary for significant affinity. Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-alpha-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki greater than 10,000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.

  DOI：

  10.1021/jm00172a016

文献信息

• C-REL INHIBITORS AND USES THEREOF
  申请人：CORNELL UNIVERSITY

  公开号：US20150218109A1

  公开（公告）日：2015-08-06

  Compounds having a c-Rel inhibiting property according to the formula: (1) wherein R 1 and R 2 are each independently selected from hydrogen atom and hydrocarbon groups having at least one and up to thirty carbon atoms and optionally substituted with one or more heteroatoms selected from halogen, nitrogen, oxygen, and sulfur; R 3 is selected from hydrocarbon groups having at least one and up to thirty carbon atoms and optionally substituted with one or more heteroatoms selected from halogen, nitrogen, oxygen, and sulfur; and X 1 , X 2 , and X 3 are each independently selected from oxygen and sulfur atoms. Methods for treating diseases and conditions associated with c-Rel overexpression by administering compounds of Formula (1) or a pharmaceutical composition thereof to a subject afflicted with such a disease or condition are also described.

  具有抑制c-Rel性质的化合物按照公式（1）：其中R1和R2各自独立地选择氢原子和至少一个碳原子至三十个碳原子的含有一个或多个杂原子（选自卤素、氮、氧和硫）的烃基，并且可以被一个或多个杂原子（选自卤素、氮、氧和硫）取代；R3选择至少一个碳原子至三十个碳原子的含有一个或多个杂原子（选自卤素、氮、氧和硫）的烃基，并且可以被一个或多个杂原子（选自卤素、氮、氧和硫）取代；X1、X2和X3各自独立地选择氧原子和硫原子。还描述了通过向患有这种疾病或情况的受试者投与公式（1）的化合物或其制剂来治疗与c-Rel过度表达相关的疾病和情况的方法。
• GLENNON, RICHARD A.;CHAURASIA, CHANDRA;TITELER, MILT, J. MED. CHEM., 33,(1990) N0, C. 2777-2784
  作者：GLENNON, RICHARD A.、CHAURASIA, CHANDRA、TITELER, MILT

  DOI：——

  日期：——
• US9873674B2
  申请人：——

  公开号：US9873674B2

  公开（公告）日：2018-01-23
• Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region
  作者：Richard A. Glennon、Chandra Chaurasia、Milt Titeler

  DOI：10.1021/jm00172a016

  日期：1990.10

  Taking advantage of a proposed hydrophobic region on 5-HT2 receptors previously identified by radioligand-binding studies utilizing various phenylisopropylamine derivatives, we prepared and evaluated several N1 - and/or C7-alkyl-substituted derivatives of alpha-methyltryptamine in order to improve its affinity and selectivity. It was determined that substitution of an n-propyl or amyl group has similar effect on affinity regardless of location (i.e., N1 or C7). The low affinity of several N1-alkylpyrroleethylamines suggests that the benzene portion of the alpha-methyltryptamines is necessary for significant affinity. Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-alpha-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki greater than 10,000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.