5-Chlor-indol-2-carbonsaeure-(2-dimethylamino-ethylamid) | 21109-17-1

• 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: 5-Chlor-indol-2-carbonsaeure-(2-dimethylamino-ethylamid)
• 英文别名: 5-chloro-N-[2-(dimethylamino)ethyl]-1H-indole-2-carboxamide
• CAS: 21109-17-1
• 化学式: C₁₃H₁₆ClN₃O
• 分子量: 265.743
• InChiKey: MLTLWPXZLVOWJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  48.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯吲哚-2-羧酸 、 N,N-二甲基乙二胺 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 5-Chlor-indol-2-carbonsaeure-(2-dimethylamino-ethylamid)
  参考文献：
  名称：

  合成和结构活性关系的吲哚和苯并咪唑哌嗪作为组胺H（4）受体拮抗剂。

  摘要：

  我们描述了一系列与最近确定的（5-氯-1H-吲哚-2-基）-（4-甲基-哌嗪-1-基）-甲酮（1）相关的配体的结构-活性关系H（4）受体（H（4）R）拮抗剂。此外，我们确定了相关的苯并咪唑类化合物作为H（4）R的新型先导化合物。配体已经通过放射性配体置换研究和功能测定法评估了它们与人类组胺H（3）和H（4）受体的相互作用，并在人类H（4）R上显示高达7.5的pK（i）值。

  DOI：

  10.1016/j.bmcl.2004.08.035

文献信息

• Indole amide derivatives: synthesis, structure–activity relationships and molecular modelling studies of a new series of histamine H1-receptor antagonists
  作者：Sandra Battaglia、Enrico Boldrini、Federico Da Settimo、Giulio Dondio、Concettina La Motta、Anna Maria Marini、Giampaolo Primofiore

  DOI：10.1016/s0223-5234(99)80044-0

  日期：1999.2

  A number of indole amide derivatives bearing a basic side chain, in which the indole ring replaces the isoster benzimidazole nucleus typical of some well-known antihistamines, were prepared and tested for their H-1-antihistaminic activity. The 1-benzyl-3-indolecarboxamides 32-42 showed antihistaminic (H-1) activity (pA(2) 6-8); the 3-indolylglyoxylylamides 7-16 and the 2-indolecarboxamides 48-56 showed little or no activity. Insertion of the basic side chain of the active 3-indolecarboxamide derivatives into a piperazine ring (compounds 57-59) led to a dramatic loss of activity. All the active compounds proved to be competitive antagonists, since the values of the regression slope were not statistically different from 1. The most active compounds, 32, 33, 38-41, were also tested both in vitro for their anticholinergic activity and in vivo for their ability to antagonize histamine-induced cutaneous vascular permeability in rats. The biological results and the structure-activity relationships of the novel compounds are discussed in the light of molecular modelling studies, taking the molecule of astemizole as a model, and referring to proposed H-1-receptor pharmacophore models. (C) Elsevier, Paris.
• Synthesis and structure–activity relationships of indole and benzimidazole piperazines as histamine H4 receptor antagonists
  作者：Nalan Terzioglu、Richard M. van Rijn、Remko A. Bakker、Iwan J.P. De Esch、Rob Leurs

  DOI：10.1016/j.bmcl.2004.08.035

  日期：2004.11

  We describe the structure-activity relationships for a series of ligands structurally related to the recently identified (5-chloro-1H-indol-2-yl)-(4-methyl-piperazin-1-yl)-methanone (1) as histamine H(4) receptor (H(4)R) antagonists. Furthermore, we identified related benzimidazoles as novel lead compounds for the H(4)R. The ligands have been evaluated by radioligand displacement studies and functional

  我们描述了一系列与最近确定的（5-氯-1H-吲哚-2-基）-（4-甲基-哌嗪-1-基）-甲酮（1）相关的配体的结构-活性关系H（4）受体（H（4）R）拮抗剂。此外，我们确定了相关的苯并咪唑类化合物作为H（4）R的新型先导化合物。配体已经通过放射性配体置换研究和功能测定法评估了它们与人类组胺H（3）和H（4）受体的相互作用，并在人类H（4）R上显示高达7.5的pK（i）值。