2-(7-ethyl-1H-indol-3-yl)-2-oxoacetyl chloride | 111478-91-2

• 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: 2-(7-ethyl-1H-indol-3-yl)-2-oxoacetyl chloride
• CAS: 111478-91-2
• 化学式: C₁₂H₁₀ClNO₂
• 分子量: 235.67
• InChiKey: DQFFTJWDMSCSHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(7-ethyl-1H-indol-3-yl)-2-oxoacetyl chloride 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 24.0h， 生成 7-ethyl-N,N-dimethyltryptamine
  参考文献：
  名称：

  Studies on several 7-substituted N,N-dimethyltryptamines

  摘要：

  Several 7-substituted derivatives of N,N-dimethyltryptamine (DMT) were prepared and evaluated in the rat fundus serotonin receptor assay and in a behavioral (discriminative stimulus) assay in rats. Both 7-Me- and 5-OMe-7-Me-DMT possess a higher pA2, and 5,7-(OMe)2-DMT a lower pA2, than that of DMT itself. Like DMT, all three of these compounds produce behavioral effects in rats which are similar to those of the hallucinogen 5-OMe-DMT. Although 7-ET- and 7-Br-DMT possess a higher serotonin receptor affinity than DMT, neither produce behavioral effects which parallel those of 5-OMe-DMT. In contrast, 6-Me-DMT and its 5-OMe derivative do not interact with the serotonin receptors in a competitive manner and are inactive in the discriminative stimulus assay.

  DOI：

  10.1021/jm00185a014
• 作为产物：
  描述：

  1-(2-氨基-3-乙基苯基)-2-氯乙烷酮 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 乙醚 、 水 为溶剂， 反应 1.5h， 生成 2-(7-ethyl-1H-indol-3-yl)-2-oxoacetyl chloride
  参考文献：
  名称：

  Studies on several 7-substituted N,N-dimethyltryptamines

  摘要：

  Several 7-substituted derivatives of N,N-dimethyltryptamine (DMT) were prepared and evaluated in the rat fundus serotonin receptor assay and in a behavioral (discriminative stimulus) assay in rats. Both 7-Me- and 5-OMe-7-Me-DMT possess a higher pA2, and 5,7-(OMe)2-DMT a lower pA2, than that of DMT itself. Like DMT, all three of these compounds produce behavioral effects in rats which are similar to those of the hallucinogen 5-OMe-DMT. Although 7-ET- and 7-Br-DMT possess a higher serotonin receptor affinity than DMT, neither produce behavioral effects which parallel those of 5-OMe-DMT. In contrast, 6-Me-DMT and its 5-OMe derivative do not interact with the serotonin receptors in a competitive manner and are inactive in the discriminative stimulus assay.

  DOI：

  10.1021/jm00185a014

文献信息

• Inhibitors of HIV-1 attachment. Part 2: An initial survey of indole substitution patterns
  作者：Nicholas A. Meanwell、Owen B. Wallace、Haiquan Fang、Henry Wang、Milind Deshpande、Tao Wang、Zhiwei Yin、Zhongxing Zhang、Bradley C. Pearce、Jennifer James、Kap-Sun Yeung、Zhilei Qiu、J.J. Kim Wright、Zheng Yang、Lisa Zadjura、Donald L. Tweedie、Suresh Yeola、Fang Zhao、Sunanda Ranadive、Brett A. Robinson、Yi-Fei Gong、Hwei-Gene Heidi Wang、Wade S. Blair、Pei-Yong Shi、Richard J. Colonno、Pin-fang Lin

  DOI：10.1016/j.bmcl.2009.02.040

  日期：2009.4

  inhibitor of the interaction between HIV gp120 and host cell CD4 receptors, on activity in an HIV entry assay was examined. Small substituents at C-4 generally resulted in increased potency whilst substitution at C-7 was readily tolerated and uniformly produced more potent HIV entry inhibitors. Substituents deployed at C-6 and, particularly, C-5 generally produced a modest to marked weakening of potency

  将简单的卤素，烷基和烷氧基取代基引入1-（4-苯甲酰基哌嗪-1-基）-2-（1 H检测了HIV gp120和宿主细胞CD4受体之间相互作用的抑制剂-吲哚-3-基）乙烷-1,2-二酮对HIV进入检测活性的抑制作用。C-4处的小取代基通常会提高效力，而C-7处的取代很容易被接受，并且会均匀产生更有效的HIV进入抑制剂。与原型相比，部署在C-6（尤其是C-5）上的替代品通常会产生一定程度的效力减弱。N-1处的小烷基取代基对活性的影响最小，同时增加了烷基部分的大小，导致抑制性能逐渐降低。这些研究建立了对HIV附着抑制剂药效团的吲哚成分的基本理解。
• HUMBER, LESLIE G.;FERDINANDI, ECKHARDT;DEMERSON, CHRISTOPHER A.;AHMED, SY+, J. MED. CHEM., 31,(1988) N 9, C. 1712-1719
  作者：HUMBER, LESLIE G.、FERDINANDI, ECKHARDT、DEMERSON, CHRISTOPHER A.、AHMED, SY+

  DOI：——

  日期：——