2-(3,5-dimethylphenyl)tryptamine | 192717-28-5

• 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-(3,5-dimethylphenyl)tryptamine
• 英文别名: 2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]-ethylamine；2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamine；2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethanamine
• CAS: 192717-28-5
• 化学式: C₁₈H₂₀N₂
• 分子量: 264.37
• InChiKey: YLWTYLPCYWJKOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethylphenyl)tryptamine 在 platinum(IV) oxide 硼烷四氢呋喃络合物 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 tert-butyl N-[4-(4-aminophenyl)butyl]-N-[2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]carbamate
  参考文献：
  名称：

  2-(3,5-Dimethylphenyl)tryptamine Derivatives that Bind to the GnRH Receptor

  摘要：

  A series of 2-(3.5-dimethylphenyl)tryptamine derivatives was prepared and evaluated on a rat gonadotropin releasing hormone receptor assay. Some para-substituents on the 4-phenylbutyl side chain attached to the tryptamine nitrogen led to com pounds with potent GnRH receptor binding. The study has helped define structural requirements for GnRH receptor binding for the 2-aryltryptamine GnRH antagonists. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00134-2
• 作为产物：
  描述：

  2-(2-(1H-吲哚-3-基)乙基)异吲哚啉-1,3-二酮 在 四(三苯基膦)钯 、 pyridinium hydrobromide perbromide 、 sodium carbonate 、 lithium chloride 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 、 甲苯 为溶剂， 生成 2-(3,5-dimethylphenyl)tryptamine
  参考文献：
  名称：

  Initial structure–activity relationship of a novel class of nonpeptidyl GnRH receptor antagonists: 2-arylindoles

  摘要：

  A nonpeptidyl GnRH receptor antagonist (1), with a unique 2-arylindole core, was identified through the Merck inhouse screening for binding affinity on the rat GnRH receptor. SAR studies directed toward the alkoxy-ethanolamine and 2-aryl groups resulted in a simpler lead structure with improved activity. This compound 50 exhibits a 60-fold improvement in binding activity over our initial lead 1. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00707-1

文献信息

• Antagonists of gonadotropin releasing hormone
  申请人：Merck & Co., Inc.

  公开号：US05756507A1

  公开（公告）日：1998-05-26

  There are disclosed compounds of formula (I) ##STR1## and pharmaceutically acceptable salts thereof which are useful as antagonists of GnRH and as such may be useful for the treatment of a variety of sex-hormone related and other conditions in both men and women.

  公式（I）的化合物及其药学上可接受的盐已被披露，它们可作为GnRH拮抗剂，并因此可能对男性和女性的各种性激素相关和其他疾病的治疗有用。
• Heterocyclic Derivatives of 2-(3,5-Dimethylphenyl)tryptamine as GnRH Receptor Antagonists
  作者：Peter Lin、Mamta Parikh、Jane-Ling Lo、Yi Tien Yang、Kang Cheng、Roy G Smith、Michael H Fisher、Matthew J Wyvratt、Mark T Goulet

  DOI：10.1016/s0960-894x(01)00133-0

  日期：2001.4

  A series of heterocyclic 2-(3,5-dimethylphenyl)tryptamine derivatives was prepared and evaluated on a rat gonadotropin releasing hormone receptor assay. The carbon tether length and heterocyclic ring attached to the amino group of 2-(3,5-dimethylphenyl)tryptamine were varied. Several of these derivatives were potent GnRH antagonists with the most potent compound having an IC50 of 16nM. (C) 2001 Elsevier Science Ltd. All rights reserved.
• EP0868178A4
  申请人：——

  公开号：EP0868178A4

  公开（公告）日：2000-03-29
• ANTAGONISTS OF GONADOTROPIN RELEASING HORMONE
  申请人：MERCK & CO., INC.

  公开号：EP0868178A1

  公开（公告）日：1998-10-07
• US5756507A
  申请人：——

  公开号：US5756507A

  公开（公告）日：1998-05-26