(S)-2-[3-(2-tert-butoxycarbonylamino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester | 217192-28-4

• 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: (S)-2-[3-(2-tert-butoxycarbonylamino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester
• 英文别名: ethyl 2-[2-(3,5-dimethylphenyl)-3-[(2S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]propan-2-yl]-1H-indol-5-yl]-2-methylpropanoate
• CAS: 217192-28-4
• 化学式: C₃₀H₄₀N₂O₄
• 分子量: 492.659
• InChiKey: UOEDPFXICGRYIJ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-[3-(2-tert-butoxycarbonylamino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester 在 氢氧化钾 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 碳酸氢钠 、 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-[(2S)-2-[5-[1-(2-azabicyclo[2.2.2]octan-2-yl)-2-methyl-1-oxopropan-2-yl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]propyl]-2,4-dinitrobenzenesulfonamide
  参考文献：
  名称：

  Orally bioavailable, indole-based nonpeptide GnRH receptor antagonists with high potency and functional activity

  摘要：

  Stereospecific introduction of a methyl group to the indole-3-side chain enhanced activity in our tryptamine-derived series of GnRH receptor antagonists. Further improvements were achieved by variation of the bicyclic amino moiety of the tertiary amide and by adjustment of the tether length to a pyridine or pyridone terminus. These modifications culminated in analogue 24, which had oral activity in a rat model and acceptable oral bioavailability and half-life in dogs and monkeys. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00512-1
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-[3-(2-tert-butoxycarbonylamino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester
  参考文献：
  名称：

  Orally bioavailable, indole-based nonpeptide GnRH receptor antagonists with high potency and functional activity

  摘要：

  Stereospecific introduction of a methyl group to the indole-3-side chain enhanced activity in our tryptamine-derived series of GnRH receptor antagonists. Further improvements were achieved by variation of the bicyclic amino moiety of the tertiary amide and by adjustment of the tether length to a pyridine or pyridone terminus. These modifications culminated in analogue 24, which had oral activity in a rat model and acceptable oral bioavailability and half-life in dogs and monkeys. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00512-1

文献信息

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

  公开号：US06017944A1

  公开（公告）日：2000-01-25

  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.

  公开了化合物的结构式(I)以及其药用可接受的盐，这些化合物可用作GnRH拮抗剂，因此可能对男性和女性的各种与性激素相关和其他疾病的治疗有用。
• EP1027046A4
  申请人：——

  公开号：EP1027046A4

  公开（公告）日：2002-04-03
• ANTAGONISTS OF GONADOTROPIN RELEASING HORMONE
  申请人：MERCK & CO., INC.

  公开号：EP1027046A1

  公开（公告）日：2000-08-16
• EP1049472A4
  申请人：——

  公开号：EP1049472A4

  公开（公告）日：2002-04-03
• US5985901A
  申请人：——

  公开号：US5985901A

  公开（公告）日：1999-11-16