{2-[5-(1-diethylcarbamoyl-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}-[4-(4-methanesulfonylaminophenyl)butyl]carbamic acid benzyl ester | 192774-13-3

• 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-[5-(1-diethylcarbamoyl-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}-[4-(4-methanesulfonylaminophenyl)butyl]carbamic acid benzyl ester
• 英文别名: benzyl N-[2-[5-[1-(diethylamino)-2-methyl-1-oxopropan-2-yl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]-N-[4-[4-(methanesulfonamido)phenyl]butyl]carbamate
• CAS: 192774-13-3
• 化学式: C₄₅H₅₆N₄O₅S
• 分子量: 765.029
• InChiKey: XZPLGPBVGKKZFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {2-[5-(1-diethylcarbamoyl-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}-[4-(4-methanesulfonylaminophenyl)butyl]carbamic acid benzyl ester 在 钯 氢气 作用下， 以 CH₂ Cl₂ -MeOH-concentrated NH₄ OH 、 乙醇 、 溶剂黄146 为溶剂， 以47.2 mg (91%)的产率得到2-(2-(3,5-dimethylphenyl)-3-{2-[4-(4-methanesulfonylaminophenyl)-butylamino]ethyl}-1H-indol-5-yl)-N,N-diethylisobutyramide
  参考文献：
  名称：

  Antagonists of gonadotropin releasing hormone

  摘要：

  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。

  公开号：

  US05756507A1
• 作为产物：
  描述：

  4-[4-(methane-sulfonamido)phenyl]butyric acid,N-methoxy-N-methylamide 在 氢氧化钾 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 硫酸二甲酯 作用下， 以 四氢呋喃 、 甲醇 、 氘代氯仿 、 二氯甲烷 为溶剂， 生成 {2-[5-(1-diethylcarbamoyl-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}-[4-(4-methanesulfonylaminophenyl)butyl]carbamic acid benzyl ester
  参考文献：
  名称：

  Substituted Indole-5-carboxamides and -acetamides as Potent Nonpeptide GnRH Receptor Antagonists

  摘要：

  The 2-aryltryptamine class of GnRH receptor antagonists has been modified to incorporate carboxamide and acetamide substituents at the indole 5-position. With either a phenol or methanesulfonamide terminus on the N-aralkyl side chain, potent binding affinity to the GnRH receptor was achieved. A functional assay for GnRH antagonism was even more sensitive to structural modification and revealed a strong preference for branched tertiary amides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00274-8

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。
• Substituted Indole-5-carboxamides and -acetamides as Potent Nonpeptide GnRH Receptor Antagonists
  作者：Wallace T. Ashton、Rosemary M. Sisco、Yi Tien Yang、Jane-Ling Lo、Joel B. Yudkovitz、Kang Cheng、Mark T. Goulet

  DOI：10.1016/s0960-894x(01)00274-8

  日期：2001.7

  The 2-aryltryptamine class of GnRH receptor antagonists has been modified to incorporate carboxamide and acetamide substituents at the indole 5-position. With either a phenol or methanesulfonamide terminus on the N-aralkyl side chain, potent binding affinity to the GnRH receptor was achieved. A functional assay for GnRH antagonism was even more sensitive to structural modification and revealed a strong preference for branched tertiary amides. (C) 2001 Elsevier Science Ltd. All rights reserved.