1-[(R)-2-{4-[2-((S)-1-amino-3-methylbutyl)-4-fluorophenyl]piperazin-1-yl}-1-(2,4-dichlorobenzyl)-2-oxoethyl]pyrrolidin-2-one | 943521-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-[(R)-2-{4-[2-((S)-1-amino-3-methylbutyl)-4-fluorophenyl]piperazin-1-yl}-1-(2,4-dichlorobenzyl)-2-oxoethyl]pyrrolidin-2-one
• 英文别名: 1-[(2R)-1-[4-[2-[(1S)-1-amino-3-methylbutyl]-4-fluorophenyl]piperazin-1-yl]-3-(2,4-dichlorophenyl)-1-oxopropan-2-yl]pyrrolidin-2-one
• CAS: 943521-53-7
• 化学式: C₂₈H₃₅Cl₂FN₄O₂
• 分子量: 549.516
• InChiKey: NUALMFMLNXDIHK-AZGAKELHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(R)-2-{4-[2-((S)-1-amino-3-methylbutyl)-4-fluorophenyl]piperazin-1-yl}-1-(2,4-dichlorobenzyl)-2-oxoethyl]pyrrolidin-2-one 、 N,N-二甲基甘氨酸 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 生成 N-((S)-1-(2-(4-((R)-3-(2,4-dichlorophenyl)-2-(2-oxopyrrolidin-1-yl)propanoyl)piperazin-1-yl)-5-fluorophenyl)-3-methylbutyl)-2-(dimethylamino)acetamide
  参考文献：
  名称：

  Pyrrolidinones as potent functional antagonists of the human melanocortin-4 receptor

  摘要：

  A series of pyrrolidinones derived from phenylalaninepiperazines were synthesized and characterized as potent and selective antagonists of the melanocortin-4 receptor. In addition to their high binding affinities, these compounds displayed high functional potencies. 12a had a K-i of 0.94 nM in binding and IC50 of 21 nM in functional activity. 12a also demonstrated efficacy in a mouse cachexia model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.097
• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 1-[(R)-2-{4-[2-((S)-1-amino-3-methylbutyl)-4-fluorophenyl]piperazin-1-yl}-1-(2,4-dichlorobenzyl)-2-oxoethyl]pyrrolidin-2-one
  参考文献：
  名称：

  Pyrrolidinones as orally bioavailable antagonists of the human melanocortin-4 receptor with anti-cachectic activity

  摘要：

  A series of pyrrolidinones derived from phenylalanines were synthesized as potent antagonists of the human melanocortin-4 receptor. These compounds showed high potencies and selectivities, and several of them had good oral bioavailabilities. In addition, 12e demonstrated in vivo efficacy in a murine cachexia model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.026