1-[(R)-2-{4-[2-((S)-1-amino-3-methylbutyl)-4-trifluoromethylphenyl]piperazin-1-yl}-1-(2,4-dichlorobenzyl)-2-oxoethyl]pyrrolidin-2-one | 626217-39-8

• 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-trifluoromethylphenyl]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-(trifluoromethyl)phenyl]piperazin-1-yl]-3-(2,4-dichlorophenyl)-1-oxopropan-2-yl]pyrrolidin-2-one
• CAS: 626217-39-8
• 化学式: C₂₉H₃₅Cl₂F₃N₄O₂
• 分子量: 599.524
• InChiKey: YXPCHDOWVWAKKP-AZGAKELHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  69.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(R)-2-{4-[2-((S)-1-amino-3-methylbutyl)-4-trifluoromethylphenyl]piperazin-1-yl}-1-(2,4-dichlorobenzyl)-2-oxoethyl]pyrrolidin-2-one 、 羟乙醛 在 三乙酰氧基硼氢化钠 作用下， 生成 1-((R)-3-(2,4-dichlorophenyl)-1-(4-(2-((S)-1-(2-hydroxyethylamino)-3-methylbutyl)-4-(trifluoromethyl)phenyl)piperazin-1-yl)-1-oxopropan-2-yl)pyrrolidin-2-one
  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， 反应 1.0h， 以78%的产率得到1-[(R)-2-{4-[2-((S)-1-amino-3-methylbutyl)-4-trifluoromethylphenyl]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