2-Methyl-propane-2-sulfinic acid [(S)-1-(5-fluoro-2-piperazin-1-yl-phenyl)-3-methyl-butyl]-amide | 910300-35-5

• 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: 2-Methyl-propane-2-sulfinic acid [(S)-1-(5-fluoro-2-piperazin-1-yl-phenyl)-3-methyl-butyl]-amide
• CAS: 910300-35-5
• 化学式: C₁₉H₃₂FN₃OS
• 分子量: 369.547
• InChiKey: KYQHNVUGYJYHBW-GKVSMKOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  44.37
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-Methyl-propane-2-sulfinic acid [(S)-1-(5-fluoro-2-piperazin-1-yl-phenyl)-3-methyl-butyl]-amide 在 盐酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-{4-[2-((S)-1-Amino-3-methyl-butyl)-4-fluoro-phenyl]-piperazin-1-yl}-3-(2,4-dichloro-phenyl)-propan-1-one
  参考文献：
  名称：

  Arylpropionylpiperazines as antagonists of the human melanocortin-4 receptor

  摘要：

  A series of 3-arylpropionylpiperazines were synthesized as antagonists of the melanocortin-4 receptor. Their potency was found to be increased by replacing the alpha-methyl substituent of the initial lead 11 with a larger s-Bu or i-Bu group. Further potency enhancement was observed when a glycine or beta-alanine was incorporated onto the benzylamine. Some compounds demonstrated good potency, moderate selectivity, and oral bioavailability. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.088
• 作为产物：
  描述：

  4-{4-fluoro-2-[((S_S)-2-methyl-propane-2-sulfinylimino)-methyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester 在 三甲基铝 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-Methyl-propane-2-sulfinic acid [(S)-1-(5-fluoro-2-piperazin-1-yl-phenyl)-3-methyl-butyl]-amide
  参考文献：
  名称：

  Arylpropionylpiperazines as antagonists of the human melanocortin-4 receptor

  摘要：

  A series of 3-arylpropionylpiperazines were synthesized as antagonists of the melanocortin-4 receptor. Their potency was found to be increased by replacing the alpha-methyl substituent of the initial lead 11 with a larger s-Bu or i-Bu group. Further potency enhancement was observed when a glycine or beta-alanine was incorporated onto the benzylamine. Some compounds demonstrated good potency, moderate selectivity, and oral bioavailability. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.088

文献信息

• Pyrrolidinones as orally bioavailable antagonists of the human melanocortin-4 receptor with anti-cachectic activity
  作者：Joe A. Tran、Fabio C. Tucci、Wanlong Jiang、Dragan Marinkovic、Caroline W. Chen、Melissa Arellano、Stacy Markison、Beth A. Fleck、Jenny Wen、Nicole S. White、Joseph Pontillo、John Saunders、Daniel Marks、Sam R. Hoare、Ajay Madan、Alan C. Foster、Chen Chen

  DOI：10.1016/j.bmc.2007.05.026

  日期：2007.8

  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.