1-[(3S,4S)-3-[4-(5-Benzyl-2-ethyl-2H-pyrazol-3-yl)-piperidin-1-ylmethyl]-4-(3-fluoro-phenyl)-pyrrolidin-1-ylmethyl]-cyclopentanecarboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-[(3S,4S)-3-[4-(5-Benzyl-2-ethyl-2H-pyrazol-3-yl)-piperidin-1-ylmethyl]-4-(3-fluoro-phenyl)-pyrrolidin-1-ylmethyl]-cyclopentanecarboxylic acid
• 英文别名: 1-[[(3S,4S)-3-[[4-(5-benzyl-2-ethyl-pyrazol-3-yl)-1-piperidyl]methyl]-4-(3-fluorophenyl)pyrrolidin-1-yl]methyl]cyclopentanecarboxylic acid；1-[[(3S,4S)-3-[[4-(5-benzyl-2-ethylpyrazol-3-yl)piperidin-1-yl]methyl]-4-(3-fluorophenyl)pyrrolidin-1-yl]methyl]cyclopentane-1-carboxylic acid
• 化学式: C₃₅H₄₅FN₄O₂
• 分子量: 572.766
• InChiKey: WYYHLSLKWWQQJK-BHDXBOSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  dibenzyl cyclopentane-1,1-dicarboxylate 在 palladium on activated charcoal 草酰氯 、 四丁基氟化铵 、 氢气 、 三乙酰氧基硼氢化钠 、 二异丁基氢化铝 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-[(3S,4S)-3-[4-(5-Benzyl-2-ethyl-2H-pyrazol-3-yl)-piperidin-1-ylmethyl]-4-(3-fluoro-phenyl)-pyrrolidin-1-ylmethyl]-cyclopentanecarboxylic acid
  参考文献：
  名称：

  CCR5 Antagonists:  3-(Pyrrolidin-1-yl)propionic Acid Analogues with Potent Anti-HIV Activity

  摘要：

  graphicA novel approach to alpha,alpha-disubstituted-beta-amino acids (beta(2,2)-amino acids) was employed in the synthesis of a series of 3-(pyrrolidin-1-yl)-propionic acids possessing high affinity for the CCR5 receptor and potent anti-HIV activity. The rat pharmacokinetics for these new analogues featured higher bioavailabilities and lower rates of clearance as compared to cyclopentane 1.

  DOI：

  10.1021/ol034707c

文献信息

• CCR5 Antagonists:  3-(Pyrrolidin-1-yl)propionic Acid Analogues with Potent Anti-HIV Activity
  作者：Christopher L. Lynch、Jeffrey J. Hale、Richard J. Budhu、Amy L. Gentry、Paul E. Finke、Charles G. Caldwell、Sander G. Mills、Malcolm MacCoss、Dong-Ming Shen、Kevin T. Chapman、Lorraine Malkowitz、Martin S. Springer、Sandra L. Gould、Julie A. DeMartino、Salvatore J. Siciliano、Margaret A. Cascieri、Anthony Carella、Gwen Carver、Karen Holmes、William A. Schleif、Renee Danzeisen、Daria Hazuda、Joseph Kessler、Janet Lineberger、Michael Miller、Emilio Emini

  DOI：10.1021/ol034707c

  日期：2003.7.1

  graphicA novel approach to alpha,alpha-disubstituted-beta-amino acids (beta(2,2)-amino acids) was employed in the synthesis of a series of 3-(pyrrolidin-1-yl)-propionic acids possessing high affinity for the CCR5 receptor and potent anti-HIV activity. The rat pharmacokinetics for these new analogues featured higher bioavailabilities and lower rates of clearance as compared to cyclopentane 1.