2-(R)-(3-(S)-((4-hydroxy-4-(3-phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester | 301184-48-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(R)-(3-(S)-((4-hydroxy-4-(3-phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester
• 英文别名: Cyclohexyl-{(S)-3-[4-hydroxy-4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-4-phenyl-pyrrolidin-1-yl}-acetic acid benzyl ester；benzyl (2R)-2-cyclohexyl-2-[(3S,4S)-3-[[4-hydroxy-4-(3-phenylpropyl)piperidin-1-yl]methyl]-4-phenylpyrrolidin-1-yl]acetate
• CAS: 301184-48-5
• 化学式: C₄₀H₅₂N₂O₃
• 分子量: 608.864
• InChiKey: MWARYVUQVJIHTP-YXWIYCFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(R)-(3-(S)-((4-hydroxy-4-(3-phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 2-cyclohexyl-2-{3-[4-hydroxy-4-(3-phenylpropyl)hexahydro-1-pyridinylmethyl]-4-phenyltetrahydro-1H-1-pyrrolyl}acetic acid
  参考文献：
  名称：

  1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 4: Synthesis of N-1 acidic functionality affording analogues with enhanced antiviral activity against HIV

  摘要：

  A series of alpha-(pyrrolidin-1-yl)acetic acids is presented as selective and potent antivirals against HIV. Several of the pyrrolidine zwitterions demonstrated reasonable in vitro properties, enhanced antiviral activities and improved pharmacokinetic profiles over pyrrolidine 1. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00606-6
• 作为产物：
  描述：

  2-(R)-(3-(R)-(t-Butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester 在 草酰氯 、 TEA 、 四丁基氟化铵 、 三乙酰氧基硼氢化钠 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-(R)-(3-(S)-((4-hydroxy-4-(3-phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester
  参考文献：
  名称：

  1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 4: Synthesis of N-1 acidic functionality affording analogues with enhanced antiviral activity against HIV

  摘要：

  A series of alpha-(pyrrolidin-1-yl)acetic acids is presented as selective and potent antivirals against HIV. Several of the pyrrolidine zwitterions demonstrated reasonable in vitro properties, enhanced antiviral activities and improved pharmacokinetic profiles over pyrrolidine 1. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00606-6

文献信息

• Pyrrolidine modulators of chemokine receptor activity
  申请人：Merck & Co., Inc.

  公开号：US06265434B1

  公开（公告）日：2001-07-24

  The present invention is directed to pyrrolidine compounds of the formula 1: (wherein R1, R2, R3, R4, R5, R6 and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.

  本发明涉及式1的吡咯烷化合物：（其中R1、R2、R3、R4、R5、R6和n在此处定义），这些化合物可用作趋化因子受体活性的调节剂。具体来说，这些化合物可用作趋化因子受体CCR-5和/或CCR-3的调节剂。
• 1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 4: Synthesis of N-1 acidic functionality affording analogues with enhanced antiviral activity against HIV
  作者：Christopher L Lynch、Jeffrey J Hale、Richard J Budhu、Amy L Gentry、Sander G Mills、Kevin T Chapman、Malcolm MacCoss、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 A Emini

  DOI：10.1016/s0960-894x(02)00606-6

  日期：2002.10

  A series of alpha-(pyrrolidin-1-yl)acetic acids is presented as selective and potent antivirals against HIV. Several of the pyrrolidine zwitterions demonstrated reasonable in vitro properties, enhanced antiviral activities and improved pharmacokinetic profiles over pyrrolidine 1. (C) 2002 Elsevier Science Ltd. All rights reserved.