(3R,4S)-1-Benzyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-phenyl-pyrrolidine | 300853-91-2

• 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: (3R,4S)-1-Benzyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-phenyl-pyrrolidine
• 英文别名: 1-Benzyl-3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidine；[(3R,4S)-1-benzyl-4-phenylpyrrolidin-3-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 300853-91-2
• 化学式: C₂₄H₃₅NOSi
• 分子量: 381.634
• InChiKey: ZJJKCVFIJFRUOY-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4S)-1-Benzyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-phenyl-pyrrolidine 在 palladium dihydroxide 碳酸氢铵 作用下， 以 甲醇 为溶剂， 以99%的产率得到(3R,4S)-3-(([tert-butyl(dimethyl)silyl]oxy)methyl)-4-phenylpyrrolidine
  参考文献：
  名称：

  1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 1: discovery of the pyrrolidine scaffold and determination of its stereochemical requirements

  摘要：

  A series of 1,3,4-trisubstituted pyrrolidines was discovered to have the ability to displace [I-125]-MIP-1 alpha from the CCR5 receptor expressed on Chinese hamster ovary (CHO) cell membranes. CCR5 activity was found to be dependent on the regiochemistry and the absolute stereochemistry of the pyrrolidine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00232-3
• 作为产物：
  描述：

  (4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3R,4S)-1-Benzyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-phenyl-pyrrolidine
  参考文献：
  名称：

  1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 1: discovery of the pyrrolidine scaffold and determination of its stereochemical requirements

  摘要：

  A series of 1,3,4-trisubstituted pyrrolidines was discovered to have the ability to displace [I-125]-MIP-1 alpha from the CCR5 receptor expressed on Chinese hamster ovary (CHO) cell membranes. CCR5 activity was found to be dependent on the regiochemistry and the absolute stereochemistry of the pyrrolidine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00232-3

文献信息

• Pyrrolidine modulators of CCR5 chemokine receptor activity
  申请人：——

  公开号：US20020198178A1

  公开（公告）日：2002-12-26

  Pyrrolidine compounds of Formula I: 1 (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8a , R 8b , j, k, l, m, and n are defined herein) are described. The compounds are modulators of CCR5 chemokine receptor activity. The compounds are useful, for example, in the prevention or treatment of infection by HIV and the treatment of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.

  本文介绍了式I：1中的吡咯烷化合物（其中R1、R2、R3、R4、R5、R6、R7、R8a、R8b、j、k、l、m和n在此定义） 。这些化合物是CCR5趋化因子受体活性的调节剂。这些化合物可用于预防或治疗HIV感染和治疗艾滋病，作为化合物或药物可接受的盐，或作为药物组合物中的成分，可选配合其他抗病毒药物、免疫调节剂、抗生素或疫苗使用。本文还介绍了治疗艾滋病的方法和预防或治疗HIV感染的方法。
• Pyrrolidine modulators of ccr5 chemokine receptor activity
  申请人：——

  公开号：US20040087552A1

  公开（公告）日：2004-05-06

  Pyrrolidine compounds of Formula (I), (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 and R 8 are defined herein) are described. The compounds are modulators of CCR5 chemokine receptor activity. The compounds are useful, for example, in the prevention or treatment of infection by HIV and the treatment of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described. 1

  本发明涉及式(I)的吡咯烷化合物（其中R1、R2、R3、R4、R5、R6a、R6b、R7和R8在此定义），这些化合物是CCR5趋化因子受体活性的调节剂。这些化合物可以作为化合物或药学上可接受的盐，或作为药物组合物中的成分使用，可选地与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用，例如用于预防或治疗HIV感染和治疗艾滋病。本发明还涉及治疗艾滋病的方法以及预防或治疗HIV感染的方法。
• Pyrrolidine modulators of chemokine receptor activity
  申请人：Merck & Co., Inc.

  公开号：US06399619B1

  公开（公告）日：2002-06-04

  The present invention is directed to pyrrolidine compounds of the formula I: (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.

  本发明涉及公式I的吡咯烷化合物：（其中R1，R2，R3，R4，R5，R6和n在此定义），该化合物可用作趋化因子受体活性的调节剂。特别地，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 2: lead optimization affording selective, orally bioavailable compounds with potent Anti-HIV activity
  作者：Jeffrey J. Hale、Richard J. Budhu、Edward B. Holson、Paul E. Finke、Bryan Oates、Sander G. Mills、Malcolm MacCoss、Sandra L. Gould、Julie A. DeMartino、Martin S. Springer、Salvatore Siciliano、Lorraine Malkowitz、William A. Schleif、Daria Hazuda、Michael Miller、Joseph Kessler、Renee Danzeisen、Karen Holmes、Janet Lineberger、Anthony Carella、Gwen Carver、Emilio Emini

  DOI：10.1016/s0960-894x(01)00545-5

  日期：2001.10

  Investigations of the structure-activity relationships of 1,3,4-trisubstituted pyrrolidine human CCR5 receptor antagonists afforded orally bioavailable compounds with the ability to inhibit HIV replication in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 1: discovery of the pyrrolidine scaffold and determination of its stereochemical requirements
  作者：Jeffrey J. Hale、Richard J. Budhu、Sander G. Mills、Malcolm MacCoss、Lorraine Malkowitz、Salvatore Siciliano、Sandra L. Gould、Julie A. DeMartino、Martin S. Springer

  DOI：10.1016/s0960-894x(01)00232-3

  日期：2001.6

  A series of 1,3,4-trisubstituted pyrrolidines was discovered to have the ability to displace [I-125]-MIP-1 alpha from the CCR5 receptor expressed on Chinese hamster ovary (CHO) cell membranes. CCR5 activity was found to be dependent on the regiochemistry and the absolute stereochemistry of the pyrrolidine. (C) 2001 Elsevier Science Ltd. All rights reserved.