1-[4-(methylsulfonyl)benzyl]-4-[3-oxo-3-{3-(tert-butyldimethylsilyloxy)phenyl}propyl]homopiperazine | 199938-51-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-(methylsulfonyl)benzyl]-4-[3-oxo-3-{3-(tert-butyldimethylsilyloxy)phenyl}propyl]homopiperazine
• 英文别名: 1-[3-[Tert-butyl(dimethyl)silyl]oxyphenyl]-3-[4-[(4-methylsulfonylphenyl)methyl]-1,4-diazepan-1-yl]propan-1-one
• CAS: 199938-51-7
• 化学式: C₂₈H₄₂N₂O₄SSi
• 分子量: 530.804
• InChiKey: XQWKAGSBDLYECE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[4-(methylsulfonyl)benzyl]-4-[3-oxo-3-{3-(tert-butyldimethylsilyloxy)phenyl}propyl]homopiperazine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 3-{1-(4-Chloro-phenyl)-1-hydroxy-3-[4-(4-methanesulfonyl-benzyl)-[1,4]diazepan-1-yl]-propyl}-phenol
  参考文献：
  名称：

  Small molecule inhibitors of the CCR2b receptor. Part 1: Discovery and optimization of homopiperazine derivatives

  摘要：

  N',N'-Disubstituted homopiperazine derivatives have been discovered as CC-chemokine receptor 2b (CCR2b) inhibitors with submicromolar activity in the CCR2b binding assay. A 4-substituted benzyl group on one homopiperazine nitroger was an important moiety for binding affinity to the CCR2b receptor. The SAR for CCR2b binding affinity correlated inversely with the a factor of the functional group on this benzyl moiety. Introduction of hydroxy groups to appropriate positions in the 3,3-diphenylpropyl group on the other homopiperazine nitrogen increased CCR2b binding activity. The synthesis of an informer library to search for alternative substructures is also described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.008
• 作为产物：
  描述：

  4-(methylsulfonyl)benzyl methanesulfonate 以 乙醇 、 二氯甲烷 为溶剂， 生成 1-[4-(methylsulfonyl)benzyl]-4-[3-oxo-3-{3-(tert-butyldimethylsilyloxy)phenyl}propyl]homopiperazine
  参考文献：
  名称：

  Small molecule inhibitors of the CCR2b receptor. Part 1: Discovery and optimization of homopiperazine derivatives

  摘要：

  N',N'-Disubstituted homopiperazine derivatives have been discovered as CC-chemokine receptor 2b (CCR2b) inhibitors with submicromolar activity in the CCR2b binding assay. A 4-substituted benzyl group on one homopiperazine nitroger was an important moiety for binding affinity to the CCR2b receptor. The SAR for CCR2b binding affinity correlated inversely with the a factor of the functional group on this benzyl moiety. Introduction of hydroxy groups to appropriate positions in the 3,3-diphenylpropyl group on the other homopiperazine nitrogen increased CCR2b binding activity. The synthesis of an informer library to search for alternative substructures is also described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.008

文献信息

• Diarylalkyl cyclic diamine derivatives as chemokine receptor antagonists
  申请人：Teijin Intellectual Property Center Limited

  公开号：US06686353B1

  公开（公告）日：2004-02-03

  Cyclic diamines of formula (I) or their pharmacologically acceptable acid addition salts, and their medical applications are described. These compounds inhibit the action of chemokines such as MIP-1a and/or MCP-1 on target cells, and are useful as a therapeutic drug and/or preventative drug in diseases, such as atherosclerosis, rheumatoid arthritis, and the like where blood monocytes and lymphocytes infiltrate into tissue.

  本文描述了式（I）的环状二胺或其药理学上可接受的酸盐以及它们的医学应用。这些化合物抑制趋化因子如MIP-1a和/或MCP-1对靶细胞的作用，可用作治疗药物和/或预防药物，用于动脉粥样硬化、类风湿性关节炎等疾病，在这些疾病中，血液单核细胞和淋巴细胞浸润组织。
• Small molecule inhibitors of the CCR2b receptor. Part 1: Discovery and optimization of homopiperazine derivatives
  作者：Minoru Imai、Tatsuki Shiota、Ken-ichiro Kataoka、Christine M. Tarby、Wilna J. Moree、Takaharu Tsutsumi、Masaki Sudo、Michele M. Ramirez-Weinhouse、Daniel Comer、Chung-Ming Sun、Shinsuke Yamagami、Hiroko Tanaka、Takuya Morita、Takahiko Hada、Jonathan Greene、Doug Barnum、John Saunders、Peter L. Myers、Yoshinori Kato、Noriaki Endo

  DOI：10.1016/j.bmcl.2004.08.008

  日期：2004.11

  N',N'-Disubstituted homopiperazine derivatives have been discovered as CC-chemokine receptor 2b (CCR2b) inhibitors with submicromolar activity in the CCR2b binding assay. A 4-substituted benzyl group on one homopiperazine nitroger was an important moiety for binding affinity to the CCR2b receptor. The SAR for CCR2b binding affinity correlated inversely with the a factor of the functional group on this benzyl moiety. Introduction of hydroxy groups to appropriate positions in the 3,3-diphenylpropyl group on the other homopiperazine nitrogen increased CCR2b binding activity. The synthesis of an informer library to search for alternative substructures is also described. (C) 2004 Elsevier Ltd. All rights reserved.