methyl 3-[4-{4-(methylsulfonyl)benzyl)homopiperazinyl] propionate | 199922-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-[4-{4-(methylsulfonyl)benzyl)homopiperazinyl] propionate
• 英文别名: Methyl 3-[4-{4-(methylsulfonyl)benzyl}homopiperazinyl]propionate；methyl 3-[4-[(4-methylsulfonylphenyl)methyl]-1,4-diazepan-1-yl]propanoate
• CAS: 199922-48-0
• 化学式: C₁₇H₂₆N₂O₄S
• 分子量: 354.47
• InChiKey: FEQYPAWDILMMMY-UHFFFAOYSA-N

物化性质

• 沸点：
  511.1±50.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  (3-chlorophenyl)magnesium bromide 、 methyl 3-[4-{4-(methylsulfonyl)benzyl)homopiperazinyl] propionate 生成 1,1-Bis-(3-chloro-phenyl)-3-[4-(4-methanesulfonyl-benzyl)-[1,4]diazepan-1-yl]-propan-1-ol
  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 在 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 methyl 3-[4-{4-(methylsulfonyl)benzyl)homopiperazinyl] propionate
  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。
• [EN] DIARYLALKYL CYCLIC DIAMINE DERIVATIVES AS CHEMOKINE RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE DIAMINE CYCLIQUE DE DIARYLAKLYLE UTILISES EN TANT QU'ANTAGONISTES DES RECEPTEURS DE CHIMIOKINES
  申请人：TEIJIN LIMITED

  公开号：WO1997044329A1

  公开（公告）日：1997-11-27

  (EN) 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-la and/or MCP-l 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 tissues.(FR) Diamines cycliques de formule (I) ou leur sels d'addition d'acide pharmaceutiquement acceptables ainsi que leurs applications médicales. Ces composés inhibent l'action de chimiokines telles que MIP-1a et/ou MCP-1 sur des cellules cibles, et sont utiles en tant que médicaments thérapeutiques et/ou préventifs dans les maladies telles que l'athérosclérose, l'arthrite rhumatoïde et similaire dans lesquelles les monocytes et les lymphocytes s'infiltrent dans les tissus.

  (I)式的环状二胺或其药学上可接受的酸盐加合物以及它们的医学应用被描述。这些化合物抑制化学趋化因子如MIP-1a和/或MCP-1在目标细胞上的作用，并且可作为治疗药物和/或预防药物在疾病中使用，例如动脉粥样硬化、类风湿性关节炎等，这些疾病中血液单核细胞和淋巴细胞渗入组织。
• DIARYLALKYL CYCLIC DIAMINE DERIVATIVES AS CHEMOKINE RECEPTOR ANTAGONISTS
  申请人：TEIJIN LIMITED

  公开号：EP0914319B1

  公开（公告）日：2001-11-21
• US6686353B1
  申请人：——

  公开号：US6686353B1

  公开（公告）日：2004-02-03
• 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.