(E)-3-(2-amino-4-chlorophenyl)-1-[(R)-4-(4-fluorobenzyl)-2-methylpiperazin-1-yl]-propenone | 685534-24-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(2-amino-4-chlorophenyl)-1-[(R)-4-(4-fluorobenzyl)-2-methylpiperazin-1-yl]-propenone
• 英文别名: (E)-3-(2-amino-4-chlorophenyl)-1-[(2R)-4-[(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]prop-2-en-1-one
• CAS: 685534-24-1
• 化学式: C₂₁H₂₃ClFN₃O
• 分子量: 387.885
• InChiKey: KOGYJMUNESOHRO-FUVBFXSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-amino-4-chlorophenyl)-1-[(R)-4-(4-fluorobenzyl)-2-methylpiperazin-1-yl]-propenone 在 氨 作用下， 以 乙醇 为溶剂， 生成 (R,E)-3-(2-(3-(4-(4-fluorobenzyl)-2-methylpiperazin-1-yl)-3-oxoprop-1-enyl)-5-chlorophenylamino)-4-aminocyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Structure–activity relationships of novel, highly potent, selective, and orally active CCR1 antagonists

  摘要：

  Design and synthesis of a series of 3-amino-4-(2-(2-(4-benzylpiperazin-1-yl)-2-oxoethoxy)phenylamino)cyclobutenedione derivatives as novel CCRI antagonists are described. Structure-activity relationship studies led to the identification of compound 22, which demonstrated potent binding activity, functional antagonism of CCR1 as well as good species cross-reactivity. In addition, compound 22 also showed desirable pharmacokinetic profiles and was selected for in vivo studies in the mouse collagen-induced arthritis model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.104
• 作为产物：
  描述：

  (R)-(-)-2-甲基哌嗪 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E)-3-(2-amino-4-chlorophenyl)-1-[(R)-4-(4-fluorobenzyl)-2-methylpiperazin-1-yl]-propenone
  参考文献：
  名称：

  Structure–activity relationships of novel, highly potent, selective, and orally active CCR1 antagonists

  摘要：

  Design and synthesis of a series of 3-amino-4-(2-(2-(4-benzylpiperazin-1-yl)-2-oxoethoxy)phenylamino)cyclobutenedione derivatives as novel CCRI antagonists are described. Structure-activity relationship studies led to the identification of compound 22, which demonstrated potent binding activity, functional antagonism of CCR1 as well as good species cross-reactivity. In addition, compound 22 also showed desirable pharmacokinetic profiles and was selected for in vivo studies in the mouse collagen-induced arthritis model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.104

文献信息

• [EN] 1-(4-BENZYL-PIPERAZIN-1-YL)-3-PHENYL-PROPENONE DERIVATIVES<br/>[FR] DERIVES DE 1-(4-BENZYL-PIPERAZINE-1-YL)-3-PHENYL-PROPENONE
  申请人：NOVARTIS AG

  公开号：WO2004037796A3

  公开（公告）日：2004-06-17
• US7645760B2
  申请人：——

  公开号：US7645760B2

  公开（公告）日：2010-01-12
• Structure–activity relationships of novel, highly potent, selective, and orally active CCR1 antagonists
  作者：Yun Feng Xie、Kirk Lake、Kathleen Ligsay、Mallareddy Komandla、Ila Sircar、Gobi Nagarajan、Jian Li、Kui Xu、Jason Parise、Lisa Schneider、Ding Huang、Juping Liu、Kevin Dines、Naoki Sakurai、Miguel Barbosa、Rick Jack

  DOI：10.1016/j.bmcl.2007.03.104

  日期：2007.6

  Design and synthesis of a series of 3-amino-4-(2-(2-(4-benzylpiperazin-1-yl)-2-oxoethoxy)phenylamino)cyclobutenedione derivatives as novel CCRI antagonists are described. Structure-activity relationship studies led to the identification of compound 22, which demonstrated potent binding activity, functional antagonism of CCR1 as well as good species cross-reactivity. In addition, compound 22 also showed desirable pharmacokinetic profiles and was selected for in vivo studies in the mouse collagen-induced arthritis model. (c) 2007 Elsevier Ltd. All rights reserved.