Ethyl 2-{1-[(2-chlorophenyl)sulfonyl]-3-oxo-2-piperazinyl}acetate | 318288-72-1

• 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: Ethyl 2-{1-[(2-chlorophenyl)sulfonyl]-3-oxo-2-piperazinyl}acetate
• 英文别名: ethyl 2-[1-(2-chlorophenyl)sulfonyl-3-oxopiperazin-2-yl]acetate
• CAS: 318288-72-1
• 化学式: C₁₄H₁₇ClN₂O₅S
• 分子量: 360.818
• InChiKey: JBNGSZRZEONQGV-UHFFFAOYSA-N

物化性质

• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 2-{1-[(2-chlorophenyl)sulfonyl]-3-oxo-2-piperazinyl}acetate 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 2-[1-(2-Chlorophenyl)sulfonyl-3-oxopiperazin-2-yl]acetic acid
  参考文献：
  名称：

  3-Oxo-2-piperazinyl acetamides as potent bradykinin B1 receptor antagonists for the treatment of pain and inflammation

  摘要：

  The discovery of novel and highly potent oxopiperazine based B1 receptor antagonists is described. Compared to the previously described arylsulfonylated (R)-3-amino-3-phenylpropionic acid series, the current compounds showed improved in vitro potency and metabolic stability. Compound 17, 2-((2R)-1-((4-methylphenyl)sulfonyl)-3-oxo-2-piperazinyl)-N-((1R)-6-(1-piperidinylmethyl)-1,2,3,4-tetrahydro-1-naphthalenyl) acetamide, showed EC(50) of 10.3 nM in a rabbit biochemical challenge model. The practical syntheses of chiral arylsulfonylated oxopiperazine acetic acids are also described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.115
• 作为产物：
  描述：

  2-(3-氧代-2-哌嗪基)乙酸乙酯 、 2-氯苯磺酰氯 在 吡啶 作用下， 生成 Ethyl 2-{1-[(2-chlorophenyl)sulfonyl]-3-oxo-2-piperazinyl}acetate
  参考文献：
  名称：

  3-Oxo-2-piperazinyl acetamides as potent bradykinin B1 receptor antagonists for the treatment of pain and inflammation

  摘要：

  The discovery of novel and highly potent oxopiperazine based B1 receptor antagonists is described. Compared to the previously described arylsulfonylated (R)-3-amino-3-phenylpropionic acid series, the current compounds showed improved in vitro potency and metabolic stability. Compound 17, 2-((2R)-1-((4-methylphenyl)sulfonyl)-3-oxo-2-piperazinyl)-N-((1R)-6-(1-piperidinylmethyl)-1,2,3,4-tetrahydro-1-naphthalenyl) acetamide, showed EC(50) of 10.3 nM in a rabbit biochemical challenge model. The practical syntheses of chiral arylsulfonylated oxopiperazine acetic acids are also described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.115

文献信息

• 3-Oxo-2-piperazinyl acetamides as potent bradykinin B1 receptor antagonists for the treatment of pain and inflammation
  作者：Jian Jeffrey Chen、Thomas Nguyen、Derin C. D’Amico、Wenyuan Qian、Jason Human、Toshihiro Aya、Kaustav Biswas、Christopher Fotsch、Nianhe Han、Qingyian Liu、Nobuko Nishimura、Tanya A.N. Peterkin、Kevin Yang、Jiawang Zhu、Babak Bobby Riahi、Randall W. Hungate、Neil G. Andersen、John T. Colyer、Margaret M. Faul、Augustus Kamassah、Judy Wang、Janan Jona、Gondi Kumar、Eileen Johnson、Benny C. Askew

  DOI：10.1016/j.bmcl.2011.03.115

  日期：2011.6

  The discovery of novel and highly potent oxopiperazine based B1 receptor antagonists is described. Compared to the previously described arylsulfonylated (R)-3-amino-3-phenylpropionic acid series, the current compounds showed improved in vitro potency and metabolic stability. Compound 17, 2-((2R)-1-((4-methylphenyl)sulfonyl)-3-oxo-2-piperazinyl)-N-((1R)-6-(1-piperidinylmethyl)-1,2,3,4-tetrahydro-1-naphthalenyl) acetamide, showed EC(50) of 10.3 nM in a rabbit biochemical challenge model. The practical syntheses of chiral arylsulfonylated oxopiperazine acetic acids are also described. (C) 2011 Elsevier Ltd. All rights reserved.