4-(5-chloro-4-oxo-3-azapentyl)-1,2-diphenyl-3,5-pyrazolidinedione | 106295-70-9

• 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: 4-(5-chloro-4-oxo-3-azapentyl)-1,2-diphenyl-3,5-pyrazolidinedione
• 英文别名: 2-chloro-N-[2-(3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)ethyl]acetamide
• CAS: 106295-70-9
• 化学式: C₁₉H₁₈ClN₃O₃
• 分子量: 371.823
• InChiKey: MOAIBTDFKDOAJL-UHFFFAOYSA-N

物化性质

• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-chloro-4-oxo-3-azapentyl)-1,2-diphenyl-3,5-pyrazolidinedione 在 1-环己基-2-吡咯烷酮 、 溴化乙啶 、 sodium bromide 作用下， 反应 96.0h， 生成 4-(5-bromo-4-oxo-3-azapentyl)-1,2-diphenyl-3,5-pyrazolidinedione
  参考文献：
  名称：

  Preparation and evaluation of electrophilic derivatives of phenylbutazone as inhibitors of prostaglandin-H-synthase

  摘要：

  The chemical syntheses and biological evaluation of several potential irreversible inhibitors for prostaglandin (PGH) synthase are described. These inhibitors were modeled after the nonsteroidal antiinflammatory (NSAI) drug phenylbutazone (4-n-butyl-1,2-diphenyl-3,5-pyrazolidinedione). Electrophilic functionalities such as an alpha-bromoacetamide, an alpha-chloroacetamide, a phenylurethane, a propargyl chloride, and several alpha,beta-unsaturated Michael acceptors were incorporated at the 4-position of the pyrazolidinedione ring structure. None of the derivatives showed evidence of irreversible inhibition of PGH synthase, although several were nearly as potent inhibitors of this enzyme as phenylbutazone. The nitrile obtained from 1,4-conjugate addition of cyanide to one of the unsaturated derivatives was considerably more potent as an inhibitor of PGH synthase than was phenylbutazone.

  DOI：

  10.1021/jm00386a020
• 作为产物：
  描述：

  4-(cyanomethyl)-1,2-diphenyl-3,5-pyrazolidinedione 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.25h， 生成 4-(5-chloro-4-oxo-3-azapentyl)-1,2-diphenyl-3,5-pyrazolidinedione
  参考文献：
  名称：

  Preparation and evaluation of electrophilic derivatives of phenylbutazone as inhibitors of prostaglandin-H-synthase

  摘要：

  The chemical syntheses and biological evaluation of several potential irreversible inhibitors for prostaglandin (PGH) synthase are described. These inhibitors were modeled after the nonsteroidal antiinflammatory (NSAI) drug phenylbutazone (4-n-butyl-1,2-diphenyl-3,5-pyrazolidinedione). Electrophilic functionalities such as an alpha-bromoacetamide, an alpha-chloroacetamide, a phenylurethane, a propargyl chloride, and several alpha,beta-unsaturated Michael acceptors were incorporated at the 4-position of the pyrazolidinedione ring structure. None of the derivatives showed evidence of irreversible inhibition of PGH synthase, although several were nearly as potent inhibitors of this enzyme as phenylbutazone. The nitrile obtained from 1,4-conjugate addition of cyanide to one of the unsaturated derivatives was considerably more potent as an inhibitor of PGH synthase than was phenylbutazone.

  DOI：

  10.1021/jm00386a020

文献信息

• Preparation and evaluation of electrophilic derivatives of phenylbutazone as inhibitors of prostaglandin-H-synthase
  作者：Jonathan L. Vennerstrom、Thomas J. Holmes

  DOI：10.1021/jm00386a020

  日期：1987.3

  The chemical syntheses and biological evaluation of several potential irreversible inhibitors for prostaglandin (PGH) synthase are described. These inhibitors were modeled after the nonsteroidal antiinflammatory (NSAI) drug phenylbutazone (4-n-butyl-1,2-diphenyl-3,5-pyrazolidinedione). Electrophilic functionalities such as an alpha-bromoacetamide, an alpha-chloroacetamide, a phenylurethane, a propargyl chloride, and several alpha,beta-unsaturated Michael acceptors were incorporated at the 4-position of the pyrazolidinedione ring structure. None of the derivatives showed evidence of irreversible inhibition of PGH synthase, although several were nearly as potent inhibitors of this enzyme as phenylbutazone. The nitrile obtained from 1,4-conjugate addition of cyanide to one of the unsaturated derivatives was considerably more potent as an inhibitor of PGH synthase than was phenylbutazone.