2-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-1H-pyrrole-3-carbonitrile | 709027-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-1H-pyrrole-3-carbonitrile
• 英文别名: 2-(4,4-dimethyl-2-oxo-1H-3,1-benzoxazin-6-yl)-1H-pyrrole-3-carbonitrile
• CAS: 709027-91-8
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: BQFWGCXTZMWESZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 2-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-1H-pyrrole-3-carbonitrile 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-1-methyl-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  Novel pyrrole-containing progesterone receptor modulators

  摘要：

  A series of 1,4-dihydro-2H-[d][3,1]-benzoxazin-2-one and 1,3-dihydro-[3H]-indol-2-one containing 6- or 5-, respectively, appended substituted pyrrole moieties were synthesized and evaluated for their ability to modulate the activity of the progesterone receptor (PR). Key structural changes to the pyrrole moieties of these molecules were shown to have a predictive influence as to whether the compounds behaved as PR agonists or antagonists. Compounds with the 5'-cyano-2'-pyrrole moiety (e.g.,.32, 33, and 38) were shown to be potent PR agonists (EC50'S Of 1.1, 1.8, and 2.8 nM, respectively). Compounds with the 5'-nitro-2'-pyrrole moiety (e.g., 34 and 36) were shown to be PR antagonists IC50'S Of 180 and 36nM, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.054
• 作为产物：
  描述：

  溴伏克辛 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium ethanolate 、 potassium carbonate 、 氯化铵 、 锌 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 为溶剂， 反应 4.0h， 生成 2-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  Novel pyrrole-containing progesterone receptor modulators

  摘要：

  A series of 1,4-dihydro-2H-[d][3,1]-benzoxazin-2-one and 1,3-dihydro-[3H]-indol-2-one containing 6- or 5-, respectively, appended substituted pyrrole moieties were synthesized and evaluated for their ability to modulate the activity of the progesterone receptor (PR). Key structural changes to the pyrrole moieties of these molecules were shown to have a predictive influence as to whether the compounds behaved as PR agonists or antagonists. Compounds with the 5'-cyano-2'-pyrrole moiety (e.g.,.32, 33, and 38) were shown to be potent PR agonists (EC50'S Of 1.1, 1.8, and 2.8 nM, respectively). Compounds with the 5'-nitro-2'-pyrrole moiety (e.g., 34 and 36) were shown to be PR antagonists IC50'S Of 180 and 36nM, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.054

文献信息

• Novel pyrrole-containing progesterone receptor modulators
  作者：Mark A Collins、Valerie Hudak、Reinhold Bender、Andrew Fensome、Puwen Zhang、Lori Miller、Richard C Winneker、Zhiming Zhang、Yuan Zhu、Jeffrey Cohen、Rayomond J Unwalla、Jay Wrobel

  DOI：10.1016/j.bmcl.2004.02.054

  日期：2004.5

  A series of 1,4-dihydro-2H-[d][3,1]-benzoxazin-2-one and 1,3-dihydro-[3H]-indol-2-one containing 6- or 5-, respectively, appended substituted pyrrole moieties were synthesized and evaluated for their ability to modulate the activity of the progesterone receptor (PR). Key structural changes to the pyrrole moieties of these molecules were shown to have a predictive influence as to whether the compounds behaved as PR agonists or antagonists. Compounds with the 5'-cyano-2'-pyrrole moiety (e.g.,.32, 33, and 38) were shown to be potent PR agonists (EC50'S Of 1.1, 1.8, and 2.8 nM, respectively). Compounds with the 5'-nitro-2'-pyrrole moiety (e.g., 34 and 36) were shown to be PR antagonists IC50'S Of 180 and 36nM, respectively). (C) 2004 Elsevier Ltd. All rights reserved.