5-(4-Chloro-phenyl)-2,2-dimethyl-4-methylene-2,3,4,5-tetrahydro-1H-6-oxa-1-aza-chrysene | 179894-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-(4-Chloro-phenyl)-2,2-dimethyl-4-methylene-2,3,4,5-tetrahydro-1H-6-oxa-1-aza-chrysene
• 英文别名: 5-(4-chlorophenyl)-2,2-dimethyl-4-methylidene-3,5-dihydro-1H-chromeno[3,4-f]quinoline
• CAS: 179894-98-5
• 化学式: C₂₅H₂₂ClNO
• 分子量: 387.909
• InChiKey: VVZDMFDMLBMVHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-Chloro-phenyl)-2,2-dimethyl-4-methylene-2,3,4,5-tetrahydro-1H-6-oxa-1-aza-chrysene 在 正丁基锂 、 二甲基硫 、 臭氧 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.05h， 生成 5-(4-Chloro-phenyl)-2,2-dimethyl-4-oxo-2,3,4,5-tetrahydro-6-oxa-1-aza-chrysene-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  5-Aryl-1,2,3,4-tetrahydrochromeno[3,4-f]quinolin-3-ones as a Novel Class of Nonsteroidal Progesterone Receptor Agonists:  Effect of A-Ring Modification

  摘要：

  Optimization of the 1,2-dihydroquinoline A-ring of a nonsteroidal human progesterone receptor (hPR) agonist pharmacophore (1) was performed by using the cotransfection and receptor binding assays as guides. The S-keto group was discovered to regain the patent agonist activity which was lost upon removal of the 3,4-olefin, and it led to a novel hPR agonist series, 5-aryl-1,2,3,4-tetrahydrochromeno[3,4-f]quinolin-3-ones. The new progestins demonstrated potent hPR agonist activity in the cotransfection assay and high binding affinity similar to progesterone. T47D human breast cancer cell line was employed for further characterization of the new progestins and a number of reference analogues. It was found that the new 3-keto analogues showed full agonist activity in the T47D assay, while the reference compounds from other related nonsteroidal hPR agonist series exhibited only partial agonist activity.

  DOI：

  10.1021/jm980723h
• 作为产物：
  描述：

  4-chlorophenyl lithium 、 2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one 在 三乙基硅烷 、 三氟乙酸 作用下， 生成 (-)-5-(4-Chlorophenyl)-1,2-dihydro-2,2,4-trimethyl-5H-chromeno[3,4-f]quinoline 、 5-(4-Chloro-phenyl)-2,2-dimethyl-4-methylene-2,3,4,5-tetrahydro-1H-6-oxa-1-aza-chrysene
  参考文献：
  名称：

  5-Aryl-1,2,3,4-tetrahydrochromeno[3,4-f]quinolin-3-ones as a Novel Class of Nonsteroidal Progesterone Receptor Agonists:  Effect of A-Ring Modification

  摘要：

  Optimization of the 1,2-dihydroquinoline A-ring of a nonsteroidal human progesterone receptor (hPR) agonist pharmacophore (1) was performed by using the cotransfection and receptor binding assays as guides. The S-keto group was discovered to regain the patent agonist activity which was lost upon removal of the 3,4-olefin, and it led to a novel hPR agonist series, 5-aryl-1,2,3,4-tetrahydrochromeno[3,4-f]quinolin-3-ones. The new progestins demonstrated potent hPR agonist activity in the cotransfection assay and high binding affinity similar to progesterone. T47D human breast cancer cell line was employed for further characterization of the new progestins and a number of reference analogues. It was found that the new 3-keto analogues showed full agonist activity in the T47D assay, while the reference compounds from other related nonsteroidal hPR agonist series exhibited only partial agonist activity.

  DOI：

  10.1021/jm980723h

文献信息

• 5-Aryl-1,2,3,4-tetrahydrochromeno[3,4-<i>f</i>]quinolin-3-ones as a Novel Class of Nonsteroidal Progesterone Receptor Agonists:  Effect of A-Ring Modification
  作者：Lin Zhi、Christopher M. Tegley、Keith B. Marschke、Dale E. Mais、Todd K. Jones

  DOI：10.1021/jm980723h

  日期：1999.4.22

  Optimization of the 1,2-dihydroquinoline A-ring of a nonsteroidal human progesterone receptor (hPR) agonist pharmacophore (1) was performed by using the cotransfection and receptor binding assays as guides. The S-keto group was discovered to regain the patent agonist activity which was lost upon removal of the 3,4-olefin, and it led to a novel hPR agonist series, 5-aryl-1,2,3,4-tetrahydrochromeno[3,4-f]quinolin-3-ones. The new progestins demonstrated potent hPR agonist activity in the cotransfection assay and high binding affinity similar to progesterone. T47D human breast cancer cell line was employed for further characterization of the new progestins and a number of reference analogues. It was found that the new 3-keto analogues showed full agonist activity in the T47D assay, while the reference compounds from other related nonsteroidal hPR agonist series exhibited only partial agonist activity.