2,2,4-Trimethyl-5-oxo-2,5-dihydro-6-oxa-1-aza-chrysene-1-carboxylic acid tert-butyl ester | 223726-55-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 2,2,4-Trimethyl-5-oxo-2,5-dihydro-6-oxa-1-aza-chrysene-1-carboxylic acid tert-butyl ester
• CAS: 223726-55-4
• 化学式: C₂₄H₂₅NO₄
• 分子量: 391.467
• InChiKey: UTRMMAKGRUALDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  29.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.75
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,2,4-Trimethyl-5-oxo-2,5-dihydro-6-oxa-1-aza-chrysene-1-carboxylic acid tert-butyl ester 在 硼烷四氢呋喃络合物 、 双氧水 、 对甲苯磺酸 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (5Z)-5-benzylidene-2,2,4-trimethyl-1,4-dihydrochromeno[3,4-f]quinolin-3-one
  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：

  二碳酸二叔丁酯 、 2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one 在 正丁基锂 作用下， 生成 2,2,4-Trimethyl-5-oxo-2,5-dihydro-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