5-(4-chlorophenyl)-1,2,3,4-tetrahydro-4-hydroxy-2,2-dimethyl-5H-chromeno[3,4-f]quinoline | 199668-74-1

• 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-chlorophenyl)-1,2,3,4-tetrahydro-4-hydroxy-2,2-dimethyl-5H-chromeno[3,4-f]quinoline
• 英文别名: 5-(4-Chlorophenyl)-2,2-dimethyl-1,3,4,5-tetrahydrochromeno[3,4-f]quinolin-4-ol
• CAS: 199668-74-1
• 化学式: C₂₄H₂₂ClNO₂
• 分子量: 391.897
• InChiKey: UNJYGSQYSIBRHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-1,2,3,4-tetrahydro-4-hydroxy-2,2-dimethyl-5H-chromeno[3,4-f]quinoline 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-(4-Chloro-phenyl)-2,2-dimethyl-2,5-dihydro-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
• 作为产物：
  描述：

  4-chlorophenyl lithium 在 三乙基硅烷 、 正丁基锂 、 二甲基硫 、 二异丁基氢化铝 、 臭氧 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.05h， 生成 5-(4-chlorophenyl)-1,2,3,4-tetrahydro-4-hydroxy-2,2-dimethyl-5H-chromeno[3,4-f]quinoline
  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

• Steroid receptor modulator compounds and methods
  申请人：——

  公开号：US20040186132A1

  公开（公告）日：2004-09-23

  Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.

  本文披露了高亲和力、高选择性的非类固醇化合物，可作为类固醇受体调节剂。同时也披露了包含这些化合物的药物组合物，以及使用这些化合物和组合物治疗需要类固醇受体激动剂或拮抗剂治疗的患者的方法，还包括制备这些化合物的中间体和制备类固醇受体调节剂化合物的方法。
• Methods for the preparation of coumarine derivatives
  申请人：LIGAND PHARMACEUTICALS INCORPORATED

  公开号：EP1041071A1

  公开（公告）日：2000-10-04

  Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.

  本发明公开了对类固醇受体具有高亲和力、高选择性调节作用的非类固醇化合物。还公开了含有此类化合物的药物组合物、使用所公开化合物和组合物治疗需要类固醇受体激动剂或拮抗剂治疗的患者的方法、制备化合物时有用的中间体以及制备类固醇受体调节剂化合物的工艺。
• STEROID RECEPTOR MODULATOR COMPOUNDS AND METHODS
  申请人：LIGAND PHARMACEUTICALS, INC.

  公开号：EP0800519A1

  公开（公告）日：1997-10-15
• US5688810A
  申请人：——

  公开号：US5688810A

  公开（公告）日：1997-11-18
• US5693646A
  申请人：——

  公开号：US5693646A

  公开（公告）日：1997-12-02