5-Methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene | 179895-20-6

• 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-Methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene
• 英文别名: 5-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline
• CAS: 179895-20-6
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: ROSXUCQGEAYHMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene 、 烯丙基三甲基硅烷 在 三氟甲磺酸三甲基硅酯 作用下， 生成 5-Allyl-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene
  参考文献：
  名称：

  5-Alkyl 1,2-dihydrochromeno[3,4-f]quinolines: a novel class of nonsteroidal progesterone receptor modulators

  摘要：

  A series of nonsteroidal human progesterone receptor (hPR) agonists, 5-alkyl 1,2-dihydrochromeno[3,4-f]quinolines, was synthesized and evaluated in cotransfection and competitive receptor binding assays. The 5-alkyl substitution was shown to be responsible for the agonist activity and substitution at C9 dramatically enhanced the potency. A number of analogues in this series showed activities similar to or better than progesterone in the cotransfection and binding assays and analogue 15 exhibited similar in vivo activity as medroxyprogesterone acetate (MPA) in murine uterine wet weight/mammary gland morphology assays. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00608-8
• 作为产物：
  描述：

  2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-Methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene
  参考文献：
  名称：

  5-Alkyl 1,2-dihydrochromeno[3,4-f]quinolines: a novel class of nonsteroidal progesterone receptor modulators

  摘要：

  A series of nonsteroidal human progesterone receptor (hPR) agonists, 5-alkyl 1,2-dihydrochromeno[3,4-f]quinolines, was synthesized and evaluated in cotransfection and competitive receptor binding assays. The 5-alkyl substitution was shown to be responsible for the agonist activity and substitution at C9 dramatically enhanced the potency. A number of analogues in this series showed activities similar to or better than progesterone in the cotransfection and binding assays and analogue 15 exhibited similar in vivo activity as medroxyprogesterone acetate (MPA) in murine uterine wet weight/mammary gland morphology assays. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00608-8

文献信息

• Steroid receptor modulator compounds and methods
  申请人：LIGAND PHARMACEUTICALS INCORPORATED

  公开号：EP1043325B1

  公开（公告）日：2004-06-16
• 5-Alkyl 1,2-dihydrochromeno[3,4-f]quinolines: a novel class of nonsteroidal progesterone receptor modulators
  作者：Lin Zhi、Christopher M Tegley、James P Edwards、Sarah J West、Keith B Marschke、Marco M Gottardis、Dale E Mais、Todd K Jones

  DOI：10.1016/s0960-894x(98)00608-8

  日期：1998.12

  A series of nonsteroidal human progesterone receptor (hPR) agonists, 5-alkyl 1,2-dihydrochromeno[3,4-f]quinolines, was synthesized and evaluated in cotransfection and competitive receptor binding assays. The 5-alkyl substitution was shown to be responsible for the agonist activity and substitution at C9 dramatically enhanced the potency. A number of analogues in this series showed activities similar to or better than progesterone in the cotransfection and binding assays and analogue 15 exhibited similar in vivo activity as medroxyprogesterone acetate (MPA) in murine uterine wet weight/mammary gland morphology assays. (C) 1998 Elsevier Science Ltd. All rights reserved.