10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysen-5-ol | 239070-99-6

• 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: 10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysen-5-ol
• 英文别名: 10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-chromeno[3,4-f]quinolin-5-ol；10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-ol
• CAS: 239070-99-6
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: RJZFVNMCFWQANQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 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：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysen-5-ol 在 盐酸 、 magnesium sulfate 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.67h， 生成 3-(2,5-dihydro-10-methoxy-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinolin-5-yl)phenol
  参考文献：
  名称：

  Synthesis and Characterization of Non-Steroidal Ligands for the Glucocorticoid Receptor:  Selective Quinoline Derivatives with Prednisolone-Equivalent Functional Activity

  摘要：

  A novel class of functional ligands for the human glucocorticoid receptor is described. Substituents in the C-10 position of the tetracyclic core are essential for glucocorticoid receptor (GR) selectivity versus other steroid receptors. The C-5 position is derivatized with meta-substituted aromatic groups, resulting in analogues with a high affinity for GR (K-i = 2.4-9.3 nM) and functional activity comparable to prednisolone in reporter gene assays of glucocorticoid-mediated gene transcription. The biological activity of these novel quinolines was also prednisolone-equivalent in whole cell assays of glucocorticoid function, and compound 13 was similar to prednisolone (po ED50 = 2.8 mpk for 13 vs ED50 = 1.2 mpk for prednisolone) in a rodent model of asthma (sephadex-induced eosinophil influx).

  DOI：

  10.1021/jm010228c
• 作为产物：
  描述：

  1-hydroxy-8-nitro-6H-dibenzo[b,d]pyran-6-one 在 palladium on activated charcoal 氢气 、 碘 、 二异丁基氢化铝 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 114.0h， 生成 10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysen-5-ol
  参考文献：
  名称：

  Synthesis and Characterization of Non-Steroidal Ligands for the Glucocorticoid Receptor:  Selective Quinoline Derivatives with Prednisolone-Equivalent Functional Activity

  摘要：

  A novel class of functional ligands for the human glucocorticoid receptor is described. Substituents in the C-10 position of the tetracyclic core are essential for glucocorticoid receptor (GR) selectivity versus other steroid receptors. The C-5 position is derivatized with meta-substituted aromatic groups, resulting in analogues with a high affinity for GR (K-i = 2.4-9.3 nM) and functional activity comparable to prednisolone in reporter gene assays of glucocorticoid-mediated gene transcription. The biological activity of these novel quinolines was also prednisolone-equivalent in whole cell assays of glucocorticoid function, and compound 13 was similar to prednisolone (po ED50 = 2.8 mpk for 13 vs ED50 = 1.2 mpk for prednisolone) in a rodent model of asthma (sephadex-induced eosinophil influx).

  DOI：

  10.1021/jm010228c

文献信息

• Process for the preparation of 5-(substituted)-10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-chromeno[3,4-F]quinolines and derivatives thereof
  申请人：Abbott Laboratories

  公开号：US06518430B1

  公开（公告）日：2003-02-11

  The present invention relates to an efficient process for the preparation of 5-(substituted)-10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-chromeno[3,4-f]quinolines.

  本发明涉及一种高效的制备5-(取代基)-10-甲氧基-2,2,4-三甲基-2,5-二氢-1H-咖啡因[3,4-f]喹啉的方法。
• Process for the preparation of 5-(substituted)-10 methoxy-2,2,4-trimethyl-2,5-dihydro- 1H-chromeno [3,4-f] quinolines and derivatives thereof
  申请人：——

  公开号：US20030069427A1

  公开（公告）日：2003-04-10

  The present invention relates to an efficient process for the preparation of 5-(substituted)-10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-chromeno[3,4-f]quinolines.

  本发明涉及一种高效的方法，用于制备5-（取代基）-10-甲氧基-2,2,4-三甲基-2,5-二氢-1H-色烯[3,4-f]喹啉。
• Process for the preparation of 5-(substituted)-10 methoxy-2,2,4-trimethyl-2,5-dihydro-1H-chromeno [3,4-F] quinolines and derivatives thereof
  申请人：——

  公开号：US06673930B2

  公开（公告）日：2004-01-06

  The present invention relates to an efficient process for the preparation of 5-(substituted)-10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-chromeno[3,4-f]quinolines.

  本发明涉及一种高效的方法，用于制备5-(取代)-10-甲氧基-2,2,4-三甲基-2,5-二氢-1H-咔啉[3,4-f]喹啉。
• A Practical and Scaleable Synthesis of A-224817.0, a Novel Nonsteroidal Ligand for the Glucocorticoid Receptor
  作者：Yi-Yin Ku、Tim Grieme、Prasad Raje、Padam Sharma、Howard E. Morton、Mike Rozema、Steve A. King

  DOI：10.1021/jo0268613

  日期：2003.4.1

  A practical and scaleable synthesis of a novel nonsteroidal ligand for the glucocorticoid receptor A-224817.0 1A is described. The synthesis proceeds in seven steps starting from 1,3-dimethoxybenzene. The biaryl intermediate 5 was prepared by an optimized high-yielding and high-throughput Negishi protocol. The quinoline core 8 was constructed by using a modified Skraup reaction. The final product was obtained by a direct allylation reaction of lactol 10 with allyltrimethylsilane. The process was accomplished efficiently to produce 1A in 25% overall yield and >99% purity with simple and practical isolation and purification procedures.
• WO2021/118728
  申请人：——

  公开号：——

  公开（公告）日：——