2,5-dihydro-10-methoxy-2,2,4-trimethyl-5-[3-(methoxymethoxy)phenyl]-1H-[1]benzopyrano[3,4-f]quinoline | 239067-67-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2,5-dihydro-10-methoxy-2,2,4-trimethyl-5-[3-(methoxymethoxy)phenyl]-1H-[1]benzopyrano[3,4-f]quinoline
• 英文别名: 10-Methoxy-5-(3-methoxymethoxy-phenyl)-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene；10-methoxy-5-[3-(methoxymethoxy)phenyl]-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline
• CAS: 239067-67-5
• 化学式: C₂₈H₂₉NO₄
• 分子量: 443.543
• InChiKey: AKWLHIKHZRXJAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-dihydro-10-methoxy-2,2,4-trimethyl-5-[3-(methoxymethoxy)phenyl]-1H-[1]benzopyrano[3,4-f]quinoline 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以98%的产率得到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：

  10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysen-5-ol 在 magnesium sulfate 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 2,5-dihydro-10-methoxy-2,2,4-trimethyl-5-[3-(methoxymethoxy)phenyl]-1H-[1]benzopyrano[3,4-f]quinoline
  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

• [EN] GLUCOCORTICOID-SELECTIVE ANTI-INFLAMMATORY AGENTS<br/>[FR] AGENTS ANTI-INFLAMMATOIRES PRESENTANT UNE SELECTIVITE POUR LES GLUCOCORTICOIDES
  申请人：ABBOTT LABORATORIES

  公开号：WO1999041256A1

  公开（公告）日：1999-08-19

  (EN) Compounds having Formula (I), are useful for partially or fully antagonizing, repressing, agonizing, or modulating the glucocorticoid receptor and treating immune, autoimmune and inflammatory diseases in a mammal. Also disclosed are pharmaceutical compositions comprising compounds of Formula (I) and methods of inhibiting immune or autoimmune diseases in a mammal.(FR) Composés représentés par la formule (I) jouant un rôle utile partiel ou total d'antagonistes, de répresseurs, d'agonistes ou de modulateurs du récepteur de glucocorticoïdes et servant à traiter des maladies immunes, auto-immunes et inflammatoires chez le mammifère. Compositions pharmaceutiques contenant les composés ci-dessus et procédés permettant d'inhiber des maladies immunes ou auto-immunes chez le mammifère.

  化合物的化学式为（I），可用于部分或完全对抗、抑制、激活或调节糖皮质激素受体，并治疗哺乳动物的免疫、自身免疫和炎症性疾病。还公开了包含化合物（I）的药物组合物和在哺乳动物中抑制免疫或自身免疫疾病的方法。
• Glucocortiocoid-selective antinflammatory agents
  申请人：Abbott Laboratories and Ligand Pharmaceuticals Incorporated

  公开号：US20030073703A1

  公开（公告）日：2003-04-17

  Compounds having Formula I 1 are useful for partially or fully antagonizing, repressing, agonizing, or modulating the glucocorticoid receptor and treating immune, autoimmune and inflammatory diseases in a mammal. Also disclosed are pharmaceutical compositions comprising compounds of Formula I and methods of inhibiting immune or autoimmune diseases in a mammal.

  具有I1式的化合物对于部分或完全对抗、抑制、激动或调节糖皮质激素受体，并治疗哺乳动物的免疫、自身免疫和炎症性疾病是有用的。此外，还揭示了包含I式化合物的制药组合物和抑制哺乳动物的免疫或自身免疫疾病的方法。
• Androgen Receptor Modulator Compounds and Methods
  申请人：Loren Jon C.

  公开号：US20090227571A1

  公开（公告）日：2009-09-10

  Provided herein are compounds that bind to androgen receptors and modulate the activity and/or the amount of androgen receptors and to methods for making and using such compounds. Also provided are compositions including such compounds and methods for making and using such compositions.

  本文提供了一些结合雄激素受体并调节雄激素受体的活性和/或数量的化合物，以及制备和使用这些化合物的方法。还提供了包括这些化合物的组合物以及制备和使用这些组合物的方法。
• GLUCOCORTICOID-SELECTIVE ANTI-INFLAMMATORY AGENTS
  申请人：ABBOTT LABORATORIES

  公开号：EP1053239A1

  公开（公告）日：2000-11-22
• US6506766B1
  申请人：——

  公开号：US6506766B1

  公开（公告）日：2003-01-14