7-Chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid pyrimidin-4-ylamide | 691857-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-Chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid pyrimidin-4-ylamide
• CAS: 691857-93-9
• 化学式: C₂₃H₁₉ClN₄O₃
• 分子量: 434.882
• InChiKey: RACHXYJKGJBALD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  107.97
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7-Chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid pyrimidin-4-ylamide 在 苯甲醚 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 7-chloro-2-oxo-N-pyrimidin-4-yl-4-[2-[(2S,6R)-6-(trifluoromethyl)piperidin-2-yl]ethoxy]-3-(3,4,5-trimethylphenyl)-1H-quinoline-6-carboxamide
  参考文献：
  名称：

  Syntheses and structure–activity relationship studies of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists

  摘要：

  Syntheses and structure-activity relationships of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists are described. Some of substituents on the piperidine ring that were investigated included a fused phenyl group, a (6R)-trifluoromethyl group, (6S) and (6R)-methyl group. This study showed that GnRH binding potency was tolerated by a small group at the 6-position of the piperidine, and blocking the 6-position by a trifluoromethyl group reduced clearance rate and increased oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.101
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到7-Chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid pyrimidin-4-ylamide
  参考文献：
  名称：

  Identification of neutral 4-O-alkyl quinolone nonpeptide GnRH receptor antagonists

  摘要：

  A series of neutral, nonbasic quinolone GnRH antagonists were prepared via Mitsunobu alkylation of protected and unprotected 4-hydroxy quinolone intermediates. The synthetic route was improved by utilization of unique reactivity and convergency afforded by the use of mono and bis-trimethylsilylethyl protected quinolones. Potent neutral GnRH antagonists were identified, including ether and lactam derivatives, that show similar in vitro binding affinity and functional activity as compared to the earlier basic 4-aminoalkyl quinolone series of nonpeptide GnRH antagonists. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.056