7-Chloro-3-(3,4,5-trimethyl-phenyl)-2,4-bis-(2-trimethylsilanyl-ethoxy)-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide | 362604-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-Chloro-3-(3,4,5-trimethyl-phenyl)-2,4-bis-(2-trimethylsilanyl-ethoxy)-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide
• 英文别名: 7-chloro-N-(1,2,5-thiadiazol-3-yl)-3-(3,4,5-trimethylphenyl)-2,4-bis(2-trimethylsilylethoxy)quinoline-6-carboxamide
• CAS: 362604-27-1
• 化学式: C₃₁H₄₁ClN₄O₃SSi₂
• 分子量: 641.382
• InChiKey: OBRNGGUGUSMZMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.02
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-Chloro-3-(3,4,5-trimethyl-phenyl)-2,4-bis-(2-trimethylsilanyl-ethoxy)-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide 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-3-(3,4,5-trimethyl-phenyl)-2-(2-trimethylsilanyl-ethoxy)-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-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
• 作为产物：
  描述：

  Methyl 7-chloro-3-(3,4,5-trimethylphenyl)-2,4-bis(2-trimethylsilylethoxy)quinoline-6-carboxylate 在 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 7-Chloro-3-(3,4,5-trimethyl-phenyl)-2,4-bis-(2-trimethylsilanyl-ethoxy)-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-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