4-chloro-2-<(2-methylphenyl)amino>thieno<3,2-d>pyrimidine | 134372-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 4-chloro-2-<(2-methylphenyl)amino>thieno<3,2-d>pyrimidine
• 英文别名: 2-(2-methylphenylamino)-4-chlorothieno[3,2-d]-pyrimidine；4-chloro-N-(2-methylphenyl)thieno[3,2-d]pyrimidin-2-amine
• CAS: 134372-87-5
• 化学式: C₁₃H₁₀ClN₃S
• 分子量: 275.761
• InChiKey: KLELAEYYNAEVQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-2-<(2-methylphenyl)amino>thieno<3,2-d>pyrimidine 、 N-甲基苯胺 在 盐酸 、 二氯甲烷 、 magnesium sulfate 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以gave the title compound, (0.75 g) m.p. 198°-200°的产率得到4-(N-methylphenylamino)-2-<(2-methylphenyl)amino>thieno<3,2-d>pyrimidine
  参考文献：
  名称：

  Thienopyrimidines

  摘要：

  本发明揭示了噻唑嘧啶化合物，作为抑制H.sup.+ K.sup.+ ATPase酶的抑制剂，用于治疗胃酸分泌。该发明的化合物是2-(2-甲基苯基氨基)-4-(N-甲基苯基氨基)噻吩[3,2-d]嘧啶。

  公开号：

  US05280026A1
• 作为产物：
  描述：

  2-<(2-methylphenyl)amino>thieno<3,2-d>pyrimidinone 在 三氯氧磷 作用下， 反应 1.0h， 以97%的产率得到4-chloro-2-<(2-methylphenyl)amino>thieno<3,2-d>pyrimidine
  参考文献：
  名称：

  Reversible Inhibitors of the Gastric (H+/K+)-ATPase. 5. Substituted 2,4-Diaminoquinazolines and Thienopyrimidines

  摘要：

  Quinazolines bearing a secondary 4-(arylamino) substituent demonstrate an SAR for inhibition of the gastric (H+/K+)-ATPase different from the previously described 3-acylquinolines, suggesting that, although these compounds are also K+-competitive, they probably bind to the enzyme in a different orientation. Compounds bearing a tertiary 4-(arylamino) substituent, however, in particular 4-(N-methylarylamino), appear to possess an SAR quite similar to the 3-acylquinolines. We show that this arises from the effect of the N-methylation, which is to orientate the 4-(arylamino) substituent syn to C-5, analogous to the 3-acylquinolines. Compounds possessing both a 4-(N-methylarylamino) substituent and a 2-(arylamino) substituent proved to be very potent, K+-competitive inhibitors of K+-stimulated ATPase activity with K-i values down to 12 nM. Some compounds also proved to be effective inhibitors of stimulated acid secretion in both the rat and dog when dosed intravenously. However, although a number of these demonstrated activity after oral administration in the dog, the level and variability precluded further evaluation.

  DOI：

  10.1021/jm00014a027

文献信息

• Substituted thienopyrimidine derivatives, their preparation, pharmaceutical compositions and medical use
  申请人：SMITHKLINE BEECHAM INTERCREDIT B.V.

  公开号：EP0404356B1

  公开（公告）日：1993-09-22
• US5280026A
  申请人：——

  公开号：US5280026A

  公开（公告）日：1994-01-18