2-(2-chloropyrimidin-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-(2-chloropyrimidin-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-2-chloropyrimidine；2-(2-chloropyrimidin-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline
• 化学式: C₁₄H₁₄ClN₃
• 分子量: 259.738
• InChiKey: NKSFOLUVXGZKOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-chloropyrimidin-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline 、 1H-苯并咪唑-2-硫醇 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 以75.2%的产率得到2-(2-(1H-benzo[d]imidazol-2-ylthio) pyrimidin-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Design, Synthesis, and Preliminary Activity Evaluation of Novel Pyrimidine Derivatives as Acid Pump Antagonists

  摘要：

  Acid‐related diseases of the upper gastrointestinal tract, especially gastroesophageal reflux disease (GERD), remain a widespread problem worldwide. In this paper, we reported the design, synthesis, and preliminary gastric antisecretory activity evaluation of novel pyrimidine derivatives as acid pump antagonists. The gastric antisecretory activity assay results showed that all compounds displayed potent gastric antisecretory activity when gastric secretion was stimulated by histamine. The most potent compound 5g exhibited even similar gastric antisecretory activity compared with the control revaprazan, and the relative inhibition rate was 93.0%, which was worthy of further investigation.

  DOI：

  10.1111/cbdd.12390
• 作为产物：
  描述：

  2,4-二氯嘧啶 、 1-甲基-1,2,3,4-四氢异喹啉 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以67.5%的产率得到2-(2-chloropyrimidin-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Design, Synthesis, and Preliminary Activity Evaluation of Novel Pyrimidine Derivatives as Acid Pump Antagonists

  摘要：

  Acid‐related diseases of the upper gastrointestinal tract, especially gastroesophageal reflux disease (GERD), remain a widespread problem worldwide. In this paper, we reported the design, synthesis, and preliminary gastric antisecretory activity evaluation of novel pyrimidine derivatives as acid pump antagonists. The gastric antisecretory activity assay results showed that all compounds displayed potent gastric antisecretory activity when gastric secretion was stimulated by histamine. The most potent compound 5g exhibited even similar gastric antisecretory activity compared with the control revaprazan, and the relative inhibition rate was 93.0%, which was worthy of further investigation.

  DOI：

  10.1111/cbdd.12390

文献信息

• Pyrimidine derivatives and processes for the preparation thereof
  申请人：Yuhan Corporation

  公开号：US05750531A1

  公开（公告）日：1998-05-12

  The present invention relates to novel pyrimidine derivatives of the formulae (I-1) and (I-2) and pharmaceutically acceptable salts thereof which possess an excellent anti-secretory activity, pharmaceutical compositions containing same as an active ingredient, their novel intermediates, and processes for the preparation thereof: ##STR1## wherein: R.sub.4 and R.sub.5, which may be the same or different, are independently hydrogen or a C.sub.1 -C.sub.3 alkyl group, or jointly form a cyclopentyl or cyclohexyl ring; A is a group of formula(II): ##STR2## wherein R.sub.1 and R.sub.2 are, independently of each other, hydrogen or a C.sub.1 -C.sub.3 alkyl group, and R.sub.3 is hydrogen, a C.sub.1 -C.sub.3 alkyl group or a halogen; and B is 1-(substituted)-1,2,3,4-tetrahydroisoquinolin-2-yl of formula (III-1) or 7-(substituted)-4,5,6,7-tetrahydrothieno\x9b2,3-c!pyridin-6-yl of formula (III-2) ##STR3## wherein R.sub.6 is hydrogen or a C.sub.1 -C.sub.3 alkyl group.

  本发明涉及式(I-1)和式(I-2)的新杂环衍生物以及可药用的盐，这些衍生物具有优异的抗分泌活性，包含它们作为活性成分的药物组合物，它们的新中间体，以及它们的制备方法：##STR1## 其中：R.sub.4 和 R.sub.5 可相同或不同，独立地是氢或C.sub.1 -C.sub.3 烷基，或者共同形成环戊基或环己基；A是式(II)的基团：##STR2## 其中R.sub.1 和 R.sub.2独立地是氢或C.sub.1 -C.sub.3 烷基，R.sub.3 是氢、C.sub.1 -C.sub.3 烷基或卤素；B是式(III-1)的1-(取代)-1,2,3,4-四氢异喹啉-2-基或式(III-2)的7-(取代)-4,5,6,7-四氢噻吩并[2,3-c]吡啶-6-基：##STR3## 其中R.sub.6 是氢或C.sub.1 -C.sub.3 烷基。
• NOVEL PYRIMIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：Yuhan Corporation

  公开号：EP0775120B1

  公开（公告）日：2003-06-04
• US5750531A
  申请人：——

  公开号：US5750531A

  公开（公告）日：1998-05-12
• Design, Synthesis, and Preliminary Activity Evaluation of Novel Pyrimidine Derivatives as Acid Pump Antagonists
  作者：Weiguo Song、Xiaopan Zhang、Shutao Li、Wenfang Xu

  DOI：10.1111/cbdd.12390

  日期：2015.3

  Acid‐related diseases of the upper gastrointestinal tract, especially gastroesophageal reflux disease (GERD), remain a widespread problem worldwide. In this paper, we reported the design, synthesis, and preliminary gastric antisecretory activity evaluation of novel pyrimidine derivatives as acid pump antagonists. The gastric antisecretory activity assay results showed that all compounds displayed potent gastric antisecretory activity when gastric secretion was stimulated by histamine. The most potent compound 5g exhibited even similar gastric antisecretory activity compared with the control revaprazan, and the relative inhibition rate was 93.0%, which was worthy of further investigation.