tert-butyl 4-(7-(4-methanesulfonylphenyl)thieno[3,2-d]pyrimidin-4-ylamino)piperidin-1-carboxylate | 1384951-52-3

• 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: tert-butyl 4-(7-(4-methanesulfonylphenyl)thieno[3,2-d]pyrimidin-4-ylamino)piperidin-1-carboxylate
• 英文别名: Tert-butyl 4-(7-(4-methanesulfonyl-phenyl)thieno[3,2-d]pyrimidin-4-ylamino)piperidin-1-carboxylate；tert-butyl 4-[[7-(4-methylsulfonylphenyl)thieno[3,2-d]pyrimidin-4-yl]amino]piperidine-1-carboxylate
• CAS: 1384951-52-3
• 化学式: C₂₃H₂₈N₄O₄S₂
• 分子量: 488.632
• InChiKey: HIBMZHKRZUIVRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(7-(4-methanesulfonylphenyl)thieno[3,2-d]pyrimidin-4-ylamino)piperidin-1-carboxylate 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-7-(4-methanesulfonylphenyl)thieno[3,2-d]pyrimidin-4-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of thienopyrimidine derivatives as GPR119 agonists

  摘要：

  A series of thienopyrimidine derivatives was synthesized and evaluated for their GPR119 agonistic ability. Several thienopyrimidine derivatives containing R(1) and R(2) substituents displayed potent GPR119 agonistic activity. Among them, compound 5d, which is a prototype, showed good in vitro activity with an EC50 value of 3 nM and human and rat liver microsomal stability. Compound 5d exhibited no CYP inhibition and induction, Herg binding, or mutagenic potential. Compound 5d showed increase insulin secretion in beta TC-6 cell and lowered the glucose excursion in mice in an oral glucose-tolerance test.

  DOI：

  10.1016/j.bmcl.2014.07.020
• 作为产物：
  描述：

  7-溴-4-氯噻酚并[3,2-D]嘧啶 在 四(三苯基膦)钯 、 sodium carbonate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 异丙醇 为溶剂， 反应 30.0h， 生成 tert-butyl 4-(7-(4-methanesulfonylphenyl)thieno[3,2-d]pyrimidin-4-ylamino)piperidin-1-carboxylate
  参考文献：
  名称：

  发现具有口服活性的磺酰基苯基噻吩并[3,2-d]嘧啶衍生物作为 GPR119 激动剂

  摘要：

  G蛋白偶联受体119（GPR119）作为治疗II型糖尿病的治疗靶点具有巨大潜力。通过生物等排替代策略发现了新型噻吩并[3,2-d]嘧啶衍生物作为 GPR119 激动剂。引入了磺酰基苯基噻吩并[3,2-d]嘧啶支架，其衍生物在基于细胞的测定中对 GPR119 显示出有效的激动活性。代表性衍生物43在啮齿动物中表现出优异的药代动力学特征，并显着改善体内葡萄糖耐量。在OGTT 研究中，化合物43显着降低小鼠和大鼠的血糖水平。

  DOI：

  10.1016/j.ejmech.2023.115584

文献信息

• NEW BICYCLIC COMPOUND FOR MODULATING G PROTEIN-COUPLED RECEPTORS
  申请人：Son Jung Beom

  公开号：US20130274268A1

  公开（公告）日：2013-10-17

  The present invention relates to a bicyclic compound for modulating G protein-coupled receptors. The inventive compound provides preventing or treating a disease associated with the modulation of G protein-coupled receptors, particularly GPR119 G protein-coupled receptors.

  本发明涉及一种用于调节G蛋白偶联受体的双环化合物。该创新化合物可用于预防或治疗与调节G蛋白偶联受体相关的疾病，特别是GPR119 G蛋白偶联受体。
• Bicyclic compound for modulating G protein-coupled receptors
  申请人：Son Jung Beom

  公开号：US08853213B2

  公开（公告）日：2014-10-07

  The present invention relates to a bicyclic compound for modulating G protein-coupled receptors. The inventive compound provides preventing or treating a disease associated with the modulation of G protein-coupled receptors, particularly GPR119 G protein-coupled receptors.

  本发明涉及一种用于调节G蛋白偶联受体的双环化合物。该发明化合物提供了预防或治疗与调节G蛋白偶联受体有关的疾病，特别是GPR119 G蛋白偶联受体的疾病。
• [EN] NEW BICYCLIC COMPOUND FOR MODULATING G PROTEIN-COUPLED RECEPTORS<br/>[FR] NOUVEAU COMPOSÉ BICYCLIQUE POUR LA MODULATION DE RÉCEPTEURS COUPLÉS À LA PROTÉINE G
  申请人：HANMI PHARM IND CO LTD

  公开号：WO2012093809A3

  公开（公告）日：2012-11-08
• US8853213B2
  申请人：——

  公开号：US8853213B2

  公开（公告）日：2014-10-07
• Synthesis and biological evaluation of thienopyrimidine derivatives as GPR119 agonists
  作者：Moon-Kook Jeon、Kyu Myung Lee、Il Hyang Kim、Yoon Kyung Jang、Seung Kyu Kang、Jun Mi Lee、Kwan-Young Jung、Jaladi Ashok Kumar、Sang Dal Rhee、Won Hoon Jung、Jin Sook Song、Myung Ae Bae、Kwang Rok Kim、Jin Hee Ahn

  DOI：10.1016/j.bmcl.2014.07.020

  日期：2014.9

  A series of thienopyrimidine derivatives was synthesized and evaluated for their GPR119 agonistic ability. Several thienopyrimidine derivatives containing R(1) and R(2) substituents displayed potent GPR119 agonistic activity. Among them, compound 5d, which is a prototype, showed good in vitro activity with an EC50 value of 3 nM and human and rat liver microsomal stability. Compound 5d exhibited no CYP inhibition and induction, Herg binding, or mutagenic potential. Compound 5d showed increase insulin secretion in beta TC-6 cell and lowered the glucose excursion in mice in an oral glucose-tolerance test.