2-amino-5-(2-pyrimidinylthio)thiazole | 133691-63-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-amino-5-(2-pyrimidinylthio)thiazole
• 英文别名: 5-pyrimidin-2-ylsulfanyl-1,3-thiazol-2-amine
• CAS: 133691-63-1
• 化学式: C₇H₆N₄S₂
• mdl: MFCD00899711
• 分子量: 210.283
• InChiKey: ZFGVHIOWIYRDOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-5-(2-pyrimidinylthio)thiazole 在 间氯过氧苯甲酸 作用下， 生成 5-(Pyrimidine-2-sulfinyl)-thiazol-2-ylamine
  参考文献：
  名称：

  Synthesis and effects of novel thiazole derivatives against thrombocytopenia

  摘要：

  5-(2-Pyridylsulfonyl)-2-thiazolamine (2) was effective both in mitomycin C (MMC)-induced thrombocytopenia and in an animal model of idiopathic thrombocytopenic purpura (ITP). It also suppressed the increase of autoantibodies against platelets in the ITP model and showed no blood toxicity. Chemical modification of 2 led to the discovery of more potent compounds against MMC-induced thrombocytopenia. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00404-1
• 作为产物：
  描述：

  5-氯-2-氨基噻唑 、 2-巯基嘧啶 在 碳酸氢钠 作用下， 生成 2-amino-5-(2-pyrimidinylthio)thiazole
  参考文献：
  名称：

  Synthesis and effects of novel thiazole derivatives against thrombocytopenia

  摘要：

  5-(2-Pyridylsulfonyl)-2-thiazolamine (2) was effective both in mitomycin C (MMC)-induced thrombocytopenia and in an animal model of idiopathic thrombocytopenic purpura (ITP). It also suppressed the increase of autoantibodies against platelets in the ITP model and showed no blood toxicity. Chemical modification of 2 led to the discovery of more potent compounds against MMC-induced thrombocytopenia. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00404-1

文献信息

• Thiazole derivatives, processes for production thereof and
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05256675A1

  公开（公告）日：1993-10-26

  Compounds of the formula: ##STR1## wherein A is S, SO, or SO2, R1 is H or acyl, R2 is H, alkyl, hydroxyalkyl, halogen or carboxy, and R3 is pyridyl are claimed. The compounds are useful as therapeutic agents for the treatment of e.g. rheumatism, nephritis and thrombocytopenia.

  该公式化合物为：##STR1## 其中A为S、SO或SO2，R1为H或酰基，R2为H、烷基、羟基烷基、卤素或羧基，R3为吡啶基。这些化合物可用作治疗药剂，用于治疗风湿病、肾炎和血小板减少症等疾病。
• N-heteroaryl indole carboxamides and analogues thereof, for use as glcokinase activators in the treatment of diabetes
  申请人：Lau F. Jesper

  公开号：US20070027140A1

  公开（公告）日：2007-02-01

  This invention relates to compounds that are activators of glucokinase and thus may be useful for the management, treatment, control, or adjunct treatment of diseases, where increasing glucokinase activity is beneficial. The compounds are of the general formula (I) wherin A and B are further defined in the application.

  本发明涉及激活葡萄糖激酶的化合物，因此可能对增加葡萄糖激酶活性有益的疾病的管理、治疗、控制或辅助治疗具有用处。这些化合物的一般式为（I）其中A和B在申请中有进一步定义。
• N-HETEROARYL INDOLE CARBOXAMIDES AND ANALOGUES THEREOF, FOR USE AS GLUCOKINASE ACTIVATORS IN THE TREATMENT OF DIABETES
  申请人：Lau Jesper F.

  公开号：US20110082144A1

  公开（公告）日：2011-04-07

  This invention relates to compounds that are activators of glucokinase and thus may be useful for the management, treatment, control, or adjunct treatment of diseases, where increasing glucokinase activity is beneficial. The compounds are of the general formula (I) wherein A and B are further defined in the application.

  本发明涉及一种激活葡萄糖激酶的化合物，因此可能有助于管理、治疗、控制或辅助治疗增加葡萄糖激酶活性有益的疾病。该化合物的一般公式为(I)，其中A和B在申请中有进一步定义。
• N-heteroaryl indole carboxamides and analogues thereof, for use as glucokinase activators in the treatment of diabetes
  申请人：TransTech Pharma, Inc.

  公开号：US07812043B2

  公开（公告）日：2010-10-12

  This invention relates to compounds that are activators of glucokinase and thus may be useful for the management, treatment, control, or adjunct treatment of diseases, where increasing glucokinase activity is beneficial. The compounds are of the general formula (I) wherein A and B are further defined in the application.

  本发明涉及一种激活葡萄糖激酶的化合物，因此可用于治疗、控制或辅助治疗增加葡萄糖激酶活性有益的疾病。该化合物的一般式为(I)，其中A和B在申请中有进一步定义。
• Synthesis and evaluation of phenylimidazole FabK inhibitors as new Anti-C. Difficile agents
  作者：Krissada Norseeda、Fahad Bin Aziz Pavel、Jacob T. Rutherford、Humna N. Meer、Chetna Dureja、Julian G. Hurdle、Kirk E. Hevener、Dianqing Sun

  DOI：10.1016/j.bmc.2023.117330

  日期：2023.6

  antibacterial activity in the low micromolar range. In these studies, we sought to expand our knowledge of the SAR of the phenylimidazole CdFabK inhibitor series while improving the potency of the compounds. Three main series of compounds were synthesized and evaluated based on: 1) pyridine head group modifications including the replacement with a benzothiazole moiety, 2) linker explorations, and 3) phenylimidazole

  以前，1-((4-(4-溴苯基)-1 H-咪唑-2-基)甲基)-3-(5-(吡啶-2-基硫基)噻唑-2-基)脲带有对溴研究表明，该取代对艰难梭菌烯酰酰基载体蛋白 (ACP) 还原酶 II 酶 FabK 具有选择性抑制活性。该化合物对Cd FabK 的抑制作用在低微摩尔范围内具有良好的抗菌活性。在这些研究中，我们试图扩大对苯基咪唑Cd FabK 抑制剂系列 SAR 的了解，同时提高化合物的效力。合成并评估了三个主要系列的化合物，基于：1）吡啶头基修饰，包括用苯并噻唑部分取代，2）接头探索，以及3）苯基咪唑尾基修饰。总体而言，在保持全细胞抗菌活性的同时，实现了Cd FabK 抑制的改善。具体地，化合物1-((4-(4-溴苯基) -1H-咪唑-2-基)甲基)-3-(5-((3-(三氟甲基)吡啶-2-基)硫基)噻唑-2 -基)脲、1-((4-(4-溴苯基) -1H-咪唑-2-基)甲基)-3-(6-(三氟甲基)苯并[