2-guanidino-4-thiazolohydrazide | 82982-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-guanidino-4-thiazolohydrazide
• 英文别名: 2-guanidino-4-thiazolecarboxylic acid hydrazide；Guanidino-4-thiazole carboxylic acid hydrazide；2-[4-(hydrazinecarbonyl)-1,3-thiazol-2-yl]guanidine
• CAS: 82982-27-2
• 化学式: C₅H₈N₆OS
• 分子量: 200.224
• InChiKey: UJLNITKVGULKNI-UHFFFAOYSA-N

物化性质

• 熔点：
  247 °C (decomp)
• 密度：
  1.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-guanidino-4-thiazolohydrazide 以88%的产率得到
  参考文献：
  名称：

  LAMATTINA, J. L.;LIPINSKI, C. A.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-胍基-4-噻唑羧酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以82%的产率得到2-guanidino-4-thiazolohydrazide
  参考文献：
  名称：

  Bioisosteric prototype design of biaryl imidazolyl and triazolyl competitive histamine H2-receptor antagonists

  摘要：

  The structural relationship of the competitive histamine H2-receptor antagonist 3-amino-5-(2-amino-4-pyridyl)-1,2,4-triazole (1) to the agonist histamine and to antagonists of the cimetidine type was explored by the design and synthesis of four series of bioisosterically designed prototypes. Biological data from these series was best interpreted as indicating a similarity between the imidazole moiety of histamine and cimetidine and the 2-amino-4-pyridyl moiety of 1. On the basis of this data, sequential replacement of 2-amino-4-pyridyl by 2-[(dimethylamino)methyl]-5-furyl and 2-guanidino-4-triazolyl moieties led to a structurally more potent series of biaryl histamine H2-receptor antagonists. The best of these, 2-methyl-4-(2-guanidino-4-thiazolyl)imidazole (29, CP-57,361-1) was 120 times more potent as a histamine H2-receptor antagonist than 1.

  DOI：

  10.1021/jm00161a005

文献信息

• Studies on Antiulcer Drugs. VI. 4-Furyl-2-guanidinothiazoles and Related Compounds as Potent Histamine H2-Receptor Antagonists.
  作者：Yousuke KATSURA、Yoshikazu INOUE、Tetsuo TOMISI、Harunobu ITOH、Hirohumi ISHIKAWA、Hisashi TAKASUGI

  DOI：10.1248/cpb.40.2432

  日期：——

  derivatives and related compounds were synthesized and evaluated for histamine H2-receptor antagonist and gastric acid antisecretory activities. Among them, compounds I-17, I-48 and I-49 showed high activities in these tests. In addition, compound I-17 possessed potent inhibitory activities on each of the gastric ulcers induced by stress, ethanol and HCl-aspirin. On the other hand, compound I-48 demonstrated

  合成了一系列的4-呋喃基-2-胍基噻唑衍生物和相关化合物，并评估了组胺H2-受体拮抗剂和胃酸的抗分泌活性。其中，化合物I-17，I-48和I-49在这些测试中显示出高活性。另外，化合物I-17对由压力，乙醇和HCl-阿司匹林诱导的每个胃溃疡具有有效的抑制活性。另一方面，化合物I-48显示出对幽门螺杆菌的抗菌活性，并且效力远强于临床使用的H2-拮抗剂。讨论了一些构效关系。
• Haloacetyl imidazoles
  申请人：Pfizer Inc.

  公开号：US04452987A1

  公开（公告）日：1984-06-05

  A series of 2-guanidino-4-heteroarylthiazoles, wherein the heteroaryl substituent is selected from thiazolyl, triazolyl, imidazolyl, and 2-alkyl, 2-amino and 2-carboxamido derivatives thereof, are disclosed. The novel compounds have activity as antisecretory agents and histamine H.sub.2 antagonists and are useful for the treatment of gastric hyperacidity and peptic ulcers. Also disclosed are pharmaceutical compositions containing the novel compounds of this invention and a method of using the compounds in the treatment of gastric hyperacidity and peptic ulcers. Novel intermediates useful in the preparation of the novel antisecretory compounds are also described.

  本发明揭示了一系列2-胍基-4-杂环芳基噻唑化合物，其中杂环芳基取代基选择自噻唑基、三唑基、咪唑基和2-烷基、2-氨基和2-羧酰胺衍生物。这些新型化合物具有抗分泌作用和组胺H.sub.2拮抗剂作用，适用于治疗胃酸过多和消化性溃疡。本发明还揭示了含有这些新型化合物的制药组合物以及使用这些化合物治疗胃酸过多和消化性溃疡的方法。还描述了制备新型抗分泌化合物的新型中间体。
• 2-Guanidino-4-heteroarylthiazoles
  申请人：Pfizer Inc.

  公开号：US04510313A1

  公开（公告）日：1985-04-09

  A series of 2-guanidino-4-heteroarylthiazoles, wherein the heteroaryl substituent is selected from thiazolyl, triazolyl, imidazolyl, and 2-alkyl, 2-amino and 2-carboxamido derivatives thereof, are disclosed. The novel compounds have activity as antisecretory agents and histamine H.sub.2 antagonists and are useful for the treatment of gastric hyperacidity and peptic ulcers. Also disclosed are pharmaceutical compositions containing the novel compounds of this invention and a method of using the compounds in the treatment of gastric hyperacidity and peptic ulcers. Novel intermediates useful in the preparation of the novel antisecretory compounds are also described.

  本发明揭示了一系列2-胍基-4-杂环芳基噻唑类化合物，其中杂环芳基取代基选自噻唑基、三唑基、咪唑基和2-烷基、2-氨基和2-羧酰胺衍生物。这些新型化合物具有抗分泌作用和组胺H.sub.2拮抗剂作用，可用于治疗胃酸过多和消化性溃疡。本发明还揭示了包含这些新型化合物的制药组合物以及使用这些化合物治疗胃酸过多和消化性溃疡的方法。还描述了制备新型抗分泌化合物的新型中间体。
• 2-guanidino-4-heteroarylthiazoles
  申请人：Pfizer Inc.

  公开号：US04590299A1

  公开（公告）日：1986-05-20

  A series of 2-guanidino-4-heteroarylthiazoles, wherein the heteroaryl substituent is selected from thiazolyl, triazolyl, imidazolyl, and 2-alkyl, 2-amino and 2-carboxamido derivatives thereof, are disclosed. The novel compounds have activity as antisecretory agents and histamine H.sub.2 antagonists and are useful for the treatment of gastric hyperacidity and peptic ulcers. Also disclosed are pharmaceutical compositions containing the novel compounds of this invention and a method of using the compounds in the treatment of gastric hyperacidity and peptic ulcers. Novel intermediates useful in the preparation of the novel antisecretory compounds are also described.

  本发明揭示了一系列2-胍基-4-杂环芳基噻唑化合物，其中杂环芳基取代基选自噻唑基、三唑基、咪唑基和2-烷基、2-氨基和2-羧酰胺衍生物。这些新型化合物具有抗分泌作用和组胺H.sub.2 拮抗剂活性，可用于治疗胃酸过多和消化性溃疡。本发明还揭示了含有这些新型化合物的制药组合物以及使用这些化合物治疗胃酸过多和消化性溃疡的方法。还描述了制备新型抗分泌化合物的新型中间体。
• Katsura Yousuke, Inoue Yoshikazu, Tomishi Tetsuo, Itoh Harunobu, Ishikawa+, Chem. and Pharm. Bull., 40 (1992) N 9, S 2432-2441
  作者：Katsura Yousuke, Inoue Yoshikazu, Tomishi Tetsuo, Itoh Harunobu, Ishikawa+

  DOI：——

  日期：——