3-Methyl-1-methylaminothioformyl-5-amino-1,2,4-triazol | 21731-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Methyl-1-methylaminothioformyl-5-amino-1,2,4-triazol
• 英文别名: 5-amino-3-methyl-[1,2,4]triazole-1-carbothioic acid methylamide；5-Amino-3-methyl-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazole；5-amino-N,3-dimethyl-1,2,4-triazole-1-carbothioamide
• CAS: 21731-97-5
• 化学式: C₅H₉N₅S
• 分子量: 171.226
• InChiKey: QDNUEVOLAMIPAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异硫氰酸甲酯 、 3-氨基-5-甲基-4H-1,2,4-三唑 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 以68%的产率得到3-Methyl-1-methylaminothioformyl-5-amino-1,2,4-triazol
  参考文献：
  名称：

  Synthesis and Pharmacological Activity of Triazole Derivatives Inhibiting Eosinophilia

  摘要：

  In order to develop novel antiasthmatic agents based on a new mechanism of action, a series of 3-substituted 5-amino-1-[(methylamino)(thiocarbonyl)]-1H-1,2,4-triazole derivatives were synthesized and evaluated in a model in which eosinophilia was induced in the ah-way through intravenous (iv) injection of Sephadex particles on days 0, 2, and 5. After screening of several hundred derivatives, we finally identified the highly potent eosinophilia inhibitor 5-amino-3-(4-chlorophenyl)-1-[(methylamino)(thiocarbonyl)]-1H-triazole (23c, GCC-AP0341), which had ID50 values of 0.3 and 0.07 mg/kg when administered orally (os) and intraperitoneally tip), respectively. This compound showed complete inhibition of the hypersensitivity induced by ascaris inhalation at an ip dose of 1 mg/kg as well as low toxicity, with an LD(50) value of > 2.0 g/kg in mice. Extensive study of its mechanism of action revealed that 23c inhibited eosinophil survival induced by interleukin-5 (IL-5), but had little or no effect on leukotriene D-4 (LTD(4)) or platelet-activating factor (PAF)-induced responses. Taken together, these results suggest 23e as a novel candidate for the treatment of chronic asthma. Further studies are now underway.

  DOI：

  10.1021/jm9507993

文献信息

• Triazole derivative and pharmaceutical use thereof
  申请人：The Green Cross Corporation

  公开号：US05750545A1

  公开（公告）日：1998-05-12

  An agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, an agent for the prophylaxis and treatment of allergic diseases, an agent for the prophylaxis and treatment of eosinophil-related diseases and an eosinophilia inhibitor, comprising, as an active ingredient, a series of triazole derivatives of the following formula (I) ##STR1## or the following formula (III) ##STR2## wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. A novel monocyclic or bicyclic triazole derivative. The agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, the agent for the prophylaxis and treatment of allergic diseases, the agent for the prophylaxis and treatment of eosinophil-related diseases, the eosinophilia inhibitor and the novel triazole derivative of the present invention all, have superior eosinophilia-inhibitory action and lymphocyte activation-inhibitory action. They are low toxic and persistent in action. They are particularly effective in the treatment of accumulation and activation of eosinophil and lymphocytes, inflammatory respiratory tract diseases, eosinophil-related diseases such as eosinophilia, and immune-related diseases.

  一种用于预防和治疗免疫相关疾病的药剂，特别是免疫抑制剂，一种用于预防和治疗过敏疾病的药剂，一种用于预防和治疗嗜酸性粒细胞相关疾病和嗜酸性粒细胞抑制剂，包括以下式（I）的一系列三唑衍生物作为活性成分：##STR1## 或以下式（III）：##STR2## 其中每个符号如规范中所定义，或其药学上可接受的盐。一种新的单环或双环三唑衍生物。本发明的嗜酸性粒细胞抑制剂和淋巴细胞激活抑制剂，以及预防和治疗免疫相关疾病，特别是免疫抑制剂，预防和治疗过敏疾病，预防和治疗嗜酸性粒细胞相关疾病，嗜酸性粒细胞抑制剂和本发明的新型三唑衍生物，都具有优越的嗜酸性粒细胞抑制作用和淋巴细胞激活抑制作用。它们毒性低且持久作用。它们在治疗嗜酸性粒细胞和淋巴细胞的积累和激活、炎症性呼吸道疾病、嗜酸性粒细胞相关疾病如嗜酸性粒细胞增多症以及免疫相关疾病方面特别有效。