methyl 1-(5-amino-1H-1,2,4-triazol-1-yl)carbodithioate | 154194-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 1-(5-amino-1H-1,2,4-triazol-1-yl)carbodithioate
• 英文别名: Methyl 5-amino-1H-1,2,4-triazole-1-carbodithioate；methyl 5-amino-1,2,4-triazole-1-carbodithioate
• CAS: 154194-74-8
• 化学式: C₄H₆N₄S₂
• 分子量: 174.25
• InChiKey: AYFOSESUCBCXAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-3-[3-(1-哌啶甲基)-苯氧基]丙胺 、 methyl 1-(5-amino-1H-1,2,4-triazol-1-yl)carbodithioate 以 二甲基亚砜 为溶剂， 以1.57 g (42%)的产率得到1-(5-Amino-1H-1,2,4-triazol-1-yl)-N-{3-[3-(1-piperidinylmethyl)phenoxy]propyl}carbothioamide
  参考文献：
  名称：

  Triazolyl thioamide derivates

  摘要：

  该发明涉及一般式(I)的新型三唑硫代酰胺，其中Q代表氢或一种可能带有一个或多个C.sub.1-4烷基取代基的杂环基，或者代表公式SR.sup.1的基团，其中R.sup.1代表由1至6个碳原子组成的直链或支链烷基基团，或者代表公式NR.sup.2 R.sup.3的基团，其中R.sup.2和R.sup.3各自代表氢、直链或支链的C.sub.1-4烷基或C.sub.2-6烯基基团，Y表示C.sub.1-4烷基，可能带有一个或多个羟基或C.sub.1-4烷氧基取代基，苯基-(C.sub.1-4烷基)，可能在苯环上带有一个或多个C.sub.1-4烷氧基，或者phenoxy-(C.sub.1-4烷基)，可能在苯环上由一个带有含氮原子的杂环基团的C.sub.1-4烷基取代，以及其药学上可接受的酸盐。此外，该发明涉及一种制备这些化合物的方法。根据该发明的化合物具有镇静、抗抑郁、解痉、抗炎、镇痛和抑制肠蠕动的效果。

  公开号：

  US05175163A1
• 作为产物：
  描述：

  3-氨基-1,2,4-三氮唑 、 二硫化碳 、 碘甲烷 在 氢氧化钾 作用下， 生成 methyl 1-(5-amino-1H-1,2,4-triazol-1-yl)carbodithioate
  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

• Synthesis and Pharmacological Activity of Triazole Derivatives Inhibiting Eosinophilia
  作者：Youichiro Naito、Fumihiko Akahoshi、Shinji Takeda、Takehiro Okada、Masahiko Kajii、Hiroko Nishimura、Masanori Sugiura、Chikara Fukaya、Yoshio Kagitani

  DOI：10.1021/jm9507993

  日期：1996.1.1

  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.
• Triazolyl thioamide derivates
  申请人：Egis Gyogyszergyar

  公开号：US05175163A1

  公开（公告）日：1992-12-29

  The invention relates to novel triazolyl thioamides of the general formula (I), ##STR1## wherein Q represents hydrogen or a heterocyclic group optionally bearing one or more C.sub.1-4 alkyl substituent(s), or a group of the formula SR.sup.1, wherein R.sup.1 stands for straight or branched chained alkyl group comprising 1 to 6 carbon atom(s), or a group of the formula NR.sup.2 R.sup.3, wherein R.sup.2 and R.sup.3 each represent hydrogen, straight or branched chained C.sub.1-4 alkyl or C.sub.2-6 alkenyl group, Y denotes C.sub.1-4 alkyl optionally bearing one or more hydroxyl or C.sub.1-4 alkoxy substituent(s), phenyl-(C.sub.1-4 alkyl) optionally bearing on the phenyl ring one or more C.sub.1-4 alkoxy group(s), or phenoxy-(C.sub.1-4 alkyl) optionally substituted on the phenyl ring by a C.sub.1-4 alkyl bearing a heterocyclic group containing a nitrogen atom, and pharmaceutically acceptable acid addition salts thereof. Furthermore the invention relates to a process for preparing these compounds. The compounds according to the invention possess tranquillant, antidepressant, spacmolytic, antiinflammatory, analgesic and antiperistaltic effects.

  该发明涉及一般式(I)的新型三唑硫代酰胺，其中Q代表氢或一种可能带有一个或多个C.sub.1-4烷基取代基的杂环基，或者代表公式SR.sup.1的基团，其中R.sup.1代表由1至6个碳原子组成的直链或支链烷基基团，或者代表公式NR.sup.2 R.sup.3的基团，其中R.sup.2和R.sup.3各自代表氢、直链或支链的C.sub.1-4烷基或C.sub.2-6烯基基团，Y表示C.sub.1-4烷基，可能带有一个或多个羟基或C.sub.1-4烷氧基取代基，苯基-(C.sub.1-4烷基)，可能在苯环上带有一个或多个C.sub.1-4烷氧基，或者phenoxy-(C.sub.1-4烷基)，可能在苯环上由一个带有含氮原子的杂环基团的C.sub.1-4烷基取代，以及其药学上可接受的酸盐。此外，该发明涉及一种制备这些化合物的方法。根据该发明的化合物具有镇静、抗抑郁、解痉、抗炎、镇痛和抑制肠蠕动的效果。