3-Methylamino-1,2,4-triazol | 15285-16-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-Methylamino-1,2,4-triazol
• 英文别名: N-methyl-1H-1,2,4-triazol-5-amine
• CAS: 15285-16-2
• 化学式: C₃H₆N₄
• mdl: MFCD02708449
• 分子量: 98.1074
• InChiKey: NOWPYQNOYJQXPV-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C
• 沸点：
  251.3±23.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methylamino-1,2,4-triazol 在 sodium nitrite 作用下， 生成 methyl-nitroso-(1H-[1,2,4]triazol-3-yl)-amine
  参考文献：
  名称：

  Pesson; Pollmanss, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 247, p. 787

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯-1,2,4-三唑 、 甲胺 以 水 为溶剂， 反应 24.0h， 生成 3-Methylamino-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

• [EN] TRICYCLIC HETEROCYLIC DERIVATIVES<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES TRICYCLIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2017202748A1

  公开（公告）日：2017-11-30

  Compounds of the formula (I) in which R1 and R2 have the meanings indicated in Claim 1,are inhibitors of ATR, and can be employed for the treatment of diseases such as cancer.

  式(I)中R1和R2具有权利要求书中指示的含义，是ATR的抑制剂，可用于治疗癌症等疾病。
• Nitroazines. 15. Contraction of the pyrimidine ring in 6-nitroazolo[1,5-a]pyrimidines
  作者：V. L. Rusinov、A. V. Myasnikov、O. N. Chupakhin、G. G. Aleksandrov

  DOI：10.1007/bf00474001

  日期：1991.5
• HANS M., WISS. Z. PAED. HOCHSCH. LISELOTTE-HERRMANN GUESTROW. MATH.-NATURWISS. FAK+
  作者：HANS M.

  DOI：——

  日期：——
• ——
  作者：E. N. Ulomsky、V. V. Voronin、V. L. Rusinov、O. N. Chupakhin

  DOI：10.1023/a:1011373131012

  日期：——

  The effects of the nature of the nucleophile and the structure of 6-nitrotriazolo[1,5-alpyrimidinones on the direction of the ring opening were investigated. The triazole ring is opened under the action of strong bases, such as alkoxides or alkalis, to form 2-cyanoamino-pyrimidinones and then 2-aminopyrimidinones. The results of the reactions with N-nucleophiles depend on the accessibility of position 5 of the heterocycle. Thus, sterically hindered secondary amines react with 5-methyltriazolopyrimidinones to give 2-guanidinopyrimidinones and then 2-aminopyrimidinones. In the absence of a substituent at position 5, the azine ring is opened to form 4-alkyl-3-amino-1,2,4-triazoles and 3-amino-2-nitroacrylamides. Under the action of primary amines, only the pyrimidine fragment is cleaved.