(1,5-Dimethyl-1H-[1,2,4]triazol-3-yl)-acetic acid hydrazide | 588728-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1,5-Dimethyl-1H-[1,2,4]triazol-3-yl)-acetic acid hydrazide
• 英文别名: 2-(1,5-Dimethyl-1,2,4-triazol-3-yl)acetohydrazide
• CAS: 588728-15-8
• 化学式: C₆H₁₁N₅O
• 分子量: 169.186
• InChiKey: MEYYMAVJAYIXSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1,5-Dimethyl-1H-[1,2,4]triazol-3-yl)-acetic acid hydrazide 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 8.25h， 生成
  参考文献：
  名称：

  Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivatives

  摘要：

  A series of 1,5-dialkyl-1,2,4-triazole derivatives of acetic acid alkylidene hydrazides 8-12, the acid 13, 1,5-dialkyl-3-(5-mercapto-4-N-aryl-1H-[1,2,4]-triazol-3-ylmethylene)-1H-[1,2,4] triazoles 14-16, their 1,3,4-oxadiazole analogues 17-21, as well as the 1,2,4-triazolo-indoles 25 and 27 were prepared. The Z/E conformations of some acetic acid alkylidene derivatives were studied by NMR spectroscopy. Most of the target compounds were evaluated in a series of human cancer cell in cultures and none have shown activity except 25 which exhibited remarkable activity against nine cancer types. No in vitro antiviral activity against HIV-1, HIV-2, HSV-1, HSV-2, SV, CV-B4, RSV, P3V, RV, SinV, PTV has been found for all the synthesized compounds.

  DOI：

  10.1016/j.farmac.2004.05.006
• 作为产物：
  描述：

  1,5-dimethyl-1H-1,2,4-triazole-3-acetic acid ethyl ester 在 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 72.0h， 以80%的产率得到(1,5-Dimethyl-1H-[1,2,4]triazol-3-yl)-acetic acid hydrazide
  参考文献：
  名称：

  新型取代的1,2,4-三唑的合成与性质：潜在的抗肿瘤药。

  摘要：

  反应性中间体4与1-（氰甲基）苯并三唑（5）及其N-2异构体9的环加成反应，在自发重排后提供了1,2,4-三唑衍生物8和10。类似地，4与氰基乙酸乙酯反应导致生成1,3,5-三取代的1,2,4-三唑12，用肼处理后得到相应的酰肼13。用半乳糖或异硫氰酸苯基酯处理13d得到1-D-半乳糖-酰基14 14和1,2,4-三唑衍生物15。化合物8c; 10b，c; 选择13a，c和14进行抗肿瘤筛选，其中8c，13a和13c显示出显着的抗白血病，卵巢癌，肾癌和肺癌活性（8c，Gl（50）为0.70 microM，0.07 microM对白血病（CCRF-CEM和RPMI-8226），针对卵巢的0.02 microM（OVCAR-3）和0。

  DOI：

  10.1016/s0968-0896(03)00043-9

文献信息

• Synthesis and properties of new substituted 1,2,4-triazoles: potential antitumor agents
  作者：Yaseen A Al-Soud、Najim A Al-Masoudi、Abd El-Rahman S Ferwanah

  DOI：10.1016/s0968-0896(03)00043-9

  日期：2003.4

  (5) and its N-2 isomer 9 furnished, after spontaneous rearrangements, the 1,2,4-triazole derivatives 8 and 10. Analogously, reaction of 4 with ethyl cyanoacetate lead to the 1,3,5-trisubstituted 1,2,4-triazoles 12, which gave on treatment with hydrazine the corresponding hydrazides 13. Treatment of 13d with galactose or phenyl isothiocayanate gave the 1-D-galactose-acylhydrazone 14 and the 1,2,4-triazole

  反应性中间体4与1-（氰甲基）苯并三唑（5）及其N-2异构体9的环加成反应，在自发重排后提供了1,2,4-三唑衍生物8和10。类似地，4与氰基乙酸乙酯反应导致生成1,3,5-三取代的1,2,4-三唑12，用肼处理后得到相应的酰肼13。用半乳糖或异硫氰酸苯基酯处理13d得到1-D-半乳糖-酰基14 14和1,2,4-三唑衍生物15。化合物8c; 10b，c; 选择13a，c和14进行抗肿瘤筛选，其中8c，13a和13c显示出显着的抗白血病，卵巢癌，肾癌和肺癌活性（8c，Gl（50）为0.70 microM，0.07 microM对白血病（CCRF-CEM和RPMI-8226），针对卵巢的0.02 microM（OVCAR-3）和0。
• Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivatives
  作者：Yaseen A. Al-Soud、Mohammad N. Al-Dweri、Najim A. Al-Masoudi

  DOI：10.1016/j.farmac.2004.05.006

  日期：2004.10

  A series of 1,5-dialkyl-1,2,4-triazole derivatives of acetic acid alkylidene hydrazides 8-12, the acid 13, 1,5-dialkyl-3-(5-mercapto-4-N-aryl-1H-[1,2,4]-triazol-3-ylmethylene)-1H-[1,2,4] triazoles 14-16, their 1,3,4-oxadiazole analogues 17-21, as well as the 1,2,4-triazolo-indoles 25 and 27 were prepared. The Z/E conformations of some acetic acid alkylidene derivatives were studied by NMR spectroscopy. Most of the target compounds were evaluated in a series of human cancer cell in cultures and none have shown activity except 25 which exhibited remarkable activity against nine cancer types. No in vitro antiviral activity against HIV-1, HIV-2, HSV-1, HSV-2, SV, CV-B4, RSV, P3V, RV, SinV, PTV has been found for all the synthesized compounds.