7-methyl-2-methylthio-1,2,4-triazolo[1,5-a]pyrimidine | 56347-12-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 7-methyl-2-methylthio-1,2,4-triazolo[1,5-a]pyrimidine
• 英文别名: 5-methyl-2-(methylthio)-[1,2,4]triazolo[1,5-a]pyrimidine；5-methyl-2-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine；5-Methyl-2-methylmercapto-[1,2,4]triazolo[1,5-a]pyrimidin；[1,2,4]Triazolo[1,5-a]pyrimidine, 5-methyl-2-(methylthio)-；5-methyl-2-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine
• CAS: 56347-12-7
• 化学式: C₇H₈N₄S
• 分子量: 180.233
• InChiKey: JAEHOUMNJIUKIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methyl-2-methylthio-1,2,4-triazolo[1,5-a]pyrimidine 在 sodium tungstate (VI) dihydrate 、 硫酸 、 水 、 双氧水 、 sodium hydride 、 溶剂黄146 作用下， 以 水 、 甲苯 为溶剂， 反应 1.0h， 生成 3-((5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)oxy)-[1,1′-biphenyl]-2-carboxylic acid
  参考文献：
  名称：

  Triazolopyrimidines as a New Herbicidal Lead for Combating Weed Resistance Associated with Acetohydroxyacid Synthase Mutation

  摘要：

  Acetohydroxyacid synthase (AHAS; also known as acetolactate synthase; EC 2.2.1.6, formerly EC 4.1.3.18) is the first common enzyme in the biosynthetic pathway leading to the branched-chain amino acids in plants and a wide range of microorganisms. Weed resistance to AHAS-inhibiting herbicides, increasing at an exponential rate, is becoming a global problem and leading to an urgent demand of developing novel compounds against both resistant and wild AHAS. In the present work, a series of novel 2-aroxyl-1,2,4-triazolopyrimidine derivatives (a total of 55) were designed and synthesized with the aim to discover an antiresistant lead compound. Fortunately, the screening results indicated that many of the newly synthesized compounds showed a better, even excellent, inhibition effect against both the wild-type Arabidopsis thaliana AHAS and P197L mutants. Among them, compounds 5-3 to 5-17, compounds 5-19 to 5-26, compounds 5-28 to 5-45, and compound 5-48 have the lower values of resistance factor (RF) and display a potential power to overcome resistance associated with the P197L mutation in the enzyme levels. Further greenhouse in vivo assay showed that compounds 5-15 and 5-20 displayed "moderate" to "good" herbicidal activity against both the wild type-and the resistant (P197L mutation) Descurainia sophia, even at a rate as low as 0.9375 (g of ai/ha). The above results indicated that these two compounds could be used as new leads for the future development of antiresistance herbicides.

  DOI：

  10.1021/acs.jafc.6b00720
• 作为产物：
  描述：

  N'-{7-methyl-2-methylthio-1,2,4-triazolo[1,5-a]pyrimidin-5-yl}-p-toluenesulphonylhydrazone hydrochloride 在 sodium carbonate 作用下， 反应 2.0h， 以82%的产率得到7-methyl-2-methylthio-1,2,4-triazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  在三唑上。加大码[1]。一些5-氯-1,2,4-三唑并[1,5- a ]嘧啶衍生物的非催化脱卤作用

  摘要：

  型的非催化脱卤方法4 5-氯1，2,4-三唑并[1,5一个基于相应的5型的水解]嘧啶衍生物p与稀释的碳酸钠水溶液甲苯磺酰腙进行详细阐述。在不可能简单氢化的情况下，该方法也提供了所需的5-未取代的衍生物6。使用氘化氢作为水解的溶剂，氘原子也可以插入衍生物6的5位。还分离了反应的不同副产物，并给出了其形成的可能解释。

  DOI：

  10.1002/jhet.5570360515

文献信息

• The Structure of Certain Polyazaindenes. II. The Product from Ethyl Acetoacetate and 3-Amino-1,2,4-triazole
  作者：C. F. H. ALLEN、H. R. BEILFUSS、D. M. BURNESS、G. A. REYNOLDS、J. F. TINKER、J. A. VanALLAN

  DOI：10.1021/jo01088a014

  日期：1959.6
• On triazoles. XL [1]. Non catalytic dehalogenation of some 5-chloro-1,2,4-triazolo[1,5-<i>a</i>]pyrimidine derivatives
  作者：Gábor Berecz、József Reiter、János Császár

  DOI：10.1002/jhet.5570360515

  日期：1999.9

  A non catalytic dehalogenation method of type 4 5-chloro-1,2,4-triazolo[1,5-a]pyrimidine derivatives based on the hydrolysis of the corresponding type 5 p-toluenesulphonyl hydrazones with diluted aqueous sodium carbonate solution was elaborated. The method provides the required 5-unsubstituted derivatives 6 also in those cases when the simple hydrogenation is not possible. Using deuterium oxide as

  型的非催化脱卤方法4 5-氯1，2,4-三唑并[1,5一个基于相应的5型的水解]嘧啶衍生物p与稀释的碳酸钠水溶液甲苯磺酰腙进行详细阐述。在不可能简单氢化的情况下，该方法也提供了所需的5-未取代的衍生物6。使用氘化氢作为水解的溶剂，氘原子也可以插入衍生物6的5位。还分离了反应的不同副产物，并给出了其形成的可能解释。
• Triazolopyrimidines as a New Herbicidal Lead for Combating Weed Resistance Associated with Acetohydroxyacid Synthase Mutation
  作者：Yu-Chao Liu、Ren-Yu Qu、Qiong Chen、Jing-Fang Yang、Niu Cong-Wei、Xi Zhen、Guang-Fu Yang

  DOI：10.1021/acs.jafc.6b00720

  日期：2016.6.22

  Acetohydroxyacid synthase (AHAS; also known as acetolactate synthase; EC 2.2.1.6, formerly EC 4.1.3.18) is the first common enzyme in the biosynthetic pathway leading to the branched-chain amino acids in plants and a wide range of microorganisms. Weed resistance to AHAS-inhibiting herbicides, increasing at an exponential rate, is becoming a global problem and leading to an urgent demand of developing novel compounds against both resistant and wild AHAS. In the present work, a series of novel 2-aroxyl-1,2,4-triazolopyrimidine derivatives (a total of 55) were designed and synthesized with the aim to discover an antiresistant lead compound. Fortunately, the screening results indicated that many of the newly synthesized compounds showed a better, even excellent, inhibition effect against both the wild-type Arabidopsis thaliana AHAS and P197L mutants. Among them, compounds 5-3 to 5-17, compounds 5-19 to 5-26, compounds 5-28 to 5-45, and compound 5-48 have the lower values of resistance factor (RF) and display a potential power to overcome resistance associated with the P197L mutation in the enzyme levels. Further greenhouse in vivo assay showed that compounds 5-15 and 5-20 displayed "moderate" to "good" herbicidal activity against both the wild type-and the resistant (P197L mutation) Descurainia sophia, even at a rate as low as 0.9375 (g of ai/ha). The above results indicated that these two compounds could be used as new leads for the future development of antiresistance herbicides.