5-((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)methyl)-1,3,4-thiadiazole-2-thiol | 936099-28-4

• 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: 5-((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)methyl)-1,3,4-thiadiazole-2-thiol
• 英文别名: 2-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-thiomethyl)-1,3,4-thiadiazol-5-thiol；5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfanylmethyl]-3H-1,3,4-thiadiazole-2-thione
• CAS: 936099-28-4
• 化学式: C₁₀H₁₀N₆S₃
• 分子量: 310.428
• InChiKey: SUDPMVAIKQSJLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)methyl)-1,3,4-thiadiazole-2-thiol 、 1-(氯甲基)-4-硝基苯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 以68%的产率得到
  参考文献：
  名称：

  基于 2-硫代乙酰肼-5,7-二甲基-1,2,4-三唑并[1,5-a]-嘧啶的二杂环化合物的合成。

  摘要：

  描述了由 2-硫代乙酰肼-5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶 (1) 合成一些二杂环化合物。化合物 1 可以转化为三唑、1,3,4-恶二唑和 1,3,4-噻二唑。中间体和目标化合物的结构经(1)H-NMR、MS和元素分析确证。

  DOI：

  10.3390/molecules13061353
• 作为产物：
  描述：

  2-hydrazinoacetylthio-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine 在 硫酸 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 5-((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)methyl)-1,3,4-thiadiazole-2-thiol
  参考文献：
  名称：

  Synthesis and antimicrobical evaluation of a novel class of 1,3,4-thiadiazole: Derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety

  摘要：

  A series of novel 1,3,4-thiadiazole derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety were synthesized by the method of splicing active substructures. Among these derivatives, compounds 12,13,15-22 and 24-31 were firstly reported. All the compounds were assayed for antimicrobial activities against five fungi strains and four bacteria strains. The preliminary results indicated that compounds 25 and 28-31 showed good antifungal activities against Physaclospora piricola and Rhizoctonia solani. Compound 26 exhibited good antifungal activities against Cercospora beticola and R. solani. Most of the compounds showed better antibacterial activities against Gram-negative bacteria strains than Gram-positive bacteria strains. Compounds 25 and 28 showed the best activities against Pseudomonas fluorescence while compounds 30-31 showed good activities against Escherichia coli. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.014

文献信息

• Efficient synthesis and antiproliferative activity of novel thioether-substituted flavonoids
  作者：Wei Huang、Qiong Chen、Wen-Chao Yang、Guang-Fu Yang

  DOI：10.1016/j.ejmech.2013.05.037

  日期：2013.8

  As widely occurring natural products, flavonoids are an important source for drug discovery, due to their structural diversity and broad-spectrum biological activity. In this work, a library of novel, thioether-substituted flavonoids with diverse heterocyclic groups was synthesized via a microwave-assisted procedure with the advantages of good yields, short times, mild conditions and ready isolation of the products. Their antiproliferative activities were evaluated against six cancer cell lines, HCCLM-7, Hela, MDA-MB-435S, SW-480, Hep-2, and MCF-7 by the MU-based assay. Compared with the positive control 5-fluorouracil, three compounds, 6a, 6b and 6j were successfully identified as the most promising candidates, due to their higher potency and broad-spectrum bioactivity with IC50 values in the range of 0.43 mu M-6.7 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Syntheses of Diheterocyclic Compounds Based on 2-Thioacetohydrazide-5,7-dimethyl-1,2,4-triazolo[1,5-a]- pyrimidine
  作者：Zu-Ming Liu、Qiong Chen、Chao-Nan Chen、Hai-Yang Tu、Guang-Fu Yang

  DOI：10.3390/molecules13061353

  日期：——

  The syntheses of some diheterocyclic compounds from 2-thioacetohydrazide- 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine (1) are described. Compound 1 can be converted into triazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles. The structures of the intermediates and the target compounds were confirmed by (1)H-NMR, MS and elemental analyses.

  描述了由 2-硫代乙酰肼-5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶 (1) 合成一些二杂环化合物。化合物 1 可以转化为三唑、1,3,4-恶二唑和 1,3,4-噻二唑。中间体和目标化合物的结构经(1)H-NMR、MS和元素分析确证。
• Synthesis and antimicrobical evaluation of a novel class of 1,3,4-thiadiazole: Derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety
  作者：Yin Luo、Shuai Zhang、Zhi-Jun Liu、Wu Chen、Jie Fu、Qing-Fu Zeng、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2013.04.014

  日期：2013.6

  A series of novel 1,3,4-thiadiazole derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety were synthesized by the method of splicing active substructures. Among these derivatives, compounds 12,13,15-22 and 24-31 were firstly reported. All the compounds were assayed for antimicrobial activities against five fungi strains and four bacteria strains. The preliminary results indicated that compounds 25 and 28-31 showed good antifungal activities against Physaclospora piricola and Rhizoctonia solani. Compound 26 exhibited good antifungal activities against Cercospora beticola and R. solani. Most of the compounds showed better antibacterial activities against Gram-negative bacteria strains than Gram-positive bacteria strains. Compounds 25 and 28 showed the best activities against Pseudomonas fluorescence while compounds 30-31 showed good activities against Escherichia coli. (C) 2013 Elsevier Masson SAS. All rights reserved.