4-amino-6-(4-methylbenzyl)-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 4-amino-6-(4-methylbenzyl)-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one
• 英文别名: 4-amino-6-(4-methylbenzyl)-3-sulfanyl-1,2,4-triazin-5(4H)-one；4-amino-6-[(4-methylphenyl)methyl]-3-sulfanylidene-2H-1,2,4-triazin-5-one
• 化学式: C₁₁H₁₂N₄OS
• 分子量: 248.308
• InChiKey: FFSJZIAPFLRBNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-6-(4-methylbenzyl)-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one 在 吡啶 、 sodium methylate 、 一水合肼 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 6.0h， 生成 8-amino-6-(4-methylbenzyl)-2,8-dihydro-3-thioxo-1,2,4-triazolo[4,3-b][1,2,4]-triazin-7(3H)-one
  参考文献：
  名称：

  Synthesis of Some Novel 6‐Benzyl(or Substituted Benzyl)‐2‐β‐d‐Glucopyranosyl‐1,2,4‐Triazolo[4,3‐b][1,2,4]Triazines as Potential Antimicrobial Chemotherapeutics

  摘要：

  Glucosidation of the new 8-amino-6-benzyl(or substituted benzyl)-2,8-dihydro-1,2,4tri azolo [4,3-b] [1,2,4]triazin-7(3 H)-ones (3a-d) with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide 4 gave the corresponding N-glucosides 5a-d. Chemical transformations leading to new functionalities have also been achieved to give compounds 7-12. Antimicrobial activity of compounds 5a-c against Aspergillus fumigatus, Penicillium italicum, Syncephalastrum racemosum, Candida albicans, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Escherichia coli is described.

  DOI：

  10.1081/ncn-200040663

文献信息

• An improved direct synthetic approach to anhydronucleosides
  作者：Ibtehal A. Al-Juwaiser、Maher R. Ibrahim、Nouria A. Al-Awadi、Yehia A. Ibrahim

  DOI：10.1016/j.tet.2008.06.016

  日期：2008.8

  The synthesis of anhydrothioglycosyls has been improved by studying the reaction under a variety of reaction conditions including gas phase pyrolysis, heating in a solvent of high boiling point, in the presence of different bases including triethylamine, DABCO, and DBU, and in a microwave reactor. (C) 2008 Published by Elsevier Ltd.
• Selective Synthesis and Reactions of 6-Substituted- 2-β-galactosyl-1,2,4-triazines of Potential Anticancer Activity
  作者：Abdel Kader Mansour、Mohga M. Eid、Nasser S. A. M. Khalil

  DOI：10.1081/ncn-120018621

  日期：2003.4

  Selective synthesis and reactions of different 6-substituted-2-beta-D-galactosyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-ones using the developed amino or aryl protecting group strategy were investigated. Primary human anticancer screening of twelve selected compounds (in vitro) resulted in an active compound against both MCF7 (Breast) and SF-268(CNS) cell lines.
• Synthesis of Some Novel 6‐Benzyl(or Substituted Benzyl)‐2‐β‐<scp>d</scp>‐Glucopyranosyl‐1,2,4‐Triazolo[4,3‐<i>b</i>][1,2,4]Triazines as Potential Antimicrobial Chemotherapeutics
  作者：Nasser S. A. M. Khalil、Abdel Kader Mansour、Mohga M. Eid

  DOI：10.1081/ncn-200040663

  日期：2004.1.12

  Glucosidation of the new 8-amino-6-benzyl(or substituted benzyl)-2,8-dihydro-1,2,4tri azolo [4,3-b] [1,2,4]triazin-7(3 H)-ones (3a-d) with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide 4 gave the corresponding N-glucosides 5a-d. Chemical transformations leading to new functionalities have also been achieved to give compounds 7-12. Antimicrobial activity of compounds 5a-c against Aspergillus fumigatus, Penicillium italicum, Syncephalastrum racemosum, Candida albicans, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Escherichia coli is described.