6-(benzylthio)-4-thioxo-3,4-dihydro-1,3,5-triazin-2(1H)-one | 32683-73-1

• 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: 6-(benzylthio)-4-thioxo-3,4-dihydro-1,3,5-triazin-2(1H)-one
• 英文别名: 6-benzylsulfanyl-4-sulfanylidene-1H-1,3,5-triazin-2-one
• CAS: 32683-73-1
• 化学式: C₁₀H₉N₃OS₂
• 分子量: 251.333
• InChiKey: LTFMWVVYTWVEHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(benzylthio)-4-thioxo-3,4-dihydro-1,3,5-triazin-2(1H)-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以71%的产率得到4-(benzylthio)-6-(propylthio)-1,3,5-triazin-2(1H)-one
  参考文献：
  名称：

  Discovery and kinetic evaluation of 6-substituted 4-benzylthio-1,3,5-triazin-2(1H)-ones as inhibitors of cathepsin B

  摘要：

  Cathepsin B is a lysosomal cysteine protease that has various physiological and pathophysiological functions. We present here the discovery of 6-substituted 4-benzylthio-1,3,5-triazin-2(1H)-ones as inhibitors of cathepsin B. starting from screening of a library of variously 2,4,6-trisubstituted 1,3,5-triazines and 1,3,5-triazin-2(1H)-ones on three different human cathepsins. The synthesis and enzymatic evaluation of a focused library of new 1,3,5-triazin-2(1H)-ones is also described. The detailed kinetics analyses have shown that these compounds can act as reversible, partial mixed-type inhibitors of cathepsin B, with K-i and K-i' values in the low micromolar range. The inhibitory activities of selected compounds were also assessed against two related cysteine proteases, cathepsin H and cathepsin L, to estimate their selectivity; these compounds have a selective profile for catB and catL over catH. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.005
• 作为产物：
  描述：

  S-苄基异硫脲盐酸盐 、 异硫氰酰甲酸乙酯 在 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 1.5h， 以75%的产率得到6-(benzylthio)-4-thioxo-3,4-dihydro-1,3,5-triazin-2(1H)-one
  参考文献：
  名称：

  The Synthesis of Novel 2,4,6-Trisubstituted 1,3,5-Triazines: A Search for Potential MurF Enzyme Inhibitors

  摘要：

  A series of new 2,4,6-trisubstituted 1,3,5-triazines, possessing a variety of substituents (-OH, -SH, -OMe, -Cl, -HNR, -SR and amino acid moieties), were synthesized and evaluated for the inhibition of the bacterial peptidoglycan biosynthesis enzyme MurF. Ethoxycarbonyl isothiocyanate successfully reacted with a variety of amidines, enabling an approach to 6-substituted-4-thioxo-1,3,5-triazin-2-ones. Also, a representative set of 2-thio-, 2-amino-, and 2-oxo-substituted 1,3,5-triazines was synthesized by the SNAr reaction, employing 2,4,6-trichloro-1,3,5-triazine and 2-chloro-4,6-dimethoxy-1,3,5-triazine as the starting materials. One compound displayed notable inhibitory activity against MurF from Escherichia coli.

  DOI：

  10.3987/com-09-11839

文献信息

• The Synthesis of Novel 2,4,6-Trisubstituted 1,3,5-Triazines: A Search for Potential MurF Enzyme Inhibitors
  作者：Bogdan Štefane、Stanislav Gobec、Izidor Sosič、Andreja Kovač、Samo Turk、Didier Blanot

  DOI：10.3987/com-09-11839

  日期：——

  A series of new 2,4,6-trisubstituted 1,3,5-triazines, possessing a variety of substituents (-OH, -SH, -OMe, -Cl, -HNR, -SR and amino acid moieties), were synthesized and evaluated for the inhibition of the bacterial peptidoglycan biosynthesis enzyme MurF. Ethoxycarbonyl isothiocyanate successfully reacted with a variety of amidines, enabling an approach to 6-substituted-4-thioxo-1,3,5-triazin-2-ones. Also, a representative set of 2-thio-, 2-amino-, and 2-oxo-substituted 1,3,5-triazines was synthesized by the SNAr reaction, employing 2,4,6-trichloro-1,3,5-triazine and 2-chloro-4,6-dimethoxy-1,3,5-triazine as the starting materials. One compound displayed notable inhibitory activity against MurF from Escherichia coli.
• Discovery and kinetic evaluation of 6-substituted 4-benzylthio-1,3,5-triazin-2(1H)-ones as inhibitors of cathepsin B
  作者：Izidor Sosič、Bojana Mirković、Samo Turk、Bogdan Štefane、Janko Kos、Stanislav Gobec

  DOI：10.1016/j.ejmech.2011.08.005

  日期：2011.9

  Cathepsin B is a lysosomal cysteine protease that has various physiological and pathophysiological functions. We present here the discovery of 6-substituted 4-benzylthio-1,3,5-triazin-2(1H)-ones as inhibitors of cathepsin B. starting from screening of a library of variously 2,4,6-trisubstituted 1,3,5-triazines and 1,3,5-triazin-2(1H)-ones on three different human cathepsins. The synthesis and enzymatic evaluation of a focused library of new 1,3,5-triazin-2(1H)-ones is also described. The detailed kinetics analyses have shown that these compounds can act as reversible, partial mixed-type inhibitors of cathepsin B, with K-i and K-i' values in the low micromolar range. The inhibitory activities of selected compounds were also assessed against two related cysteine proteases, cathepsin H and cathepsin L, to estimate their selectivity; these compounds have a selective profile for catB and catL over catH. (C) 2011 Elsevier Masson SAS. All rights reserved.