4-(benzylthio)-6-((cyanomethyl)thio)-1,3,5-triazin-2(1H)-one | 1334681-54-7

• 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-(benzylthio)-6-((cyanomethyl)thio)-1,3,5-triazin-2(1H)-one
• 英文别名: 2-[(4-benzylsulfanyl-6-oxo-1H-1,3,5-triazin-2-yl)sulfanyl]acetonitrile
• CAS: 1334681-54-7
• 化学式: C₁₂H₁₀N₄OS₂
• 分子量: 290.37
• InChiKey: XPMCNCTVSVWOEE-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：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  S-苄基异硫脲盐酸盐 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 3.33h， 生成 4-(benzylthio)-6-((cyanomethyl)thio)-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

文献信息

• 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.