1-{2-[(1,3-benzodioxol-5-yl)methylthio]-4-chloro-5-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]benzenesulfonyl}-3-hydroxyguanidine | 1398564-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-{2-[(1,3-benzodioxol-5-yl)methylthio]-4-chloro-5-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]benzenesulfonyl}-3-hydroxyguanidine
• 英文别名: 2-[2-(1,3-Benzodioxol-5-ylmethylsulfanyl)-4-chloro-5-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]phenyl]sulfonyl-1-hydroxyguanidine；2-[2-(1,3-benzodioxol-5-ylmethylsulfanyl)-4-chloro-5-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]phenyl]sulfonyl-1-hydroxyguanidine
• CAS: 1398564-86-7
• 化学式: C₂₃H₁₇Cl₂N₅O₅S₃
• 分子量: 610.522
• InChiKey: WVJCSSAIUWTYRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  211
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N-{2-[(1,3-benzodioxol-5-yl)methylthio]-4-chloro-5-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]benzenesulfonyl}cyanamide potassium salt 在 盐酸羟胺 作用下， 以 乙腈 为溶剂， 以80%的产率得到1-{2-[(1,3-benzodioxol-5-yl)methylthio]-4-chloro-5-[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]benzenesulfonyl}-3-hydroxyguanidine
  参考文献：
  名称：

  1-(2-Mercaptobenzenesulfonyl)-3-hydroxyguanidines – Novel potent antiproliferatives, synthesis and in vitro biological activity

  摘要：

  Twenty four 1-[2-alkylthio-5-(azol-2 or 5-yl)-4-chlorobenzenesulfonyl]-3-hydroxyguanidines 6a-x have been synthesized in order to evaluate their biological activity. Compounds 6a, 6c, 6d, 6f, 6g, 6i-p, 6r-t, and 6v-x were tested for their in vitro anticancer activity at the US National Cancer Institute. The highest in vitro anticancer activity was found for compounds 6d, 6g and 6k with GI(50) average value in the range 1.62-1.86 mu M, and TGI mean values 3.72-4.47 mu M, whereas the remaining compounds showed broad spectrum of anticancer activity at low micromolar GI(50) level against all tested cancer cell lines. These results were subjected to CoMSIA analysis to establish quantitative structure activity relationships. The results evidence that potency of these compounds correlates mainly with hydrophobic and polar surface properties of substituents located both at 2 and 5 positions of 1-(4-chlorobenzenesulfonyl) moiety of investigated 3-hydroxyguanidine series. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.042

文献信息

• 1-(2-Mercaptobenzenesulfonyl)-3-hydroxyguanidines – Novel potent antiproliferatives, synthesis and in vitro biological activity
  作者：Kamil Brożewicz、Jarosław Sławiński

  DOI：10.1016/j.ejmech.2012.07.042

  日期：2012.9

  Twenty four 1-[2-alkylthio-5-(azol-2 or 5-yl)-4-chlorobenzenesulfonyl]-3-hydroxyguanidines 6a-x have been synthesized in order to evaluate their biological activity. Compounds 6a, 6c, 6d, 6f, 6g, 6i-p, 6r-t, and 6v-x were tested for their in vitro anticancer activity at the US National Cancer Institute. The highest in vitro anticancer activity was found for compounds 6d, 6g and 6k with GI(50) average value in the range 1.62-1.86 mu M, and TGI mean values 3.72-4.47 mu M, whereas the remaining compounds showed broad spectrum of anticancer activity at low micromolar GI(50) level against all tested cancer cell lines. These results were subjected to CoMSIA analysis to establish quantitative structure activity relationships. The results evidence that potency of these compounds correlates mainly with hydrophobic and polar surface properties of substituents located both at 2 and 5 positions of 1-(4-chlorobenzenesulfonyl) moiety of investigated 3-hydroxyguanidine series. (C) 2012 Elsevier Masson SAS. All rights reserved.