2-[4-[4-[[Amino-(hydroxyamino)methylidene]amino]phenyl]sulfanylphenyl]-1-hydroxyguanidine | 1418793-62-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[4-[4-[[Amino-(hydroxyamino)methylidene]amino]phenyl]sulfanylphenyl]-1-hydroxyguanidine
• 英文别名: 2-[4-[4-[[amino-(hydroxyamino)methylidene]amino]phenyl]sulfanylphenyl]-1-hydroxyguanidine
• CAS: 1418793-62-0
• 化学式: C₁₄H₁₆N₆O₂S
• 分子量: 332.386
• InChiKey: ADUYOPVBXVJZMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  167
• 氢给体数：
  6
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4-[4-[[Amino-(hydroxyamino)methylidene]amino]phenyl]sulfanylphenyl]-1-hydroxyguanidine 在 盐酸 作用下， 以 乙醚 为溶剂， 以19%的产率得到2-[4-[4-[[Amino-(hydroxyamino)methylidene]amino]phenyl]sulfanylphenyl]-1-hydroxyguanidine;hydrochloride
  参考文献：
  名称：

  Aromatic Bis-N-hydroxyguanidinium Derivatives: Synthesis, Biophysical, and Biochemical Evaluations

  摘要：

  In this paper we report the synthesis of a new family of hydroxyguanidinium aromatic derivatives (4a-g) as potential minor groove binders and cytotoxic agents. Their DNA affinity was evaluated by thermal denaturation experiments using salmon sperm DNA. The antiproliferative effects of derivatives 4a, 4d, and 4f were evaluated in human promyelocytic HL-60, breast carcinoma MCF-7, and neuroblastoma Kelly cell lines using the AlamarBlue viability assay, and IC50 values were obtained. All three compounds were active in the HL-60 cell line. In particular, 4b exhibits antiproliferative effects in all three cell lines while 4d reduced HL-60 and Kelly viability. Both 4b and 4d produced considerable antiproliferative activity in the Kelly cell line. Derivative 4d was chosen for further cell cycle and apoptosis studies using flow cytometric analysis of cellular DNA content.

  DOI：

  10.1021/jm301358s
• 作为产物：
  描述：

  4,4-二氨基二苯硫醚 在 N,N-二甲基乙酰胺 、 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-[4-[4-[[Amino-(hydroxyamino)methylidene]amino]phenyl]sulfanylphenyl]-1-hydroxyguanidine
  参考文献：
  名称：

  Aromatic Bis-N-hydroxyguanidinium Derivatives: Synthesis, Biophysical, and Biochemical Evaluations

  摘要：

  In this paper we report the synthesis of a new family of hydroxyguanidinium aromatic derivatives (4a-g) as potential minor groove binders and cytotoxic agents. Their DNA affinity was evaluated by thermal denaturation experiments using salmon sperm DNA. The antiproliferative effects of derivatives 4a, 4d, and 4f were evaluated in human promyelocytic HL-60, breast carcinoma MCF-7, and neuroblastoma Kelly cell lines using the AlamarBlue viability assay, and IC50 values were obtained. All three compounds were active in the HL-60 cell line. In particular, 4b exhibits antiproliferative effects in all three cell lines while 4d reduced HL-60 and Kelly viability. Both 4b and 4d produced considerable antiproliferative activity in the Kelly cell line. Derivative 4d was chosen for further cell cycle and apoptosis studies using flow cytometric analysis of cellular DNA content.

  DOI：

  10.1021/jm301358s