4-hydroxy-benzaldehyde 4-m-tolyl-thiosemicarbazone | 7762-92-7

• 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: 4-hydroxy-benzaldehyde 4-m-tolyl-thiosemicarbazone
• 英文别名: 4-hydroxy-benzaldehyde 4-m-tolyl-thiosemicarbazone；4-Hydroxy-benzaldehyd-<4-(3-methyl-phenyl)-thiosemicarbazon>
• CAS: 7762-92-7
• 化学式: C₁₅H₁₅N₃OS
• 分子量: 285.37
• InChiKey: BOZBVLIPFSLIEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  56.65
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-benzaldehyde 4-m-tolyl-thiosemicarbazone 、 2-氯丙酸 生成 4-hydroxy-benzaldehyde (5-methyl-4-oxo-3-m-tolyl-thiazolidin-2-ylidene)-hydrazone
  参考文献：
  名称：

  Trivedi,J.P.; Shah,I.D., Journal of the Indian Chemical Society, 1966, vol. 43, p. 275 - 276

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl N-[(4-hydroxyphenyl)methylideneamino]carbamodithioate 、 3-甲基苯胺 以 乙醇 为溶剂， 以61%的产率得到4-hydroxy-benzaldehyde 4-m-tolyl-thiosemicarbazone
  参考文献：
  名称：

  Synthesis and Ribonucleotide reductase inhibitory activity of thiosemicarbazones

  摘要：

  Ribonucleotide reductase (RR) is an important therapeutic target for anticancer drugs. The structure of human RR features a 1: 1 complex of two homodimeric subunits, hRRM1 and hRRM2. Prokaryotically expressed and highly purified recombinant human RR subunits, hRRM1 and hRRM2, were used for holoenzyme-based [(3)H] CDP reduction in vitro assay. Ten new thiosemicarbazones (7-16) were synthesized and screened for their RR inhibitory activity. Two thiosemicarbazones derived from p-hydroxy benzaldehyde (9 and 10) were found to be active but less potent than the standard, Hydroxyurea (HU). Guided by the activity of compounds 9 and 10, 11 new thiosemicarbazones (17-27) derived from p-hydroxy benzaldehyde were prepared and screened for their RR inhibitory activity. All the 11 compounds were more potent than HU. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.097

文献信息

• Trivedi,J.P.; Shah,I.D., Journal of the Indian Chemical Society, 1966, vol. 43, p. 275 - 276
  作者：Trivedi,J.P.、Shah,I.D.

  DOI：——

  日期：——
• Synthesis and Ribonucleotide reductase inhibitory activity of thiosemicarbazones
  作者：Kesavan Krishnan、Kumari Prathiba、Venkatesan Jayaprakash、Arijit Basu、Nibha Mishra、Bingsen Zhou、Shuya Hu、Yun Yen

  DOI：10.1016/j.bmcl.2008.09.097

  日期：2008.12

  Ribonucleotide reductase (RR) is an important therapeutic target for anticancer drugs. The structure of human RR features a 1: 1 complex of two homodimeric subunits, hRRM1 and hRRM2. Prokaryotically expressed and highly purified recombinant human RR subunits, hRRM1 and hRRM2, were used for holoenzyme-based [(3)H] CDP reduction in vitro assay. Ten new thiosemicarbazones (7-16) were synthesized and screened for their RR inhibitory activity. Two thiosemicarbazones derived from p-hydroxy benzaldehyde (9 and 10) were found to be active but less potent than the standard, Hydroxyurea (HU). Guided by the activity of compounds 9 and 10, 11 new thiosemicarbazones (17-27) derived from p-hydroxy benzaldehyde were prepared and screened for their RR inhibitory activity. All the 11 compounds were more potent than HU. (C) 2008 Elsevier Ltd. All rights reserved.