6-hydroxy chromone-3-carbaldehyde thiosemicarbazone | 863982-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-hydroxy chromone-3-carbaldehyde thiosemicarbazone
• 英文别名: 6-hydroxy-chromone-3-carbaldehyde thiosemicarbazone；[(6-Hydroxy-4-oxochromen-3-yl)methylideneamino]thiourea
• CAS: 863982-29-0
• 化学式: C₁₁H₉N₃O₃S
• 分子量: 263.277
• InChiKey: JVLHVDYXVOCPDL-UHFFFAOYSA-N

物化性质

• 熔点：
  256-258 °C(Solv: acetone (67-64-1))
• 沸点：
  489.2±55.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  nickel(II) nitrate 、 6-hydroxy chromone-3-carbaldehyde thiosemicarbazone 以 甲醇 为溶剂， 生成 (6-hydroxy chromone-3-carbaldehyde thiosemicarbazone)nickel(II) nitrate
  参考文献：
  名称：

  Synthesis, characterization, cytotoxic activity and DNA binding Ni(II) complex with the 6-hydroxy chromone-3-carbaldehyde thiosemicarbazone

  摘要：

  A new ligand L, 6-hydroxy chromone-3-carbaldehyde thiosemicarbazone, and its Ni(II) complex have been synthesized and characterized. The crystal structure of Ni(II) complex was determined by single crystal X-ray diffraction. Ni(II) complex and ligand L were subjected to biological tests in vitro using THP-1, Raji and Hela cancer cell lines. Compared with the ligand, Ni(II) complex showed significant cytotoxic activity against these three cancer cell lines. The interactions of Ni(II) complex and ligand L with calf thymus DNA were then investigated by spectrometric titration, ethidium bromide displacement experiments and viscosity measurements methods. The experimental results indicated that Ni(II) complex bound to DNA by intercalative mode via the ligand L. The intrinsic binding constants of Ni(II) complex and ligand L with DNA were (1.10 +/- 0.65) x 10(6) M-1 and (1.48 +/- 0.57) x 10(5) M-1, respectively. (C) 2009 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.08.024
• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 6-hydroxy chromone-3-carbaldehyde thiosemicarbazone
  参考文献：
  名称：

  使用 6-羟基-4H-4-氧代[1]-苯并吡喃-3-甲醛作为通用起始材料合成一些新型唑、氮杂、吡啶和嘧啶衍生物

  摘要：

  3-甲酰基色酮 1 与盐酸羟胺缩合得到相应的肟 2，该肟 2 转化为腈 3。将肟 2 和/或腈 3 与乙酸或马尿酸回流得到 16 和 17。用氨基脲盐酸盐和氨基硫脲处理 1 得到相应的卡巴腙 5-6 与溴乙酸乙酯和/或氯丙酮进行环化，得到 7-8。1 还与无环活性亚甲基试剂（例如丙二腈、氰基乙酸乙酯和乙酰乙酸乙酯）反应以形成化合物 11、12 和 13。 1 与双功能试剂（例如苄基、邻苯二胺、邻氨基苯酚和邻氨基苯硫酚）的反应产生相应的咪唑基苯并吡喃酮和氮杂衍生物 14-20。1与含有活性亚甲基的无环或杂环化合物的缩合，例如。G。马尿酸形成缩合产物 21-27。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:20–27, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc

  DOI：

  10.1002/hc.20048

文献信息

• Synthesis of some new azole, azepine, pyridine, and pyrimidine derivatives using 6-hydroxy-4H-4-oxo[1]-benzopyran-3- carboxaldehyde as a versatile starting material
  作者：A. H. Abdel-Rahman、M. A. A. Hammouda、S. I. El-Desoky

  DOI：10.1002/hc.20048

  日期：——

  malononitrile, ethyl cyanoacetate, and ethyl acetoacetate to form compounds 11, 12, and 13. Reaction of 1 with bifunctional reagents, e.g. benzil, o-phenylenediamine, o-aminophenol, and o-aminothiophenol yielding the corresponding imidazolyl bezopyranone and azepine derivatives 14–20. Condensation of 1 with acyclic or heterocyclic compounds containing active methylene group, e.g. hippuric acid forming the

  3-甲酰基色酮 1 与盐酸羟胺缩合得到相应的肟 2，该肟 2 转化为腈 3。将肟 2 和/或腈 3 与乙酸或马尿酸回流得到 16 和 17。用氨基脲盐酸盐和氨基硫脲处理 1 得到相应的卡巴腙 5-6 与溴乙酸乙酯和/或氯丙酮进行环化，得到 7-8。1 还与无环活性亚甲基试剂（例如丙二腈、氰基乙酸乙酯和乙酰乙酸乙酯）反应以形成化合物 11、12 和 13。 1 与双功能试剂（例如苄基、邻苯二胺、邻氨基苯酚和邻氨基苯硫酚）的反应产生相应的咪唑基苯并吡喃酮和氮杂衍生物 14-20。1与含有活性亚甲基的无环或杂环化合物的缩合，例如。G。马尿酸形成缩合产物 21-27。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:20–27, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc
• Synthesis, characterization, cytotoxic activity and DNA binding Ni(II) complex with the 6-hydroxy chromone-3-carbaldehyde thiosemicarbazone
  作者：Bao-dui Wang、Zheng-Yin Yang、Ming-hua Lü、Jun Hai、Qin Wang、Zhong-Ning Chen

  DOI：10.1016/j.jorganchem.2009.08.024

  日期：2009.12

  A new ligand L, 6-hydroxy chromone-3-carbaldehyde thiosemicarbazone, and its Ni(II) complex have been synthesized and characterized. The crystal structure of Ni(II) complex was determined by single crystal X-ray diffraction. Ni(II) complex and ligand L were subjected to biological tests in vitro using THP-1, Raji and Hela cancer cell lines. Compared with the ligand, Ni(II) complex showed significant cytotoxic activity against these three cancer cell lines. The interactions of Ni(II) complex and ligand L with calf thymus DNA were then investigated by spectrometric titration, ethidium bromide displacement experiments and viscosity measurements methods. The experimental results indicated that Ni(II) complex bound to DNA by intercalative mode via the ligand L. The intrinsic binding constants of Ni(II) complex and ligand L with DNA were (1.10 +/- 0.65) x 10(6) M-1 and (1.48 +/- 0.57) x 10(5) M-1, respectively. (C) 2009 Elsevier B. V. All rights reserved.