N-(2,6-diisopropylphenyl)hydrazinecarbothioamide | 63299-73-0

• 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: N-(2,6-diisopropylphenyl)hydrazinecarbothioamide
• 英文别名: 4-(2.6-Diisopropylphenyl)thiosemicarbazid；4-(2,6-Diisopropylphenyl)thiosemicarbazide；1-amino-3-[2,6-di(propan-2-yl)phenyl]thiourea
• CAS: 63299-73-0
• 化学式: C₁₃H₂₁N₃S
• 分子量: 251.396
• InChiKey: MLBRTISQROZFBI-UHFFFAOYSA-N

物化性质

• 熔点：
  188 °C
• 沸点：
  341.9±52.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2,6-diisopropylphenyl)hydrazinecarbothioamide 生成 4-(2.6-Diisopropylphenyl)thiosemicarbazid-S.S.S-trioxid
  参考文献：
  名称：

  Walter,W.; Rohloff,C., Justus Liebigs Annalen der Chemie, 1977, p. 463 - 484

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二异丙基异硫氰酸苯酯 在 肼 作用下， 以 水 、 异丙醇 为溶剂， 反应 0.5h， 以72%的产率得到N-(2,6-diisopropylphenyl)hydrazinecarbothioamide
  参考文献：
  名称：

  A Series of α-Heterocyclic Carboxaldehyde Thiosemicarbazones Inhibit Topoisomerase IIα Catalytic Activity

  摘要：

  A series of novel thiosemicarbazone derivatives bearing condensed heterocyclic carboxaldehyde moieties were designed and synthesized. Among them, TSC24 exhibited broad antiproliferative activity in a panel of human tumor cells and suppressed tumor growth in mice. The mechanism research revealed that TSC24 was not only an iron chelator but also a topoisomerase II alpha catalytic inhibitor. Its inhibition on topoisomerase II alpha was due to direct interaction with the ATPase domain of topoisomerase I la which led to the block of ATP hydrolysis. Molecular docking predicted that TSC24 might bind at the ATP binding site, which was confirmed by the competitive inhibition assay. These results about the mechanisms involved in the anticancer activities of thiosemicarbazones will aid in the rational design of novel topoisomerase II-targeted drugs and will provide insights into the discovery and development of novel cancer therapeutics based on the dual activity to chelate iron and to inhibit the catalytic activity of topoisomerase II alpha.

  DOI：

  10.1021/jm9014394

文献信息

• Habib; Rieker; Tawil, Il Farmaco, 1994, vol. 49, # 7-8, p. 519 - 526
  作者：Habib、Rieker、Tawil

  DOI：——

  日期：——
• WALTER W.; ROHLOFF C., J. LIEBIGS ANN. CHEM. <JLAC-BF>, 1977, NO 3, 463-484
  作者：WALTER W.、 ROHLOFF C.

  DOI：——

  日期：——
• A Series of α-Heterocyclic Carboxaldehyde Thiosemicarbazones Inhibit Topoisomerase IIα Catalytic Activity
  作者：He Huang、Qin Chen、Xin Ku、Linghua Meng、Liping Lin、Xiang Wang、Caihua Zhu、Yi Wang、Zhi Chen、Ming Li、Hualiang Jiang、Kaixian Chen、Jian Ding、Hong Liu

  DOI：10.1021/jm9014394

  日期：2010.4.22

  A series of novel thiosemicarbazone derivatives bearing condensed heterocyclic carboxaldehyde moieties were designed and synthesized. Among them, TSC24 exhibited broad antiproliferative activity in a panel of human tumor cells and suppressed tumor growth in mice. The mechanism research revealed that TSC24 was not only an iron chelator but also a topoisomerase II alpha catalytic inhibitor. Its inhibition on topoisomerase II alpha was due to direct interaction with the ATPase domain of topoisomerase I la which led to the block of ATP hydrolysis. Molecular docking predicted that TSC24 might bind at the ATP binding site, which was confirmed by the competitive inhibition assay. These results about the mechanisms involved in the anticancer activities of thiosemicarbazones will aid in the rational design of novel topoisomerase II-targeted drugs and will provide insights into the discovery and development of novel cancer therapeutics based on the dual activity to chelate iron and to inhibit the catalytic activity of topoisomerase II alpha.
• Walter,W.; Rohloff,C., Justus Liebigs Annalen der Chemie, 1977, p. 463 - 484
  作者：Walter,W.、Rohloff,C.

  DOI：——

  日期：——