2,4,5-trihydroxybenzaldehyde-4-phenyl-3-thiosemicarbazone | 1415358-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,4,5-trihydroxybenzaldehyde-4-phenyl-3-thiosemicarbazone
• CAS: 1415358-89-2
• 化学式: C₁₄H₁₃N₃O₃S
• 分子量: 303.342
• InChiKey: ZAMTYZNUTJTWQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.11
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2,4,5-三羟基苯甲醛 、 4-苯基-3-硫代氨基脲 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以65%的产率得到2,4,5-trihydroxybenzaldehyde-4-phenyl-3-thiosemicarbazone
  参考文献：
  名称：

  Phenolic thio- and selenosemicarbazones as multi-target drugs

  摘要：

  A series of isosteric phenolic thio- and selenosemicarbazones have been obtained by condensation of naturally-occurring phenolic aldehydes and thio(seleno)semicarbazides. Title compounds were designed as potential multi-target drugs, and a series of structure-activity relationships could be established upon their in vitro assays: antioxidant activity, alpha-glucosidase inhibition and antiproliferative activity against six human tumor cell lines: A549 (non-small cell lung), HBL-100 (breast), HeLa (cervix), SW1573 (non-small cell lung), T-47D (breast) and WiDr (colon). For the antiradical activity, selenium atom and 2 or 3 phenolic hydroxyl groups proved to be essential motifs; remarkably, the compound with the most potent activity, with a trihydroxyphenyl scaffold (EC50 = 4.87 +/- 1.57 mu M) was found to be stronger than natural hydroxytyrosol, a potent antioxidant present in olive oil (EC50 = 13.80 +/- 1.41 mu M). Furthermore, one of the thiosemicarbazones was found to be a strong non-competitive inhibitor of alpha-glucosidase (K-i = 9.6 +/- 1.6 mu M), with an 8-fold increase in activity compared to acarbose (K-i = 77.9 +/- 11.4 mu M), marketed for the treatment of type-2 diabetes. Most of the synthesized compounds also exhibited relevant antiproliferative activities; in particular, seleno derivatives showed GI(50) values lower than 6.0 mu M for all the tested cell lines; N-naphthyl mono- and dihydroxylated derivatives behaved as more potent antiproliferative agents than 5-fluorouracil or cisplatin. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.037

文献信息

• Evaluating anti-Toxoplasma gondii activity of new serie of phenylsemicarbazone and phenylthiosemicarbazones in vitro
  作者：Marco Antônio G. B. Gomes、Laís P. Carvalho、Barbara S. Rocha、Rodrigo R. Oliveira、Edésio J. T. de Melo、Edmilson J. Maria

  DOI：10.1007/s00044-012-0347-9

  日期：2013.8

  While Toxoplasma gondii is able to infect and replicate within all eukaryotic cells, tachyzoites are the infective form of T. gondii that invades all eukaryotic cells leading to tissue rupture, the main features of toxoplasmosis. The present study evaluates the activity of (benzaldehyde)-4-phenyl-3-thiosemicarbazone and (benzaldehyde)-(4 or 1)-phenylsemicarbazone against intracellular T. gondii. The nine new compounds were incubated in infected Vero cells at concentrations of 0.01, 0.1, 0.5, and 1.0 mM and evaluated for three main effects: cytotoxicity, infection, and number of intracellular parasites. The cytotoxicity test showed a pattern by analyzing the substituent arylhydrazone, where trihydroxy Compounds 4-9 were cytotoxic at concentrations of 0.5 and 1.0 mM. The results highlight Compound 8, which reduced the number of intracellular parasites by 82 % in a concentration of 0.01 mM and showed a LD50 of 0.3 mM in cell culture. These different biological actions are due to changes in the molecular structure and type of radical present in each compound. All compounds tested were more efficient than the control drug sulfadizine.