1-(4-methoxyphenyl)-3-[(E)-thiophen-2-ylmethylideneamino]thiourea

• 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: 1-(4-methoxyphenyl)-3-[(E)-thiophen-2-ylmethylideneamino]thiourea
• 化学式: C₁₃H₁₃N₃OS₂
• 分子量: 291.398
• InChiKey: UDXDSWVZNFIGLG-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基苯基 异硫氰酸酯 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-(4-methoxyphenyl)-3-[(E)-thiophen-2-ylmethylideneamino]thiourea
  参考文献：
  名称：

  Synthesis of thiophene-thiosemicarbazone derivatives and evaluation of their in vitro and in vivo antitumor activities

  摘要：

  A series of thiophene-2-thiosemicarbazones derivatives (5-14) was synthesized, characterized and evaluated for their antitumor activity. They were tested in vitro against human tumor cell lines through the colorimetric method. The results revealed that compounds 7 and 9 were the most effective in inhibiting 50% of the cell growth after 48 h of treatment. As compound 7 showed a potent anti-proliferative profile, it has been chosen for further studies in 786-0 cell line by flow cytometry. Treatments with compound 7 (50 mu M) induced early phosphatidylserine exposure after 18 h of exposure and this process progressed phosphatidylserine exposure with loss of cell membrane integrity after 24 h of treatment, suggesting a time-dependent cell death process. Regarding the cell cycle profile, no changes were observed after treatment with compound 7 (25 mu m), suggesting a mechanism of cell death independent on the cell cycle. The in vivo studies show that compound 7 possess low acute toxicity, being the doses of 30-300 mgK(-1) chosen for studies in Ehrlich solid tumor model in mice. All doses were able to inhibit tumor development being the lowest one the most effective. Our findings highlight thiophene-2-thiosemicarbazones as a promising class of compounds for further studies concerning new anticancer therapies. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.036

文献信息

• Synthesis of thiophene-thiosemicarbazone derivatives and evaluation of their in vitro and in vivo antitumor activities
  作者：Jamerson Ferreira de Oliveira、Anekécia Lauro da Silva、Débora Barbosa Vendramini-Costa、Cezar Augusto da Cruz Amorim、Júlia Furtado Campos、Amélia Galdino Ribeiro、Ricardo Olímpio de Moura、Jorge Luiz Neves、Ana Lúcia Tasca Gois Ruiz、João Ernesto de Carvalho、Maria do Carmo Alves de Lima

  DOI：10.1016/j.ejmech.2015.09.036

  日期：2015.11

  A series of thiophene-2-thiosemicarbazones derivatives (5-14) was synthesized, characterized and evaluated for their antitumor activity. They were tested in vitro against human tumor cell lines through the colorimetric method. The results revealed that compounds 7 and 9 were the most effective in inhibiting 50% of the cell growth after 48 h of treatment. As compound 7 showed a potent anti-proliferative profile, it has been chosen for further studies in 786-0 cell line by flow cytometry. Treatments with compound 7 (50 mu M) induced early phosphatidylserine exposure after 18 h of exposure and this process progressed phosphatidylserine exposure with loss of cell membrane integrity after 24 h of treatment, suggesting a time-dependent cell death process. Regarding the cell cycle profile, no changes were observed after treatment with compound 7 (25 mu m), suggesting a mechanism of cell death independent on the cell cycle. The in vivo studies show that compound 7 possess low acute toxicity, being the doses of 30-300 mgK(-1) chosen for studies in Ehrlich solid tumor model in mice. All doses were able to inhibit tumor development being the lowest one the most effective. Our findings highlight thiophene-2-thiosemicarbazones as a promising class of compounds for further studies concerning new anticancer therapies. (C) 2015 Elsevier Masson SAS. All rights reserved.