4-α-naphthylselenosemicarbazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-α-naphthylselenosemicarbazide
• 化学式: C₁₁H₁₁N₃Se
• 分子量: 264.188
• InChiKey: HNBFDFGYINEJEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  15.0
• 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：
  50.08
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-α-naphthylselenosemicarbazide 、 3,4-二羟基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以90%的产率得到1-(3',4'-dihydroxybenzylidene)-4-(α-naphthyl)-3-selenosemicarbazone
  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
• 作为产物：
  描述：

  1-naphthyl isoselenocyanate 在 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到4-α-naphthylselenosemicarbazide
  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

• Selective synthesis of novel 2-imino-1,3-selenazolidin-4-ones and 2-amino-1,3,4-selenadiazin-5-ones from isoselenocyanates
  作者：Yuanyuan Xie、Junli Liu、Jianjun Li

  DOI：10.1016/j.tetlet.2010.12.068

  日期：2011.2

  An efficient and regioselective synthesis of 2-imino-1,3-selenazolidin-4-ones and 2-amino-1,3,4-selenadiazin-5-ones was achieved via one-pot reaction of isoselenocyanates, hydrazines, and ethyl chloroacetate or chloroacetyl chloride, respectively. Plausible mechanisms for these transformations were given. (C) 2010 Elsevier Ltd. All rights reserved.
• Phenolic thio- and selenosemicarbazones as multi-target drugs
  作者：Verónica Calcatierra、Óscar López、José G. Fernández-Bolaños、Gabriela B. Plata、José M. Padrón

  DOI：10.1016/j.ejmech.2015.02.037

  日期：2015.4

  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.