3-(acridin-9-yl)-1-tert-butylthiourea | 162406-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(acridin-9-yl)-1-tert-butylthiourea
• 英文别名: 1-acridin-9-yl-3-tert-butylthiourea
• CAS: 162406-23-7
• 化学式: C₁₈H₁₉N₃S
• 分子量: 309.435
• InChiKey: OHCBUABJPJSUBE-UHFFFAOYSA-N

物化性质

• 沸点：
  474.6±37.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(acridin-9-yl)-1-tert-butylthiourea 在 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 3-Acridin-9-yl-2-[(E)-tert-butylimino]-thiazolidin-4-one
  参考文献：
  名称：

  含a啶骨架的1,3-噻唑烷丁-4-酮的区域专一性合成，结构和电子电离质谱

  摘要：

  区域异构的3-烷基（芳基）-2-（ac啶-9'-基）亚氨基-1,3-噻唑烷丁-4-酮（8b-i）和2-烷基（芳基）亚氨基-3-（ac啶）的合成通过使3-（ac啶酮-9-基）-1-烷基（芳基）硫脲5a-i与溴乙酸甲酯反应来进行-9'-基）-1,3-噻唑烷-4-酮（11a-i）分别通过相应的异硫脲氢溴酸盐和溴乙酰溴，具有良好的区域选择性。讨论了所得化合物的结构，NMR光谱和质谱行为。

  DOI：

  10.1002/jhet.5570420524
• 作为产物：
  描述：

  9-异硫氰酸酯吖啶 、 叔丁胺 以 乙腈 为溶剂， 生成 3-(acridin-9-yl)-1-tert-butylthiourea
  参考文献：
  名称：

  Kinetics of Reactions of 9-Isothiocyanatoacridine with Aromatic and Aliphatic Amines and Fluorescence Properties of the 1-Acridin-9-yl-3-alkyl(aryl)thioureas Obtained

  摘要：

  采用可见光光谱法研究了9-异硫氰酸基蒽的亲核加成反应动力学，该反应在有机溶剂中与十七种脂肪族和芳香族胺反应。9-异硫氰酸基蒽的反应速率比苯基异硫氰酸酯快约两个数量级。脂肪族胺的反应速率受立体效应的影响明显。除1-蒽基-9-丁基硫脲（IIIo）外，所得产物的荧光强度均弱于起始的9-异硫氰酸基蒽。

  DOI：

  10.1135/cccc19942632

文献信息

• DNA binding acridine–thiazolidinone agents affecting intracellular glutathione
  作者：Helena Paulíková、Zuzana Vantová、Ľuba Hunáková、Lýdia Čižeková、Mária Čarná、Mária Kožurková、Danica Sabolová、Pavol Kristian、Slávka Hamuľaková、Ján Imrich

  DOI：10.1016/j.bmc.2012.09.068

  日期：2012.12

  Three new acridine-thiazolidinone derivatives (2a-2c) have been synthesized and their interactions with calf thymus DNA and a number of cell lines (leukemic cells HL-60 and L1210 and human epithelial ovarian cancer cell lines A2780) were studied. The compounds 2a-2c possessed high affinity to calf thymus DNA and their binding constants determined by spectrofluorimetry were in the range of 1.37 x 10(6)-5.89 x 10(6) M (1). All of the tested derivatives displayed strong cytotoxic activity in vitro, the highest activity in cytotoxic tests was found for 2c with IC50 = 1.3 +/- 0.2 mu M (HL-60), 3.1 +/- 0.4 mu M (L1210), and 7.7 +/- 0.5 mu M (A2780) after 72 h incubation. The cancer cells accumulated acridine derivatives very fast and the changes of the glutathione level were confirmed. The compounds inhibited proliferation of the cells and induced an arrest of the cell cycle and cell death. Their influence upon cells was associated with their reactivity towards thiols and DNA binding activity. (C) 2012 Elsevier Ltd. All rights reserved.
• Regiospecific synthesis, structure and electron ionization mass spectra of 1,3-thiazolidin-4-ones containing the acridine skeleton
  作者：Imrich Géci、Ján Imrich、Pavol Kristian、Henri Kivelä、Pauliina Valtamo、Kalevi Pihlaja

  DOI：10.1002/jhet.5570420524

  日期：2005.7

  no-1,3-thiazolidin-4-ones (8b-i) and 2-alkyl(aryl)imino-3-(acridin-9′-yl)-1,3-thiazolidin-4-ones (11a-i) was performed by the reaction of 3-(acridin-9-yl)-1-alkyl(aryl)thioureas 5a-i with methyl bromoacetate and bromoacetyl bromide, respectively, via the corresponding isothiourea hydrobromides with excellent regioselectivity. The structure, NMR spectra and mass spectrometric behavior of the resulting

  区域异构的3-烷基（芳基）-2-（ac啶-9'-基）亚氨基-1,3-噻唑烷丁-4-酮（8b-i）和2-烷基（芳基）亚氨基-3-（ac啶）的合成通过使3-（ac啶酮-9-基）-1-烷基（芳基）硫脲5a-i与溴乙酸甲酯反应来进行-9'-基）-1,3-噻唑烷-4-酮（11a-i）分别通过相应的异硫脲氢溴酸盐和溴乙酰溴，具有良好的区域选择性。讨论了所得化合物的结构，NMR光谱和质谱行为。
• Kinetics of Reactions of 9-Isothiocyanatoacridine with Aromatic and Aliphatic Amines and Fluorescence Properties of the 1-Acridin-9-yl-3-alkyl(aryl)thioureas Obtained
  作者：Dana Mazagová、Pavol Kristian、Gejza Suchár、Ján Imrich、Marián Antalík

  DOI：10.1135/cccc19942632

  日期：——

  Kinetics of nucleophilic addition reaction of 9-isothiocyanatoacridine with seventeen aliphatic and aromatic amines in organic solvents has been studied by the VIS spectroscopic method. 9-Isothiocyanatoacridine reacted by about two orders of magnitude faster than phenyl isothiocyanate. The reaction rates of aliphatic amines were markedly affected by steric effects. Excepting 1-acridin-9-yl-3-butylthiourea (IIIo), the products obtained exhibited weaker fluorescence than the starting 9-isothiocyanatoacridine.

  采用可见光光谱法研究了9-异硫氰酸基蒽的亲核加成反应动力学，该反应在有机溶剂中与十七种脂肪族和芳香族胺反应。9-异硫氰酸基蒽的反应速率比苯基异硫氰酸酯快约两个数量级。脂肪族胺的反应速率受立体效应的影响明显。除1-蒽基-9-丁基硫脲（IIIo）外，所得产物的荧光强度均弱于起始的9-异硫氰酸基蒽。