1-allyl-3-(4-ethoxyphenyl)-thiourea | 1142-30-9

• 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-allyl-3-(4-ethoxyphenyl)-thiourea
• 英文别名: N-Allyl-N'-(4-EtO-Phenyl)thiocarbamid；N-allyl-N'-(4-ethoxyphenyl)thiourea；N-(4-ethoxy-phenyl)-N'-allyl-thiourea；N-(4-Aethoxy-phenyl)-N'-allyl-thioharnstoff；Thiourea, N-(4-ethoxyphenyl)-N'-2-propenyl-；1-(4-ethoxyphenyl)-3-prop-2-enylthiourea
• CAS: 1142-30-9
• 化学式: C₁₂H₁₆N₂OS
• mdl: MFCD00625520
• 分子量: 236.338
• InChiKey: JUYGRDKXJBNWHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-allyl-3-(4-ethoxyphenyl)-thiourea 在 溶剂黄146 、 mercury(II) oxide 作用下， 生成 N-allyl-N'-(4-ethoxy-phenyl)-urea
  参考文献：
  名称：

  Bergmann; Camacho; Dreyer, Berichte der Deutschen Pharmazeutischen Gesellschaft, vol. 32, p. 256

  摘要：

  DOI：
• 作为产物：
  描述：

  对乙氧基苯胺 、 天然芥菜籽油 以 乙醇 为溶剂， 反应 3.0h， 生成 1-allyl-3-(4-ethoxyphenyl)-thiourea
  参考文献：
  名称：

  Synthesis of New Thioureas Derivatives and Evaluation of Their Efficacy as Proliferation Inhibitors in MCF-7 Breast Cancer Cells by Using 99mTc-MIBI Radiotracer

  摘要：

  <节><标题>背景与目的：<段>文献中已充分记载某些硫脲衍生物的抗肿瘤活性，并受到广泛关注。本研究旨在合成并表征一些新型硫脲及羰基硫脲，作为体外和体内针对MCF-7乳腺癌细胞的抗肿瘤药物。<节><标题>材料与方法：<段>合成了几种1-烯丙基-3-(取代苯基)、N,N'-(苯撑)双(3-烯丙基二硫代硫脲)以及1-环丙烷羰基-3-(取代苯基)硫脲衍生物，并通过FT-IR光谱、NMR和¹³C-NMR进行了确认。通过MTT、肿瘤体积测量以及^99mTc-MIBI在MCF-7荷瘤裸鼠中的摄取等多种体外和体内试验，评估了这些化合物的抗肿瘤活性。<节><标题>结果：<段>在所有合成的化合物中，某些硫脲衍生物[3i]和[4b]在100nM浓度下对MCF-7细胞体外增殖表现出显著的抑制作用。然而，在HUVEC人脐静脉内皮正常细胞中未观察到这种抑制。体内抗肿瘤效果显示，合成的化合物在MCF-7异种移植小鼠模型中，以2至10 mg/kg的不同浓度处理21天后，肿瘤体积有所减少。这些效果与作为标准抗雌激素药物的他莫昔芬相当。根据^99mTc-MIBI生物分布结果，对携带MCF-7的裸鼠使用[3i]和[4b]化合物在最大浓度（10 mg/kg）处理后，^99mTc-MIBI的肿瘤摄取显著减少。<节><标题>结论：<段>化合物[3i]和[4b]在耐受剂量下抑制了异种移植裸鼠中MCF-7细胞的生长。我们的研究表明，这些具有显著抗肿瘤效果的新化合物可能作为乳腺癌治疗的潜在候选药物。

  DOI：

  10.2174/1573406416666200425224921

文献信息

• Facile and regioselective synthesis of thiazolidin-4-one derivatives catalyzed by basic ionic liquid [bmim]OH under ultrasonic irradiation
  作者：Manouchehr Mamaghani、Mozhgan Pourranjbar、Roghayeh Hossein Nia

  DOI：10.1080/17415993.2013.800061

  日期：2014.1.2

  synthesized regioselectively in good to high yields by condensation of N,N-disubstituted thioureas and ethyl chloroacetate in the presence of basic ionic liquid [bmim]OH as a catalyst under conventional and ultrasonic irradiation conditions. Under ultrasonic irradiation, the reaction furnished the desired 2-iminothiazolidinones in higher yields (76–87%) and lower reaction times (30–55 min). GRAPHICAL ABSTRACT

  在碱性离子液体[bmim]OH作为催化剂存在下，在常规和超声辐照条件下，通过N，N-二取代硫脲和氯乙酸乙酯的缩合反应，区域选择性地合成了2-Iminothiazolidin-4-one衍生物。在超声波照射下，该反应以更高的产率（76-87%）和更短的反应时间（30-55 分钟）提供了所需的 2-亚氨基噻唑烷酮。图形概要
• Oeriu et al, Academia Republicii Populare Romine, Baza de Cercetari Stiintifice, Timisoara, Studii si Cercetari, Stiinte Chimice, 1958, vol. 6, p. 155,156
  作者：Oeriu et al

  DOI：——

  日期：——
• Bergmann; Camacho; Dreyer, Berichte der Deutschen Pharmazeutischen Gesellschaft, vol. 32, p. 255
  作者：Bergmann、Camacho、Dreyer

  DOI：——

  日期：——
• Synthesis of new 2,5-diamino-1,3-thiazole and 2-thiohydantoin derivatives by condensation of N-(2-Aryl-1-chloro-2-oxoethyl) carboxamides with thioureas
  作者：A. G. Balya、A. N. Chernega、S. A. But、A. N. Vasilenko、V. S. Brovarets、B. S. Drach

  DOI：10.1134/s1070363208070268

  日期：2008.7

  N-(2-Aryl-1-chloro-2-oxoethyl) carboxamides react under mild conditions with thiourea, N-alkyl-and N-arylthioureas, and various N,N'-disubstituted thioureas, following the Hantzsch reaction scheme. The reactions are selective, and the resulting 2,5-diamino-1,3-thiazole derivatives undergo recyclization acid followed by hydrolysis to give substituted 2-thiohydantoins on heating with hydrochloric acid in ethanol.
• Synthesis of New Thioureas Derivatives and Evaluation of Their Efficacy as Proliferation Inhibitors in MCF-7 Breast Cancer Cells by Using 99mTc-MIBI Radiotracer
  作者：Ahmad Hormati、Jafar Abbasi Shiran、Mikaeil Molazadeh、Babak Kaboudin、Sajjad Ahmadpour

  DOI：10.2174/1573406416666200425224921

  日期：2021.8

  Anti-tumor activity of some thioureas derivatives is well documented in literature and received considerable attention. The present study aims to synthesize and characterize some novel thioureas and carbonylthioureas as anti-tumor agents for MCF-7 breast cancer cells in vitro and in vivo.

  Several 1-allyl-3-(substituted phenyl), N,N'-(phenylene) bis(3- allyldithithiourea) and 1-cyclopropanecarbonyl-3-(substituted phenyl)-thioureas derivatives were synthesized and confirmed by FT-IR spectroscopy, NMR and ¹³C-NMR. Anti-tumor activity of these compounds was determined by various in vitro and in vivo assays including; MTT, tumor volume measurement as well as,^99mTc-MIBI tumor uptake in MCF-7 tumor bearing nude mice.

  Among all of the synthesized compounds, some thioureas derivatives [3i] and [4b] at 100 nM concentration exhibited significant inhibitory effects on the proliferation of MCF-7 cell in vitro. However, this inhibition was not observed in HUVEC human endothelial normal cells. In vivo anti-tumor effects of the synthesized compounds on MCF-7 xenograft mouse models demonstrated a reduction in the tumor volume for various concentrations between 2 to 10 mg/kg after 21 days. These effects were comparable with Tamoxifen as standard anti-estrogen drug. According to the ^99mTc-MIBI biodistribution result, treatment of MCF-7 bearing nude mice with both [3i] and [4b] compounds at the maximum concentration (10 mg/kg) can lead to a significant decrease of ^99mTc- MIBI tumor uptake.

  Compounds [3i] and [4b] suppressed the growth of MCF-7 cells in the xenograft nude mice at the doses that were well-tolerated. Our study suggests that these new compounds with their significant anti-tumor effects, may serve as useful candidates for breast cancer therapy.

  <节><标题>背景与目的：<段>文献中已充分记载某些硫脲衍生物的抗肿瘤活性，并受到广泛关注。本研究旨在合成并表征一些新型硫脲及羰基硫脲，作为体外和体内针对MCF-7乳腺癌细胞的抗肿瘤药物。<节><标题>材料与方法：<段>合成了几种1-烯丙基-3-(取代苯基)、N,N'-(苯撑)双(3-烯丙基二硫代硫脲)以及1-环丙烷羰基-3-(取代苯基)硫脲衍生物，并通过FT-IR光谱、NMR和¹³C-NMR进行了确认。通过MTT、肿瘤体积测量以及^99mTc-MIBI在MCF-7荷瘤裸鼠中的摄取等多种体外和体内试验，评估了这些化合物的抗肿瘤活性。<节><标题>结果：<段>在所有合成的化合物中，某些硫脲衍生物[3i]和[4b]在100nM浓度下对MCF-7细胞体外增殖表现出显著的抑制作用。然而，在HUVEC人脐静脉内皮正常细胞中未观察到这种抑制。体内抗肿瘤效果显示，合成的化合物在MCF-7异种移植小鼠模型中，以2至10 mg/kg的不同浓度处理21天后，肿瘤体积有所减少。这些效果与作为标准抗雌激素药物的他莫昔芬相当。根据^99mTc-MIBI生物分布结果，对携带MCF-7的裸鼠使用[3i]和[4b]化合物在最大浓度（10 mg/kg）处理后，^99mTc-MIBI的肿瘤摄取显著减少。<节><标题>结论：<段>化合物[3i]和[4b]在耐受剂量下抑制了异种移植裸鼠中MCF-7细胞的生长。我们的研究表明，这些具有显著抗肿瘤效果的新化合物可能作为乳腺癌治疗的潜在候选药物。