1-allyl-3-(4-hydroxyphenyl)-thiourea | 20680-01-7

• 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-hydroxyphenyl)-thiourea
• 英文别名: 1-(4-Hydroxyphenyl)-3-prop-2-enylthiourea
• CAS: 20680-01-7
• 化学式: C₁₀H₁₂N₂OS
• mdl: MFCD00020152
• 分子量: 208.284
• InChiKey: UCVFACUXEHCDOR-UHFFFAOYSA-N

物化性质

• 沸点：
  340.9±52.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76.4
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  1-allyl-3-(4-hydroxyphenyl)-thiourea 在 氨基磺酰氯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以65%的产率得到4-(3-allylthioureido)phenyl sulfamate
  参考文献：
  名称：

  [EN] CARBONIC ANHYDRASE INHIBITORS
  [FR] INHIBITEURS D'ANHYDRASE CARBONIQUE

  摘要：

  一种碳酸酐酶IX（CA IX）抑制剂，包括一般式化合物：R-NH-CX-NH-(CH2)n-Ar-Q-SO2-NH2或其药用可接受的盐、衍生物或前药；其中n = 0、1或2；Q为O或NH；X为O或S；R包括有机取代基。

  公开号：

  WO2011098610A1
• 作为产物：
  描述：

  对氨基苯酚 、 天然芥菜籽油 以 乙醇 为溶剂， 反应 28.0h， 生成 1-allyl-3-(4-hydroxyphenyl)-thiourea
  参考文献：
  名称：

  新型3-烯丙基-2-(取代亚氨基)-4-苯基-3H-噻唑和2,2'-(1,3-亚苯基)双(3-取代-2-亚氨基-4-苯基-3H)的区域选择性合成-噻唑）衍生物作为抗菌剂

  摘要：

  摘要 通过烯丙基硫脲与2-溴苯乙酮反应合成了多种新型3-烯丙基-2-(取代亚氨基)-4-苯基-3H-噻唑衍生物。我们还报告了使用各种异硫氰酸酯和 1,3-苯二胺的反应合成双烯丙基-3 H 噻唑。所有化合物的结构均通过光谱和元素分析表征。大多数合成的化合物对沙门氏菌、藤黄微球菌、枯草芽孢杆菌和铜绿假单胞菌均表现出有效的抗菌活性。

  DOI：

  10.1016/j.molstruc.2013.02.003

文献信息

• 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。
• CARBONIC ANHYDRASE INHIBITORS
  申请人：Ebbesen Peter

  公开号：US20130053392A1

  公开（公告）日：2013-02-28

  A carbonic anhydrase IX (CA IX) inhibitor which comprises a compound of general formula: R—NH—CX—NH—(CH 2 ) n —Ar-Q-SO 2 —NH 2 or a pharmaceutically-acceptable salt, derivative or prodrug thereof; wherein n=0, 1 or 2; Q is O or NH; X is O or S; and R comprises an organic substituent group.

  一种碳酸酐酶IX（CA IX）抑制剂，包括一种一般化学式为：R—NH—CX—NH—（CH2）n—Ar-Q-SO2—NH2的化合物或其药用可接受的盐、衍生物或前药；其中n=0、1或2；Q为O或NH；X为O或S；R包括一个有机取代基。
• Some Phenylthiourea Derivatives and their Antituberculous Activity
  作者：L. Doub、L. M. Richardson、D. R. Herbst、M. L. Black、O. L. Stevenson、L. L. Bambas、G. P. Youmans、A. S. Youmans

  DOI：10.1021/ja01542a043

  日期：1958.5
• Two-component initiator system (amine-free) with very good storage stability and particular suitability for acid systems
  申请人：Utterodt Andreas

  公开号：US20070040151A1

  公开（公告）日：2007-02-22

  A two-component initiator system having accelerators for curing polymerizable materials comprising the following components: (a) a hydroperoxide compound containing one or more hydroperoxide groups that are bound to a tertiary carbon; (b) a thiourea derivative; and (c) as accelerator, a copper compound which is soluble in the preparation is preferably free of amine and is particularly suited for polymerizable dental compositions.
• Regioselective synthesis of novel 3-allyl-2-(substituted imino)-4-phenyl-3H-thiazole and 2,2′-(1,3-phenylene)bis(3-substituted-2-imino-4-phenyl-3H-thiazole) derivatives as antibacterial agents
  作者：Jafar Abbasi Shiran、Asieh Yahyazadeh、Manouchehr Mamaghani、Mehdi Rassa

  DOI：10.1016/j.molstruc.2013.02.003

  日期：2013.5

  Abstract Several novel 3-allyl-2-(substituted imino)-4-phenyl-3 H -thiazole derivatives were synthesized by the reaction of allyl-thioureas and 2-bromoacetophenone. We also report the synthesis of bis-allyl-3 H thiazoles using the reaction of various isothiocyanates and 1,3-phenylenediamine. The structures of all compounds were characterized by spectral and elemental analysis. Most of the synthesized

  摘要 通过烯丙基硫脲与2-溴苯乙酮反应合成了多种新型3-烯丙基-2-(取代亚氨基)-4-苯基-3H-噻唑衍生物。我们还报告了使用各种异硫氰酸酯和 1,3-苯二胺的反应合成双烯丙基-3 H 噻唑。所有化合物的结构均通过光谱和元素分析表征。大多数合成的化合物对沙门氏菌、藤黄微球菌、枯草芽孢杆菌和铜绿假单胞菌均表现出有效的抗菌活性。