1-(4-氯苯基)-3-丙-2-烯-1-基硫代脲 | 14255-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-氯苯基)-3-丙-2-烯-1-基硫代脲
• 英文名称: 1-allyl-4-(chlorophenyl) thiourea
• 英文别名: 1-allyl-3-(4-chlorophenyl)thiourea；1-allyl-3-parachlorophenyl-thiourea；N-allyl-N'-(4-chloro-phenyl)-thiourea；N-Allyl-N'-(4-chlor-phenyl)-thioharnstoff；N-Allyl-N'-(4-chlorophenyl)thiourea；1-(4-chlorophenyl)-3-prop-2-enylthiourea
• CAS: 14255-79-9
• 化学式: C₁₀H₁₁ClN₂S
• mdl: MFCD00090701
• 分子量: 226.73
• InChiKey: CIYHLGZJXIQQNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)-3-丙-2-烯-1-基硫代脲 在 phosphate buffer 作用下， 以 乙醇 为溶剂， 以83%的产率得到N-allyl-N'-chlorophenylurea
  参考文献：
  名称：

  Kamal, Ahmed; Rao, Maddamsetty V.; Rao, Adari B., Chemistry Letters, 1990, # 4, p. 655 - 656

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯胺 、 天然芥菜籽油 以 氯仿 为溶剂， 生成 1-(4-氯苯基)-3-丙-2-烯-1-基硫代脲
  参考文献：
  名称：

  通过胺，异硫氰酸盐和1,2-二氮杂-1,3-二烯的三组分顺序反应，杂环骨架多样性的有效方法

  摘要：

  通过高效的一锅三组分反应，将一组1,2-二氮杂-1,3-二烯（DDs），伯胺和异硫氰酸酯按不同的顺序添加，可以实现杂环骨架多样性实现。区分不同杂环核心形成的关键特征是N或S异源亲核试剂可用于提供第一步迈克尔加成步骤，从而提供区域选择性取代的2-硫代乙内酰脲或2-iminothiazolidinones。两个杂环的5位上的或enehydrazino侧链代表有价值的功能，可达到难以通过其他方法获得的新型5-羟基亚乙基衍生物。

  DOI：

  10.1021/jo2021949

文献信息

• Synthesis, characterization, and antibacterial activity of some thiazoles derived from allyl thioureas
  作者：R. Khare、J. Sharma、A. Sharma

  DOI：10.1134/s1070363216030312

  日期：2016.3

  Synthesis of thiazoles was carried out from allyl thioureas using different cyclizing agents such as hydrogen chloride gas and bromine. Synthesized compounds were characterized by IR, 1H and 13C NMR, mass spectrometry, and elemental analysis. The synthesized thiazoles were evaluated for their antibacterial activity against Gram postitive (Lactobacillus bulgaris and Streptococcus mitis) and Gram negative

  噻唑的合成是使用不同的环化剂，例如氯化氢气体和溴，从烯丙基硫脲进行的。通过IR，1 H和13 C NMR，质谱和元素分析对合成的化合物进行表征。评价合成的噻唑对革兰氏阳性（保加利亚乳杆菌和链球菌）和革兰阴性（耶尔森氏菌）的抗菌活性，以及​​对黑曲霉真菌的抑菌活性。
• 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。
• Dains; Roberts; Brewster, Journal of the American Chemical Society, 1916, vol. 38, p. 138
  作者：Dains、Roberts、Brewster

  DOI：——

  日期：——
• Novel Synthesis of Dihydrothiazoles from the Selenium‐Induced Cyclization of Allyl Thioureas
  作者：Hao Qian、Yanhong Lian

  DOI：10.1080/00397910701845761

  日期：2008.2.1

  The reaction of allylic thioureas with phenylselenenyl chloride affords 2-amino dihydrothiazoles in excellent yields by selenium-induced cyclization of allylic thioureas.
• KAMAL, AHMED;RAO, MADDAMSETTY V.;RAO, ADARI B., CHEM. LETT.,(1990) N, C. 655-656
  作者：KAMAL, AHMED、RAO, MADDAMSETTY V.、RAO, ADARI B.

  DOI：——

  日期：——