1-cyclopropanecarbonyl-3-(p-methylphenyl)-thiourea

• 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-cyclopropanecarbonyl-3-(p-methylphenyl)-thiourea
• 英文别名: N-[(4-methylphenyl)carbamothioyl]cyclopropanecarboxamide
• 化学式: C₁₂H₁₄N₂OS
• 分子量: 234.322
• InChiKey: DZBGFAGUIRJAMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环丙烷羰基异硫氰酸酯 、 乙烷,三氯氟- 以 乙腈 为溶剂， 反应 1.5h， 生成 1-cyclopropanecarbonyl-3-(p-methylphenyl)-thiourea
  参考文献：
  名称：

  新型 N-环烷基羰基-N'-芳基-硫脲：合成、设计、抗真菌活性和基因毒性

  摘要：

  开发了一种新型N-环烷基羰基-N'-芳基硫脲的合成方法。它包括将等分子量的异硫氰酸铵和取代的苯胺依次添加到环烷基羰基氯中。产品的特性和纯度通过 LC/MS 光谱确认，其结构通过元素分析、IR 和 1H-NMR 光谱确认。标准微生物的初步抗菌筛选和分子对接允许选择几种结构进行抗真菌和遗传毒性研究。对 9 种化合物对 11 种植物病原真菌和三种疫霉属菌株的抗真菌潜力进行了体外筛选，结果表明，浓度为 50 μg/ml 的两种 N-（芳基氨基甲硫酰）环丙烷甲酰胺表现出与标准抗真菌剂“环丙康唑”相当的活性。

  DOI：

  10.1002/cbdv.202000212

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。
• One-pot and two-step synthesis of novel carbonylthioureas and dicarbonyldithioureas derivatives
  作者：Alireza Banaei、Jafar Abbasi Shiran、Afshin Saadat、Farnaz Fazlalizadeh Ardabili、Patrick McArdle

  DOI：10.1016/j.molstruc.2015.06.074

  日期：2015.11

  One-pot, two-step synthesis of several 1-cyclopropanecarbony1-3-(substituted phenyl)-thioureas and 1(phenylene-1,4-dione)-3,3'-(substituted phenyl)-dithioureas have been successfully prepared. The structures of the synthesized compounds were confirmed by elemental analysis, FT-IR spectroscopy and NMR. Also the crystal structure one of these compounds was determined by X-ray crystallography. All synthesized compounds were evaluated for antibacterial activity using Salmonella enterica (SE), Micrococcus luteus (ML), Bacillus subtilis (BS) and Pseudomonas aeruginosa (PS). (C) 2015 Elsevier B.V. All rights reserved.
• 1-Cycloalkanecarbonyl-substituted thioureas and thiosemicarbazides as effective dihydrofolate reductase inhibitors with antibacterial activity
  作者：O. V. Kholodniak、M. Tniguer、I. S. Nosulenko、A. O. Kinichenko、K. I. Kandybey、O. M. Antypenko、S. I. Kovalenko

  DOI：10.7124/bc.000a6f

  日期：2022.7.25
• Novel <i>N</i> ‐Cycloalkylcarbonyl‐ <i>N</i> ′‐arylthioureas: Synthesis, Design, Antifungal Activity and Gene Toxicity
  作者：Olena V. Kholodniak、Maksym S. Kazunin、Fatuma Meyer、Sergiy I. Kovalenko、Karl G. Steffens

  DOI：10.1002/cbdv.202000212

  日期：2020.7

  A synthesis method of novel N‐cycloalkylcarbonyl‐N′‐arylthioureas was developed. It consists of sequential addition of equimolecular amounts of ammonium isothiocyanate and substituted anilines to cycloalkylcarbonyl chlorides. The identity and purity of products were confirmed by LC/MS spectra, their structure by elemental analysis, IR and 1H‐NMR spectra. Preliminary antimicrobial screening for standard

  开发了一种新型N-环烷基羰基-N'-芳基硫脲的合成方法。它包括将等分子量的异硫氰酸铵和取代的苯胺依次添加到环烷基羰基氯中。产品的特性和纯度通过 LC/MS 光谱确认，其结构通过元素分析、IR 和 1H-NMR 光谱确认。标准微生物的初步抗菌筛选和分子对接允许选择几种结构进行抗真菌和遗传毒性研究。对 9 种化合物对 11 种植物病原真菌和三种疫霉属菌株的抗真菌潜力进行了体外筛选，结果表明，浓度为 50 μg/ml 的两种 N-（芳基氨基甲硫酰）环丙烷甲酰胺表现出与标准抗真菌剂“环丙康唑”相当的活性。