1-allyl-3-(1-naphthyl)-thiourea | 17073-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-allyl-3-(1-naphthyl)-thiourea
• 英文别名: N-α-naphthyl-N'-allylthiourea；1-allyl-3-naphthalen-1-yl-thiourea；N-allyl-N'-[1]naphthyl-thiourea；N-Allyl-N'-[1]naphthyl-thioharnstoff；N-Allyl-N'-α-naphthyl-thioharnstoff；1-Allyl-3-(naphthalen-1-yl)thiourea；1-naphthalen-1-yl-3-prop-2-enylthiourea
• CAS: 17073-29-9
• 化学式: C₁₄H₁₄N₂S
• 分子量: 242.345
• InChiKey: XKOOYYGMASECMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-allyl-3-(1-naphthyl)-thiourea 在 盐酸 作用下， 生成 (5-methyl-4,5-dihydro-thiazol-2-yl)-[1]naphthyl-amine
  参考文献：
  名称：

  Prager, Chemische Berichte, 1889, vol. 22, p. 2992

  摘要：

  DOI：
• 作为产物：
  描述：

  1-萘胺 、 天然芥菜籽油 以 乙醇 为溶剂， 反应 28.0h， 生成 1-allyl-3-(1-naphthyl)-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。
• Non-toxic corrosion-protection pigments based on manganese
  申请人：——

  公开号：US20040011252A1

  公开（公告）日：2004-01-22

  Corrosion-inhibiting pigments based on manganese are described that contain a trivalent or tetravalent manganese/valence stabilizer complex. An inorganic or organic material is used to stabilize the trivalent or tetravalent manganese ion to form a compound that is sparingly soluble, exhibits low solubility, or is insoluble in water, depending upon the intended usage. Specific stabilizers are chosen to control the release rate of trivalent or tetravalent manganese during exposure to water and to tailor the compatibility of the powder when used as a pigment in a chosen binder system. Stabilizers may also modify the processing and handling characteristics of the formed powders. Manganese/valence stabilizer combinations are chosen based on the well-founded principles of manganese coordination chemistry. Many manganese-valence stabilizer combinations are presented that can equal the performance of conventional hexavalent chromium or tetravalent lead systems. It is emphasized that this abstract is provided to comply with the rules requiring an abstract which will allow a searcher or other reader to quickly ascertain the subject matter of the technical disclosure. It is submitted with the understanding that it will not be used to interpret or limit the scope or meaning of the claims.

  以锰为基础的缓蚀颜料含有三价或四价锰/价稳定剂复合物。一种无机或有机材料可用于稳定三价或四价锰离子，从而形成一种可少量溶解、溶解度低或不溶于水的化合物，具体取决于预期用途。选择特定的稳定剂是为了控制三价锰或四价锰在遇水时的释放率，并调整粉末在所选粘合剂体系中用作颜料时的相容性。稳定剂还可以改变成型粉末的加工和处理特性。锰/价稳定剂组合的选择是基于锰配位化学的基本原理。文中介绍了许多锰价稳定剂组合，其性能与传统的六价铬或四价铅体系相当。需要强调的是，提供本摘要是为了符合要求提供摘要的规则，以便检索者或其他读者快速确定技术公开的主题。提交本摘要的前提是，本摘要不用于解释或限制权利要求的范围或含义。
• Non-toxic corrosion-protection pigments based on rare earth elements
  申请人：——

  公开号：US20040104377A1

  公开（公告）日：2004-06-03

  A corrosion-inhibiting pigment comprising a rare earth element and a valence stabilizer combinded to form a rare earth/valence stabilizer complex. The rare earth element is selected from cerium, terbium, praseodymium, or a combination thereof, and at least one rare earth element is in the tetravalent oxidation state. An inorganic or organic material is used to stabilize the tetravalent rare earth ion to form a compound that is sparingly soluble in water. Specific stabilizers are chosen to control the release rate of tetravalent cerium, terbium, or praseodymium during exposure to water and to tailor the compatibility of the powder when used as a pigment in a chosen binder system. Stabilizers may also modify the processing and handling characteristics of the formed powders. Many rare earth-valence stabilizer combinations are presented that can equal the performance of conventional hexavalent chromium systems.

  一种缓蚀颜料，由稀土元素和价态稳定剂结合形成稀土/价态稳定剂复合物。稀土元素选自铈、铽、镨或它们的组合，至少有一种稀土元素处于四价氧化态。使用无机或有机材料来稳定四价稀土离子，以形成稀溶于水的化合物。选择特定的稳定剂是为了控制四价铈、铽或镨在遇水时的释放率，并调整粉末在所选粘合剂体系中用作颜料时的相容性。稳定剂还可以改变成型粉末的加工和处理特性。本文介绍了许多稀土-价稳定剂组合，其性能可与传统的六价铬体系媲美。
• Zinin, Justus Liebigs Annalen der Chemie, 1852, vol. 84, p. 348
  作者：Zinin

  DOI：——

  日期：——
• Mudrovcic, Zeitschrift fur Wissenschaftliche Photographie, Photophysik und Photochemie, vol. 26, p. 172 Anm.2
  作者：Mudrovcic

  DOI：——

  日期：——