octadecyl 4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: octadecyl 4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: octadecyl 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₃₀H₄₈N₂O₃S
• 分子量: 516.789
• InChiKey: UJVIBIQYTHCPHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  36
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硬脂醇 在 indium(III) chloride 、 氨基磺酸 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 octadecyl 4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Novel hybrid DHPM-fatty acids: Synthesis and activity against glioma cell growth in vitro

  摘要：

  We described the first synthesis of fatty acid 3,4-dihydropyrimidinones (DHPM-fatty acids) using the Biginelli multicomponent reaction. Antiproliferative activity on two glioma cell lines (C6 rat and U-138-MG human) was also reported. The novel DHPM-fatty acids reduced glioma cell viability relative to temozolomide. Hybrid oxo-monastrol-palmitic acid was the most potent, reducing U-138-MG human cell viability by ca. 50% at 10 mu M. In addition, the DHPM-fatty acids showed a large safety range to neural cells, represented by the organotypic hippocampal culture. These results suggest that the increased lipophilicity of DHPM-fatty acids offer a promising approach to overcoming resistance to chemotherapy and may play an important role in the development of new antitumor drugs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.062

文献信息

• N-Alkylated Sulfamic Acid Derivatives as Organocatalyst in Multicomponent Synthesis of Fatty Dihydropyrimidinones
  作者：Carolina Hack、Larissa Porciuncula、Andressa Weber、Caroline D’Oca、Dennis Russowsky、Jaqueline Moura、Luiz Pinto、Marcelo D’Oca

  DOI：10.21577/0103-5053.20180112

  日期：——

  3-dicarbonyl compounds and long-chain 1,3-dicarbonyl derivatives, demonstrating catalytic efficiency. N-Alkylated sulfamic acid derived from benzylamine showed good results (ca. 80% yields). In addition, excellent results were obtained with organocatalysts based on sulfamic acid and thiourea (ca. 80-97% yields), demonstrating the catalytic efficiency of new derivatives of thiourea organosulfamic catalysts.

  在这项工作中，N-烷基化氨基磺酸衍生物被引入作为有希望的酸性有机催化剂，具有方便的酸度和易于合成。将来自不同含氮化合物（胺，壳聚糖，尿素和硫脲）的新型有机催化剂应用于多组分反应，以合成几种二氢嘧啶酮（DHPM）。使用经典的1,3-二羰基化合物和长链1,3-二羰基衍生物，所有测试过的有机催化剂均具有良好的DHPM收率，证明了催化效率。衍生自苄胺的N-烷基氨基磺酸显示出良好的结果（约80％的收率）。此外，使用基于氨基磺酸和硫脲的有机催化剂获得了优异的结果（约80-97％的收率），证明了硫脲有机氨基磺酸催化剂的新衍生物的催化效率。
• Novel hybrid DHPM-fatty acids: Synthesis and activity against glioma cell growth in vitro
  作者：Tamara G.M. Treptow、Fabrício Figueiró、Elisa H.F. Jandrey、Ana M.O. Battastini、Christianne G. Salbego、Juliana B. Hoppe、Priscila S. Taborda、Sabrina B. Rosa、Luciana A. Piovesan、Caroline Da R. Montes D'Oca、Dennis Russowsky、Marcelo G. Montes D'Oca

  DOI：10.1016/j.ejmech.2015.03.062

  日期：2015.5

  We described the first synthesis of fatty acid 3,4-dihydropyrimidinones (DHPM-fatty acids) using the Biginelli multicomponent reaction. Antiproliferative activity on two glioma cell lines (C6 rat and U-138-MG human) was also reported. The novel DHPM-fatty acids reduced glioma cell viability relative to temozolomide. Hybrid oxo-monastrol-palmitic acid was the most potent, reducing U-138-MG human cell viability by ca. 50% at 10 mu M. In addition, the DHPM-fatty acids showed a large safety range to neural cells, represented by the organotypic hippocampal culture. These results suggest that the increased lipophilicity of DHPM-fatty acids offer a promising approach to overcoming resistance to chemotherapy and may play an important role in the development of new antitumor drugs. (C) 2015 Elsevier Masson SAS. All rights reserved.