hexadecyl 4-(3-hydroxyphenyl)-6-methyl-2-oxo-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: hexadecyl 4-(3-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: hexadecyl 4-(3-hydroxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₂₈H₄₄N₂O₄
• 分子量: 472.668
• InChiKey: GAECSBBAMXVWNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  34
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-十六烷醇 在 indium(III) chloride 、 氨基磺酸 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 hexadecyl 4-(3-hydroxyphenyl)-6-methyl-2-oxo-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

• Synthesis and antitumoral activity of novel analogues monastrol–fatty acids against glioma cells
  作者：Franciele S. De Oliveira、Patrick M. De Oliveira、Luana M. Farias、Rafael C. Brinkerhoff、Rui Carlos M. A. Sobrinho、Tamara M. Treptow、Caroline R. Montes D'Oca、Marcelo A. G. Marinho、Mariana A. Hort、Ana P. Horn、Dennis Russowsky、Marcelo G. Montes D'Oca

  DOI：10.1039/c8md00169c

  日期：——

  long-chain monastrol analogues against rat glioblastoma cells. The novel analogues C6-substituted monastrol and oxo-monastrol were synthesized via Biginelli multicomponent condensation of fatty β-ketoester in good yields using a simple approach catalyzed by nontoxic and free-metal sulfamic acid. Following synthesis, their in vitro antitumoral activities were investigated. Notably, all analogues tested were

  莫纳斯特罗尔是一种可渗透细胞的小分子，被认为是有丝分裂驱动蛋白Eg5的抑制剂。杂环脂肪酸衍生物是一类具有广泛生物活性的新型化合物。这项工作描述了一系列新的长链monastrol类似物对大鼠胶质母细胞瘤细胞体外抗肿瘤活性的比较研究。通过使用无毒和游离金属氨基磺酸催化的简单方法，通过脂肪β-酮酸酯的Biginelli多组分缩合反应，合成了新的类似物C6取代的Monastrol和oxo-monastrol 。合成后，在体外抗肿瘤活性进行了调查。值得注意的是，所有测试的类似物均对大鼠胶质母细胞瘤细胞具有活性。衍生自棕榈酸和硬脂酸脂肪酸链的类似物观察到了优异的活性。这些化合物是最有效的分子，显示出比莫那妥尔高13倍的效价，IC 50值分别为5.11和6.85μM 。这些化合物可以为更有效的抗肿瘤药物提供有希望的新的前导衍生物。
• 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。