(Z)-octadec-9-enyl 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: (Z)-octadec-9-enyl 4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: [(Z)-octadec-9-enyl] 4-(3-hydroxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₃₀H₄₆N₂O₃S
• 分子量: 514.773
• InChiKey: PTAWRTXRCJLGSA-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  36
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  油醇 在 indium(III) chloride 、 氨基磺酸 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 (Z)-octadec-9-enyl 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

• 10.1039/d4ra03292f
  作者：Rios、Dea、dos Santos、Rampon、Guzman、Moore-Carrasco、D'Oca、Nachtigall、Santos、Rebolledo-Mira

  DOI：10.1039/d4ra03292f

  日期：——

  the synthesis and antitumoral activity of novel C5-substituted fatty-DHPMs against breast and gastric cancer cell lines. The compounds were synthesized via Biginelli multicomponent reaction from oleyl β-ketoester in good yields (40–72%) using a simple approach catalyzed by nontoxic and free-metal sulfamic acid. Among the compounds tested, the compound 10c, derived from 3-hydroxybenzaldehyde and urea,

  Monastrol 是二氢嘧啶酮/硫酮 (DHPM) 杂环家族中最著名的小化合物，是一种细胞渗透性分子，被认为是有丝分裂驱动蛋白 Eg5 的抑制剂，在肿瘤细胞中过度表达，是一个非常有前途的开发靶点抗癌新药。 DHPM 的亲脂特性已被证明在新分子的设计中至关重要。这项工作描述了新型 C5 取代的脂肪-DHPM 的合成及其对乳腺癌和胃癌细胞系的抗肿瘤活性。这些化合物是通过Biginelli 多组分反应从油基 β-酮酯合成的，采用无毒且游离金属氨基磺酸催化的简单方法，收率良好（40-72%）。在测试的化合物中，衍生自3-羟基苯甲醛和尿素的化合物10c对正常细胞(C2C12)表现出77%的细胞活力，并被选择用于针对肿瘤乳腺(MCF-7)和胃(AGS)细胞系进行评估。获得的结果显示乳腺癌细胞的 IC 50为 2.3 μM，证明该分子是最有效的分子，并使其成为未来体内实验有前途的化合物。
• 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.