morpholinyl-(12R)-hydroxy-(9Z)-octadecenamide | 1246776-24-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: morpholinyl-(12R)-hydroxy-(9Z)-octadecenamide
• 英文别名: 4-((R)-12-hydroxy-octadec-9c-enoyl)-morpholine；4-((R)-12-Hydroxy-octadec-9c-enoyl)-morpholin；(Z,12R)-12-hydroxy-1-morpholino-octadec-9-en-1-one；(Z,12R)-12-hydroxy-1-morpholin-4-yloctadec-9-en-1-one
• CAS: 1246776-24-8
• 化学式: C₂₂H₄₁NO₃
• 分子量: 367.572
• InChiKey: XTHBDBXHFQJGHN-ZDKIGPTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙烯腈 、 morpholinyl-(12R)-hydroxy-(9Z)-octadecenamide 在 1,4-二氧六环 、 苄基三甲基氢氧化铵 作用下， 生成 4-[12-(2-cyano-ethoxy)-octadec-9-enoyl]-morpholine
  参考文献：
  名称：

  Dupuy et al., Journal of the American Oil Chemists' Society, 1959, vol. 36, p. 659,660

  摘要：

  DOI：
• 作为产物：
  描述：

  蓖麻油酸 在 硫酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 morpholinyl-(12R)-hydroxy-(9Z)-octadecenamide
  参考文献：
  名称：

  Antiproliferative activity of synthetic fatty acid amides from renewable resources

  摘要：

  In the work, the in vitro antiproliferative activity of a series of synthetic fatty acid amides were investigated in seven cancer cell lines. The study revealed that most of the compounds showed antiproliferative activity against tested tumor cell lines, mainly on human glioma cells (U251) and human ovarian cancer cells with a multiple drug-resistant phenotype (NCI-ADR/RES). In addition, the fatty methyl benzylamide derived from ricinoleic acid (with the fatty acid obtained from castor oil, a renewable resource) showed a high selectivity with potent growth inhibition and cell death for the glioma cell line-the most aggressive CNS cancer. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.019

文献信息

• Synthesis of (<i>R</i>)- and (<i>S</i>)-Ricinoleic Acid Amides and Evaluation of Their Antimicrobial Activity
  作者：Sylwia Matysiak、Julia Zabielska、Józef Kula、Alina Kunicka-Styczyńska

  DOI：10.1002/aocs.12013

  日期：2018.1

  fatty acid amides derived from (R)‐ and (S)‐ricinoleic acid and 4 cyclic and acyclic amines were synthesized in a proecological solvent‐free process with yields ranging from 43 to 88%. All S‐configured compounds and both enantiomers of amide with 2‐amino‐2‐methyl‐1‐propanol were obtained and studied in terms of biological activity for the first time. The evaluation of antimicrobial activity of (R)‐ and

  在无保护性溶剂的过程中合成了一系列衍生自（R）和（S）蓖麻油酸的脂肪酸酰胺和4个环胺和无环胺，收率范围为43％至88％。首次获得了所有S构型的化合物以及酰胺与2-氨基-2-甲基-1-丙醇的两种对映异构体，并首次就生物学活性进行了研究。（R）和（S）-蓖麻油酸衍生物对代表革兰氏阴性和革兰氏阳性细菌，酵母和霉菌的13种不同微生物的抗菌活性评估显示出对革兰氏阳性细菌特别是黄球菌和微球菌的显着抑制活性。枯草芽孢杆菌，并针对选定的霉菌。乙醇胺和吡咯烷衍生的酰胺显示出最有希望的抗菌和抗霉菌潜力。蓖麻油酸和吡咯烷的衍生物对选择的两种霉菌，巴西曲霉和扩张青霉的活性最高。而且，R-构型的类似物对枯草芽孢杆菌最有效。蓖麻油酸与乙醇胺的酰胺对金黄色葡萄球菌显示出显着的潜力，这使它们与该细菌具有很高抗性的其余测试衍生物区分开来。
• Magne et al., Journal of the American Oil Chemists' Society, 1959, vol. 36, p. 635
  作者：Magne et al.

  DOI：——

  日期：——
• Dupuy et al., Journal of the American Oil Chemists' Society, 1958, vol. 35, p. 99,100
  作者：Dupuy et al.

  DOI：——

  日期：——
• Antiproliferative activity of synthetic fatty acid amides from renewable resources
  作者：Daiane S. dos Santos、Luciana A. Piovesan、Caroline R. Montes D’Oca、Carolina R. Lopes Hack、Tamara G.M. Treptow、Marieli O. Rodrigues、Débora B. Vendramini-Costa、Ana Lucia T.G. Ruiz、João Ernesto de Carvalho、Marcelo G. Montes D’Oca

  DOI：10.1016/j.bmc.2014.11.019

  日期：2015.1

  In the work, the in vitro antiproliferative activity of a series of synthetic fatty acid amides were investigated in seven cancer cell lines. The study revealed that most of the compounds showed antiproliferative activity against tested tumor cell lines, mainly on human glioma cells (U251) and human ovarian cancer cells with a multiple drug-resistant phenotype (NCI-ADR/RES). In addition, the fatty methyl benzylamide derived from ricinoleic acid (with the fatty acid obtained from castor oil, a renewable resource) showed a high selectivity with potent growth inhibition and cell death for the glioma cell line-the most aggressive CNS cancer. (C) 2014 Elsevier Ltd. All rights reserved.
• Dupuy et al., Journal of the American Oil Chemists' Society, 1959, vol. 36, p. 659,660
  作者：Dupuy et al.

  DOI：——

  日期：——