methyl N-(abiet-8,11,13-trien-18-oyl)-L-phenylalaninate | 1449310-87-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl N-(abiet-8,11,13-trien-18-oyl)-L-phenylalaninate
• 英文别名: methyl (2S)-2-[[(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carbonyl]amino]-3-phenylpropanoate
• CAS: 1449310-87-5
• 化学式: C₃₀H₃₉NO₃
• 分子量: 461.645
• InChiKey: ABWOYWZNJHHWCD-FFDQPCAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-(abiet-8,11,13-trien-18-oyl)-L-phenylalaninate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以93%的产率得到N-(abiet-8,11,13-trien-18-oyl)-L-phenylalanine
  参考文献：
  名称：

  New derivatives of dehydroabietic acid target planktonic and biofilm bacteria in Staphylococcus aureus and effectively disrupt bacterial membrane integrity

  摘要：

  The combination of the dehydroabietic acid scaffold with different amino acids resulted in the discovery of a new class of hybrid compounds that targets both planktonic and biofilms bacteria in Staphylococcus aureus strains and are far more potent anti-biofilm agents than conventional antibiotics. Unlike dehydroabietic acid, these compounds can disrupt biofilms within a short time period and compromise the integrity of the bacterial membrane. Two of the compounds identified in our study are the most potent abietane-type anti-biofilm agents reported so far and display robust activity against pre-formed biofilms at concentrations only 3-6-fold higher than those required to inhibit biofilm formation. Their easy preparation based on proteolysis-resistant D- and unusual amino acids makes them useful chemical probes to gain a deeper understanding of bacterial biofilms and outstanding candidates for further development into new drugs to fight infections. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.038
• 作为产物：
  描述：

  脱氢松香酸 、 L-苯丙氨酸甲酯盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以39%的产率得到methyl N-(abiet-8,11,13-trien-18-oyl)-L-phenylalaninate
  参考文献：
  名称：

  abinetane型双萜类氨基酸共轭衍生物对人癌细胞的细胞毒活性。

  摘要：

  分别从松香酸（1）和脱氢松香酸（11）制备九种氨基酸共轭衍生物，分别为2-10和12-20，并评估了它们对四种人类癌细胞系（即白血病）的细胞毒性。 HL60），肺（A549），胃（AZ521）和乳房（SK-BR-3）。所有化合物均显示出针对HL60的细胞毒性，IC50值为2.3-37.3μM。另外，大多数衍生物对其他癌细胞系表现出中等的细胞毒性。在这些衍生物中，N- [18-氧杂芳基-8,11,13-三烯-18-基] -L-酪氨酸甲酯（19）对四种癌细胞具有较强的细胞毒活性，IC50值为2.3（HL60），7.1 （A549），3.9（AZ521）和8.1μM（SK-BR-3）。此外，所有衍生物均显示出对白血病细胞具有高选择性的细胞毒活性，

  DOI：

  10.1002/cbdv.201300043

文献信息

• Cytotoxic Activities of Amino Acid-Conjugate Derivatives of Abietane-Type Diterpenoids against Human Cancer Cell Lines
  作者：Motohiko Ukiya、Takuma Kawaguchi、Kenta Ishii、Eri Ogihara、Yosuke Tachi、Masahiro Kurita、Yoichiro Ezaki、Makoto Fukatsu、Yasunori Kushi、Toshihiro Akihisa

  DOI：10.1002/cbdv.201300043

  日期：2013.7

  the derivatives exhibited moderate cytotoxicities against the other cancer cell lines. Among the derivatives, methyl N-[18-oxoabieta-8,11,13-trien-18-yl]-L-tyrosinate (19) exhibited potent cytotoxic activities against four cancer cell lines with IC50 values of 2.3 (HL60), 7.1 (A549), 3.9 (AZ521), and 8.1 μM (SK-BR-3). Furthermore, all derivatives were shown to possess high selective cytotoxic activities

  分别从松香酸（1）和脱氢松香酸（11）制备九种氨基酸共轭衍生物，分别为2-10和12-20，并评估了它们对四种人类癌细胞系（即白血病）的细胞毒性。 HL60），肺（A549），胃（AZ521）和乳房（SK-BR-3）。所有化合物均显示出针对HL60的细胞毒性，IC50值为2.3-37.3μM。另外，大多数衍生物对其他癌细胞系表现出中等的细胞毒性。在这些衍生物中，N- [18-氧杂芳基-8,11,13-三烯-18-基] -L-酪氨酸甲酯（19）对四种癌细胞具有较强的细胞毒活性，IC50值为2.3（HL60），7.1 （A549），3.9（AZ521）和8.1μM（SK-BR-3）。此外，所有衍生物均显示出对白血病细胞具有高选择性的细胞毒活性，
• ABIETANE-TYPE DITERPENOIDS
  申请人：UNIVERSITY OF HELSINKI

  公开号：US20170247409A1

  公开（公告）日：2017-08-31

  The present invention relates to the field of wood rosin and resin acid derivatives and more particularly to abietane-type diterpenoids as well as different uses thereof. Furthermore, the present invention relates to methods of coating surfaces, preventing, reducing or inhibiting bacterial biofilm formation, and treating or preventing disorders caused by microbial growth and viability as well as bacterial colonization.
• New derivatives of dehydroabietic acid target planktonic and biofilm bacteria in Staphylococcus aureus and effectively disrupt bacterial membrane integrity
  作者：Suvi Manner、Mikko Vahermo、Malena E. Skogman、Sara Krogerus、Pia M. Vuorela、Jari Yli-Kauhaluoma、Adyary Fallarero、Vânia M. Moreira

  DOI：10.1016/j.ejmech.2015.07.038

  日期：2015.9

  The combination of the dehydroabietic acid scaffold with different amino acids resulted in the discovery of a new class of hybrid compounds that targets both planktonic and biofilms bacteria in Staphylococcus aureus strains and are far more potent anti-biofilm agents than conventional antibiotics. Unlike dehydroabietic acid, these compounds can disrupt biofilms within a short time period and compromise the integrity of the bacterial membrane. Two of the compounds identified in our study are the most potent abietane-type anti-biofilm agents reported so far and display robust activity against pre-formed biofilms at concentrations only 3-6-fold higher than those required to inhibit biofilm formation. Their easy preparation based on proteolysis-resistant D- and unusual amino acids makes them useful chemical probes to gain a deeper understanding of bacterial biofilms and outstanding candidates for further development into new drugs to fight infections. (C) 2015 Elsevier Masson SAS. All rights reserved.