methyl N-oleoyl-L-tyrosinate | 727425-00-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl N-oleoyl-L-tyrosinate
• 英文别名: methyl (2S)-3-(4-hydroxyphenyl)-2-[[(Z)-octadec-9-enoyl]amino]propanoate
• CAS: 727425-00-5
• 化学式: C₂₈H₄₅NO₄
• 分子量: 459.67
• InChiKey: RDFXMFXIBYNJCQ-SGAGCNABSA-N

物化性质

• 沸点：
  621.7±55.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  33
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl N-oleoyl-L-tyrosinate 在 四氮唑 、 sodium tetrahydroborate 、 N,N-二异丙基乙胺 、 calcium chloride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 Phosphoric acid di-tert-butyl ester (S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-((Z)-octadec-9-enoylamino)-propyl ester
  参考文献：
  名称：

  Initial structure–activity relationships of lysophosphatidic acid receptor antagonists: discovery of a high-affinity LPA1/LPA3 receptor antagonist

  摘要：

  A recently reported dual LPA(1)/LPA(3) receptor antagonist (VPC12249, 1) has been modified herein so as to optimize potency and selectivity at LPA receptors. Compounds containing variation in the acyl lipid chain and linker region have been synthesized and screened for activity at individual LPA receptors. LPA(1)-selective (14b) and LPA(3)-selective (10g,m) compounds of modest potency have been discovered. Additionally, 2-pyridyl derivative 10t exhibits a K-i value of 18 nM at the LPA(1) receptor and is significantly more potent than 1 at the LPA(3) receptor. This paper describes the synthetic methods, biological evaluation, and structure-activity relationships (SARs) of LPA receptor antagonists. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.076
• 作为产物：
  描述：

  L-酪氨酸 在 硫酸 、 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 二氯甲烷 为溶剂， 反应 16.33h， 生成 methyl N-oleoyl-L-tyrosinate
  参考文献：
  名称：

  糖和脂肪酸对N-脂肪酰基-L-酪氨酸糖苷配基生物活性的影响

  摘要：

  摘要在本研究中，一系列的脂肪酸为基础的（短期，中期和长期的不饱和链）糖基化的ñ -脂肪酸酰基大号-tyrosines和Ñ -lipoyl-大号-酪氨酸甲酯的合成和评价了它们的细胞毒性和抗菌活性。使用不同的化学试剂合成糖苷配基部分。使用路易斯酸\（\ hbox {BF} _ {3。} \ hbox {Et} _ {2} \ hbox {O} \）对糖苷配基部分与不同的碳水化合物进行糖基化。针对一组四个癌细胞系测试了所有合成的化合物。糖基化的N-脂肪酰基-L-酪氨酸对所有细胞系均具有中等活性\（\ hbox {IC} _ {50} \）值在\（15.6 {-} 45.6 \; {\ upmu} \ hbox {M} \）范围内。但是，油酸类似物（10a，10d）对MDA的\（\ hbox {IC} _ {50} \）值分别为15.6，\（17.6 \; {\ upmu} \ hbox {M} \）

  DOI：

  10.1007/s12039-017-1298-y

文献信息

• Synthesis, physicochemical, and biological activities of novel N-acyl tyrosine monomeric and Gemini surfactants in single and SDS/CTAB-mixed micellar system
  作者：Nausheen Joondan、Sabina Jhaumeer-Laulloo、Prakashanand Caumul、Matthew Akerman

  DOI：10.1002/poc.3675

  日期：2017.10

  Mixed micellar behavior of the N‐acyl Gemini surfactant with conventional cationic (CTAB) and anionic (SDS) surfactants in aqueous solution was studied. The negative value of the interaction parameter β12 observed for the N‐acyl Gemini in binary mixture with CTAB surfactant indicated a synergistic interaction within the mixed micellar system. However, the binary mixture with SDS displayed antagonistic

  合成了一系列具有不同链长（C 10 -C 18）和不饱和度的单链N-酰基酪氨酸表面活性剂，以及链长为C 12的N-酰基双子酪氨酸表面活性剂，结构为使用光谱分析确认。评估了链长和不饱和度对N-酰基酪氨酸表面活性剂的理化和抗菌性能的影响。C 12该衍生物在单链表面活性剂中显示出最佳的抗菌活性，并且油酰衍生物中双键的存在增强了其饱和类似物的抗菌活性。N-酰基双子叶表面活性剂在该系列中表现出最高的抗菌活性，并且比其单链类似物还显示出更大的胶束形成能力。研究了N-酰基双子叶表面活性剂与常规阳离子（CTAB）和阴离子（SDS）表面​​活性剂在水溶液中的混合胶束行为。相互作用参数的负值β 12在与CTAB表面活性剂的二元混合物中观察到的N-酰基双子座表明混合胶束体系内有协同作用。但是，具有SDS的二元混合物表现出拮抗作用。N-酰基双子叶表面活性剂与CTAB的二元混合物比SDS混合物具有更好的抗菌活性和发
• In Situ Synthesis of Gold and Silver Nanoparticles by Using Redox-Active Amphiphiles and Their Phase Transfer to Organic Solvents
  作者：Satyabrata Si、Enakshi Dinda、Tarun K. Mandal

  DOI：10.1002/chem.200701014

  日期：——

  An in situ reduction approach to synthesizing gold and silver nanoparticles by using a series of newly designed, redox-active amphiphiles at basic pH is described. These amphiphiles are the conjugates of a fatty acid (e.g., oleic acid, stearic acid, and lauric acid) and a redox-active amino acid (e.g., tryptophan or tyrosine). The amphiphile-coated nanoparticles are then efficiently transferred from

  描述了一种通过在碱性pH下使用一系列新设计的氧化还原活性两亲物来原位合成金和银纳米粒子的方法。这些两亲物是脂肪酸（例如油酸，硬脂酸和月桂酸）和氧化还原活性氨基酸（例如色氨酸或酪氨酸）的缀合物。然后，仅通过酸处理就可以将两亲涂层纳米颗粒从水中有效转移到不同的非极性有机介质（例如苯，甲苯，二甲苯，环己烷和己烷）中。通过紫外/可见光谱和透射电子显微镜监测相转移过程，结果表明，转移到有机介质后，平均粒径和粒径分布几乎保持不变。通过FTIR光谱和热重分析证实了两亲物对纳米颗粒表面的锚定。提出了一种机制来描述原位形成的胶态金纳米粒子和银纳米粒子的稳定性以及它们向有机溶剂中的相转移。两亲物的存在增加了胶体金纳米颗粒共轭物在有机溶剂中的热稳定性。
• Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials
  作者：Yazmin M. Osornio、Peter Uebelhart、Silvan Bosshard、Fabian Konrad、Jay S. Siegel、Ehud M. Landau

  DOI：10.1021/jo301659c

  日期：2012.12.7

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.
• [EN] NOVEL LYSOPHOSPHATIDIC ACID RECEPTOR SELECTIVE ANTAGONISTS<br/>[FR] NOUVEAUX ANTAGONISTES SELECTIFS DU RECEPTEUR DE L'ACIDE LYSOPHOSPHATIDIQUE
  申请人：UNIV VIRGINIA

  公开号：WO2005115150A3

  公开（公告）日：2006-05-04
• A novel series of 2-pyridyl-containing compounds as lysophosphatidic acid receptor antagonists: development of a nonhydrolyzable LPA3 receptor-selective antagonist
  作者：Brian H Heasley、Renata Jarosz、Karen M Carter、S Jenny Van、Kevin R Lynch、Timothy L Macdonald

  DOI：10.1016/j.bmcl.2004.05.023

  日期：2004.8

  A recently reported dual LPA(1)/LPA(3) receptor antagonist (1) has been modified so as to modulate the basicity, sterics, and dipole moment of the 2-pyridyl moiety. Additionally, the implications of installing nonhydrolyzable phosphate head group isosteres with regard to antagonist potency and selectivity at LPA receptors is described. This study has resulted in the development of the first nonhydrolyzable and presumably phosphatase-resistant LPA(3)-selective antagonist reported to date. (C) 2004 Elsevier Ltd. All rights reserved.