N-硬脂酰酪氨酸甲酯 | 122445-70-9

• 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
• 中文名称: N-硬脂酰酪氨酸甲酯
• 英文名称: N-stearoyl-L-tyrosine methyl ester
• 英文别名: N-stearoyl-L-tyrosine methyl ester；N-Stearoyl-L-tyrosin-methylester；N-Stearoyltyrosine methyl ester；methyl (2S)-3-(4-hydroxyphenyl)-2-(octadecanoylamino)propanoate
• CAS: 122445-70-9
• 化学式: C₂₈H₄₇NO₄
• 分子量: 461.685
• InChiKey: BXGLCPSPURNXQE-SANMLTNESA-N

物化性质

• 熔点：
  102.5-105 °C
• 沸点：
  612.4±45.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  33
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  N-硬脂酰酪氨酸甲酯 在 sodium hydroxide 作用下， 生成 N-硬脂酰酪氨酸
  参考文献：
  名称：

  Synthesis and evaluation of anti-tumor activities of N4 fatty acyl amino acid derivatives of 1-β-arabinofuranosylcytosine

  摘要：

  1-beta-D-Arabinofuranosylcytosine (Ara-C, Cytarabine) is one of the drugs used for acute nonlympbocytic leukemia (ANLL). However, the bioavailability of Ara-C is relatively low due to its low lipophilicity. In order to improve the lipophilicity and bioavailability of Ara-C, a series of N-4 derivatives of Ara-C, i.e., (fatty acid)-(amino acid)-Ara-C analogues, were prepared. The 15 derivatives synthesized were characterized by their melting points, optical rotations and partition coefficients. It was found that the Ara-C derivatives synthesized in this study were more lipophilic than Ara-C as determined by their partition coefficients. Their in vitro cytotoxicity and in vivo anti-tumor activity were determined and compared with that of Ara-C. It was found that the derivatives were more active than Ara-C in Hela cells, but not in HL-60 cells. The in vivo results showed that some of the derivatives were more effective than Ara-C in mice bearing S-180 tumor while others showed a decreased activity in comparison with Ara-C. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.02.028
• 作为产物：
  描述：

  L-酪氨酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 生成 N-硬脂酰酪氨酸甲酯
  参考文献：
  名称：

  STEAROYL AMINO ACID SALT AND PREPARATION METHOD AND APPLICATION THEREOF

  摘要：

  一种具有通式（I）的结构式的硬脂酰氨基酸盐，其中R1为H或能够被一个或多个取代基取代的芳香基，或为C1-4直链或带有支链的烷基，取代基为醇羟基或酚羟基；R2为C11-25饱和或不饱和脂肪族基团。还提供了制备硬脂酰氨基酸盐的方法，以及使用硬脂酰氨基酸盐的方法。与原型药物硬脂酰氨基酸相比，本文描述的硬脂酰氨基酸盐具有优异的理化性质，良好的稳定性，高相对生物利用度，强大的药效和高安全系数。因此，预计将成为神经退行性疾病和急性脑损伤的临床治疗候选药物，以及减重的临床药物，具有广泛的应用前景。

  公开号：

  US20160326096A1

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
• Synthesis and biological evaluation of phosphonate derivatives as autotaxin (ATX) inhibitors
  作者：Peng Cui、Jose L. Tomsig、William F. McCalmont、Sangderk Lee、Christopher J. Becker、Kevin R. Lynch、Timothy L. Macdonald

  DOI：10.1016/j.bmcl.2006.12.114

  日期：2007.3

  Autotaxin (ATX) is an autocrine motility factor that promotes cancer cell invasion, cell migration, and angiogenesis. ATX, originally discovered as a nucleotide phosphodiesterase, is known now to be responsible for the lysophospholipid-preferring phospholipase D activity in plasma. As such, it catalyzes the production of lysophosphatidic acid (LPA) from lysophophatidylcholine (LPC). ATX is thus an attractive drug target; small molecular inhibitors might be efficacious in slowing the spread of cancers. With this study we have generated a series of P-keto and P-hydroxy phosphonate derivatives of LPA, some of which are potent ATX inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.
• Zeelen; Havinga, Recueil des Travaux Chimiques des Pays-Bas, 1958, vol. 77, p. 267,271
  作者：Zeelen、Havinga

  DOI：——

  日期：——
• PHARMACEUTICAL COMPOSITION WITH GELLING PROPERTIES CONTAINING A TYROSINE DERIVATIVE
  申请人：ETHYPHARM

  公开号：EP2254550A1

  公开（公告）日：2010-12-01
• US8815944B2
  申请人：——

  公开号：US8815944B2

  公开（公告）日：2014-08-26