N-硬脂酰酪氨酸 | 57993-25-6

• 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
• 英文名称: L-stearoyltyrosine
• 英文别名: N-stearoyl-L-tyrosine；N-stearoyl tyrosine；N-Stearoyl-L-tyrosin；N-Stearoyltyrosine；(2S)-3-(4-hydroxyphenyl)-2-(octadecanoylamino)propanoic acid
• CAS: 57993-25-6
• 化学式: C₂₇H₄₅NO₄
• 分子量: 447.659
• InChiKey: YKWCFTGLODSOSB-VWLOTQADSA-N

物化性质

• 熔点：
  134.5-138 °C
• 沸点：
  639.9±50.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  32
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-硬脂酰酪氨酸 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以95.6%的产率得到N-stearoyl tyrosine potassium salt
  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
• 作为产物：
  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

文献信息

• Synthetic libraries of tyrosine-derived bacterial metabolites
  作者：Savvas N. Georgiades、Jon Clardy

  DOI：10.1016/j.bmcl.2007.10.058

  日期：2008.5

  The preparation of a collection of 131 small molecules, reminiscent of families of long chain N-acyl tyrosines, enamides and enol esters that have been isolated from heterologous expression of environmental DNA (eDNA) in Escherichia coli, is reported. The synthetic libraries of N-acyl tyrosines and their 3-keto counterparts were prepared via solid-phase routes, whereas the enamides and enol esters

  据报道，制备了 131 个小分子的集合，让人联想到长链 N-酰基酪氨酸、烯酰胺和烯醇酯家族，这些分子是从大肠杆菌环境 DNA (eDNA) 的异源表达中分离出来的。N-酰基酪氨酸及其3-酮对应物的合成库是通过固相途径制备的，而烯酰胺和烯醇酯是在溶液相中合成的。
• Synthesis of Lipoamino Acids and Their Activity against Cerebral Ischemic Injury
  作者：Li-Yun Yao、Qi Lin、Yin-Yao Niu、Ke-Min Deng、Jian-Hua Zhang、Yang Lu

  DOI：10.3390/molecules14104051

  日期：——

  A series of lipoamino acids were synthesized and their neuroprotective effect against brain ischemia induced by oxygen-glucose deprivation (OGD) on rat cerebral slices was evaluated. Among these compounds, N-stearoyl-L-tyrosine (4), N-stearoyl-L-serine (5) and N-stearoyl-L-threonine (6) exhibited good neuroprotective activity. We found that the neuroprotective activity of lipoamino acids depended on the acyl group, the presence of a free carboxylic function and a free hydroxyl group at the branched chain of the amino acids. The results also showed that 5 was the most active compound, protecting rat brain slices against OGD as well as hydrogen peroxide (H2O2) insult at the range of 1–10 M.

  一系列脂氨基酸被合成，并评估了它们对大鼠脑片由氧葡萄糖剥夺（OGD）诱导的脑缺血的神经保护作用。在这些化合物中，N-硬脂酰基-L-酪氨酸（4）、N-硬脂酰基-L-丝氨酸（5）和N-硬脂酰基-L-苏氨酸（6）表现出了良好的神经保护活性。我们发现，脂氨基酸的神经保护活性依赖于酰基团、氨基酸支链上自由羧基和自由羟基的存在。结果还显示，5是最活跃的化合物，在1-10 M的范围内保护大鼠脑片免受OGD和过氧化氢（H2O2）的损伤。
• Liposome delivery of compositions to enhance tanning and repair UV damage
  申请人：CALIFORNIA SUNCARE INC.

  公开号：EP0707844A2

  公开（公告）日：1996-04-24

  The present invention concerns the delivery in carrier liposomes of novel combinations of two or more active ingredients designed to enhance tanning and ameliorate damage to skin and DNA caused by UV radiation.

  本发明涉及在载体脂质体中输送两种或两种以上活性成分的新型组合，旨在增强美黑效果并改善紫外线辐射对皮肤和 DNA 造成的损伤。
• Antigen-adjuvant coupling reagents and methods of use
  申请人：Massachusetts Institute of Technology

  公开号：US11224648B2

  公开（公告）日：2022-01-18

  The present disclosure relates to compositions and methods for coupling an antigen to an adjuvant, immunogenic compositions and vaccines. The methods of the invention can be used to increase an immune response, or to treat cancer or an infectious disease.

  本公开涉及将抗原与佐剂、免疫原性组合物和疫苗偶联的组合物和方法。本发明的方法可用于增加免疫反应，或治疗癌症或传染病。
• Tanning preparation for the skin
  申请人：DIJA ZEIST B.V.

  公开号：US20030118527A1

  公开（公告）日：2003-06-26

  The invention relates to a tanning preparation for the skin comprising at least one tyrosine derivative of formula 1, where R<1>=—H, —(CH2)x-CH3, x being an integer from 1 to 20, R<2>=CH3CO—, CH3-(CH2)yCO—, y being an integer from 1 to 20, and an activator consisting of an aliphatic polyol having at least 10 C atoms in the molecule. The aliphatic polyol preferably consists of a hexadecanetriol, in particular phytantriol. Expediently, the tanning preparation is a gel, lotion, cream, foam, spray or emulsion. The invention further relates to a controlled release tanning preparation for the skin

  本发明涉及一种皮肤鞣制制剂，它包含至少一种式 1 的酪氨酸衍生物，其中 R=-H, -(CH2)x-CH3, x 是 1 到 20 的整数，R=CH3CO-, CH3-(CH2)yCO-, y 是 1 到 20 的整数，以及由分子中至少有 10 个 C 原子的脂肪族多元醇组成的活化剂。脂肪族多元醇最好是十六烷三醇，特别是植烷三醇。美黑制剂最好是凝胶、乳液、膏霜、泡沫、喷雾或乳液。本发明还涉及一种用于皮肤的控释美黑制剂