N-stearoyl-DL-phenylalanine | 133849-18-0

• 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: N-stearoyl-DL-phenylalanine
• 英文别名: N-stearoyl-phenylalanine；N-Stearoyl-phenylalanin；N-Octadecanoyl-D-phenylalanine；2-(octadecanoylamino)-3-phenylpropanoic acid
• CAS: 133849-18-0
• 化学式: C₂₇H₄₅NO₃
• 分子量: 431.659
• InChiKey: PHZQULSGYVCYNC-UHFFFAOYSA-N

物化性质

• 熔点：
  95.5 °C
• 沸点：
  600.5±48.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  31
• 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：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 1,4-二氧六环 、 sodium hydroxide 作用下， 生成 N-stearoyl-DL-phenylalanine
  参考文献：
  名称：

  Zeelen; Havinga, Recueil des Travaux Chimiques des Pays-Bas, 1958, vol. 77, p. 267,271

  摘要：

  DOI：

文献信息

• 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。
• STEAROYL AMINO ACID SALT AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：SHANGHAI JIAOTONG UNIVERSITY SCHOOL OF MEDICINE

  公开号：US20160326096A1

  公开（公告）日：2016-11-10

  A stearoyl amino acid salt having a structural formula of the general formula (I), wherein R 1 is H or an aromatic base capable of being substituted by one or more substituents, or a C 1-4 straight chain or an alkyl with a branched chain, the substituent being an alcoholic hydroxyl group or a phenolic hydroxyl group; and R 2 is a C 11-25 saturated or unsaturated aliphatic group. Also provided are methods of preparing the stearoyl amino acid salt, and methods of using the stearoyl amino acid salt. Compared to a prototype drug stearoyl amino acid, the stearoyl amino acid salt described herein has excellent physicochemical properties, good stability, high relative bioavailability, a strong drug effect and a high safety factor. It is thus expected to become a candidate for clinical treatment of neurodegenerative diseases and acute brain injury, and a clinical drug for weight loss, thus having broad application prospects.

  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。
• CHEMICAL UNCOUPLERS OF RESPIRATION AND METHODS OF USE THEREOF
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US20200317613A1

  公开（公告）日：2020-10-08

  Uncoupling of respiration is a well-recognized process that increases respiration and heat production in cells. Provided herein are chemical uncouplers of respiration that are compounds of Formula (I). Also provided are methods for preventing or treating metabolic disorders and modulating metabolic processes using compound of Formula (I).

  解耦呼吸是一个众所周知的过程，可以增加细胞的呼吸和产热。本文提供了化学解耦剂，这些解耦剂是化合物(I)的化合物。还提供了使用化合物(I)预防或治疗代谢性疾病和调节代谢过程的方法。
• Chemical uncouplers of respiration and methods of use thereof
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US11365177B2

  公开（公告）日：2022-06-21

  Uncoupling of respiration is a well-recognized process that increases respiration and heat production in cells. Provided herein are chemical uncouplers of respiration that are compounds of Formula (I). Also provided are methods for preventing or treating metabolic disorders and modulating metabolic processes using compound of Formula (I).

  呼吸解偶联是一个公认的过程，可增加细胞的呼吸和产热。本文提供的呼吸化学解偶联剂是式（I）化合物。还提供了使用式（I）化合物预防或治疗代谢紊乱和调节代谢过程的方法。
• AN ENZYME-CATALYZED PROCESS FOR PREPARING N-ACYL AMINO ACIDS AND N-ACYL AMINO ACID AMIDES
  申请人：NOVO NORDISK A/S

  公开号：EP0473700A1

  公开（公告）日：1992-03-11