(S)-2-phenylacetylamino-3-(4-hydroxyphenyl)propionic acid | 54614-13-0

• 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: (S)-2-phenylacetylamino-3-(4-hydroxyphenyl)propionic acid
• 英文别名: N-phenylacetyl-L-tyrosine；N-Phenylacetyl-L-tyrosin；(2S)-3-(4-hydroxyphenyl)-2-[(2-phenylacetyl)amino]propanoic acid
• CAS: 54614-13-0
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: KJACRUBFUHSJLG-HNNXBMFYSA-N

物化性质

• 沸点：
  610.6±55.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (S)-2-phenylacetylamino-3-(4-hydroxyphenyl)propionic acid 、 glycylglycyl-L-phenylalanyl-L-leucine methyl ester 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， 生成
  参考文献：
  名称：

  An Effective and Safe Enkephalin Analog for Antinociception

  摘要：

  阿片类药物每年在全球造成69,000起过量死亡，并引起严重副作用。迫切需要更安全的镇痛药物。内源性阿片肽Leu-Enkephalin（Leu-ENK）在外周引入时由于稳定性差和有限的膜通透性而无效。我们开发了一个含有小的疏水修饰的Leu-ENK类似物的专注库。N-戊二酰基类似物KK-103显示出最高的与δ阿片受体的结合亲和力（相对于Leu-ENK的68%）和37小时的延长血浆半衰期。在小鼠热板模型中，皮下注射KK-103相对于Leu-ENK（14%MPE·h）显示出10倍改善的抗痉挛作用（142%MPE·h）。在福尔马林模型中，KK-103将舔舐和咬咬时间减少到相对于车组约50%。KK-103被证明是通过中枢神经系统中的阿片受体起作用。与吗啡相比，KK-103持续时间更长，不会引起呼吸抑制、身体依赖和耐受性，显示出作为安全有效镇痛药物的潜力。

  DOI：

  10.3390/pharmaceutics13070927
• 作为产物：
  描述：

  L-酪氨酸乙酯 、 苯乙酰氯 在 氯仿 作用下， 生成 (S)-2-phenylacetylamino-3-(4-hydroxyphenyl)propionic acid
  参考文献：
  名称：

  Isotopic composition characteristics and identification of immature and lowmature oils

  摘要：

  Isotopic composition characteristics and the significance of immature and low-mature oils are first systematically discussed. The carbon isotopes of the whole oil can be divided into two groups, one has delta C-13 main peak values ranging from -30 parts per thousand to -29 and the other from -27 parts per thousand to -25 parts per thousand, they are related to lacustrine and salt-lake facies or swamp facies, respectively. The carbon isotopic fractionation among different group components is relatively small, usually less than 2 parts per thousand and the biggest difference in fractionation often occurs between saturated and aromatic fractions. Their deltaD values vary between -180 parts per thousand, and -130 parts per thousand. The main peak of their deltaD values concentrates between -170 parts per thousand and -150 parts per thousand, suggesting a domination of lacustrine facies. However, the secondary peak ranges from -160 parts per thousand to -150 parts per thousand, showing a requent salinization of paleo-water bodies. The average delta C-13 values of the methane vary between -50 parts per thousand and -52 parts per thousand, about 10 parts per thousand lighter than those of mature oils. There is a relatively good correlationship between immature and low-mature oils and their source rocks in carbon isotopic compositions of group fractions and monohydrocarbons; moreover, compared with the source rocks of mature oils, that of immature oils is often relatively depleted in C-13, which is one of the characteristics of immature oils, differing from those of mature oils.

  DOI：

  10.1007/bf02901173

文献信息

• Alcaligenes faecalis penicillin G acylase-catalyzed enantioselective acylation of dl-phenylalanine and derivatives in aqueous medium
  作者：Xiangyu Gong、Erzheng Su、Pixiang Wang、Dongzhi Wei

  DOI：10.1016/j.tetlet.2011.08.056

  日期：2011.10

  A new strategy based on enantioselective acylation properties of relatively unknown penicillin G acylase from Alcaligenes faecalis has been developed for the production of pharmacologically interesting enantiomerically pure d-phenylalanine. In order to get high reaction rate and enantioselectivity, two key factors (pH and temperature) and eight different acyl donors were optimized, and the optimal

  已经开发了基于相对未知的粪便产青霉素的青霉素G酰基转移酶的对映选择性酰化性质的新策略，用于生产药理学上有趣的对映体纯的d-苯丙氨酸。为了获得高反应速率和对映选择性，对两个关键因素（pH和温度）和八个不同的酰基供体进行了优化，并使用苯乙酰胺作为酰基供体，在pH 10、35°C下进行了最佳的酰化反应。该对映选择性酰化方法还通过在对映纯中有效产生五种不同的对位取代的苯丙氨酸衍生物来说明。
• Peptidartige Aminosäurederivate
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0310918A2

  公开（公告）日：1989-04-12

  Verbindung der Formel worin R1, R2, R3, R4 und A die in Anspruch 1 angegebene Bedeutung haben, sowie pharmazeutisch verwendbare Salze davon besitzen Renin-inhibierende Eigenschaften und können demnach in Form pharmazeutischer Präparate als Arzneimittel verwendet werden. Sie können nach an sich bekannten Methoden hergestellt werden.

  式中的化合物 其中 R1、R2、R3、R4 和 A 具有权利要求 1 中给出的含义，其药用盐具有抑制肾素的特性，因此可以以药物制剂的形式用作药物。它们可以通过本身已知的方法制备。
• PHENYL-CONTAINING N-ACYL AMINE AND AMINOACID DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF, A PHARMACEUTICAL COMPOSITION AND THE USE THEREOF
  申请人：Obschestvo S Ogranichennoi Otvetstennostiyu "Pharmenterprises"

  公开号：EP1876169B1

  公开（公告）日：2015-12-30
• NOVEL N-AND C-TERMINAL SUBSTITUTED ANTAGONISTIC ANALOGS OF HUMAN GH-RH
  申请人：The University of Miami

  公开号：EP2288374B1

  公开（公告）日：2017-02-01
• Phenyl-containing n-acyl amine and aminoacid derivatives, methods for the production thereof, a pharmaceutical composition and the use thereof
  申请人：Nebolsin Vladimir Evgenievich

  公开号：US20090111874A1

  公开（公告）日：2009-04-30

  The present invention relates to novel phenyl-N-acyl derivatives of biogenic amines and amino acids of general formula (I) as cyclooxynease inhibitors, possessing analgetic and anti-inflammatory properties and devoid of side effects in particular ulcerogeneity and pro-spasmodic actions, as well as capability to potentiate effect of other analgetics, and possessing in addition antihypoxic, antidepressant and anti-Parkinsonistic action; as well as to the processes for the preparation novel and known phenyl-N-acyl derivatives of biogenic amines, to a pharmaceutical composition and to an agent comprising compounds of general formula (I) as well as to use thereof and a method of treating.