(S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid | 1075238-11-7

• 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-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid
• 英文别名: N-Acetyl-3-prenyl-L-tyrosine；(2S)-2-acetamido-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]propanoic acid
• CAS: 1075238-11-7
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: LJFWHSLCSLLNMJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl (2S)-2-acetamido-3-(4-prop-2-enoxyphenyl)propanoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 lithium hydroxide monohydrate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 29.0h， 生成 (S)-2-acetamido-3-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)propanoic acid
  参考文献：
  名称：

  SYNTHESIS OF (S)-2-ACETAMIDO-3-(4-HYDROXY-3-(3-METHYLBUT-2-ENYL) PHENYL) PROPANOIC ACID DERIVATIVES

  摘要：

  本发明公开了一种制备式(I)化合物或其药学上可接受的盐、溶剂化物、互变异构体或立体异构体的方法，例如化合物1和化合物2。该方法通过一种O-烯丙基化的基于酪氨酸的化合物，例如化合物3进行，最好包括[3,3]sigmatropic Claisen重排和烯烃交叉重聚反应。此外，本发明还公开了一种包含式(I)化合物、肿瘤坏死因子(TNF)相关的凋亡诱导配体(TRAIL)和药学上可接受的载体或赋形剂的制药组合物。

  公开号：

  US20170114004A1

文献信息

• Uncatalyzed sigmatropic rearrangement of tyrosine-based compounds
  申请人：King Fahd University of Petroleum and Minerals

  公开号：US10023527B2

  公开（公告）日：2018-07-17

  A method for producing a compound of formula (I) or a pharmaceutically acceptable salt, solvate, tautomer or stereoisomer, such as compound 1 and compound 2 is disclosed. The method proceeds through an O-allylated tyrosine-based compound, such as compound 3 and preferably comprises [3,3] sigmatropic Claisen rearrangement and olefin cross metathesis reactions. In addition, a pharmaceutical composition comprising a compound of formula (I) a tumor necrosis factor (TNF) related apoptosis inducing ligand (TRAIL) and a pharmaceutically acceptable carrier or excipient is disclosed.

  本发明公开了一种生产式（I）化合物或药学上可接受的盐、溶液剂、同分异构体或立体异构体（如化合物 1 和化合物 2）的方法。该方法通过 O-烯丙基化的酪氨酸基化合物（如化合物 3）进行，最好包括 [3,3] sigmatropic Claisen 重排和烯烃交叉偏析反应。此外，还公开了一种药物组合物，该组合物包含式（I）化合物、肿瘤坏死因子（TNF）相关凋亡诱导配体（TRAIL）和药学上可接受的载体或赋形剂。
• Method for making a prenyl group-substituted tyrosine compound
  申请人：King Fahd University of Petroleum and Minerals

  公开号：US10329245B2

  公开（公告）日：2019-06-25

  A method for producing a compound of formula (I) or a pharmaceutically acceptable salt, solvate, tautomer or stereoisomer, such as compound 1 and compound 2 is disclosed. The method proceeds through an O-allylated tyrosine-based compound, such as compound 3 and preferably comprises [3,3] sigmatropic Claisen rearrangement and olefin cross metathesis reactions. In addition, a pharmaceutical composition comprising a compound of formula (I) a tumor necrosis factor (TNF) related apoptosis inducing ligand (TRAIL) and a pharmaceutically acceptable carrier or excipient is disclosed.

  本发明公开了一种生产式（I）化合物或药学上可接受的盐、溶液剂、同分异构体或立体异构体（如化合物 1 和化合物 2）的方法。该方法通过 O-烯丙基化的酪氨酸基化合物（如化合物 3）进行，最好包括 [3,3] sigmatropic Claisen 重排和烯烃交叉偏析反应。此外，还公开了一种药物组合物，该组合物包含式（I）化合物、肿瘤坏死因子（TNF）相关凋亡诱导配体（TRAIL）和药学上可接受的载体或赋形剂。
• Enzymatic Basis of Ribosomal Peptide Prenylation in Cyanobacteria
  作者：John A. McIntosh、Mohamed S. Donia、Satish K. Nair、Eric W. Schmidt

  DOI：10.1021/ja205458h

  日期：2011.8.31

  The enzymatic basis of ribosomal peptide natural product prenylation has not been reported. Here, we characterize a prenyltransferase, LynF, from the TruF enzyme family. LynF is the first characterized representative of the TruF protein family, which is responsible for both reverse- and forward-O-prenylation of tyrosine, serine, and threonine in cyclic peptides known as cyanobactins. We show that LynF reverse O-prenylates tyrosine in macrocyclic peptides. Based upon these results, we propose that the TruF family prenylates mature cyclic peptides, from which the leader sequence and other enzyme recognition elements have been excised. This differs from the common model of ribosomal peptide biosynthesis, in which a leader sequence is required to direct post-translational modifications. In addition, we find that reverse O-prenylated tyrosine derivatives undergo a facile Claisen rearrangement at 'physiological' temperature in aqueous buffers, leading to forward C-prenylated products. Although the Claisen rearrangement route to natural products has been chemically anticipated for at least 40 years, it has not been demonstrated as a route to prenylated natural products. Here, we show that the Claisen rearrangement drives phenolic C-prenylation in at least one case, suggesting that this route should be reconsidered as a mechanism for the biosynthesis of prenylated phenolic compounds.
• Microwave-Assisted Claisen Rearrangement: Synthesis of Naturally Occurring TRAIL-Resistance-Overcoming Tyrosine Derivative
  作者：M. Mansha、Y. Abbas、N. Ullah

  DOI：10.1080/00397911.2014.974614

  日期：2015.3.4

  Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is a tumor necrosis factor (TNF) family ligand that binds on the death receptors, DR4 and DR5, activating apoptotic pathways selectively in cancer cells and thus has become a promising cancer therapeutic agent. Compound 1, isolated from Streptomyces sp. IFM 10937, has shown activity in overcoming TRAIL resistance in AGS cells. Synthesis of 1 has been accomplished from L-tyrosine in an overall high-yielding reaction sequence.
• UNCATALYZED SIGMATROPIC REARRANGEMENT OF TYROSINE-BASED COMPOUNDS
  申请人：King Fahd University of Petroleum and Minerals

  公开号：US20170217877A1

  公开（公告）日：2017-08-03

  A method for producing a compound of formula (I) or a pharmaceutically acceptable salt, solvate, tautomer or stereoisomer, such as compound 1 and compound 2 is disclosed. The method proceeds through an O-allylated tyrosine-based compound, such as compound 3 and preferably comprises [3,3] sigmatropic Claisen rearrangement and olefin cross metathesis reactions. In addition, a pharmaceutical composition comprising a compound of formula (I) a tumor necrosis factor (TNF) related apoptosis inducing ligand (TRAIL) and a pharmaceutically acceptable carrier or excipient is disclosed.