N-acetyltyrosine N-ethylamide | 49577-69-7

• 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: N-acetyltyrosine N-ethylamide
• 英文别名: 2-acetamido-N-ethyl-3-(4-hydroxyphenyl)propanamide
• CAS: 49577-69-7
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: IEOQUJJRIYTWBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-acetyltyrosine N-ethylamide 、 5-碘尿苷 以 水 为溶剂， 反应 7.0h， 以30%的产率得到2-Acetylamino-3-{3-[1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-4-hydroxy-phenyl}-N-ethyl-propionamide
  参考文献：
  名称：

  Mechanistic Studies of the 5-Iodouracil Chromophore Relevant to Its Use in Nucleoprotein Photo-Cross-Linking

  摘要：

  The photoreactivity of the 5-iodouracil chromophore was investigated toward understanding photo-cross-linking of nucleic acids bearing the chromophore to functionality in associated proteins. Irradiation of 5-iodouridine (TCT) in the presence of a 10-fold excess of N-acetyltyrosine N-ethylamide (1) at 308 nm with a XeCl excimer laser or at 325 nm with a HeCd laser yields uridine (U) and N-acetyl-m-(5-uridinyl)tyrosine N-ethylamide (2) in a 1:2 mole ratio. In the presence of N-acetylphenylalanine N-ethylamide, uridine and analogous ortho, meta, and para regioisomeric adducts (3o, 3m, and 3p) were formed in a similar U to adduct mole ratio. The primary photochemical process leading to products was established as carbon-iodine bond homolysis in the first excited singlet state from a deuterium labeling experiment, photoacoustic calorimetry, and quantum yield measurements. Photoreduction of IU in 2-propanol-d solvent gave U with no deuterium incorporation. Photoacoustic calorimetric measurements established that triplet benzophenone transferred energy to IU with a rate constant of 2 x 10(9) M(-1) s(-1). Further, the reaction of IU with 1 to form 2 was sensitized by benzophenone; however, comparison of quantum yields upon direct and sensitized excitation indicated that, at most, only a small portion of the reactions occurred via the triplet state. With direct excitation of IU, quantum yields as a function of the concentration of 1 showed that U and adduct 2 resulted from a common intermediate proposed to be the 5-uridinyl radical. Uridine formation was enhanced by the presence of hydrogen atom donors at the expense of formation of 2. Quantum yields were independent of excitation wavelength in the region 310-330 nm but not the reaction medium. The quantum yield of uridine formation but not adduct formation was approximately an order of magnitude higher in 90% acetonitrile-10% water than in pH 7 water. The results are discussed in terms of high-yield cross-linking of nucleic acids bearing the 5-iodouracil chromophore to associated proteins in light of cocrystal X-ray structural data.

  DOI：

  10.1021/ja9607852

文献信息

• 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：EP1876169A1

  公开（公告）日：2008-01-09

  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.

  本发明涉及作为环氧化酶抑制剂的通式（I）生物胺和氨基酸的新型苯基-N-酰基衍生物，该衍生物具有镇痛和抗炎特性，无副作用，特别是无溃疡性和促痉挛作用，并能增强其他镇痛药的效果，此外还具有抗缺氧、抗抑郁和抗帕金森病作用；以及生物胺的新型和已知苯基-N-酰基衍生物的制备工艺、药物组合物和包含通式（I）化合物的制剂及其用途和治疗方法。
• Systematic evolution of ligands by exponential enrichment: photoselection of nucleic acid ligands and solution selex
  申请人：Somalogic, Inc.

  公开号：EP1889910A2

  公开（公告）日：2008-02-20

  A method for identifying nucleic acid ligands to target molecules using the SELEX procedure wherein the candidate nucleic acids contain photoreactive groups and nucleic acid ligands identified thereby are claimed. The complexes of increased affinity nucleic acids and target molecules formed in the procedure are crosslinked by irradiation to facilitate separation from unbound nucleic acids. In other methods partitioning of high and low affinity nucleic acids is facilitated by primer extension steps as shown in the figure in which chain termination nucleotides, digestion resistant nucleotides or nucleotides that allow retention of the cDNA product on an affinity matrix are differentially incorporated into the cDNA products of either the high or low affinity nucleic acids and the cDNA products are treated accordingly to amplification, enzymatic or chemical digestion or by contact with an affinity matrix.

  一种利用 SELEX 程序鉴定核酸与靶分子配体的方法，其中候选核酸含有光活性基团，并要求由此鉴定核酸配体。在该程序中形成的亲和力增强的核酸和靶分子的复合物通过辐照交联，以便于与未结合的核酸分离。在其他方法中，高亲和力核酸和低亲和力核酸的分离是通过引物延伸步骤来促进的，如图所示，其中链终止核苷酸、抗消化核苷酸或可使 cDNA 产物保留在亲和基质上的核苷酸被不同地掺入高亲和力核酸或低亲和力核酸的 cDNA 产物中，cDNA 产物被相应地放大、酶解或化学消化或与亲和基质接触来处理。
• GADD45BETA TARGETING AGENTS
  申请人：Imperial Innovations Limited

  公开号：EP3178836A1

  公开（公告）日：2017-06-14

  Compounds based around tetrapeptide, tripeptide and dipeptide moeties and corresponding peptiod moeties. Related methods and pharmaceutical compositions for use in treatment of cancer, inflammatory diseases, and other disorders.

  以四肽、三肽和二肽分子及相应的肽基分子为基础的化合物。用于治疗癌症、炎症性疾病和其他疾病的相关方法和药物组合物。
• Mechanistic Studies Relevant to Bromouridine-Enhanced Nucleoprotein Photocrosslinking: Possible Involvement of an Excited Tyrosine Residue of the Protein
  作者：Christopher L. Norris、Kristen M. Meisenheimer、Tad H. Koch

  DOI：10.1111/j.1751-1097.1997.tb08546.x

  日期：1997.2

  AbstractThe results of mechanistic studies on formation of uridine (U) and N‐acetyl‐in‐(5‐uridinyl)tyrosine N‐ethylam‐ide (2) from irradiation of aqueous, pH 7 solutions of bromouridine (BrU) and N‐acetyltyrosine JV‐ethylamide (1) are reported. Solutions were irradiated with monochromatic laser emission at 266, 308 and 325 nm. Quantum yield measurements as a function of excitation wavelength suggest that both products result from excitation of the tyrosine derivative followed by electron transfer to BrU, possibly with intermediacy of the hydrated electron. The BrU radical anion ejects bromide to form the uri‐dinyl radical, which then abstracts a hydrogen atom from 1 or adds to the aromatic ring of 1. Formation of adduct 2 is a model for photocrosslinking of nucleic acids bearing the bromouracil chromophore to adjacent tyrosine residues of proteins in nucleoprotein complexes. The value of 325 nm excitation in photocrosslinking, where the tyrosine chromophore is more competitive for photons, was demonstrated with an RNA bound to the MS2 bacteriophage coat protein; more than a 60% increase in the yield of photocrosslinking relative to that obtained with 308 nm excitation was achieved.
• SYSTEMATIC EVOLUTION OF LIGANDS BY EXPONENTIAL ENRICHMENT: PHOTOSELECTION OF NUCLEIC ACID LIGANDS AND SOLUTION SELEX
  申请人：UNIVERSITY RESEARCH CORPORATION

  公开号：EP0736105A1

  公开（公告）日：1996-10-09