3-phenyl-2-[(pyridine-4-carbonyl)amino]propionic acid methyl ester | 98874-13-6

• 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
• 英文名称: 3-phenyl-2-[(pyridine-4-carbonyl)amino]propionic acid methyl ester
• 英文别名: L-phenylalanine-N-(4-pyridylcarbonyl) methyl ester；methyl (2S)-3-phenyl-2-(pyridine-4-carbonylamino)propanoate
• CAS: 98874-13-6
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: JQHJGTIBSGEBHH-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-phenyl-2-[(pyridine-4-carbonyl)amino]propionic acid methyl ester 在 N-甲基吗啉 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 N-(N-4-pyridinylformyl-L-phenylalanyl)-4-nitro-L-phenylalanine methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of Matijing-Su derivatives as potent anti-HBV agents

  摘要：

  A series of Matijing-Su (MTS, N-(N-benzoyl-L-phenylalanyl)-O-acetyl-L-phenylalanol) derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity in 2.2.15 cells. The IC50 of compounds 14a (0.71 mu M), 13c (2.85 mu M), 13b (4.37 mu M), etc. and the selective index of 13g (161.01), 13c (90.45), 13a (85.09) etc. of the inhibition on the replication of HBV DNA were better than those of the positive control lamivudine (IC50: 82.42 mu M, SI: 41.59). Compounds 13o, 13p, and 16a also exhibited significant anti-HBV activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.001
• 作为产物：
  描述：

  异烟酸 、 L-苯丙氨酸甲酯盐酸盐 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3-phenyl-2-[(pyridine-4-carbonyl)amino]propionic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of Matijing-Su derivatives as potent anti-HBV agents

  摘要：

  A series of Matijing-Su (MTS, N-(N-benzoyl-L-phenylalanyl)-O-acetyl-L-phenylalanol) derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity in 2.2.15 cells. The IC50 of compounds 14a (0.71 mu M), 13c (2.85 mu M), 13b (4.37 mu M), etc. and the selective index of 13g (161.01), 13c (90.45), 13a (85.09) etc. of the inhibition on the replication of HBV DNA were better than those of the positive control lamivudine (IC50: 82.42 mu M, SI: 41.59). Compounds 13o, 13p, and 16a also exhibited significant anti-HBV activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.001

文献信息

• Photochemical tyrosine oxidation with a hydrogen-bonded proton acceptor by bidirectional proton-coupled electron transfer
  作者：Arturo A. Pizano、Jay L. Yang、Daniel G. Nocera

  DOI：10.1039/c2sc20113e

  日期：——

  appended to a rhenium(I) tricarbonyl 1,10-phenanthroline core to yield rhenium-amino acid complexes with tyrosine ([Re]-Y-OH) and phenylalanine ([Re]-F). The emission from the [Re] center is more significantly quenched for [Re]-Y-OH upon addition of base. Time-resolved studies establish that excited-state quenching occurs by a combination of static and dynamic mechanisms. The degree of quenching depends

  氨基酸自由基的产生和运输对于许多重要的生物学过程至关重要，小分子模型为这些生物学过程提供了宝贵的机理见解。吡啶基-氨基酸-甲基酯被附加到carbonyl羰基（I）三羰基1,10-菲咯啉核上，生成具有酪氨酸（[Re] -Y-OH）和苯丙氨酸（[Re] -F）的rh-氨基酸配合物。添加碱后，[Re] -Y-OH的[Re]中心发射更加明显地被淬灭。时间分辨的研究表明，激发态猝灭是通过静态和动态机制的结合而发生的。淬灭的程度取决于碱的强度，这与质子耦合电子转移（PCET）的淬灭机理相一致。对[Re] -Y-OH和[Re] -F的比较研究可以对双向PCET过程进行详细的机理分析。
• Photoinduced Intramolecular Tryptophan Oxidation and Excited-State Behavior of [Re(L-AA)(CO)₃(α-diimine)]⁺(L = Pyridine or Imidazole, AA = Tryptophan, Tyrosine, Phenylalanine)
  作者：Ana María Blanco-Rodríguez、Mike Towrie、J. Sýkora、Stanislav Záliš、Antonín Vlček

  DOI：10.1021/ic200252z

  日期：2011.7.4

  complexes [Re(L-AA)(CO)3(N,N)]+ (N,N = bpy, phen) containing an aromatic amino acid (AA), phenylalanine (Phe), tyrosine (Tyr), or tryptophan (Trp), linked to Re by a pyridine-amido or imidazole-amido ligand L have been synthesized and their excited-state properties investigated by nanosecond time-resolved IR (TRIR) and emission spectroscopy. Near-UV optical excitation populates a ReI(CO)3→N,N 3MLCT excited

  Re I羰基-二亚胺络合物[Re（L-AA）（CO）3（N，N）] +（N，N = bpy，phen）包含芳香族氨基酸（AA），苯丙氨酸（Phe），酪氨酸（Tyr合成了通过吡啶-酰胺基或咪唑-酰胺基配体L与Re连接的色氨酸（Trp）或色氨酸（Trp），并通过纳秒时间分辨IR（TRIR）和发射光谱研究了它们的激发态性质。近紫外光激发形成Re I（CO）3 →N，N 3 MLCT激发态* [Re II（L-AA）（CO）3（N，N •–）] +。在Phe和Tyr配合物的情况下，观察到衰变到基态（寿命为50-300 ns）是唯一的激发态失活过程，而含Trp的物质经历Trp（吲哚）→* Re II电子转移（ET ）产生电荷分离（CS）状态[Re I（L-Trp •+）（CO）3（N，N •–）] +。取决于L，N，N和溶剂，ET的寿命为8–40 ns。CS状态的特征是ν（CO）IR波段从其各自的基
• Bioconjugated Rhenium(I) Complexes with Amino Acid Derivatives: Synthesis, Photophysical Properties, and Cell Imaging Studies
  作者：Vanesa Fernández-Moreira、M. Lourdes Ortego、Catrin F. Williams、Michael P. Coogan、M. Dolores Villacampa、M. Concepción Gimeno

  DOI：10.1021/om300610j

  日期：2012.8.27

  nm) suggested the new bioconjugated rhenium complexes could be strong candidates for cell imaging applications. All species were taken up by MCF-7 cells and seemed to have a distinct localization pattern. However, while cells incubated with para derivatives had an anomalous cellular growth pattern and suffered from photobleaching upon irradiation, promoting cellular death, those incubated with the meta

  报道了一系列生物共轭的fac三羰基rh双亚胺配合物与氨基酸酯衍生物的合成及其在荧光显微镜细胞成像中的应用。合成了一系列间-和对-生物共轭的吡啶基衍生物，并通过与fac- [Re（bipy）（CO）3（CF 3 SO 3）配位，分析了它们的光物理性质）]。它们的长寿命（270–370 ns）和大的斯托克斯位移（> 140 nm）表明，新的生物共轭rh配合物可能是细胞成像应用的强力候选者。所有种类均被MCF-7细胞吸收，并且似乎具有独特的定位模式。然而，虽然与对位衍生物一起孵育的细胞具有异常的细胞生长模式，并且在照射时遭受光漂白，从而促进了细胞死亡，但与间位衍生物孵育的那些细胞却表现正常，没有光漂白，从而强调了配体设计的重要性。为了获得最佳结果是必要的：即细胞成像或光疗应用。
• Group 11 complexes with amino acid derivatives: Synthesis and antitumoral studies
  作者：Lourdes Ortego、Margarida Meireles、Cornelia Kasper、Antonio Laguna、M. Dolores Villacampa、M. Concepción Gimeno

  DOI：10.1016/j.jinorgbio.2015.12.018

  日期：2016.3

  and copper(I) complexes with modified amino acid esters and phosphine ligands have been prepared in order to test their cytotoxic activity. Two different phosphine fragments, PPh3 and PPh2py (py = pyridine), have been used. The amino acid esters have been modified by introducing an aromatic amine as pyridine that coordinates metal fragments through the nitrogen atom, giving complexes of the type [M(L)(PR3)]+

  为了测试它们的细胞毒性活性，已经制备了具有修饰的氨基酸酯和膦配体的金（I），金（III），银（I）和铜（I）配合物。使用了两个不同的膦片段PPh 3和PPh 2 py（py =吡啶）。通过引入芳香胺作为吡啶来修饰氨基酸酯，吡啶可通过氮原子配位金属片段，从而形成[M（L）（PR 3）] +或[AuCl 3（L）]类型的络合物（L = 升-缬氨酸- N-（4-吡啶基羰基）甲基酯（L1），升丙氨酸-N-（4-吡啶基羰基）甲基酯（L2），升-苯丙氨酸-N-（4-吡啶基羰基）甲酯）（L3）; M ＝ Au（I），Ag（I），Cu（I），PR 3  ＝ PPh 3，PPh 2 py）。在体外的金属配合物的细胞毒性活性对四名肿瘤人细胞系和一种肿瘤的小鼠细胞系测试。使用代谢活性测试（3-（4,5-二甲基噻唑-2-基）-2,5-二苯基溴化四氮唑，MTT），并将IC 50值与顺铂的IC 50值进行比较。几种复
• A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics
  作者：Zhengyan Fu、Yongmei Xie、Jiangpeng He、Aiping Tong、Yuquan Wei

  DOI：10.1055/s-0033-1339550

  日期：——

  We have developed a convenient and efficient method for the synthesis of dipeptidyl benzoxaboroles and their peptidomimetics. The novel dipeptidyl benzoxaboroles were obtained by the protecting-group-free coupling of 6-amino-1,3-dihydro-2,1-benzoxaborol-1-ol with various N-(arylcarbonyl)phenylalanines. Bioisosteric replacement of the terminal amide moiety of dipeptidyl benzoxaboroles by 1,3,4-oxadiazoles or 4H-3,1-benzothiazin-4-one provided their peptidomimetics with good molecular diversity. These transformations were based on the pluripotency of methyl (S)-2-isothiocyanato-3-phenylpropanoate and were highlighted by mild reaction conditions, high atom efficiency, and good to excellent isolated yields. This method is a valuable addition to the development of novel drug-like boronic acid molecules.