(S)-2-(nicotinamido)-3-phenylpropanoic acid | 17274-89-4

• 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-(nicotinamido)-3-phenylpropanoic acid
• 英文别名: nicotinoyl-L-phenylalanine；Nia-Phe-OH；N-nicotinoyl-L-phenylalanine；N-Nicotinoyl-L-phenylalanin；L-2-Nicotinoylamino-3-phenyl-propionsaeure；(2S)-3-phenyl-2-(pyridine-3-carbonylamino)propanoic acid
• CAS: 17274-89-4；36724-78-4；74204-45-8
• 化学式: C₁₅H₁₄N₂O₃
• mdl: MFCD00420584
• 分子量: 270.288
• InChiKey: KSZPRUJKMRILRZ-ZDUSSCGKSA-N

物化性质

• 沸点：
  561.3±45.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(nicotinamido)-3-phenylpropanoic acid 在 双氧水 、 溶剂黄146 作用下， 生成 N-(1-oxy-nicotinoyl)-L-phenylalanine
  参考文献：
  名称：

  The α-Chymotrypsin-catalyzed Hydrolysis of α-N-Benzoyl-β-(4-pyridyl-1-oxide)-L-alanine Methyl Ester and of α-N-(Nicotinyl-1-oxide)-L-phenylalanine Methyl Ester¹

  摘要：

  DOI：

  10.1021/ja01544a033
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 在 水 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-2-(nicotinamido)-3-phenylpropanoic acid
  参考文献：
  名称：

  A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics

  摘要：

  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.

  DOI：

  10.1055/s-0033-1339550

文献信息

• Synthesis and biological evaluation of novel hydrogen sulfide releasing nicotinic acid derivatives
  作者：Yinxing Sun、Yusuo Zhang、Yuyao Li、Jian Cheng、Shiyu Chen、Yunqi Xiao、Guizhen Ao

  DOI：10.1016/j.bmc.2016.08.060

  日期：2016.11

  Twelve novel hybrids of slowly releasing hydrogen sulfide donor ADT-OH combined with nicotinic acid were synthesized. All of their structures had been confirmed by 1H NMR, 13C NMR and MS spectra. The target compounds were evaluated for their neuroprotective effects on hippocampal neuron HT22 cells against glutamate-induced injury at the concentrations of 1–100 μM with MTT assay, and their toxicity

  合成了十二种新的缓释硫化氢供体ADT-OH与烟酸结合的杂种。所有结构均通过1 H NMR确证，131 H NMR和MS光谱。用MTT分析评估目标化合物对谷氨酸诱导的损伤对海马神经元HT22细胞的神经保护作用，并在100μM浓度对未经谷氨酰胺处理的HT22细胞的毒性。在永久性大脑中动脉闭塞（pMCAO）小鼠模型中，在缺血后3小时通过腹膜内注射进一步研究了该活性化合物对缺血性梗死体积的影响。结果表明，所有化合物在大多数实验浓度下均能显着保护HT22细胞免受谷氨酸诱导的损伤，并且在高浓度下对正常HT22细胞没有或只有很少的神经毒性。更重要的是，化合物A6在pMCAO模型中显着减少了梗塞体积。这些结果表明，化合物A6可能有望用于进一步评估对脑缺血损伤的干预。
• Synthesis and Biochemical Evaluation of Nicotinamide Derivatives as NADH Analogue Coenzymes in Ene Reductase
  作者：Natashya Falcone、Zhe She、Jebreil Syed、Alan Lough、Heinz‐Bernhard Kraatz

  DOI：10.1002/cbic.201800661

  日期：2019.3.15

  Nicotinamide and pyridine-containing conjugates have attracted a lot of attention in research as they have found use in a wide range of applications including as redox flow batteries and calcium channel blockers, in biocatalysis, and in metabolism. The interesting redox character of the compounds' pyridine/dihydropyridine system allows them to possess very similar characteristics to the natural chiral

  含烟酰胺和吡啶的共轭物已在研究中引起了广泛关注，因为它们发现了广泛的应用，包括用作氧化还原液流电池和钙通道阻滞剂，生物催化和代谢。化合物的吡啶/二氢吡啶体系有趣的氧化还原特性使它们具有与天然手性氧化还原剂NAD + / NADH极为相似的特性，甚至模仿了它们的功能。设计和合成具有类似氧化还原特性的NAD + / NADH模拟物引起了人们极大的兴趣。在这项研究中，设计，合成和表征了三种烟酰胺共轭物。通过X射线晶体学获得的分子结构获得了两种缀合物，从而提供了有关化合物键合和结构的更多详细信息。然后进一步评估这些化合物的生化特性，发现其中一种缀合物具有与天然NADH相似的功能和特性。在活性酶烯酸还原酶中评估了该化合物。像NADH一样，它可以帮助减少三个底物的C = C双键，甚至胜过天然辅酶。报告了动力学数据。
• Palladium-Catalyzed Aminocarbonylation in Solid-Phase Peptide Synthesis: A Method for Capping, Cyclization, and Isotope Labeling
  作者：Anna Skogh、Stig D. Friis、Troels Skrydstrup、Anja Sandström

  DOI：10.1021/acs.orglett.7b01068

  日期：2017.6.2

  A new synthetic approach for introducing N-capping groups onto peptides attached to a solid support, combining aminocarbonylation under mild conditions using a palladacycle precatalyst and solid-phase peptide synthesis, is reported. The use of a silacarboxylic acid as an in situ CO-releasing molecule allowed the reaction to be performed in a single vial. The method also enables versatile substitution

  报道了一种新的合成方法，该方法用于在结合有固相支持物的肽上引入N封端基团，并在适度条件下使用Palladacycle预催化剂和固相肽合成方法将氨基羰基化结合在一起。使用硅烷羧酸作为原位释放CO的分子使得反应可以在单个小瓶中进行。该方法还可以实现侧链的通用取代，侧链至侧链的环化以及修饰肽的选择性[ 13 C]酰基标记。
• Microwave-Assisted Formation of Peptide-Vitamin Conjugates
  作者：Claudia El-Nachef、Kiran Bajaj、Jacqueline Koblick、Alan R. Katritzky

  DOI：10.1002/ejoc.201200323

  日期：2012.8

  Amino acid and peptide conjugates with vitamin B3, H, E and D3 were synthesized by using microwave irradiation in good to satisfactory yields. In addition, a novel benzotriazole-activated biotin intermediate has been introduced, which could serve as an alternative biotinylation agent.

  通过使用微波辐射以良好到令人满意的产率合成了具有维生素 B3、H、E 和 D3 的氨基酸和肽缀合物。此外，还引入了一种新型苯并三唑活化的生物素中间体，可作为替代生物素化剂。
• Neue Lokalanästhetika
  作者：H. Rinderknecht

  DOI：10.1002/hlca.19590420430

  日期：——

  The mixed anhydride method has been used successfully in the synthesis of a series of pyridinecarboxamides. Hydrogenation of some of these products furnished piperidinecarboxarnides which were found to possess excellent local anesthetic properties and low toxicities.

  混合酸酐法已成功用于一系列吡啶甲酰胺的合成中。这些产品中的一些加氢提供了哌啶甲酰胺，发现它们具有出色的局部麻醉性能和低毒性。