2-[(4-氰基苯甲酰基)氨基]乙酸 | 90290-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[(4-氰基苯甲酰基)氨基]乙酸
• 英文名称: 2-(4-cyanobenzamido)acetic acid
• 英文别名: 2-[(4-Cyanophenyl)formamido]acetic acid；2-[(4-cyanobenzoyl)amino]acetic acid
• CAS: 90290-83-8
• 化学式: C₁₀H₈N₂O₃
• mdl: MFCD09734720
• 分子量: 204.185
• InChiKey: QWURZCQBKCZXAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(4-氰基苯甲酰基)氨基]乙酸 在 TEA 、 sodium acetate 、 乙酸酐 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Highly selective conversion of N-aroyl-α-dehydronaphthylalaninamides into 3,4-dihydrobenzoquinolinone derivatives via photoinduced intermolecular electron transfer

  摘要：

  The irradiation of substituted (Z)-N-aroyl-alpha-dehydronaphthylalaninamides [(Z)-1] in methanol containing triethylamine (TEA) with Pyrex-filtered light was found to give 3,4-dihydrobenzoquinolinone derivatives (2) in high yields along with minor amounts of 4,5-dihydrooxazole derivatives (3). Analysis of the substituent effects on product composition revealed that both the photoreactivity of 1 and the selectivity of 2 are decreased with increasing electron-withdrawing ability of the substituent introduced at the para-position on the N-benzoyl benzene ring. From the analysis of the dependence of the quantum yield for the formation of 2 on the TEA concentration, it was found that back electron transfer occurs efficiently within an (E)-1 anion radical-TEA cation radical pair intermediate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.096
• 作为产物：
  描述：

  对氨基马尿酸 生成 2-[(4-氰基苯甲酰基)氨基]乙酸
  参考文献：
  名称：

  Bray et al., Biochemical Journal, 1951, vol. 48, p. 192,193

  摘要：

  DOI：

文献信息

• Method for binding albumin and means to be used in the method
  申请人：Amersham Pharmacia Biotech AB

  公开号：US05994507A1

  公开（公告）日：1999-11-30

  A method for binding albumin by contacting an aqueous liquid containing an albumin with an albumin-binding compound is selected from albumin-binding compounds containing the scaffold --CO--NH--C(.dbd.C--)--CO--, and conjugates that are capable of binding albumin and exhibiting the scaffold --CO--NH--C(.dbd.C--)--CO--.

  通过将含有白蛋白的水性液体与一种选择自含有支架--CO--NH--C(.dbd.C--)--CO--的白蛋白结合化合物接触的方法被选中，这些结合化合物能够结合白蛋白并展示支架--CO--NH--C(.dbd.C--)--CO--。
• Preferential formation of cis-4,5-dihydrooxazole derivatives via photoinduced electron transfer-initiated cyclization of N-acyl-α-dehydroarylalanine alkyl esters
  作者：Kei Maekawa、Norikazu Hishikawa、Kanji Kubo、Tetsutaro Igarashi、Tadamitsu Sakurai

  DOI：10.1016/j.tet.2007.08.089

  日期：2007.11

  aryl, and acyl substituent effects on the photoinduced electron transfer-initiated cyclization reaction of the title compounds (1) were investigated in polar solvents from mechanistic and synthetic points of view. The irradiation of (Z)-1 in methanol containing triethylamine (TEA) was found to quantitatively give cis- and trans-4,5-dihydrooxazole derivatives (cis-2 and trans-2). In addition to thermodynamic

  从机理和合成的观点出发，研究了极性溶剂中烷基，芳基和酰基取代基对标题化合物（1）的光诱导电子转移引发的环化反应的影响。的照射（ż） - 1在含有三乙胺（TEA）的甲醇被发现，定量得到顺式-和反式-4,5-二氢恶唑衍生物（顺式- 2和反式- 2）。除了热力学考虑为对发光强度的电子转移和荧光猝灭在TEA，酰基和芳基取代基效应的存在和光反应1证实了形成（E）-芳基亚甲基自由基阴离子和（E）-N-酰基自由基阴离子中间体的连续电子转移反应的参与。还证实了后者中间体的环化最终导致2。这样的发现为选择性的基础顺- 2大大随的烷基和芳基取代基的空间体积增加1，可以得出结论，在的环化双基中间，前体的这些取代基对氢移的空间位阻2负责该中间体的动力学控制的氢转移。产物组成分析表明，质子性极性溶剂甲醇具有氢键合溶剂化能力，是最适合检测的光环化反应的溶剂。
• Orthopalladation of GFP-Like Fluorophores Through C-H Bond Activation: Scope and Photophysical Properties
  作者：Sandra Collado、Alejandro Pueyo、Christine Baudequin、Laurent Bischoff、Ana Isabel Jiménez、Carlos Cativiela、Christophe Hoarau、Esteban P. Urriolabeitia

  DOI：10.1002/ejoc.201800966

  日期：2018.12.2

  C. H. and E. P. U. thank the European Cooperation in Science and Technology (COST) program under CA15106 grant: CH Activation in Organic Synthesis (CHAOS). A. I. J., C. C. and E. P. U. thank Ministerio de Economia y Competitividad MINECO (Spain, Project CTQ2013‐40855R) and Gobierno de Aragon‐FEDER (Spain, research group E19_17R: Aminoacidos y Peptidos) for financial support. This work has been partially

  CH 和 EPU 感谢 CA15106 资助下的欧洲科学技术合作 (COST) 计划：有机合成中的 CH 激活 (CHAOS)。AIJ、CC 和 EPU 感谢Ministryio de Economia y Competitividad MINECO（西班牙，CTQ2013-40855R 项目）和 Gobierno de Aragon-FEDER（西班牙，研究组 E19_17R：Aminoacidos y Peptidos）提供的资金支持。这项工作得到了鲁昂大学、鲁昂国家应用科学研究院 (INSA Rouen)、国家科学研究中心 (CNRS)、卓越实验室 (Labex) SynOrg 和诺曼底地区的部分支持。
• Discovery of a Necroptosis Inhibitor Improving Dopaminergic Neuronal Loss after MPTP Exposure in Mice
  作者：Sara R. Oliveira、Pedro A. Dionísio、Maria M. Gaspar、Maria B. T. Ferreira、Catarina A. B. Rodrigues、Rita G. Pereira、Mónica S. Estevão、Maria J. Perry、Rui Moreira、Carlos A. M. Afonso、Joana D. Amaral、Cecília M. P. Rodrigues

  DOI：10.3390/ijms22105289

  日期：——

  Parkinson’s disease (PD) is the second most common neurodegenerative disorder, mainly characterized by motor deficits correlated with progressive dopaminergic neuronal loss in the substantia nigra pars compacta (SN). Necroptosis is a caspase-independent form of regulated cell death mediated by the concerted action of receptor-interacting protein 3 (RIP3) and the pseudokinase mixed lineage domain-like protein (MLKL). It is also usually dependent on RIP1 kinase activity, influenced by further cellular clues. Importantly, necroptosis appears to be strongly linked to several neurodegenerative diseases, including PD. Here, we aimed at identifying novel chemical inhibitors of necroptosis in a PD-mimicking model, by conducting a two-step screening. Firstly, we phenotypically screened a library of 31 small molecules using a cellular model of necroptosis and, thereafter, the hit compound effect was validated in vivo in a sub-acute 1-methyl-1-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride (MPTP) PD-related mouse model. From the initial compounds, we identified one hit—Oxa12—that strongly inhibited necroptosis induced by the pan-caspase inhibitor zVAD-fmk in the BV2 murine microglia cell line. More importantly, mice exposed to MPTP and further treated with Oxa12 showed protection against MPTP-induced dopaminergic neuronal loss in the SN and striatum. In conclusion, we identified Oxa12 as a hit compound that represents a new chemotype to tackle necroptosis. Oxa12 displays in vivo effects, making this compound a drug candidate for further optimization to attenuate PD pathogenesis.

  帕金森病（PD）是第二常见的神经退行性疾病，主要特征是与黑质致密部（SN）中进行性多巴胺能神经元丧失相关的运动缺陷。坏死凋亡是一种受调控的细胞死亡形式，不依赖半胱氨酸蛋白酶的介导，由受体相互作用蛋白3（RIP3）和伪激酶混合谱系结构域类蛋白（MLKL）协同作用介导。通常还依赖于RIP1激酶活性，并受进一步细胞信号的影响。重要的是，坏死凋亡似乎与包括PD在内的几种神经退行性疾病密切相关。在这里，我们旨在通过进行两步筛选，在模拟PD的模型中鉴定新的坏死凋亡化学抑制剂。首先，我们使用细胞模型对包含31种小分子的化合物库进行表型筛选，然后验证击中化合物在亚急性1-甲基-1-4-苯基-1,2,3,6-四氢吡啶盐酸盐（MPTP）PD相关小鼠模型中的体内效果。从最初的化合物中，我们确定了一个击中物—Oxa12，它强烈抑制了BV2小鼠微胶质细胞系中由泛半胱氨酸蛋白酶抑制剂zVAD-fmk诱导的坏死凋亡。更重要的是，暴露于MPTP并进一步接受Oxa12治疗的小鼠显示出对MPTP诱导的SN和纹状体中多巴胺能神经元丧失的保护作用。总之，我们确定了Oxa12作为一个击中化合物，代表了一种新的化学类型来对抗坏死凋亡。Oxa12在体内显示出效果，使得这种化合物成为进一步优化以减轻PD发病机制的药物候选化合物。
• Synthesis and spectroscopic analysis of benzylidene imidazolone linked to P-porphyrins through axial ligand
  作者：Jin Matsumoto、Kyosuke Takemori、Jun Ishikawa、Yu Nabetani、Mamoru Fujitsuka、Tetsuro Majima、Masahide Yasuda

  DOI：10.1007/s00044-018-2255-0

  日期：2018.12

  Tetraphenylporphyrinatophosphorus(V) complexes (1) comprising two axially linked benzylidene imidazolone (Biz) moieties, which are chromophores of the green fluorescent protein, were prepared. In medical applications such as photodynamic therapy, the P-porphyrin part (Ptp) is expected to sensitize to generate singlet oxygen, whereas the Biz units act as fluorescent probes. The fluorescence spectra

  制备了包含两个轴向连接的亚苄基咪唑酮（Biz）部分的四苯基卟啉对磷（V）络合物（1），其为绿色荧光蛋白的发色团。在诸如光动力疗法的医学应用中，预计P-卟啉部分（Ptp）会敏化产生单线态氧，而Biz单位则充当荧光探针。在370 nm的Biz激发下分析1的荧光光谱。分别在460和610 nm处观察到由Biz和Ptp激发态引起的荧光。发生了由Ptp激发的单重态Biz的分子内猝灭，导致Biz发出的荧光弱。在Biz单位1中引入氰基提高了他们的荧光量子产率高达7.7×10 -4。在550 nm的Ptp激发下1的荧光光谱与不含Biz发色团的二甲氧基四苯基卟啉氯化磷的对-卟啉参考化合物的荧光光谱极为相似。在对卟啉的轴向位置引入Biz后，Ptp的理化参数保持不变。