2-amino-N-(2-fluorophenyl) acetamide

• 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: 2-amino-N-(2-fluorophenyl) acetamide
• 英文别名: N-(2-fluorophenyl)glycinamide；2-amino-N-(2-fluorophenyl)acetamide
• 化学式: C₈H₉FN₂O
• mdl: MFCD09724242
• 分子量: 168.171
• InChiKey: FTIAWEJHCFHJJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-N-(2-fluorophenyl) acetamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium sulfate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (S)-2-(benzylideneamino)-2-(2-fluorophenyl)acetamide
  参考文献：
  名称：

  Isotopically Directed Symmetry Breaking and Enantioenrichment in Attrition-Enhanced Deracemization

  摘要：

  The evolution of homochirality via attrition-enhanced deracemization (AED) of enantiomorphic solids is carried out using molecules that differ only in the isotopic composition of a phenyl group positioned remote from the chiral center. Enantioenrichment consistently favors the enantiomorph containing a deuterated phenyl group over the protio or C-13 version, and the protio version is consistently favored over the C-13 version. While these isotopic compounds exhibit identical crystal structures and solubilities, the trend in deracemization correlates with melting points. Understanding the origin of this isotope bias provides fundamental clues about overcoming stochastic behavior to direct the stereochemical outcome in attrition-enhanced deracemization processes. The energy required for breaking symmetry with chiral bias is compared for this near-equilibrium AED process and the far-from-equilibrium Soai autocatalytic reaction. Implications for the origin of biological homochirality are discussed.

  DOI：

  10.1021/jacs.9b11422
• 作为产物：
  描述：

  2-氯-N-(2-氟苯基)乙酰胺 在 ammonium hydroxide 作用下， 反应 6.0h， 以60%的产率得到2-amino-N-(2-fluorophenyl) acetamide
  参考文献：
  名称：

  用于阿尔茨海默氏病治疗的新型自然启发多功能分子的设计，合成和生物学评估。

  摘要：

  为了克服克服与天然产物有关的阿尔茨海默氏病管理的局限性并开发体内活性多功能胆碱能抑制剂的总体目标，我们着手开发阿魏酸类似物。进行了系统的SAR研究，以改善LogP值较低的类似物对阿魏酸对胆碱酯酶的抑制作用。酶抑制和动力学研究确定化合物7a为具有优先乙酰胆碱酯酶抑制作用的先导分子（AChE IC50 = 5.74±0.13μM; BChE IC50 = 14.05±0.10μM）与母体阿魏酸（20μM时AChE和BChE的抑制％ ，分别为15.19±0.59和19.73±0.91）。分子对接和动力学研究表明7a非常适合AChE和BChE的活性位点，与AChE中的关键残基Asp74，Trp286和Tyr337以及BChE中的Tyr128，Trp231，Leu286，Ala328，Phe329和Tyr341形成稳定而强的相互作用。在DPPH分析中发现化合物7a是有效的抗氧化剂（IC50 = 57

  DOI：

  10.1016/j.ejmech.2020.112257

文献信息

• Design, synthesis and biological evaluation of novel naturally-inspired multifunctional molecules for the management of Alzheimer’s disease
  作者：Yash Pal Singh、Gullanki Naga Venkata Charan Tej、Amruta Pandey、Khushbu Priya、Pankaj Pandey、Gauri Shankar、Prasanta Kumar Nayak、Geeta Rai、Amar G. Chittiboyina、Robert J. Doerksen、Swati Vishwakarma、Gyan Modi

  DOI：10.1016/j.ejmech.2020.112257

  日期：2020.7

  the management of Alzheimer's disease and to develop in-vivo active multifunctional cholinergic inhibitors, we embarked on the development of ferulic acid analogs. A systematic SAR study to improve upon the cholinesterase inhibition of ferulic acid with analogs that also had lower logP was carried out. Enzyme inhibition and kinetic studies identified compound 7a as a lead molecule with preferential

  为了克服克服与天然产物有关的阿尔茨海默氏病管理的局限性并开发体内活性多功能胆碱能抑制剂的总体目标，我们着手开发阿魏酸类似物。进行了系统的SAR研究，以改善LogP值较低的类似物对阿魏酸对胆碱酯酶的抑制作用。酶抑制和动力学研究确定化合物7a为具有优先乙酰胆碱酯酶抑制作用的先导分子（AChE IC50 = 5.74±0.13μM; BChE IC50 = 14.05±0.10μM）与母体阿魏酸（20μM时AChE和BChE的抑制％ ，分别为15.19±0.59和19.73±0.91）。分子对接和动力学研究表明7a非常适合AChE和BChE的活性位点，与AChE中的关键残基Asp74，Trp286和Tyr337以及BChE中的Tyr128，Trp231，Leu286，Ala328，Phe329和Tyr341形成稳定而强的相互作用。在DPPH分析中发现化合物7a是有效的抗氧化剂（IC50 = 57
• Discovery of aromatic 2-(3-(methylcarbamoyl) guanidino)-N-aylacetamides as highly potent chitinase inhibitors
  作者：Zhixiang Zhao、Fang Li、Wei Chen、Qing Yang、Huizhe Lu、Jianjun Zhang

  DOI：10.1016/j.bmc.2023.117172

  日期：2023.2

  Chitinases are important glycoside hydrolases that are closely related to bacterial pathogenesis, fungal cell wall remodelling, and insect moulting. Consequently, chitinases have become attractive targets for therapeutic drugs and pesticides. In this study, we designed and synthesised a series of novel chitinase inhibitors based on the N-methylcarbamoylguanidinyl group of the natural product argifin

  几丁质酶是重要的糖苷水解酶，与细菌发病机制、真菌细胞壁重塑和昆虫蜕皮密切相关。因此，几丁质酶已成为治疗药物和杀虫剂的有吸引力的目标。在本研究中，我们基于天然产物argifin的N-甲基氨基甲酰基胍基设计并合成了一系列新型几丁质酶抑制剂。活性最强的化合物8h对 I 组几丁质酶Hs Chit1、Sm ChiB 和Of Chi-h 表现出强烈的抑制活性，IC 50值分别为 0.19 µM、4.2 nM 和 25 nM。结合模式研究表明化合物8h在几丁质酶的 +1 或 +2 亚位点形成 π-π 堆积/疏水相互作用。此外，在药效团N-甲基氨基甲酰基胍基和 -1 亚位点的关键残基之间形成关键氢键网。总之，这项研究的结果为使用平面结构和N-甲基氨基甲酰基胍基的组合开发有效的小分子几丁质酶抑制剂提供了新的见解。
• Design, synthesis and anti-osteosarcoma activity study of novel pyrido[2,3-d]pyrimidine derivatives by inhibiting DKK1-Wnt/β-catenin pathway
  作者：Yanni Shen、Qian Xie、Yiling Wang、Jianhui Liang、Cuilu Jiang、Xiaoping Liu、Yan Wang、Chun Hu

  DOI：10.1016/j.bioorg.2023.106848

  日期：2023.12

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• Isotopically Directed Symmetry Breaking and Enantioenrichment in Attrition-Enhanced Deracemization
  作者：James I. Murray、Jacob N. Sanders、Paul F. Richardson、K. N. Houk、Donna G. Blackmond

  DOI：10.1021/jacs.9b11422

  日期：2020.2.26

  The evolution of homochirality via attrition-enhanced deracemization (AED) of enantiomorphic solids is carried out using molecules that differ only in the isotopic composition of a phenyl group positioned remote from the chiral center. Enantioenrichment consistently favors the enantiomorph containing a deuterated phenyl group over the protio or C-13 version, and the protio version is consistently favored over the C-13 version. While these isotopic compounds exhibit identical crystal structures and solubilities, the trend in deracemization correlates with melting points. Understanding the origin of this isotope bias provides fundamental clues about overcoming stochastic behavior to direct the stereochemical outcome in attrition-enhanced deracemization processes. The energy required for breaking symmetry with chiral bias is compared for this near-equilibrium AED process and the far-from-equilibrium Soai autocatalytic reaction. Implications for the origin of biological homochirality are discussed.
• Extraction, isolation, synthesis, and biological evaluation of novel piperic acid derivatives for the treatment of Alzheimer’s disease
  作者：Jitendra Kumar、Gauri Shankar、Sunil Kumar、Jobin Thomas、Neha Singh、Saripella Srikrishna、Jitendra Satija、Sairam Krishnamurthy、Gyan Modi、Sunil Kumar Mishra

  DOI：10.1007/s11030-023-10667-x

  日期：——

  inhibition and its kinetic data suggested 6j as the lead molecule (AChE IC50 = 2.13 ± 0.015 µM, BChE = 28.19 ± 0.20%), in comparison to PA (AChE = 7.14 ± 0.98%) which was further selected for various biological studies in AD models. 6j, exhibited interaction with the peripheral anionic site of AChE, BBB permeability (Pe = 7.98), and antioxidant property (% radical scavenging activity = 35.41 ± 1.09, 2.43 ± 1

   抽象的 在本文中，我们开发了一系列胡椒酸（ PA ）类似物，旨在克服天然产品在治疗阿尔茨海默病（AD）方面的局限性。进行了全面的 SAR 研究以增强PA的胆碱酯酶抑制作用。乙酰胆碱酯酶抑制及其动力学数据表明6j作为先导分子（AChE IC 50 = 2.13 ± 0.015 µM ，BChE = 28.19 ± 0.20%），与进一步选择用于各种生物活性的PA （AChE = 7.14 ± 0.98%）相比。 AD 模型研究。 6j表现出与 AChE 外周阴离子位点的相互作用、BBB 通透性 ( Pe = 7.98) 和抗氧化性能（% 自由基清除活性 = 35.41 ± 1.09、2.43 ± 1.65，对于6j和PA在 20 M \(\mu \) ， 分别）。金属螯合研究的结果表明， 6j不能有效地螯合铁。分子模型研究表明6j可以有效地与AChE的Ser293、Phe295、Arg29