2-氨基-3-(4-氟苯基)丙腈 | 753414-47-0

• 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-氨基-3-(4-氟苯基)丙腈
• 英文名称: 2-amino-3-(4-fluorophenyl)propanenitrile
• CAS: 753414-47-0
• 化学式: C₉H₉FN₂
• 分子量: 164.182
• InChiKey: MBIJHJYDUDWVFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-((diphenylmethylene)amino)-3-(4-fluorophenyl)propanenitrile 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以93%的产率得到2-氨基-3-(4-氟苯基)丙腈
  参考文献：
  名称：

  Heterocycle amide isosteres: An approach to overcoming resistance for HIV-1 integrase strand transfer inhibitors

  摘要：

  A series of heterocyclic pyrimidinedione-based HIV-1 integrase inhibitors was prepared and screened for activity against purified integrase enzyme and/or viruses modified with the following mutations within integrase: Q148R, Q148H/G140S and N155H. These are mutations that result in resistance to the first generation integrase inhibitors raltegravir and elvitegravir. Based on consideration of drug-target interactions, an approach was undertaken to replace the amide moiety of the first generation pyrimidinedione inhibitor with azole heterocycles that could retain potency against these key resistance mutations. An imidazole moiety was found to be the optimal amide substitute and the observed activity was rationalized with the use of calculated properties and modeling. Rat pharmacokinetic (PK) studies of the lead imidazole compounds demonstrated moderate clearance and moderate exposure.

  DOI：

  10.1016/j.bmcl.2019.126784

文献信息

• Flow Synthesis of Fluorinated α-Amino Acids
  作者：Stella Vukelić、Dmitry B. Ushakov、Kerry Gilmore、Beate Koksch、Peter H. Seeberger

  DOI：10.1002/ejoc.201500300

  日期：2015.5

  semi-continuous process for the synthesis of racemic fluorinated α-amino acids from fluorinated amines is described. Following a singlet-oxygen-driven photooxidative cyanation, an acid-mediated hydrolysis of the intermediate α-amino nitrile yields the desired α-amino acid. Aliphatic, benzylic, and homobenzylic residues with different fluorination degrees are tolerated, providing good overall yields (50–67 %). This

  氟化 α-氨基酸是用途广泛的化合物，可用于医学和生物化学的多种用途。然而，它们的合成仍然是一个重大障碍，通常需要多个步骤、多个保护基团和/或使用剧毒试剂。这些挑战限制了氟化α-氨基酸的应用。描述了一种从氟化胺合成外消旋氟化 α-氨基酸的方便、无保护基团和半连续的方法。在单线态氧驱动的光氧化氰化作用之后，中间体 α-氨基腈的酸介导水解产生所需的 α-氨基酸。可以耐受具有不同氟化度的脂肪族、苄基和高苄基残基，提供良好的总产率 (50–67%)。
• [EN] HIV INTEGRASE INHIBITORS<br/>[FR] INHIBITEURS DE L'INTÉGRASE DU VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011046873A1

  公开（公告）日：2011-04-21

  The disclosure generally relates to the novel compounds of formula I, including their salts, which inhibit HIV integrase and prevent viral integration into human DNA. This action makes the compounds useful for treating HIV infection and AIDS. The invention also encompasses pharmaceutical compositions and methods for treating those infected with HIV.

  该披露通常涉及到式I的新化合物，包括它们的盐，这些化合物抑制HIV整合酶并阻止病毒整合到人类DNA中。这种作用使得这些化合物对治疗HIV感染和艾滋病有用。该发明还涵盖了用于治疗HIV感染者的药物组合物和方法。
• [EN] HIV INTEGRASE INHIBITORS<br/>[FR] INHIBITEURS D'INTÉGRASE DU VIH
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012078844A1

  公开（公告）日：2012-06-14

  The disclosure generally relates to the novel compounds of formula (I), including their salts, which inhibit HIV integrase and prevent viral integration into human DNA. This action makes the compounds useful for treating HIV infection and AIDS. The invention also encompasses pharmaceutical compositions and methods for treating those infected with HIV.

  该披露通常涉及公式（I）的新化合物，包括它们的盐，这些化合物抑制HIV整合酶并防止病毒整合到人类DNA中。这种作用使得这些化合物在治疗HIV感染和艾滋病方面非常有用。该发明还涵盖了用于治疗HIV感染者的药物组合物和方法。
• HIV Integrase Inhibitors
  申请人：Naidu B. Narasimhulu

  公开号：US20110245241A1

  公开（公告）日：2011-10-06

  The disclosure generally relates to the novel compounds of formula I, including their salts, which inhibit HIV integrase and prevent viral integration into human DNA. This action makes the compounds useful for treating HIV infection and AIDS. The invention also encompasses pharmaceutical compositions and methods for treating those infected with HIV.

  该披露通常涉及到公式I的新化合物及其盐，这些化合物抑制HIV整合酶并防止病毒整合到人类DNA中。这种作用使化合物对治疗HIV感染和艾滋病有用。该发明还包括用于治疗HIV感染者的药物组合物和方法。
• Inhibitors of Human Immunodeficiency Virus Replication
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160000771A1

  公开（公告）日：2016-01-07

  The disclosure generally relates to compounds of formula (I), including compositions and methods for treating human immunodeficiency virus (HIV) infection. The disclosure provides novel inhibitors of HIV, pharmaceutical compositions containing such compounds, and methods for using these compounds in the treatment of HIV infection.

  该披露通常涉及到公式(I)的化合物，包括治疗人类免疫缺陷病毒（HIV）感染的组合物和方法。该披露提供了HIV的新型抑制剂，含有这些化合物的药物组合物，以及使用这些化合物治疗HIV感染的方法。