N-乙酰基-3-(4-三氟甲基)苯丙氨酸 | 82337-58-4

• 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
• 中文名称: N-乙酰基-3-(4-三氟甲基)苯丙氨酸
• 英文名称: 2-acetamido-3-(4-(trifluoromethyl)phenyl)propanoic acid
• 英文别名: 2-Acetamino-3-<4-trifluormethyl-phenyl>-propionsaeure；2-Acetamino-3-(4-trifluormethyl-phenyl)-propionsaeure；2-acetamido-3-[4-(trifluoromethyl)phenyl]propanoic Acid
• CAS: 82337-58-4
• 化学式: C₁₂H₁₂F₃NO₃
• 分子量: 275.227
• InChiKey: MPQGVZVPMHZXNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-乙酰基-3-(4-三氟甲基)苯丙氨酸 在 三氟化硼乙醚 作用下， 反应 1.0h， 生成 methyl (R)-2-acetamido-3-(4-(trifluoromethyl)phenyl)propanoate
  参考文献：
  名称：

  Synthesis and biological activity of some very hydrophobic superagonist analogs of luteinizing hormone-releasing hormone

  摘要：

  The effect of increased hydrophobicity at position 6 of luteinizing hormone-releasing hormone (LH-RH) has been investigated by the incorporation of a series of 15 very hydrophobic, unnatural D-amino acids at this position. The unnatural amino acids studied can be considered analogues of phenylalanine with carbocyclic aromatic side chains consisting of substituted phenyl (e.g., 2,4,6-trimethylphenyl, p-biphenyl) or polycyclic aromatic (e.g., naphthalene, anthracene) units. When enzymatic resolution (subtilisin Carlsberg) of the most hydrophobic amino acids failed, the racemic amino acids were incorporated, and the diastereomeric LH-RH analogues were resolved by preparative high-performance liquid chromatography. The analogues were synthesized by the solid-phase technique. All of the synthetic compounds were very potent LH-RH superagonists, but [6-(3-(2-naphthyl)-D-alanine)]LH-RH, [6-(3-(2-naphthyl)-D-alanine), 7-(N alpha-methylleucine)]LH-RH and [6-(3-(2,4,6-trimethylphenyl)-D-alanine)]LH-RH appear to be among the most potent LH-RH agonist analogues yet reported when tested in a rat estrus cyclicity suppression assay designed to show the paradoxical antifertility effects of these compounds [ED50 approximately 7 x 10(-8) g; twice daily in saline]. These analogues are twice as potent as [D-Trp6,ProNHEt9]LH-RH in this assay system (i.e., approximately 200 times the potency of LH-RH).

  DOI：

  10.1021/jm00349a006
• 作为产物：
  描述：

  diethyl 2-acetamido-2-<<4-(trifluoromethyl)phenyl>methyl>malonate 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 以75%的产率得到N-乙酰基-3-(4-三氟甲基)苯丙氨酸
  参考文献：
  名称：

  [EN] BORON CONTAINING POLYBASIC BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTICS USES THEREOF
  [FR] INHIBITEURS DES POMPES À EFFLUX BACTÉRIENNES POLYBASIQUES CONTENANT DU BORE ET UTILISATIONS THÉRAPEUTIQUES DE CES DERNIERS

  摘要：

  本文披露了含硼酸功能的多碱性细菌外流泵抑制剂及其合成方法、使用方法和药物组合物。一些实施例包括通过向感染细菌或有细菌感染风险的受试者共同给予外流泵抑制剂和另一种抗菌剂的方法来治疗或预防细菌感染。

  公开号：

  WO2012109164A1

文献信息

• [EN] BORON CONTAINING POLYBASIC BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTICS USES THEREOF<br/>[FR] INHIBITEURS DES POMPES À EFFLUX BACTÉRIENNES POLYBASIQUES CONTENANT DU BORE ET UTILISATIONS THÉRAPEUTIQUES DE CES DERNIERS
  申请人：REMPEX PHARMACEUTICALS INC

  公开号：WO2012109164A1

  公开（公告）日：2012-08-16

  Disclosed herein are polybasic bacterial efflux pump inhibitors containing boronic acid functionality and their methods of synthesis, methods of use, and pharmaceutical compositions. Some embodiments include methods of treating or preventing a bacterial infection by co¬ administering to a subject infected with bacteria or at risk of infection with bacteria the efflux pump inhibitor with another anti-bacterial agent.

  本文披露了含硼酸功能的多碱性细菌外流泵抑制剂及其合成方法、使用方法和药物组合物。一些实施例包括通过向感染细菌或有细菌感染风险的受试者共同给予外流泵抑制剂和另一种抗菌剂的方法来治疗或预防细菌感染。
• QUATERNARY ALKYL AMMONIUM BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTIC USES THEREOF
  申请人：GLINKA TOMASZ

  公开号：US20120165276A1

  公开（公告）日：2012-06-28

  Disclosed are compounds having at least one quaternary alkyl ammonium functionality. The compounds inhibit bacterial efflux pump inhibitors and are used in combination with an anti-bacterial agent to treat or prevent bacterial infections. These combinations can be effective against bacterial infections that have developed resistance to anti-bacterial agents through an efflux pump mechanism.

  本发明涉及具有至少一个季铵基团的化合物。这些化合物抑制细菌外排泵抑制剂，并与抗菌剂结合使用以治疗或预防细菌感染。这些组合物可以有效地对抗通过外排泵机制对抗菌剂产生耐药性的细菌感染。
• BORON CONTAINING POLYBASIC BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTIC USES THEREOF
  申请人：Glinka Tomasz

  公开号：US20130316943A1

  公开（公告）日：2013-11-28

  Disclosed herein are polybasic bacterial efflux pump inhibitors containing boronic acid functionality and their methods of synthesis, methods of use, and pharmaceutical compositions. Some embodiments include methods of treating or preventing a bacterial infection by co-administering to a subject infected with bacteria or at risk of infection with bacteria the efflux pump inhibitor with another anti-bacterial agent.

  本文披露了含有硼酸官能团的多碱性细菌外排泵抑制剂及其合成方法、使用方法和制药组合物。其中一些实施例包括通过向感染细菌或有细菌感染风险的受试者联合给予外排泵抑制剂和另一种抗菌剂来治疗或预防细菌感染的方法。
• Boron containing polybasic bacterial efflux pump inhibitors and therapeutic uses thereof
  申请人：Glinka Tomasz

  公开号：US08933018B2

  公开（公告）日：2015-01-13

  Disclosed herein are polybasic bacterial efflux pump inhibitors containing boronic acid functionality and their methods of synthesis, methods of use, and pharmaceutical compositions. Some embodiments include methods of treating or preventing a bacterial infection by co-administering to a subject infected with bacteria or at risk of infection with bacteria the efflux pump inhibitor with another anti-bacterial agent.

  本文披露了含有硼酸官能团的多碱性细菌外排泵抑制剂及其合成方法、使用方法和制药组合物。其中某些实施例包括通过向感染细菌或有感染细菌风险的受试者共同给予外排泵抑制剂和另一种抗菌剂来治疗或预防细菌感染的方法。
• 一种N-乙酰基-4-三氟甲基苯丙氨酸的拆分方法及其应用
  申请人：瑞博（杭州）医药科技有限公司

  公开号：CN117623973A

  公开（公告）日：2024-03-01

  本发明提供了一种N‑乙酰基‑4‑三氟甲基苯丙氨酸的拆分方法及其应用，该拆分方法以廉价易得的N‑乙酰基‑4‑三氟甲基苯丙氨酸为拆分底物，经济成本低，经拆分剂R‑(+)‑1‑苯基乙胺拆分后得到的(S)‑N‑乙酰基‑4‑三氟甲基苯丙氨酸‑(R)‑1‑苯乙胺盐，经游离后再脱保护基，最终可得到高手性纯度的(S)‑4‑三氟甲基苯丙氨酸，纯度＞99.5％，且收率较高，可达到70～90％。另外，N‑乙酰基‑4‑三氟甲基苯丙氨酸在经拆分后的另一构型(R)‑N‑乙酰基‑4‑三氟甲基苯丙氨酸经消旋后，可以重新得到N‑乙酰基‑4‑三氟甲基苯丙氨酸，回收使用再用于拆分，具有高利用率。