(3R,4R)-4-(4-溴苯氧基)四氢呋喃-3-胺 | 1258963-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (3R,4R)-4-(4-溴苯氧基)四氢呋喃-3-胺
• 英文名称: (3R,4R)-4-(4-bromophenoxy)tetrahydrofuran-3-amine
• 英文别名: (3R,4R)-rel-4-(4-bromophenoxy)oxolan-3-amine；(3R,4R)-4-(4-bromophenoxy)oxolan-3-amine
• CAS: 1258963-55-1
• 化学式: C₁₀H₁₂BrNO₂
• 分子量: 258.115
• InChiKey: GRTOEAAOPRPWSN-ZJUUUORDSA-N

物化性质

• 沸点：
  349.6±42.0 °C(Predicted)
• 密度：
  1.491±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-(4-溴苯氧基)四氢呋喃-3-胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 正庚烷 、 二氯甲烷 、 二乙胺 、 异丙醇 为溶剂， 反应 20.0h， 生成 N-[(3S,4S)-4-(4-bromophenoxy)tetrahydrofuran-3-yl]propane-2-sulfonamide
  参考文献：
  名称：

  The Discovery and Characterization of the α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptor Potentiator N-{(3S,4S)-4-[4-(5-Cyano-2-thienyl)phenoxy]tetrahydrofuran-3-yl}propane-2-sulfonamide (PF-04958242)

  摘要：

  A unique tetrahydrofuran ether class of highly potent alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor potentiators has been identified using rational and structure-based drug design. An acyclic lead compound, containing an ether-linked isopropylsulfonamide and biphenyl group, was pharmacologically augmented by converting it to a conformationally constrained tetrahydrofuran to improve key interactions with the human GluA2 ligand-binding domain. Subsequent replacement of the distal phenyl motif with 2-cyanothiophene to enhance its potency, selectivity, and metabolic stability afforded N-{(3S,4S)-4-[4-(5-cyano-2-thienyl)-phenoxy]tetrahydrofuran-3-yl}propane-2-sulfonamide (PF-04958242, 3), whose preclinical characterization suggests an adequate therapeutic index, aided by low projected human oral pharmacokinetic variability, for clinical studies exploring its ability to attenuate cognitive deficits in patients with schizophrenia.

  DOI：

  10.1021/acs.jmedchem.5b00300
• 作为产物：
  描述：

  cis-3-azido-4-(4-bromophenoxy)tetrahydrofuran 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 (3R,4R)-4-(4-溴苯氧基)四氢呋喃-3-胺
  参考文献：
  名称：

  [EN] ANTIBACTERIAL COMPOUNDS
  [FR] COMPOSÉS ANTIBACTÉRIENS

  摘要：

  本文提供了杂环化合物和含有该化合物的药物组合物，可用于抑制革兰氏阴性细菌的生长。该化合物和组合物可用于治疗细菌感染，如肺炎。

  公开号：

  WO2022173758A1

文献信息

• Amino-oxetanes as amide isosteres by an alternative defluorosulfonylative coupling of sulfonyl fluorides
  作者：Juan J. Rojas、Rosemary A. Croft、Alistair J. Sterling、Edward L. Briggs、Daniele Antermite、Daniel C. Schmitt、Luka Blagojevic、Peter Haycock、Andrew J. P. White、Fernanda Duarte、Chulho Choi、James J. Mousseau、James A. Bull

  DOI：10.1038/s41557-021-00856-2

  日期：2022.2

  This disconnection, comparable to a typical amidation, will allow the application of vast existing amine libraries. The reaction is tolerant to a wide range of polar functionalities and is suitable for array formats. Ten oxetane analogues of bioactive benzamides and marketed drugs are prepared. Kinetic and computational studies support the formation of an oxetane carbocation as the rate-determining

  生物等排体提供了有价值的设计元素，药物化学家可以使用这些元素将生物活性化合物的结构和药代动力学特征调整为可行的候选药物。芳基氧杂环丁胺作为苯甲酰胺（非常常见的药效团）的生物等排体具有令人兴奋的潜力，但由于缺乏可用的合成方法而很少被检查。在这里，我们描述了磺酰氟通过已建立的 SuFEx（磺酰氟交换）点击反应性的替代途径形成氨基氧杂环丁烷的一类反应。脱氟磺酰化仅在加热时形成平面氧杂环丁烷碳正离子。这种断开与典型的酰胺化相当，将允许应用大量现有的胺库。该反应对多种极性官能团具有耐受性，适用于阵列形式。制备了十种具有生物活性的苯甲酰胺和已上市药物的氧杂环丁烷类似物。动力学和计算研究支持氧杂环丁烷碳正离子的形成作为速率决定步骤，然后是化学选择性亲核偶联步骤。
• [EN] HETEROCYCLIC SULFONAMIDES, USES AND PHARMACEUTICAL COMPOSITIONS THEREOF<br/>[FR] SULFONAMIDES HÉTÉROCYCLIQUES, UTILISATIONS ET COMPOSITIONS PHARMACEUTIQUES ASSOCIÉES
  申请人：PFIZER

  公开号：WO2010150192A1

  公开（公告）日：2010-12-29

  The invention is directed to a class of compounds, including the pharmaceutically acceptable salts of the compounds, having the structure of formula (I) as defined in the specification. The invention is also directed to compositions containing and uses of the compounds of formula I.

  该发明涉及一类化合物，包括该化合物的药用可接受盐，其具有规范中定义的式(I)的结构。该发明还涉及含有和使用式I化合物的组合物。
• Heterocyclic sulfonamides, uses and pharmaceutical compositions thereof
  申请人：Pfizer Inc.

  公开号：US08278457B2

  公开（公告）日：2012-10-02

  The invention is directed to a class of compounds, including the pharmaceutically acceptable salts of the compounds, having the structure of formula I: as defined in the specification. The invention is also directed to compositions containing and uses of the compounds of formula I.

  本发明涉及一类化合物，包括化合物的药用可接受盐，其结构式为公式I所定义。本发明还涉及含有公式I化合物的组合物和其用途。
• Heterocyclic Sulfonamides, Uses and Pharmaceutical Compositions Thereof
  申请人：Fliri Anton F. J.

  公开号：US20110105533A1

  公开（公告）日：2011-05-05

  The invention is directed to a class of compounds, including the pharmaceutically acceptable salts of the compounds, having the structure of formula I: as defined in the specification. The invention is also directed to compositions containing and uses of the compounds of formula I.

  本发明涉及一类化合物，包括化合物的药用可接受盐，其结构如式I所定义。本发明还涉及含有式I化合物的组合物和其用途。
• HETEROCYCLIC SULFONAMIDES, USES AND PHARMACEUTICAL COMPOSITIONS THEREOF
  申请人：Fliri Anton F. J.

  公开号：US20120322823A1

  公开（公告）日：2012-12-20

  The invention is directed to a class of compounds, including the pharmaceutically acceptable salts of the compounds, having the structure of formula I: as defined in the specification. The invention is also directed to compositions containing and uses of the compounds of formula I.

  本发明涉及一类化合物，包括化合物的药学上可接受的盐，其结构如公式I所定义。本发明还涉及含有公式I化合物的组合物和其用途。