5-(4-(dimethylamino)phenyl)isoxazole-3-carboxylic acid | 1391625-43-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(4-(dimethylamino)phenyl)isoxazole-3-carboxylic acid
• 英文别名: 5-[4-(Dimethylamino)phenyl]isoxazole-3-carboxylic Acid；5-[4-(dimethylamino)phenyl]-1,2-oxazole-3-carboxylic acid
• CAS: 1391625-43-6
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: ZAYBMRVNLSQVQL-UHFFFAOYSA-N

物化性质

• 沸点：
  474.1±40.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,6S)-3,6-diisobutylpiperazin-2-one 、 5-(4-(dimethylamino)phenyl)isoxazole-3-carboxylic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以26%的产率得到(3S,6S)-4-(5-(4-(dimethylamino)phenyl)isoxazole-3-carbonyl)-3,6-diisobutylpiperazin-2-one
  参考文献：
  名称：

  Discovery of a Novel Class of Potent HCV NS4B Inhibitors: SAR Studies on Piperazinone Derivatives

  摘要：

  HTS screening identified compound 2a (piper-azinone derivative) as a low micromolar HCV genotype 1 (GT-1) inhibitor. Resistance mapping studies suggested that this piperazinone chemotype targets the HCV nonstructural protein NS4B. Extensive SAR studies were performed around 2a and the amide function and the C-3/C-6 cis stereochemistry of the piperazinone core were essential for HCV activity. A 10-fold increase in GT-1 potency was observed when the chiral phenylcyclopropyl amide side chain of 2a was replaced with p-fluorophenylisoxazole-carbonyl moiety (67). Replacing the C-6 nonpolar hydrophobic moiety of 67 with a phenyl moiety (95) did not diminish the GT-1 potency. A heterocyclic thiophene moiety (103) and an isoxazole moiety (108) were incorporated as isosteric replacements for the C-6 phenyl moiety (95), resulting in significant improvement in GT-1b and la potency. However, the piperazonone class of compounds lacks GT-2 activity and, consequently, were not pursued further into development.

  DOI：

  10.1021/jm4012643
• 作为产物：
  描述：

  二甲氨基苯乙酮 、 5-(3-Chloro-4-fluoro-phenyl)-isoxazole-3-carboxylic acid 以to afford the product 43 (1.65 g, overall yield 14.6%) as a white solid的产率得到5-(4-(dimethylamino)phenyl)isoxazole-3-carboxylic acid
  参考文献：
  名称：

  COMPOUNDS

  摘要：

  本文公开了用于治疗病毒感染，如HCV的化合物。

  公开号：

  US20120202794A1

文献信息

• [EN] PYRAZINE AND IMIDAZOLIDINE DERIVATIVES AND THEIR USES TO TREAT HEPATITIS C<br/>[FR] DÉRIVÉS DE PYRAZINE ET D'IMIDAZOLIDINE ET LEURS UTILISATIONS EN VUE DU TRAITEMENT DE L'HÉPATITE C
  申请人：GILEAD PHARMASSET LLC

  公开号：WO2012103113A1

  公开（公告）日：2012-08-02

  Disclosed herein are compounds useful for treating a viral infection, such HCV.

  本文披露了一些用于治疗病毒感染，如HCV的化合物。