3-Allyl-4-fluoro-benzoic acid | 1027295-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Allyl-4-fluoro-benzoic acid
• 英文别名: 4-Fluoro-3-prop-2-enylbenzoic acid
• CAS: 1027295-98-2
• 化学式: C₁₀H₉FO₂
• 分子量: 180.179
• InChiKey: LVDFQYAVAFGXIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Allyl-4-fluoro-benzoic acid 在 palladium dihydroxide 草酰氯 、 氢气 、 三甲基铝 、 N,N-二异丙基乙胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 苯 为溶剂， -20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 25.5h， 生成 (R)-2-(3-propyl-4-fluorophenyl)-4,5-dihydrooxazole-4-carboxylic acid hydroxamic acid
  参考文献：
  名称：

  Potent, Novel in Vitro Inhibitors of the Pseudomonas aeruginosa Deacetylase LpxC

  摘要：

  Deacetylation of uridyldiphospho-3-O-(R-hydroxydecanoyl)-N-acetylglucosamine by LpxC is the first committed step in the Pseudomonas aeruginosa biosynthetic pathway to lipid A; homologous enzymes are found widely among Gram-negative bacteria. As an essential enzyme for which no inhibitors have yet been reported, the P. aeruginosa LpxC represents a highly attractive target for a novel antibacterial drug. We synthesized several focused small-molecule libraries, each composed of a variable aromatic ring, one of four heterocyclic/spacer moieties, and a hydroxamic acid and evaluated the LpxC inhibition of these compounds against purified P. aeruginosa enzyme. To ensure that the in vitro assay would be as physiologically relevant as possible, we synthesized a tritiated form of the specific P. aeruginosa glycolipid substrate and measured directly the enzymatically released acetate. Several of our novel compounds, predominantly those having fluorinated substituents on the aromatic ring and an oxazoline as the heterocyclic moiety, demonstrated in vitro IC50 values less than 1 muM. We now report the synthesis and in vitro evaluation of these P. aeruginosa LpxC inhibitors.

  DOI：

  10.1021/jm010579r
• 作为产物：
  描述：

  3-溴-4-氟苯甲酸甲酯 在 氢氧化钾 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 3-Allyl-4-fluoro-benzoic acid
  参考文献：
  名称：

  Potent, Novel in Vitro Inhibitors of the Pseudomonas aeruginosa Deacetylase LpxC

  摘要：

  Deacetylation of uridyldiphospho-3-O-(R-hydroxydecanoyl)-N-acetylglucosamine by LpxC is the first committed step in the Pseudomonas aeruginosa biosynthetic pathway to lipid A; homologous enzymes are found widely among Gram-negative bacteria. As an essential enzyme for which no inhibitors have yet been reported, the P. aeruginosa LpxC represents a highly attractive target for a novel antibacterial drug. We synthesized several focused small-molecule libraries, each composed of a variable aromatic ring, one of four heterocyclic/spacer moieties, and a hydroxamic acid and evaluated the LpxC inhibition of these compounds against purified P. aeruginosa enzyme. To ensure that the in vitro assay would be as physiologically relevant as possible, we synthesized a tritiated form of the specific P. aeruginosa glycolipid substrate and measured directly the enzymatically released acetate. Several of our novel compounds, predominantly those having fluorinated substituents on the aromatic ring and an oxazoline as the heterocyclic moiety, demonstrated in vitro IC50 values less than 1 muM. We now report the synthesis and in vitro evaluation of these P. aeruginosa LpxC inhibitors.

  DOI：

  10.1021/jm010579r

文献信息

• INHIBITORS OF BETA-SECRETASE
  申请人：CACATIAN Salvacion

  公开号：US20110071126A1

  公开（公告）日：2011-03-24

  The present invention is directed to a compound represented by the following structural formula or a pharmaceutically acceptable salt thereof. Pharmaceutical compositions and method of use of the compounds are also described.

  本发明涉及下述结构式所代表的化合物或其药学上可接受的盐。同时还描述了该化合物的药物组合物和使用方法。
• Inhibitors of beta-secretase
  申请人：Vitae Pharmaceuticals, Inc.

  公开号：EP2801570A1

  公开（公告）日：2014-11-12

  The present invention is directed to a compound represented by the following structural formula or a pharmaceutically acceptable salt thereof. Pharmaceutical compositions and method of use of the compounds are also described.

  本发明涉及一种由以下结构式表示的化合物 或其药学上可接受的盐。本发明还描述了该化合物的药物组合物和使用方法。
• US8633212B2
  申请人：——

  公开号：US8633212B2

  公开（公告）日：2014-01-21
• US9212153B2
  申请人：——

  公开号：US9212153B2

  公开（公告）日：2015-12-15
• [EN] INHIBITORS OF BETA-SECRETASE<br/>[FR] INHIBITEURS DE BÊTA-SÉCRÉTASE
  申请人：VITAE PHARMACEUTICALS INC

  公开号：WO2010105179A2

  公开（公告）日：2010-09-16

  The present invention is directed to a compound represented by the following structural formula or a pharmaceutically acceptable salt thereof. Pharmaceutical compositions and method of use of the compounds are also described.