3-(4-fluorophenyl)-4,5-dihydroisoxazole-5-carboxylic acid | 522615-28-7

• 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-(4-fluorophenyl)-4,5-dihydroisoxazole-5-carboxylic acid
• 英文别名: 3-(4-fluorophenyl)-2-isoxazoline-5-carboxylic acid；3-(4-Fluorophenyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid
• CAS: 522615-28-7
• 化学式: C₁₀H₈FNO₃
• mdl: MFCD06011106
• 分子量: 209.177
• InChiKey: PBZBMHSUDXPYCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090
• 储存条件：
  室温下密封保存，并保持干燥。

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-4,5-dihydroisoxazole-5-carboxylic acid 在 吡啶 、 甲基磺酰氯 作用下， 以 乙腈 为溶剂， 生成 N-(4-chloro-2-(diethylcarbamoyl)-6-methylphenyl)-3-(4-fluorophenyl)-4,5-dihydroisoxazole-5-carboxamide
  参考文献：
  名称：

  Anthranilic acid-based diamides derivatives incorporating aryl-isoxazoline pharmacophore as potential anticancer agents: Design, synthesis and biological evaluation

  摘要：

  A series of novel anthranilic diamides derivatives containing aryl-isoxazoline moiety were designed and synthesized as a part of our ongoing search for potential anticancer agents. Their structures were confirmed by H-1 NMR, C-13 NMR and ESI-MS analyses. The preliminary assays showed that some of the compounds displayed moderate to good antitumor activities against human lung cancer (NCI-H460), hepatocellular liver carcinoma (HepG2), gastric cancer (SGC-7901 and BGC-823) and breast epithelial adenocarcinoma (MCF-7) cell lines at mu M level, which might be developed as novel lead scaffold for potential anticancer agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.001
• 作为产物：
  描述：

  Ethyl 3-(4-fluorophenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 3-(4-fluorophenyl)-4,5-dihydroisoxazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of isoxazolinyl oxazolidinones: Search for potent antibacterial

  摘要：

  A series of (5S) N-(3-{3-fluoro-4-[4-(3-aryl-4,5-dihydro-isoxazole-5-carbonyl)-piperazin-1-yl]-phenyl}2-oxo-oxazolidin-5-ylmethyl)-acetamide(6a-o) were synthesized and their in vitro antibacterial activity against various resistant Gram-positive and Gram-negative bacteria were evaluated. Most of the synthesized compounds showed 2 to 10 fold lower MIC values compared to linezolid against Staphylococcus aureus ATCC 25923, ATCC 70069, ATCC 29213, Bacillus cereus MTCC 430, Enterococcus faecalis MTCC439, Klebsiella pneumoniae ATCC 27736, and Streptococcus pyogens. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.133

文献信息

• US4889551A
  申请人：——

  公开号：US4889551A

  公开（公告）日：1989-12-26
• US4906277A
  申请人：——

  公开号：US4906277A

  公开（公告）日：1990-03-06
• Synthesis and antibacterial evaluation of isoxazolinyl oxazolidinones: Search for potent antibacterial
  作者：Vandana Varshney、Nripendra N. Mishra、Praveen K. Shukla、Devi P. Sahu

  DOI：10.1016/j.bmcl.2009.04.133

  日期：2009.7

  A series of (5S) N-(3-3-fluoro-4-[4-(3-aryl-4,5-dihydro-isoxazole-5-carbonyl)-piperazin-1-yl]-phenyl}2-oxo-oxazolidin-5-ylmethyl)-acetamide(6a-o) were synthesized and their in vitro antibacterial activity against various resistant Gram-positive and Gram-negative bacteria were evaluated. Most of the synthesized compounds showed 2 to 10 fold lower MIC values compared to linezolid against Staphylococcus aureus ATCC 25923, ATCC 70069, ATCC 29213, Bacillus cereus MTCC 430, Enterococcus faecalis MTCC439, Klebsiella pneumoniae ATCC 27736, and Streptococcus pyogens. (C) 2009 Elsevier Ltd. All rights reserved.
• Anthranilic acid-based diamides derivatives incorporating aryl-isoxazoline pharmacophore as potential anticancer agents: Design, synthesis and biological evaluation
  作者：Liqiao Shi、Rui Hu、Yanhong Wei、Ying Liang、Ziwen Yang、Shaoyong Ke

  DOI：10.1016/j.ejmech.2012.06.001

  日期：2012.8

  A series of novel anthranilic diamides derivatives containing aryl-isoxazoline moiety were designed and synthesized as a part of our ongoing search for potential anticancer agents. Their structures were confirmed by H-1 NMR, C-13 NMR and ESI-MS analyses. The preliminary assays showed that some of the compounds displayed moderate to good antitumor activities against human lung cancer (NCI-H460), hepatocellular liver carcinoma (HepG2), gastric cancer (SGC-7901 and BGC-823) and breast epithelial adenocarcinoma (MCF-7) cell lines at mu M level, which might be developed as novel lead scaffold for potential anticancer agents. (C) 2012 Elsevier Masson SAS. All rights reserved.