4-(3-(4-fluorophenyl)isoxazol-5-yl)butan-1-ol

• 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: 4-(3-(4-fluorophenyl)isoxazol-5-yl)butan-1-ol
• 英文别名: 4-[3-(4-Fluorophenyl)-1,2-oxazol-5-yl]butan-1-ol；4-[3-(4-fluorophenyl)-1,2-oxazol-5-yl]butan-1-ol
• 化学式: C₁₃H₁₄FNO₂
• 分子量: 235.258
• InChiKey: KMALZXQMMASFRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-(4-fluorophenyl)isoxazol-5-yl)butan-1-ol 在 silica gel 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 4-[3-(4-Fluorophenyl)-1,2-oxazol-5-yl]butanal
  参考文献：
  名称：

  Design and synthesis of a piperazinylalkylisoxazole library for subtype selective dopamine receptor ligands

  摘要：

  A piperazinylbutylisoxazole libary was designed, synthesized and screened for the binding affinities to dopamine D-2, D-3, and D-4 receptors. Several ligands were identified to possess high binding affinity and selectivity for the D-3 and D-4 receptors over the D-2 receptor. Compounds 6s and 6t showed K-i values of 2.6 nM and 3.9 nM for the D-3 receptor with 46- and 50-fold selectivity over the D-3 receptor, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00179-8
• 作为产物：
  描述：

  syn-4-氟苯甲醛肟 在 吡啶 、 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 4-(3-(4-fluorophenyl)isoxazol-5-yl)butan-1-ol
  参考文献：
  名称：

  Design and synthesis of a piperazinylalkylisoxazole library for subtype selective dopamine receptor ligands

  摘要：

  A piperazinylbutylisoxazole libary was designed, synthesized and screened for the binding affinities to dopamine D-2, D-3, and D-4 receptors. Several ligands were identified to possess high binding affinity and selectivity for the D-3 and D-4 receptors over the D-2 receptor. Compounds 6s and 6t showed K-i values of 2.6 nM and 3.9 nM for the D-3 receptor with 46- and 50-fold selectivity over the D-3 receptor, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00179-8

文献信息

• Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents
  作者：Prasanta Das、Sarah Boone、Dipanwita Mitra、Lindsay Turner、Ritesh Tandon、Drazen Raucher、Ashton T. Hamme

  DOI：10.1039/d0ra06148d

  日期：——

  Electrophilic fluorine-mediated dearomative spirocyclization has been developed to synthesize a range of fluoro-substituted spiro-isoxazoline ethers and lactones. The in vitro biological assays of synthesized compounds were probed for anti-viral activity against human cytomegalovirus (HCMV) and cytotoxicity against glioblastomas (GBM6) and triple negative breast cancer (MDA MB 231). Interestingly,

  亲电氟介导的脱芳香螺环化已被开发用于合成一系列氟取代的螺异恶唑啉醚和内酯。对合成化合物进行体外生物学测定，探讨其对人巨细胞病毒 (HCMV) 的抗病毒活性以及对胶质母细胞瘤 (GBM6) 和三阴性乳腺癌 (MDA MB 231) 的细胞毒性。有趣的是，化合物4d和4n显示出显着的抗HCMV活性（IC 50 ∼ 10 μM），而4l和5f显示出最高的细胞毒性，IC 50 = 36 〜 80 μM。合成功效和生物学相关性为进一步开发氟螺螺异恶唑啉作为新型抗病毒和抗癌药物提供了机会。