5-(4-fluorophenyl)-2-furoylhydrazone | 732251-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-(4-fluorophenyl)-2-furoylhydrazone
• 英文别名: 5-(4-Fluorophenyl)furan-2-carbohydrazide
• CAS: 732251-99-9
• 化学式: C₁₁H₉FN₂O₂
• mdl: MFCD08051035
• 分子量: 220.203
• InChiKey: DCWMJMZWFNAANF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-fluorophenyl)-2-furoylhydrazone 、 2,6-二氟苯甲酰异氰酸酯 以 甲苯 为溶剂， 反应 2.0h， 以75.8%的产率得到4-(2,6-difluorobenzoyl)-1-[5-(4-fluorophenyl)-2-furoyl]semicarbazide
  参考文献：
  名称：

  N-苯甲酰基-N'-[5-(2'-取代苯基)-2-呋喃酰基]氨基脲衍生物的合成及生物活性

  摘要：

  为了寻找具有良好活性的新型几丁质合成抑制剂（CSIs），选择典型的CSIs类苯甲酰苯脲作为先导化合物，通过将苯甲酰苯脲的脲键转化为氨基脲基团并改变其结构，设计了15种含有呋喃部分的新型衍生物。苯胺部分变成糠酰基。标题化合物由取代苯甲酰异氰酸酯与5-(取代苯基)-2-呋喃酰肼反应合成，结构经IR、1H-NMR、元素分析和单晶X射线衍射分析(化合物E2 ）。生物测定结果表明，标题化合物表现出良好的杀虫活性，尤其是对小菜蛾（Plutella xylostella L.），但杀真菌活性较低。令人鼓舞的是，标题化合物对人早幼粒细胞白血病细胞系（HL-60）具有明显的抗癌活性，部分标题化合物对人肝癌细胞系（Bel-7402）、人胃癌细胞系（BGC-823）也有活性, 和人鼻咽癌细胞系 (KB)。结果表明，先导化合物中的连接对生物活性和光谱很重要。尿素键的修饰是发现新农药和候选药物的有效策略。结果表明，

  DOI：

  10.3390/molecules15064267
• 作为产物：
  描述：

  5-(4-fluorophenyl)furan-2-carboxylic acid methyl ester 在 一水合肼 作用下， 生成 5-(4-fluorophenyl)-2-furoylhydrazone
  参考文献：
  名称：

  New class of potent antitumor acylhydrazone derivatives containing furan

  摘要：

  A pair of chemical isomeric structures of N-acylhydrazone compounds I and II were designed and synthesized. The reaction was carried out with high diastereoselectivity to obtain one configurational isomer in excellent yields. The exact configuration and conformation of IIa and IIe were confirmed by the X-ray single crystal diffraction. The antitumor bioassay revealed that some compounds exhibited excellent activity against the selected cancer cell lines. In particular, IIf (IC50 =16.4 mu M) was better than doxorubicin (IC50=53.3 mu M) against human promyelocytic leukemic cells (HL-60). Their toxicities were predicted in silico. The results showed that compounds II were safe and eligible to be development candidates. IIf showed great promise as a novel lead compound for further anticancer discovery. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.007

文献信息

• Synthesis and Fungicidal Activity of Novel 2,5-Disubstituted-1,3,4-oxadiazole Derivatives
  作者：Zi-Ning Cui、Yan-Xia Shi、Li Zhang、Yun Ling、Bao-Ju Li、Yoshihiro Nishida、Xin-Ling Yang

  DOI：10.1021/jf303807a

  日期：2012.11.28

  A novel series of 1,3,4-oxadiazole derivatives containing a 5-phenyl-2-furan moiety were synthesized from the intermediates diacylhydrazine 3 and acylhydrazone 5 via an efficient approach under microwave irradiation in good yields. Their structures were characterized by IR, H-1 NMR, and elemental analysis. The antifungal tests indicated that the title compounds showed in vivo fungicidal activity against Botrytis cinerea and Rhizoctonia solanii at 500 mu g/mL obviously. Some tested compounds even had a superiority effect over the commercial fungicides 40% Pyrimethanil SC and 3% Validamycin AS. The activity between the title compound and their precursors diacylhydrazine 3 and acylhydrazone 5 was also compared and discussed.
• Synthesis and Bioactivity of N-Benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] Semicarbazide Derivatives
  作者：Zining Cui、Yun Ling、Baoju Li、Yongqiang Li、Changhui Rui、Jingrong Cui、Yanxia Shi、Xinling Yang

  DOI：10.3390/molecules15064267

  日期：——

  novel chitin synthesis inhibitors (CSIs) with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 15 novel derivatives containing furan moieties were designed by converting the urea linkage of benzoylphenylureas into a semicarbazide and changing the aniline part into furoyl groups. The title compounds were synthesized by the reaction of substituted benzoyl isocyanates

  为了寻找具有良好活性的新型几丁质合成抑制剂（CSIs），选择典型的CSIs类苯甲酰苯脲作为先导化合物，通过将苯甲酰苯脲的脲键转化为氨基脲基团并改变其结构，设计了15种含有呋喃部分的新型衍生物。苯胺部分变成糠酰基。标题化合物由取代苯甲酰异氰酸酯与5-(取代苯基)-2-呋喃酰肼反应合成，结构经IR、1H-NMR、元素分析和单晶X射线衍射分析(化合物E2 ）。生物测定结果表明，标题化合物表现出良好的杀虫活性，尤其是对小菜蛾（Plutella xylostella L.），但杀真菌活性较低。令人鼓舞的是，标题化合物对人早幼粒细胞白血病细胞系（HL-60）具有明显的抗癌活性，部分标题化合物对人肝癌细胞系（Bel-7402）、人胃癌细胞系（BGC-823）也有活性, 和人鼻咽癌细胞系 (KB)。结果表明，先导化合物中的连接对生物活性和光谱很重要。尿素键的修饰是发现新农药和候选药物的有效策略。结果表明，
• New class of potent antitumor acylhydrazone derivatives containing furan
  作者：Zining Cui、Ying Li、Yun Ling、Juan Huang、Jingrong Cui、Ruiqing Wang、Xinling Yang

  DOI：10.1016/j.ejmech.2010.09.007

  日期：2010.12

  A pair of chemical isomeric structures of N-acylhydrazone compounds I and II were designed and synthesized. The reaction was carried out with high diastereoselectivity to obtain one configurational isomer in excellent yields. The exact configuration and conformation of IIa and IIe were confirmed by the X-ray single crystal diffraction. The antitumor bioassay revealed that some compounds exhibited excellent activity against the selected cancer cell lines. In particular, IIf (IC50 =16.4 mu M) was better than doxorubicin (IC50=53.3 mu M) against human promyelocytic leukemic cells (HL-60). Their toxicities were predicted in silico. The results showed that compounds II were safe and eligible to be development candidates. IIf showed great promise as a novel lead compound for further anticancer discovery. (C) 2010 Elsevier Masson SAS. All rights reserved.