5-(2-fluorophenyl)-2-furoylhydrazone | 1216141-38-6

• 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-(2-fluorophenyl)-2-furoylhydrazone
• 英文别名: 5-(2-Fluorophenyl)furan-2-carbohydrazide；5-(2-fluorophenyl)furan-2-carbohydrazide
• CAS: 1216141-38-6
• 化学式: C₁₁H₉FN₂O₂
• mdl: MFCD12402243
• 分子量: 220.203
• InChiKey: CTHJLLHBBHMIKK-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-(2-fluorophenyl)-2-furoylhydrazone 、 4-氯苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以98.09%的产率得到(E)-4-chlorobenzaldehyde 5-(2-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
• 作为产物：
  描述：

  5-(2-fluorophenyl)furan-2-carboxylic acid methyl ester 在 一水合肼 作用下， 生成 5-(2-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.