2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid [(5-nitro-2-furyl)methylene]hydrazide | 662157-82-6

• 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: 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid [(5-nitro-2-furyl)methylene]hydrazide
• 英文别名: 5-(2,4-difluorophenyl)-2-hydroxy-N-[(5-nitrofuran-2-yl)methylideneamino]benzamide
• CAS: 662157-82-6
• 化学式: C₁₈H₁₁F₂N₃O₅
• 分子量: 387.299
• InChiKey: BTKDUJWQOAKMNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117.97
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  巯基乙酸 、 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid [(5-nitro-2-furyl)methylene]hydrazide 以 苯 为溶剂， 生成 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid [2-(5-nitro-2-furyl)-4-thiazolidinon-3-yl]amide
  参考文献：
  名称：

  Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide

  摘要：

  Two novel series of 4-thiazolidinone derivatives, namely 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid [2-(5-nitro-2-furyl/substituted phenyl)-4-thiazol idinone-3 -y1jam ides (5a-g) and 2-(2',4'-difluoro4-hydroxybipheiiyl-3-carbonylhydrazono)-3-alkyl/ary1-4-thiazolidinones (6ae) together with 5-(2',4'-difluoro4-hydroxybiphenyl-5-yi)-2-cyclohexylamino-1,3,4-oxadiazole (7a) have been synthesized as title compounds. 1-(2',4'-Difluoro-4-hydroxybiphenyl-3-carbonyl)4-alkyl/atylthiosemicarbazides (4a-g) were also obtained and used as intermediate to give the title compounds. All synthesized compounds were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv, antiviral and antimicrobial activities against various virus, bacteria and fungi strains. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.11.005
• 作为产物：
  描述：

  二氟尼柳 在 硫酸 、 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.0h， 生成 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid [(5-nitro-2-furyl)methylene]hydrazide
  参考文献：
  名称：

  Synthesis and biological activities of diflunisal hydrazide–hydrazones

  摘要：

  Several diflunisal hydrazide-hydrazone derivatives namely 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid [(5-nitro-2-furyl/substitutedphenyl)methylene] hydrazide (3a-o) have been synthesised. Methyl 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylate (1) and 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid hydrazide (2) were also synthesised and used as intermediate compounds. All synthesised compounds were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37 Rv, antimicrobial activities against various bacteria, fungi and yeast species. Compound 3a have shown activity against Staphylococcus epidermis HE-5 and Staphylococcus aureus HE-9 at 18.75 and 37.5 mug mL(-1), respectively. Compound 3o have exhibited activity against Acinetobacter calcoaceticus IO-16 at a concentration of 37.5 mug mL(-1), whereas Cefepime, the drug used as standard, have been found less active against the microorganisms mentioned above. The synthesised compounds were found to provide 12-34% inhibition of mycobacterial growth of M. tuberculosis H37 Rv in the primary screen at 6.25 mug mL-1. Anticonvulsant activity of the compounds were also determined by maximal electroshock (MES) and subcutaneous metrazole (scMET) tests in mice and rats following the procedures of antiepileptic drug development (ADD) program of the National Institutes of Health (NIH). Compound 3k showed 25% protection against MES induced seizures in p.o. rat screening at a dose level of 30 mg kg(-1) whereas 3n and 3o showed neurotoxicity after 4 and 0.5 h at a dose level of 100 and 300 mg kg(-1) respectively. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.08.004

文献信息

• Synthesis and biological activities of diflunisal hydrazide–hydrazones
  作者：S.Güniz Küçükgüzel、Adil Mazi、Fikrettin Sahin、Suzan Öztürk、James Stables

  DOI：10.1016/j.ejmech.2003.08.004

  日期：2003.11

  Several diflunisal hydrazide-hydrazone derivatives namely 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid [(5-nitro-2-furyl/substitutedphenyl)methylene] hydrazide (3a-o) have been synthesised. Methyl 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylate (1) and 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid hydrazide (2) were also synthesised and used as intermediate compounds. All synthesised compounds were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37 Rv, antimicrobial activities against various bacteria, fungi and yeast species. Compound 3a have shown activity against Staphylococcus epidermis HE-5 and Staphylococcus aureus HE-9 at 18.75 and 37.5 mug mL(-1), respectively. Compound 3o have exhibited activity against Acinetobacter calcoaceticus IO-16 at a concentration of 37.5 mug mL(-1), whereas Cefepime, the drug used as standard, have been found less active against the microorganisms mentioned above. The synthesised compounds were found to provide 12-34% inhibition of mycobacterial growth of M. tuberculosis H37 Rv in the primary screen at 6.25 mug mL-1. Anticonvulsant activity of the compounds were also determined by maximal electroshock (MES) and subcutaneous metrazole (scMET) tests in mice and rats following the procedures of antiepileptic drug development (ADD) program of the National Institutes of Health (NIH). Compound 3k showed 25% protection against MES induced seizures in p.o. rat screening at a dose level of 30 mg kg(-1) whereas 3n and 3o showed neurotoxicity after 4 and 0.5 h at a dose level of 100 and 300 mg kg(-1) respectively. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide
  作者：Güniz Küçükgüzel、Ayla Kocatepe、Erik De Clercq、Fikrettin Şahin、Medine Güllüce

  DOI：10.1016/j.ejmech.2005.11.005

  日期：2006.3

  Two novel series of 4-thiazolidinone derivatives, namely 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid [2-(5-nitro-2-furyl/substituted phenyl)-4-thiazol idinone-3 -y1jam ides (5a-g) and 2-(2',4'-difluoro4-hydroxybipheiiyl-3-carbonylhydrazono)-3-alkyl/ary1-4-thiazolidinones (6ae) together with 5-(2',4'-difluoro4-hydroxybiphenyl-5-yi)-2-cyclohexylamino-1,3,4-oxadiazole (7a) have been synthesized as title compounds. 1-(2',4'-Difluoro-4-hydroxybiphenyl-3-carbonyl)4-alkyl/atylthiosemicarbazides (4a-g) were also obtained and used as intermediate to give the title compounds. All synthesized compounds were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv, antiviral and antimicrobial activities against various virus, bacteria and fungi strains. (c) 2006 Elsevier SAS. All rights reserved.