3-(benzofuran-2-yl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbonyl chloride | 1388834-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(benzofuran-2-yl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbonyl chloride
• 英文别名: 5-(1-Benzofuran-2-yl)-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydropyrazole-2-carbonyl chloride
• CAS: 1388834-33-0
• 化学式: C₁₉H₁₅ClN₂O₄
• 分子量: 370.792
• InChiKey: DQNGCPGJQQGUMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(benzofuran-2-yl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbonyl chloride 、 4-氨基-1,2-苯二醇 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到3-(benzofuran-2-yl)-N-(3,4-dihydroxyphenyl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide
  参考文献：
  名称：

  Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility

  摘要：

  In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo[5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.061
• 作为产物：
  描述：

  2-乙酰基苯并呋喃 在 ClZr₄ 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 3-(benzofuran-2-yl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbonyl chloride
  参考文献：
  名称：

  Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility

  摘要：

  In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo[5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.061

文献信息

• Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility
  作者：Javarappa Rangaswamy、Honnaiah Vijay Kumar、Salakatte Thammaiah Harini、Nagaraja Naik

  DOI：10.1016/j.bmcl.2012.05.061

  日期：2012.7

  In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo[5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively. (C) 2012 Elsevier Ltd. All rights reserved.