1-(5-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)-4, 5-dihydro-1H-pyrazol-1-yl)ethanone | 1412774-73-2

• 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: 1-(5-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)-4, 5-dihydro-1H-pyrazol-1-yl)ethanone
• 英文别名: 1-[3-(4-Aminophenyl)-5-(3,4-dimethoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone；1-[3-(4-aminophenyl)-5-(3,4-dimethoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 1412774-73-2
• 化学式: C₁₉H₂₁N₃O₃
• 分子量: 339.394
• InChiKey: HFLLGMZSIRKBJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  间甲苯磺酰氯 、 1-(5-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)-4, 5-dihydro-1H-pyrazol-1-yl)ethanone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到N-(4-(1-acetyl-3-(3,4-dimethoxyphenyl)-4, 5-dihydro-1H-pyrazol-5-yl)phenyl)-3-methylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis, anti-inflammatory and antimicrobial evaluation of novel 1-acetyl-3,5-diaryl-4,5-dihydro (1H) pyrazole derivatives bearing urea, thiourea and sulfonamide moieties

  摘要：

  A series of novel 1-acetyl-3-(3,4-dimethoxypheny)-5-(4-(3-(arylureido/arylthioureido/arylsulfonamido) phenyl)-4,5-dihydropyrazole derivatives of biological interest have been prepared by sequential cyclization of 1-(4-nitrophenyl)-3-(3,4-dimethoxyphenyl)-pro-2-ene-1 with hydrazine hydrate, reduction followed by reaction of resulting amine with different arylisocyanates or arylisothiocyanates or arylsulfonyl chlorides. All the synthesized compounds (1- 32) have been screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Biological evaluation study showed, the compounds 4, 5, 9, 11, 14 and 16 found to have promising anti-inflammatory activity (up to 61-85% TNF-alpha and 76-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (76% TNF-alpha and 86% IL-6 inhibitory activity at 1 mu M). Compounds 24, 26, 27, 28 and 29 exhibited promising antimicrobial activity at MIC values ranging from 70 to 10 mu g/mL against all the selected pathogenic bacteria and fungi. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.118
• 作为产物：
  描述：

  1-(3-(3,4-dimethoxyphenyl)-5-(4-nitrophenyl)-4, 5-dihydro-1H-pyrazol-1-yl)ethanone 在 tin(ll) chloride 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以70%的产率得到1-(5-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)-4, 5-dihydro-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis, anti-inflammatory and antimicrobial evaluation of novel 1-acetyl-3,5-diaryl-4,5-dihydro (1H) pyrazole derivatives bearing urea, thiourea and sulfonamide moieties

  摘要：

  A series of novel 1-acetyl-3-(3,4-dimethoxypheny)-5-(4-(3-(arylureido/arylthioureido/arylsulfonamido) phenyl)-4,5-dihydropyrazole derivatives of biological interest have been prepared by sequential cyclization of 1-(4-nitrophenyl)-3-(3,4-dimethoxyphenyl)-pro-2-ene-1 with hydrazine hydrate, reduction followed by reaction of resulting amine with different arylisocyanates or arylisothiocyanates or arylsulfonyl chlorides. All the synthesized compounds (1- 32) have been screened for their pro-inflammatory cytokines (TNF-alpha and IL-6) and antimicrobial activity (antibacterial and antifungal). Biological evaluation study showed, the compounds 4, 5, 9, 11, 14 and 16 found to have promising anti-inflammatory activity (up to 61-85% TNF-alpha and 76-93% IL-6 inhibitory activity) at concentration of 10 mu M with reference to standard dexamethasone (76% TNF-alpha and 86% IL-6 inhibitory activity at 1 mu M). Compounds 24, 26, 27, 28 and 29 exhibited promising antimicrobial activity at MIC values ranging from 70 to 10 mu g/mL against all the selected pathogenic bacteria and fungi. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.118