1-(4-(1-acetyl-3-(3,4-dimethoxyphenyl)-4, 5-dihydro-1H-pyrazol-5-yl) phenyl)-3-(4-chlorophenyl)thiourea | 1412775-54-2

• 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-(4-(1-acetyl-3-(3,4-dimethoxyphenyl)-4, 5-dihydro-1H-pyrazol-5-yl) phenyl)-3-(4-chlorophenyl)thiourea
• 英文别名: 1-[4-[2-Acetyl-5-(3,4-dimethoxyphenyl)-3,4-dihydropyrazol-3-yl]phenyl]-3-(4-chlorophenyl)thiourea；1-[4-[2-acetyl-5-(3,4-dimethoxyphenyl)-3,4-dihydropyrazol-3-yl]phenyl]-3-(4-chlorophenyl)thiourea
• CAS: 1412775-54-2
• 化学式: C₂₆H₂₅ClN₄O₃S
• 分子量: 509.029
• InChiKey: AKDWYWDIRJSIIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 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 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 1-(4-(1-acetyl-3-(3,4-dimethoxyphenyl)-4, 5-dihydro-1H-pyrazol-5-yl) phenyl)-3-(4-chlorophenyl)thiourea
  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

文献信息

• 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
  作者：Ashish P. Keche、Girish D. Hatnapure、Rajesh H. Tale、Atish H. Rodge、Vandana M. Kamble

  DOI：10.1016/j.bmcl.2012.08.118

  日期：2012.11

  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.