3-[(3-benzo[b]furan-2-yl-5-(4-hydroxyphenyl)-4,5-dihydro-1H-1-pyrazolyl)carbonyl]-1-ethyl-7-methyl-1,4-dihydro[1,8]naphthyridin-4-one | 1246467-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-[(3-benzo[b]furan-2-yl-5-(4-hydroxyphenyl)-4,5-dihydro-1H-1-pyrazolyl)carbonyl]-1-ethyl-7-methyl-1,4-dihydro[1,8]naphthyridin-4-one
• 英文别名: 3-[5-(Benzofuran-2-yl)-3-(4-hydroxyphenyl)-3,4-dihydropyrazole-2-carbonyl]-1-ethyl-7-methyl-1,8-naphthyridin-4-one；3-[5-(1-benzofuran-2-yl)-3-(4-hydroxyphenyl)-3,4-dihydropyrazole-2-carbonyl]-1-ethyl-7-methyl-1,8-naphthyridin-4-one
• CAS: 1246467-71-9
• 化学式: C₂₉H₂₄N₄O₄
• 分子量: 492.534
• InChiKey: XPHLXQVKRAOQJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(1-苯并呋喃-2-基)-3-(4-羟基苯基)丙-2-烯-1-酮 、 nalidixic acid hydrazide 在 溶剂黄146 作用下， 120.0 ℃ 、1.0 MPa 条件下， 反应 0.23h， 以89%的产率得到3-[(3-benzo[b]furan-2-yl-5-(4-hydroxyphenyl)-4,5-dihydro-1H-1-pyrazolyl)carbonyl]-1-ethyl-7-methyl-1,4-dihydro[1,8]naphthyridin-4-one
  参考文献：
  名称：

  Design, synthesis, and antitubercular evaluation of novel series of 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs

  摘要：

  Twenty-eight newer 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs were synthesized by microwave irradiation method and evaluated for in-vitro and in-vivo antitubercular activity against multidrug-resistant M. tuberculosis stains. Structure activity relationship study was carried out and found NO2 (o) substituted 3-benzo-furan-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin was most potent antitubercular agent against M. tuberculosis, even better than standard drug isoniazid and comparable with rifampin. Other synthesized compounds 7j, 7f, 7a, 7e and 5d, 5f were found moderate to good activity in in-vitro model at lower IC50 values 85 mu M, 154 mu M, 157 mu M, 164 mu M, 170 mu M and 190 mu ML respectively. In in-vivo animal model compound 7j was drastically reduced the bacterial load in lung and spleen tissues at the dose of 25 mg/kg body weight. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.035