2-[3-(1-Benzofuran-2-yl)-3-oxoprop-1-en-1-yl]benzoic acid | 766529-55-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-[3-(1-Benzofuran-2-yl)-3-oxoprop-1-en-1-yl]benzoic acid
• 英文别名: 2-[3-(1-benzofuran-2-yl)-3-oxoprop-1-enyl]benzoic acid
• CAS: 766529-55-9
• 化学式: C₁₈H₁₂O₄
• 分子量: 292.291
• InChiKey: OSKPTNCBYABGDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  173-175 °C
• 沸点：
  506.6±50.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[3-(1-Benzofuran-2-yl)-3-oxoprop-1-en-1-yl]benzoic acid 、 nalidixic acid hydrazide 在 溶剂黄146 作用下， 120.0 ℃ 、1.0 MPa 条件下， 反应 0.23h， 以87%的产率得到3-[(3-benzo[b]furan-2-yl-5-(2-carboxyphenyl)-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
• 作为产物：
  描述：

  2-乙酰基苯并呋喃 、 邻羧基苯甲醛 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 130.0 ℃ 、1.0 MPa 条件下， 反应 0.17h， 生成 2-[3-(1-Benzofuran-2-yl)-3-oxoprop-1-en-1-yl]benzoic acid
  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

文献信息

• 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
  作者：Kuntal Manna、Yadvendra K. Agrawal

  DOI：10.1016/j.ejmech.2010.05.035

  日期：2010.9

  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.