2-[3-(4-Nitrophenyl)acryloyl]-3H-naphtho[2,1-b]pyran-3-one | 107096-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-[3-(4-Nitrophenyl)acryloyl]-3H-naphtho[2,1-b]pyran-3-one
• 英文别名: 2-[3-(4-nitrophenyl)prop-2-enoyl]benzo[f]chromen-3-one
• CAS: 107096-89-9
• 化学式: C₂₂H₁₃NO₅
• 分子量: 371.349
• InChiKey: RIUHIBIWHUVSTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-(4-Nitrophenyl)acryloyl]-3H-naphtho[2,1-b]pyran-3-one 、 2-(4-氟-苯基)-乙脒盐酸盐 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以80%的产率得到2-(2-(4-fluorobenzyl)-6-(4-nitrophenyl)pyrimidin-4-yl)-3H-benzo[f]chromen-3-one
  参考文献：
  名称：

  Design, synthesis of benzocoumarin-pyrimidine hybrids as novel class of antitubercular agents, their DNA cleavage and X-ray studies

  摘要：

  A series of 2-(2-(4-fluorobenzyl)-6-(substituted phenyl) pyrimidin-4-yl)-3H-benzo[f]chromen-3-one derivatives (1a-1o) were selectively prepared in high yields under microwave irradiation. The synthesized compounds were characterized by elemental and spectroscopic analysis; in addition the structures of compound (1a), (1b) and (1j) were elucidated by the X-ray diffraction technique. Compounds (1a-1o) were evaluated for their in-vitro antitubercular activity while the most active compounds were further subjected for their cytotoxicity and DNA cleavage study. Results revealed that most of the tested compounds displayed potent antitubercular activity with MIC in the range 0.05-2.81 mu g/mL. Among them, compound (1b) possessed excellent activity (MIC 0.05 mu g/mL) against M.tb H(37)Rv, strain and exhibited low level of cytotoxicity against Vero cells, which suggested compound (1b) is a promising lead for subsequent investigation in search of new antitubercular agents. DNA cleavage by gel electrophoresis method revealed that compounds (1b, 1g, 1k and 1n) were found to cleave the DNA completely. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.056

文献信息

• Design, synthesis of benzocoumarin-pyrimidine hybrids as novel class of antitubercular agents, their DNA cleavage and X-ray studies
  作者：Dinesh S. Reddy、Kallappa M. Hosamani、Hirihalli C. Devarajegowda

  DOI：10.1016/j.ejmech.2015.06.056

  日期：2015.8

  A series of 2-(2-(4-fluorobenzyl)-6-(substituted phenyl) pyrimidin-4-yl)-3H-benzo[f]chromen-3-one derivatives (1a-1o) were selectively prepared in high yields under microwave irradiation. The synthesized compounds were characterized by elemental and spectroscopic analysis; in addition the structures of compound (1a), (1b) and (1j) were elucidated by the X-ray diffraction technique. Compounds (1a-1o) were evaluated for their in-vitro antitubercular activity while the most active compounds were further subjected for their cytotoxicity and DNA cleavage study. Results revealed that most of the tested compounds displayed potent antitubercular activity with MIC in the range 0.05-2.81 mu g/mL. Among them, compound (1b) possessed excellent activity (MIC 0.05 mu g/mL) against M.tb H(37)Rv, strain and exhibited low level of cytotoxicity against Vero cells, which suggested compound (1b) is a promising lead for subsequent investigation in search of new antitubercular agents. DNA cleavage by gel electrophoresis method revealed that compounds (1b, 1g, 1k and 1n) were found to cleave the DNA completely. (C) 2015 Elsevier Masson SAS. All rights reserved.