ethyl-3-methyl-1-(thiophen-2-yl)-1H-benzo(f)chromene-2-carboxylate | 1539312-37-2

• 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: ethyl-3-methyl-1-(thiophen-2-yl)-1H-benzo(f)chromene-2-carboxylate
• 英文别名: ethyl 3-methyl-1-thiophen-2-yl-1H-benzo[f]chromene-2-carboxylate
• CAS: 1539312-37-2
• 化学式: C₂₁H₁₈O₃S
• 分子量: 350.438
• InChiKey: VCGXVFYPEZBJLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 乙酰乙酸乙酯 、 2-萘酚 在 fluoroboric acid adsorbed on silica 作用下， 以 neat (no solvent) 为溶剂， 以74%的产率得到ethyl-3-methyl-1-(thiophen-2-yl)-1H-benzo(f)chromene-2-carboxylate
  参考文献：
  名称：

  Microwave assisted synthesis of naphthopyrans catalysed by silica supported fluoroboric acid as a new class of non purine xanthine oxidase inhibitors

  摘要：

  A series of naphthopyrans was synthesized employing silica supported fluoroboric acid under solvent free conditions in a microwave reactor. The catalytic influence of HBF4-SiO2 was investigated in detail to optimize the reaction conditions. The synthesised compounds were evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Structure-activity relationship analyses have also been presented. Among the synthesised compounds, NP-17, NP-19, NP-20, NP-23, NP-24, NP-25 and NP-26 were the active inhibitors with an IC50 ranging from 4 to 17 mu M. Compound NP-19 with a thiophenyl ring at position 1 emerged as the most potent xanthine oxidase inhibitor (IC50 = 4 mu M) in comparison to allopurinol (IC50 = 11.10 mu M) and febuxostat (IC50 = 0.025 mu M). The basis of significant inhibition of xanthine oxidase by NP-19 was rationalized by its molecular docking at MTE binding site of xanthine oxidase. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.031

文献信息

• Microwave assisted synthesis of naphthopyrans catalysed by silica supported fluoroboric acid as a new class of non purine xanthine oxidase inhibitors
  作者：Sahil Sharma、Kirti Sharma、Ritu Ojha、Dinesh Kumar、Gagandip Singh、Kunal Nepali、P.M.S. Bedi

  DOI：10.1016/j.bmcl.2013.12.031

  日期：2014.1

  A series of naphthopyrans was synthesized employing silica supported fluoroboric acid under solvent free conditions in a microwave reactor. The catalytic influence of HBF4-SiO2 was investigated in detail to optimize the reaction conditions. The synthesised compounds were evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Structure-activity relationship analyses have also been presented. Among the synthesised compounds, NP-17, NP-19, NP-20, NP-23, NP-24, NP-25 and NP-26 were the active inhibitors with an IC50 ranging from 4 to 17 mu M. Compound NP-19 with a thiophenyl ring at position 1 emerged as the most potent xanthine oxidase inhibitor (IC50 = 4 mu M) in comparison to allopurinol (IC50 = 11.10 mu M) and febuxostat (IC50 = 0.025 mu M). The basis of significant inhibition of xanthine oxidase by NP-19 was rationalized by its molecular docking at MTE binding site of xanthine oxidase. (C) 2013 Elsevier Ltd. All rights reserved.