1-(5-hydroxy-7,8,9,10a-tetrahydro-6bH-naphtho[2′,1′:4,5]furo[2,3-b]pyran-6-yl)ethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 1-(5-hydroxy-7,8,9,10a-tetrahydro-6bH-naphtho[2′,1′:4,5]furo[2,3-b]pyran-6-yl)ethanone
• 英文别名: cis-1-(5-hydroxy-7,8,9,10a-tetrahydro-6bH-naphtho[2',1':4,5]furo[2,3-b]pyran-6-yl)ethanone；1-[(11S,16R)-8-hydroxy-15,17-dioxatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),2,4,6,8-pentaen-9-yl]ethanone
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: GWONZTGUOZNNPG-YVEFUNNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-二羟基萘 在 4-二甲氨基吡啶 、 ammonium cerium (IV) nitrate 、 三氟化硼乙醚 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 7.0h， 生成 1-(5-hydroxy-7,8,9,10a-tetrahydro-6bH-naphtho[2′,1′:4,5]furo[2,3-b]pyran-6-yl)ethanone
  参考文献：
  名称：

  Anti-tyrosinase, antioxidant, and antibacterial activities of novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans

  摘要：

  Novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans (7a-k) were synthesized using ceric ammonium nitrate (CAN)-catalyzed formal [3 + 21 cycloaddition. Synthesized compounds were evaluated for their tyrosinase inhibitory, antioxidant, and antibacterial activities. A modified spectrophotometric method using L-DOPA as substrate was used to determine tyrosinase inhibitory activities, and a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay was used to evaluate antioxidant properties. Antibacterial activities against gram-negative Escherichia colt (KTC-1924) and gram-positive Staphylococcus aureus (KTC-1916) were evaluated using the disc diffusion technique. Of the synthesized compounds, 7b with a 4-acetyl and an electron-enriched dihydronaphthofuran ring showed the highest tyrosinase-inhibition activity (IC50 = 8.91 mu g/mL), which was comparable with that of standard kojic acid (IC50 = 10.16 mu g/ mL), potent antioxidant activity (IC50 = 3.33 mu g/mL), which was comparable with that of BHT (IC50 = 34.67 mu g/mL), and excellent antibacterial activities (MICs: 0.50 mu g/mL against E. coli and S. aureus strains). A mechanistic analysis of 7b demonstrated that its tyrosinase inhibitory activity was reversible and competitive. Compounds 7c and 7d showed potent antioxidant activities (IC50: 6.30 and 5.01 mu g/mL), and compound 7d also exhibited potent inhibitory activity against E. coli with a MIC of 0.5 mu g/mL. Furthermore, compounds 7a, 7e, 7f, and 7i showed potent antibacterial activities against S. aureus with MICs of 0.5 mu g/mL, which was comparable to that of ampicillin (MIC = 0.5 mu g/mL). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.025

文献信息

• A novel and efficient synthesis of diverse dihydronaphtho[1,2-b]furans using the ceric ammonium nitrate-catalyzed formal [3 + 2] cycloaddition of 1,4-naphthoquinones to olefins and its application to furomollugin
  作者：Likai Xia、Yong Rok Lee

  DOI：10.1039/c3ob40977e

  日期：——

  A novel approach was developed for the synthesis of diverse dihydronaphtho[1,2-b]furans from 1,4-naphthoquinones and olefins in the presence of ceric ammonium nitrate. This reaction provides a rapid route for the synthesis of a variety of dihydronaphtho[1,2-b]furans and naphtho[1,2-b]furans bearing different substituents. This methodology was also used to synthesize the biologically important natural

  开发了一种新的方法，用于在硝酸铈铵的存在下，由1,4-萘醌和烯烃合成各种二氢萘[1,2- b ]呋喃。该反应为合成各种带有不同取代基的二氢萘并[1,2- b ]呋喃和萘并[1,2- b ]呋喃提供了一条快速途径。该方法也仅用两个步骤就可以合成生物学上重要的天然产物呋喃洛金。
• KR2015/64952
  申请人：——

  公开号：——

  公开（公告）日：——
• Anti-tyrosinase, antioxidant, and antibacterial activities of novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans
  作者：Likai Xia、Akber Idhayadhulla、Yong Rok Lee、Young-Jung Wee、Sung Hong Kim

  DOI：10.1016/j.ejmech.2014.09.025

  日期：2014.10

  Novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans (7a-k) were synthesized using ceric ammonium nitrate (CAN)-catalyzed formal [3 + 21 cycloaddition. Synthesized compounds were evaluated for their tyrosinase inhibitory, antioxidant, and antibacterial activities. A modified spectrophotometric method using L-DOPA as substrate was used to determine tyrosinase inhibitory activities, and a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay was used to evaluate antioxidant properties. Antibacterial activities against gram-negative Escherichia colt (KTC-1924) and gram-positive Staphylococcus aureus (KTC-1916) were evaluated using the disc diffusion technique. Of the synthesized compounds, 7b with a 4-acetyl and an electron-enriched dihydronaphthofuran ring showed the highest tyrosinase-inhibition activity (IC50 = 8.91 mu g/mL), which was comparable with that of standard kojic acid (IC50 = 10.16 mu g/ mL), potent antioxidant activity (IC50 = 3.33 mu g/mL), which was comparable with that of BHT (IC50 = 34.67 mu g/mL), and excellent antibacterial activities (MICs: 0.50 mu g/mL against E. coli and S. aureus strains). A mechanistic analysis of 7b demonstrated that its tyrosinase inhibitory activity was reversible and competitive. Compounds 7c and 7d showed potent antioxidant activities (IC50: 6.30 and 5.01 mu g/mL), and compound 7d also exhibited potent inhibitory activity against E. coli with a MIC of 0.5 mu g/mL. Furthermore, compounds 7a, 7e, 7f, and 7i showed potent antibacterial activities against S. aureus with MICs of 0.5 mu g/mL, which was comparable to that of ampicillin (MIC = 0.5 mu g/mL). (C) 2014 Elsevier Masson SAS. All rights reserved.