4-(7-methoxy-2,3-dihydrobenzo[1,4]oxathiin-2-yl)phenol | 1046446-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(7-methoxy-2,3-dihydrobenzo[1,4]oxathiin-2-yl)phenol
• 英文别名: 4'-hydroxy-7-methoxy-4-thiaflavan；4-(7-Methoxy-2,3-dihydro-1,4-benzoxathiin-2-yl)phenol
• CAS: 1046446-88-1
• 化学式: C₁₅H₁₄O₃S
• 分子量: 274.34
• InChiKey: VMYISDREFRJQAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-hydroxy-4-methoxyphenylthio)phthalimide 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 4-(7-methoxy-2,3-dihydrobenzo[1,4]oxathiin-2-yl)phenol
  参考文献：
  名称：

  Thiaflavan scavenges radicals and inhibits DNA oxidation: A story from the ferrocene modification

  摘要：

  4-Thiaflavan is a sulfur-substituted flavonoid with a benzoxathiin scaffold. The aim of this work is to compare abilities of sulfur and oxygen atom, hydroxyl groups, and ferrocene moiety at different positions of 4-thiaflavan to trap radicals and to inhibit DNA oxidation. It is found that abilities of thiaflavans to trap radicals and to inhibit DNA oxidation are increased in the presence of ferrocene moiety and are further improved by the electron-donating group attaching to thiaflavan skeleton. It can be concluded that the ferrocene moiety plays the major role for thiaflavans to be antioxidants even in the absence of phenolic hydroxyl groups. On the other hand, the antioxidant effectiveness of phenolic hydroxyl groups in thiaflavans can be improved by the electron-donating group. The influences of sulfur and oxygen atoms in thiaflavans on the antioxidant property of para-hydroxyl group exhibit different manners when the thiaflavans are used to trap radicals and to inhibit DNA oxidation. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.081

文献信息

• Antimycotic activity of 4-thioisosteres of flavonoids towards yeast and yeast-like microorganisms
  作者：Pietro Buzzini、Stefano Menichetti、Chiara Pagliuca、Caterina Viglianisi、Eva Branda、Benedetta Turchetti

  DOI：10.1016/j.bmcl.2008.05.048

  日期：2008.7

  Different substituted methoxy- and hydroxy-4-thioisosteres of flavonoids were prepared and their in vitro antimycotic activity towards yeast (Candida spp., Clavispora spp., Cryptococcus spp., Filobasidiella spp., Issatchenkia spp., Pichia spp., Kluyveromyces spp., Saccharomyces spp. and Yarrowia spp.) and yeast-like (Prototheca spp.) microorganisms was tested. Further insights in the biological activities of these antioxidant, oestrogenic and antimicrobial biomimetic derivatives were obtained. (C) 2008 Elsevier Ltd. All rights reserved.
• Thiaflavan scavenges radicals and inhibits DNA oxidation: A story from the ferrocene modification
  作者：Hai-Wang Lai、Zai-Qun Liu

  DOI：10.1016/j.ejmech.2014.04.081

  日期：2014.6

  4-Thiaflavan is a sulfur-substituted flavonoid with a benzoxathiin scaffold. The aim of this work is to compare abilities of sulfur and oxygen atom, hydroxyl groups, and ferrocene moiety at different positions of 4-thiaflavan to trap radicals and to inhibit DNA oxidation. It is found that abilities of thiaflavans to trap radicals and to inhibit DNA oxidation are increased in the presence of ferrocene moiety and are further improved by the electron-donating group attaching to thiaflavan skeleton. It can be concluded that the ferrocene moiety plays the major role for thiaflavans to be antioxidants even in the absence of phenolic hydroxyl groups. On the other hand, the antioxidant effectiveness of phenolic hydroxyl groups in thiaflavans can be improved by the electron-donating group. The influences of sulfur and oxygen atoms in thiaflavans on the antioxidant property of para-hydroxyl group exhibit different manners when the thiaflavans are used to trap radicals and to inhibit DNA oxidation. (C) 2014 Elsevier Masson SAS. All rights reserved.