1,3-dihydroxy-5,8-dimethoxyxanthone | 114567-42-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1,3-dihydroxy-5,8-dimethoxyxanthone
• 英文别名: 1,3‐dihydroxy‐5,8‐dimethoxy‐9H‐xanthen‐9‐one；1,3-Dihydroxy-5,8-dimethoxy-9H-xanthen-9-one；1,3-dihydroxy-5,8-dimethoxyxanthen-9-one
• CAS: 114567-42-9
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: NZEMKDUWMYIOOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-dihydroxy-5,8-dimethoxyxanthone 在 吗啉 作用下， 生成 1,3,5,8-四羟基-2,4-双(3-甲基-2-丁烯基)-9H-氧杂蒽-9-酮
  参考文献：
  名称：

  1,3,5,8-四氧合氧杂蒽在热水溶液吗啉中的重排

  摘要：

  2-异戊烯基-1-羟基-3,5,8-三甲氧基黄酮的吗啉去甲基化反应可得到1,3,5,8-和1,3,7,8-四氧杂蒽酮的混合物。

  DOI：

  10.1016/s0040-4039(01)93954-1
• 作为产物：
  描述：

  1-glucosyloxy-3-hydroxy-5,8-dimethoxyxanthone 在 emulsin 作用下， 生成 1,3-dihydroxy-5,8-dimethoxyxanthone
  参考文献：
  名称：

  来自 Swertia petiolata 的三和四氧化氧杂蒽酮

  摘要：

  摘要 一种新的四氧化氧杂蒽酮糖苷：1-葡糖氧基-3-羟基-5,8-二甲氧基氧杂蒽酮与1,8-二羟基-3,5-二甲氧基氧杂蒽酮；1,3-二羟基-7-甲氧基氧杂蒽酮和1,7-二羟基-3-甲氧基氧杂蒽酮。

  DOI：

  10.1016/0031-9422(90)85439-m

文献信息

• 1,3,5,8-四羟基呫吨酮和1,3,7,8-四羟基呫吨酮的制备方法
  申请人：广州药本君安医药科技股份有限公司

  公开号：CN110156739A

  公开（公告）日：2019-08-23

  本发明公开了1,3,5,8‑四羟基呫吨酮和1,3,7,8‑四羟基呫吨酮的制备方法，该方法包括以下步骤：以1,2,4‑三甲氧基苯为起始原料，加入正丁基锂和氯甲酸酯反应，生成2,3,6‑三甲氧基苯甲酸甲酯；加入碱反应，生成2,3,6‑三甲氧基苯甲酸；加入均苯三酚，再加入伊顿试剂反应，生成1,3‑二羟基‑5(7),8‑二甲氧基呫吨酮异构体混合物；最后加入试剂A反应，生成1,3,5,8‑四羟基呫吨酮和1,3,7,8‑四羟基呫吨酮异构体混合物，经过分离，得到产物。本发明中1,3,5,8‑四羟基呫吨酮和1,3,7,8‑四羟基呫吨酮的制备方法，具有反应条件温和、合成试剂环境友好、步骤简洁、反应总收率较高的特点。
• BENNETT, GRAHAM J.;LEE, HIOK-HUANG, TETRAHEDRON LETT., 30,(1989) N1, C. 7265-7268
  作者：BENNETT, GRAHAM J.、LEE, HIOK-HUANG

  DOI：——

  日期：——
• KHETWAL, KHADGA S.;JOSHI, BINITA;BISHT, R. S., PHYTOCHEMISTRY, 29,(1990) N, C. 1265-1267
  作者：KHETWAL, KHADGA S.、JOSHI, BINITA、BISHT, R. S.

  DOI：——

  日期：——
• KULANTHAIVEL, PALANIAPPAN;PELLETIER, S. WILLIAM;KHETWAL, KHADGA S.;VERMA,+, J. NATUR. PROD., 51,(1988) N 2, 379-381
  作者：KULANTHAIVEL, PALANIAPPAN、PELLETIER, S. WILLIAM、KHETWAL, KHADGA S.、VERMA,+

  DOI：——

  日期：——
• Xanthones with multiple roles against diabetes: their synthesis, structure‐activity relationship, and mechanism studies
  作者：Youhong Ke、Qinfang Xu、Jianling Hu、Jianrun Zhang、Shijian Chen、Zhijun Liu、Shuling Peng、Chao Zhang、Zhenqiang Chen、Heru Chen

  DOI：10.1002/ddr.22170

  日期：2024.4

  A four‐step synthetic process has been developed to prepare 1,3,5,8‐tetrahydroxyxanthone (2a) and its isomer 1,3,7,8‐tetrahydroxyxanthone (2b). 25 more xanthones were also synthesized by a modified scheme. Xanthone 2a was identified as the most active inhibitor against both α‐glucosidase and aldose reductase (ALR2), with IC₅₀ values of 7.8 ± 0.5 μM and 63.2 ± 0.6 nM, respectively, which was far active than acarbose (35.0 ± 0.1 μM), and a little more active than epalrestat (67.0 ± 3.0 nM). 2a was also confirmed as the most active antioxidant in vitro with EC₅₀ value of 8.9 ± 0.1 μM. Any structural modification including methylation, deletion, and position change of hydroxyl group in 2a will cause an activity loss in inhibitory and antioxidation. By applying a H₂O₂‐induced oxidative stress nematode model, it was confirmed that xanthone 2a can be absorbed by Caenorhabditis elegans and is bioavailable to attenuate in vivo oxidative stress, including the effects on lifespan, superoxide dismutase, Catalase, and malondialdehyde. 2a was verified with in vivo hypoglycemic effect and mitigation of embryo malformations in high glucose. All our data support that xanthone 2a behaves triple roles and is a potential agent to treat diabetic mellitus, gestational diabetes mellitus, and diabetic complications.