5-chloro-1,3,8-trihydroxyxanthone | 134369-96-3

• 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: 5-chloro-1,3,8-trihydroxyxanthone
• 英文别名: 1,3,8‐trihydroxy‐5‐chloro‐9H‐xanthen‐9‐one；5-Chloro-1,3,8-trihydroxyxanthen-9-one
• CAS: 134369-96-3
• 化学式: C₁₃H₇ClO₅
• 分子量: 278.649
• InChiKey: VVSMUFLGGRLGLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3,8-Trihydroxy-5-nitroxanthen-9-one 在 盐酸 、 palladium 10% on activated carbon 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 13.0h， 生成 5-chloro-1,3,8-trihydroxyxanthone
  参考文献：
  名称：

  Xanthones with multiple roles against diabetes: their synthesis, structure‐activity relationship, and mechanism studies

  摘要：

  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.

  DOI：

  10.1002/ddr.22170

文献信息

• Patel G N; Trivedi K N, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 4, p. 437 - 439
  作者：Patel G N、Trivedi K N

  DOI：——

  日期：——