5,7-Dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5,7-Dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
• 英文别名: 5,7-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
• 化学式: C₁₆H₁₄O₆
• 分子量: 302.28
• InChiKey: OKZDPTMCZVSTDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲氧基-4-(甲氧基甲氧基)苯甲醛 在 盐酸 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 水 为溶剂， 反应 30.0h， 生成 5,7-Dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  10.1002/cmdc.202400056

  摘要：

  Neuroinflammation is an inflammatory immune response that arises in the central nervous system. It is one of the primary causes of neurodegenerative diseases, such as Alzheimer’s disease and Parkinson’s disease. Phloroglucinol (PG) is a natural product contained in extracts of plant, algae and microbe and has been reported to have antioxidant and anti‐inflammatory properties. In this study, we synthesized PG derivatives to enhance their antioxidant and anti‐inflammatory activity. Among PG derivatives, 6a suppressed pro‐oxidative and inflammatory molecule nitric oxide (NO) production more effectively than PG. Moreover, 6a dose‐dependently reduced the expression of proinflammatory cytokines such as IL‐6, IL‐1β, TNF‐α, and NO producing enzyme iNOS in lipopolysaccharide (LPS)‐stimulated BV‐2 microglial cells. Additionally, we confirmed that 6a alleviated cognitive impairment and glial activation in mouse model of LPS‐induced neuroinflammation. These findings suggest that novel PG derivative, 6a, is a potential treatment for neurodegenerative diseases.

  DOI：

  10.1002/cmdc.202400056

文献信息

• 10.1002/cmdc.202400056
  作者：Kim, Jushin、Won Choi, Ji、Jeong Kim, Hyeon、Kim, Byungeun、Kim, Yoowon、Hwejin Lee, Elijah、Kim, Rium、Kim, Jaehwan、Park, Jiwoo、Jeong, Yeeun、Park, Jong-Hyun、Duk Park, Ki

  DOI：10.1002/cmdc.202400056

  日期：——

  Neuroinflammation is an inflammatory immune response that arises in the central nervous system. It is one of the primary causes of neurodegenerative diseases, such as Alzheimer’s disease and Parkinson’s disease. Phloroglucinol (PG) is a natural product contained in extracts of plant, algae and microbe and has been reported to have antioxidant and anti‐inflammatory properties. In this study, we synthesized PG derivatives to enhance their antioxidant and anti‐inflammatory activity. Among PG derivatives, 6a suppressed pro‐oxidative and inflammatory molecule nitric oxide (NO) production more effectively than PG. Moreover, 6a dose‐dependently reduced the expression of proinflammatory cytokines such as IL‐6, IL‐1β, TNF‐α, and NO producing enzyme iNOS in lipopolysaccharide (LPS)‐stimulated BV‐2 microglial cells. Additionally, we confirmed that 6a alleviated cognitive impairment and glial activation in mouse model of LPS‐induced neuroinflammation. These findings suggest that novel PG derivative, 6a, is a potential treatment for neurodegenerative diseases.