2,3-dihydro-2,5-dihydroxy-4H-chromen-4-one | 55818-37-6

• 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: 2,3-dihydro-2,5-dihydroxy-4H-chromen-4-one
• 英文别名: 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one；2,5-Dihydroxy-2,3-dihydro-4H-1-benzopyran-4-one；2,5-dihydroxy-2,3-dihydrochromen-4-one
• CAS: 55818-37-6
• 化学式: C₉H₈O₄
• 分子量: 180.16
• InChiKey: SFJMPMHMKPKFLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-[2,6-bis(benzyloxy)phenyl]-3-oxopropanal 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 26.0h， 以33%的产率得到2,3-dihydro-2,5-dihydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Towards the first inhibitors of trihydroxynaphthalene reductase from Curvularia lunata: Synthesis of artificial substrate, homology modelling and initial screening

  摘要：

  Trihydroxynaphthalene reductase (3HNR) is an essential enzyme in the biosynthesis of fungal melanin and it represents an emerging target for the development of new fungicides and antimicotics. To promote the discovery of new inhibitors, an improved chemical synthesis of the artificial substrate 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one (DDBO) was developed. A series of compounds were screened on 3HNR from Curvularia lunata, a known plant pathogen and an opportunistic human pathogen, and several structurally diverse hits were obtained. Homology modelling of 3HNR from C. lunata can explain their binding modes and will enable further structure-based design of new and improved inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.066

文献信息

• Towards the first inhibitors of trihydroxynaphthalene reductase from Curvularia lunata: Synthesis of artificial substrate, homology modelling and initial screening
  作者：Mojca Brunskole、Bogdan Štefane、Karmen Zorko、Marko Anderluh、Jure Stojan、Tea Lanišnik Rižner、Stanislav Gobec

  DOI：10.1016/j.bmc.2008.04.066

  日期：2008.6

  Trihydroxynaphthalene reductase (3HNR) is an essential enzyme in the biosynthesis of fungal melanin and it represents an emerging target for the development of new fungicides and antimicotics. To promote the discovery of new inhibitors, an improved chemical synthesis of the artificial substrate 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one (DDBO) was developed. A series of compounds were screened on 3HNR from Curvularia lunata, a known plant pathogen and an opportunistic human pathogen, and several structurally diverse hits were obtained. Homology modelling of 3HNR from C. lunata can explain their binding modes and will enable further structure-based design of new and improved inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.