6,7-dihydroxy-5-methoxy-2-methyl-4H-[1]benzopyran-4-one | 16623-15-7

• 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: 6,7-dihydroxy-5-methoxy-2-methyl-4H-[1]benzopyran-4-one
• 英文别名: 5-methoxy-6,7-di-hydroxy-2-methylchromone；6,7-dihydroxy-5-methoxy-2-methyl-chromen-4-one；6,7-Dihydroxy-5-methoxy-2-methyl-chromen-4-on；6,7-Dihydroxy-5-methoxy-2-methyl-chromon；6,7-Dihydroxy-5-methoxy-2-methylchromen-4-one
• CAS: 16623-15-7
• 化学式: C₁₁H₁₀O₅
• 分子量: 222.197
• InChiKey: MQDLSRDVQWNJHN-UHFFFAOYSA-N

物化性质

• 熔点：
  229 °C(Solv: water (7732-18-5))
• 沸点：
  483.6±45.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-dihydroxy-5-methoxy-2-methyl-4H-[1]benzopyran-4-one 在 盐酸 作用下， 生成 5,6,7-三羟基-2-甲基-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  Furo-chromones and -Coumarins. IX. Reactions of Khellol Glucoside, Visnagin and Bergapten

  摘要：

  DOI：

  10.1021/ja01609a066
• 作为产物：
  描述：

  7-羟基-5-甲氧基-2-甲基-4-氧代-4H-1-苯并吡喃-6-甲醛 在 sodium hydroxide 、 水 、 双氧水 、 盐酸 作用下， 以86%的产率得到6,7-dihydroxy-5-methoxy-2-methyl-4H-[1]benzopyran-4-one
  参考文献：
  名称：

  4-Phenoxybutoxy-substituted heterocycles – A structure–activity relationship study of blockers of the lymphocyte potassium channel Kv1.3

  摘要：

  The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC(50) of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC(50)s of 150 nM to 10 mu M in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC(50) 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.10.033

文献信息

• Concise Synthesis of 5-Methoxy-6-hydroxy-2-methylchromone-7-<i>O</i>- and 5-Hydroxy-2-methylchromone-7-<i>O</i>-rutinosides. Investigation of Their Cytotoxic Activities against Several Human Tumor Cell Lines
  作者：Baolin Wu、Wenpeng Zhang、Zhonghua Li、Li Gu、Xin Wang、Peng George Wang

  DOI：10.1021/jo102325s

  日期：2011.4.1

  The synthesis of two novel 2-methylchromone-7-O-rutinosides is reported, and the in vitro biological activities of these compounds and their synthetic precursors have been investigated on the basis of their cytotoxicity against several human tumor cell lines. The synthesis features early stage assembly of the acidic labile glycosidic bond between sugar and 2-methylchromone aglycon under phase transfer catalyzed glycosidation conditions, whereas all the other standard glycosylation conditions specific to a wide array of rutinosyl donors bearing different anomeric leaving groups (e.g., SPh, OC(NH)CCl3, Br, OH groups) failed to furnish any detectable products.
• 4-Phenoxybutoxy-substituted heterocycles – A structure–activity relationship study of blockers of the lymphocyte potassium channel Kv1.3
  作者：Silke B. Bodendiek、Cédrick Mahieux、Wolfram Hänsel、Heike Wulff

  DOI：10.1016/j.ejmech.2008.10.033

  日期：2009.5

  The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC(50) of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC(50)s of 150 nM to 10 mu M in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC(50) 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Furo-chromones and -Coumarins. IX. Reactions of Khellol Glucoside, Visnagin and Bergapten
  作者：Alexander Schönberg、Nasry Badran、Nicolas A. Starkowsky

  DOI：10.1021/ja01609a066

  日期：1955.2