5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2:5,4-b'>dipyran | 106038-24-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2:5,4-b'>dipyran
• 英文别名: 5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2-b:5,4-b'>dipyran；2,6-dihydro-5-methoxy-8-methylpyrano[3,2-g][1]benzopyran-2,6-dione；5-methoxy-8-methylpyrano[3,2-g]chromen-2,6-dione；5-Methoxy-8-methylpyrano[3,2-g]chromene-2,6-dione
• CAS: 106038-24-8
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: MJWKARBCOYYLJA-UHFFFAOYSA-N

物化性质

• 沸点：
  493.8±45.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2:5,4-b'>dipyran 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到7-Hydroxy-5-methoxy-6-(5-methyl-1H-pyrazol-3-yl)-chromen-2-one
  参考文献：
  名称：

  Soliman, Fouad M.; Khalil, Khairia M.; Elnaem, Shweekar I., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 60, # 3/4, p. 183 - 187

  摘要：

  DOI：
• 作为产物：
  描述：

  7-hydroxy-5-methoxy-2-methyl-6-[(phenylimino)methyl]-4H-chromen-4-one 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.0h， 生成 5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2:5,4-b'>dipyran
  参考文献：
  名称：

  磷叶立德化学。第 34 部分 Chromenone Phosphanylidene 和 Cyclobutylidene 衍生物的合成

  摘要：

  摘要 亲核磷杂草烯叶立德与visnaginone 和khellinone 反应得到相应的亚膦基和呋喃色烯衍生物。此外，吡喃色烯是从色烯甲醛与磷枯草烯的反应中获得的。另一方面，亚膦基-亚环丁基及其二聚体是由呋喃色烯甲醛与相同的鏻试剂反应产生的。图形概要

  DOI：

  10.1080/10426507.2011.600741

文献信息

• 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.
• Atta, Sanaa M. S.; Hafez, Taghrid S.; Mahran, Mohamed R., Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 80, # 1-4, p. 109 - 116
  作者：Atta, Sanaa M. S.、Hafez, Taghrid S.、Mahran, Mohamed R.

  DOI：——

  日期：——