2-hydroxymethyl-5-methoxy-3-methylbenzofuran-4,7-dione | 1435059-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxymethyl-5-methoxy-3-methylbenzofuran-4,7-dione
• 英文别名: 4,7-dihydro-2-(hydroxymethyl)-5-methoxy-3-methylbenzofuran-4,7-dione；2-(Hydroxymethyl)-5-methoxy-3-methyl-1-benzofuran-4,7-dione；2-(hydroxymethyl)-5-methoxy-3-methyl-1-benzofuran-4,7-dione
• CAS: 1435059-21-4
• 化学式: C₁₁H₁₀O₅
• 分子量: 222.197
• InChiKey: BJNUVBZVSJJFPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxymethyl-5-methoxy-3-methylbenzofuran-4,7-dione 、 N,N-二甲基乙二胺 以 乙腈 为溶剂， 反应 3.0h， 以100%的产率得到4,7-dihydro-5-(2-(dimethylamino)ethylamino)-2-(hydroxymethyl)-3-methylbenzofuran-4,7-dione
  参考文献：
  名称：

  Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation

  摘要：

  一系列苯并呋喃醌类化合物，作为海洋代谢物annulin A的类似物，已被合成并评估为人类吲哚胺2,3-双加氧酶（IDO）的抑制剂。合成过程通过铜(II)介导的溴化苯醌与1,3-二羰基化合物的反应，随后进行官能团转化。最具活性的化合物是含有3位CH2OR基团的5-甲氧基-2-甲基苯并呋喃醌，其IC50约为0.2 mM。相应的一氢醌无活性。基于苯并咪唑醌结构的化合物也是活性IDO抑制剂。醌类在抑制IDO的浓度下不会产生显著的氧化应激水平。

  DOI：

  10.1039/c3ob42258e
• 作为产物：
  描述：

  methyl 5-methoxy-3-methylbenzofuran-2-carboxylate 在 硝酸 、 溶剂黄146 、 盐酸 、 tin 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以53%的产率得到2-hydroxymethyl-5-methoxy-3-methylbenzofuran-4,7-dione
  参考文献：
  名称：

  Benzofuran-, benzothiophene-, indazole- and benzisoxazole-quinones: Excellent substrates for NAD(P)H:quinone oxidoreductase 1

  摘要：

  A series of heterocyclic quinones based on benzofuran, benzothiophene, indazole and benzisoxazole has been synthesized, and evaluated for their ability to function as substrates for recombinant human NAD(P)H:quinone oxidoreductase (NQO1), a two-electron reductase upregulated in tumor cells. Overall, the quinones are excellent substrates for NQO1, approaching the reduction rates observed for menadione. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.071

文献信息

• Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation
  作者：Catarina Carvalho、David Siegel、Martyn Inman、Rui Xiong、David Ross、Christopher J. Moody

  DOI：10.1039/c3ob42258e

  日期：——

  A series of benzofuranquinones, analogues of the marine metabolite annulin A, has been synthesized and evaluated as inhibitors of human indoleamine 2,3-dioxygenase (IDO). The synthesis was carried out by copper(II)-mediated reaction of bromobenzoquinones with 1,3-dicarbonyl compounds followed by functional group interconversions. The most potent compounds were 5-methoxy-2-methylbenzofuranquinones containing a CH2OR group at position-3 with IC50 ∼ 0.2 mM. The corresponding hydroquinones were inactive. Compounds based on the benzimidazolequinone framework are also active IDO inhibitors. The quinones do not generate significant levels of oxidative stress at concentrations that inhibit IDO.

  一系列苯并呋喃醌类化合物，作为海洋代谢物annulin A的类似物，已被合成并评估为人类吲哚胺2,3-双加氧酶（IDO）的抑制剂。合成过程通过铜(II)介导的溴化苯醌与1,3-二羰基化合物的反应，随后进行官能团转化。最具活性的化合物是含有3位CH2OR基团的5-甲氧基-2-甲基苯并呋喃醌，其IC50约为0.2 mM。相应的一氢醌无活性。基于苯并咪唑醌结构的化合物也是活性IDO抑制剂。醌类在抑制IDO的浓度下不会产生显著的氧化应激水平。
• Benzofuran-, benzothiophene-, indazole- and benzisoxazole-quinones: Excellent substrates for NAD(P)H:quinone oxidoreductase 1
  作者：Jeffery J. Newsome、Mary Hassani、Elizabeth Swann、Jane M. Bibby、Howard D. Beall、Christopher J. Moody

  DOI：10.1016/j.bmc.2013.03.071

  日期：2013.6

  A series of heterocyclic quinones based on benzofuran, benzothiophene, indazole and benzisoxazole has been synthesized, and evaluated for their ability to function as substrates for recombinant human NAD(P)H:quinone oxidoreductase (NQO1), a two-electron reductase upregulated in tumor cells. Overall, the quinones are excellent substrates for NQO1, approaching the reduction rates observed for menadione. (C) 2013 Elsevier Ltd. All rights reserved.