(7-methoxybenzofuran-2-yl)(3-methoxyphenyl)methanone | 497058-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7-methoxybenzofuran-2-yl)(3-methoxyphenyl)methanone
• 英文别名: 7-Methoxy-2-(3-methoxybenzoyl)benzofuran；(7-methoxy-1-benzofuran-2-yl)-(3-methoxyphenyl)methanone
• CAS: 497058-32-9
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: DPDDHDGIOOMGKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2Z)-7-methoxy-2-[(3-methoxyphenyl)methylidene]-1-benzofuran-3-one 在 盐酸 、 manganese(IV) oxide 、 sodium tetrahydroborate 、 水 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 1.84h， 生成 (7-methoxybenzofuran-2-yl)(3-methoxyphenyl)methanone
  参考文献：
  名称：

  A straightforward conversion of aurones to 2-benzoylbenzofurans: transformation of one class of natural products into another

  摘要：

  The naturally occurring aurones (2-benzylidene-3(2H)-benzofuran-3-ones) can be easily converted to another class of natural products 2-benzoylbenzo[b]furans, via an effective reduction, acid-mediated rearrangement, and oxidation cascade. This easy conversion was conducted without purification of intermediates. This straightforward conversion may be considered as a possible biosynthesis pathway of 2-benzoylbenzo[b]furans in plants. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.011

文献信息

• Exploration of benzofuran-based compounds as potent and selective Plasmodium falciparum glycogen synthase kinase-3 (PfGSK-3) inhibitors
  作者：Chantalle Moolman、Rencia van der Sluis、Richard M. Beteck、Lesetja J. Legoabe

  DOI：10.1016/j.bioorg.2021.104839

  日期：2021.7

  inhibited PfGSK-3, with four of these compounds exhibiting IC50 values in the sub-micromolar range (0.00048–0.440 µM). Evaluation of the structure-activity relationships required for PfGSK-3 selective inhibition indicated that a C6-OCH3 substitution on ring A is preferred, while the effect of the ring B substituent on activity, in decreasing order is: C4′-CN > C4′-F > C3′-OCH3 > C3′,4′-diCl. To date,

  恶性疟原虫糖原合酶激酶-3 ( Pf GSK-3) 已被确定为开发针对多药耐药疟疾的新型药物的潜在靶标。合成并评估了一系列基于苯并呋喃的化合物作为重组表达和纯化的Pf GSK-3 和人糖原合酶激酶-3 β ( Hs GSK-3β) 的抑制剂。在该系列中，五种化合物（5k、5m、5p、5r、5s）优先抑制Pf GSK-3，其中四种化合物表现出 IC 50亚微摩尔范围内的值 (0.00048–0.440 µM)。对Pf GSK-3 选择性抑制所需的构效关系的评估表明，A 环上的 C6-OCH 3取代是优选的，而 B 环取代基对活性的影响按降序排列为：C4'-CN > C4'-F > C3'-OCH 3  > C3',4'-diCl。迄今为止，Pf GSK-3 抑制剂的开发仅限于 4-苯基噻吩并[2,3- b ]吡啶类。基于查尔酮的支架，例如本文所述的苯并呋喃，是有希望的新命中，可用于未来设计Pf
• Synthesis and evaluation of methoxy substituted 2-benzoyl-1-benzofuran derivatives as lead compounds for the development adenosine A1 and/or A2A receptor antagonists
  作者：Helena D. Janse van Rensburg、Lesetja J. Legoabe、Gisella Terre'Blanche、Janine Aucamp

  DOI：10.1016/j.bioorg.2019.103459

  日期：2020.1

  of fourteen methoxy substituted 2-benzoyl-1-benzofuran derivatives were synthesised and their affinities determined for adenosine A1 and A2A receptors via radioligand binding assays to establish the structure activity relationships pertinent for A1 and A2A affinity. Compound 3j (6,7-dimethoxybenzofuran-2-yl)(3-methoxyphenyl)methanone exhibited A1 affinity (A1Ki (rat) = 6.880 µM) as well as A2A affinity

  合成了一系列十四个甲氧基取代的2-苯甲酰基-1-苯并呋喃衍生物，并通过放射性配体结合试验确定了它们对腺苷A1和A2A受体的亲和力，以建立与A1和A2A亲和力相关的结构活性关系。化合物3j（6，7-二甲氧基苯并呋喃-2-基）（3-甲氧基苯基）甲酮表现出A1亲和力（A1Ki（大鼠）＝6.880μM）以及A2A亲和力（A2AKi（大鼠）＝0.5161μM）。化合物3a-b和3i-k对A1表现出选择性亲和力，Ki值低于10 µM。结果表明，环A上的C6,7-diOCH3取代与环B上的间（C3'）-OCH3取代相结合对A1和A2A的亲和力和活性是有益的。化合物3a-b和3j-k显示出低细胞毒性。经过体外和计算机分析后，化合物3j可以被认为是铅样的（即
• A straightforward conversion of aurones to 2-benzoylbenzofurans: transformation of one class of natural products into another
  作者：Samir Yahiaoui、Marine Peuchmaur、Ahcène Boumendjel

  DOI：10.1016/j.tet.2011.08.011

  日期：2011.10

  The naturally occurring aurones (2-benzylidene-3(2H)-benzofuran-3-ones) can be easily converted to another class of natural products 2-benzoylbenzo[b]furans, via an effective reduction, acid-mediated rearrangement, and oxidation cascade. This easy conversion was conducted without purification of intermediates. This straightforward conversion may be considered as a possible biosynthesis pathway of 2-benzoylbenzo[b]furans in plants. (C) 2011 Elsevier Ltd. All rights reserved.