2-(3-methoxyphenyl)-5-nitrobenzofuran

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(3-methoxyphenyl)-5-nitrobenzofuran
• 英文别名: 2-(3-Methoxyphenyl)-5-nitro-1-benzofuran；2-(3-methoxyphenyl)-5-nitro-1-benzofuran
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: BDQKXWUFZNSZCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenyl)-5-nitrobenzofuran 在 palladium on activated charcoal 、 氢气 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 3-(5-aminobenzofuran-2-yl)phenol
  参考文献：
  名称：

  Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents

  摘要：

  Eight 2-phenylnaphthalenoids (2PNs) (3a h) and twenty four 2-phenylbenzofuranoids (2PBF5) (4a-4j, 5a-5j, 6a, 6f-6h) were successfully designed, synthesized and their antiproliferative and in vitro DNA topoisomerase inhibitory activities were evaluated. Nine compounds (four 2PNs and five 2PBFs) showed either Topol or TopoII alpha inhibitory activities. Six compounds (four 2PNs and two 2PBFs) exhibited potent cytotoxicity with IC50 values for 72 h exposure ranging from 0.3 to above 20 mu M against MDA-MB-231, MDA-MB-435, HepG2 and PC3 cell lines. The two 2PBFs displayed comparable and even better antiproliferative as well as TopoII alpha inhibitory activities than 2PNs. Interestingly, the active 2PBFs displayed different mechanisms of TopoII alpha inhibition from that of 2PNs, suggesting that the chromophore scaffold replacement may result in a change of the binding site of inhibitors to TopoII alpha. Furthermore, the mechanisms of antiproliferation on MDA-MB-231 cells indicate that compounds 5a and 5f are promising for further development of anticancer agents. The results of this study reveal that the evolutionary strategy of medicinal chemistry through scaffold hopping is a promising strategy for structure optimization of TopoII alpha inhibitors. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.048
• 作为产物：
  描述：

  2-羟基-5-硝基苄醇 在 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 2-(3-methoxyphenyl)-5-nitrobenzofuran
  参考文献：
  名称：

  寻找新的黄嘌呤氧化酶抑制剂：3-苯基香豆素与2-苯基苯并呋喃。

  摘要：

  体内尿酸的过度产生会导致高尿酸血症，这也与痛风密切相关。黄嘌呤氧化酶（XO）抑制剂可降低尿酸的产生。还已经提出抑制XO作为改善心血管健康的机制。因此，寻找新的有效XO抑制剂是药物发现中一个有趣的话题。3-苯基香豆素和2-苯基苯并呋喃是药物化学中的特有支架。它们的结构相似性使其成为有趣的分子以进行比较研究。在两个支架中都引入了甲氧基和硝基取代基。当前的研究对这些分子针对该重要靶标的合成和生物学活性提供了一些见识。对于该系列中最好的化合物，3-（4-甲氧基苯基）-6-硝基香豆素（4），确定IC 50值，抑制类型，对B16F10细胞的细胞毒性和ADME理论性质。还进行了对接研究，以更好地了解该分子与XO结合口袋的相互作用。这项工作是初步筛选，以进一步设计和合成新的非嘌呤能衍生物，作为潜在的参与炎症抑制的化合物，特别是与痛风有关。

  DOI：

  10.1016/j.ijbiomac.2020.06.152

文献信息

• Fabrication of an amyloid fibril-palladium nanocomposite: a sustainable catalyst for C–H activation and the electrooxidation of ethanol
  作者：Ramasamy Jayarajan、Rakesh Kumar、Jagriti Gupta、Gayathri Dev、Pradeep Kadu、Debdeep Chatterjee、Dhirendra Bahadur、Debabrata Maiti、Samir K. Maji

  DOI：10.1039/c8ta11134k

  日期：——

  used as a heterogeneous catalyst in C–H bond activation and the electrooxidation of ethanol. The study demonstrated α-Syn-PdNPs to be a superior heterogeneous catalyst for the synthesis of pharmaceutically valuable benzofuran, naphthofuran, coumarin and N-arylindole via C–H activation. Further, the electrooxidation of ethanol using α-Syn-PdNPs displayed an electrochemically active surface area of 160.6

  淀粉样蛋白是高度有序的纳米原纤维，其抗张强度与钢相似，因此可以抵抗极端的pH和温度。基于此原理，我们证明了以α-突触核蛋白（α-Syn）原纤维为模板，可以轻松合成钯，铜，铂，金和银纳米复合材料。我们表明，α-Syn-原纤维-钯纳米颗粒（α-Syn-PdNPs）复合材料可以用作C–H键活化和乙醇电氧化的非均相催化剂。研究表明，α-Syn-PdNPs是一种优异的非均相催化剂，可通过以下方法合成药学上有价值的苯并呋喃，萘并呋喃，香豆素和N-芳基吲哚。C–H激活。此外，使用α-Syn-PdNPs对乙醇进行的电氧化表现出160.6 m 2 g -1的电化学活性表面积，该表面积比先前报道的负载Pd纳米复合材料的值高得多。
• Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human monoamine oxidase inhibitors
  作者：Giovanna L. Delogu、Amit Kumar、Gianluca Gatto、Fernando Bustelo、Lucía M. Saavedra、Maria Isabel Rodríguez-Franco、Reyes Laguna、Dolores Viña

  DOI：10.1016/j.bioorg.2020.104616

  日期：2021.2

  A new series of 2-phenylbenzofuran derivatives were designed and synthesized to determine relevant structural features for the MAO inhibitory activity and selectivity. Methoxy substituents were introduced in the 2-phenyl ring, whereas the benzofuran moiety was not substituted or substituted at the positions 5 or 7 with a nitro group. Substitution patterns on both the phenyl ring and the benzofuran

  设计并合成了一系列新的 2-苯基苯并呋喃衍生物，以确定 MAO 抑制活性和选择性的相关结构特征。在 2-苯环中引入了甲氧基取代基，而苯并呋喃部分未被取代或在 5 或 7 位被硝基取代。苯环和苯并呋喃部分的取代模式决定了对 MAO-A 或 MAO-B 的亲和力。2-(3-甲氧基苯基)-5-硝基苯并呋喃9是该系列中最有效的 MAO-B 抑制剂 (IC 50  = 0.024 µM)，而 7-硝基-2-苯基苯并呋喃7是最有效的 MAO-A 抑制剂(IC 50 = 0.168 µM)，两者都作为可逆抑制剂。2-苯环上甲氧基的数量和位置对抑制活性有重要影响。分子对接研究证实了实验结果，并强调了关键残基在酶抑制中的重要性。
• Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents
  作者：Huilin Hao、Wang Chen、Jing Zhu、Chunhua Lu、Yuemao Shen

  DOI：10.1016/j.ejmech.2015.07.048

  日期：2015.9

  Eight 2-phenylnaphthalenoids (2PNs) (3a h) and twenty four 2-phenylbenzofuranoids (2PBF5) (4a-4j, 5a-5j, 6a, 6f-6h) were successfully designed, synthesized and their antiproliferative and in vitro DNA topoisomerase inhibitory activities were evaluated. Nine compounds (four 2PNs and five 2PBFs) showed either Topol or TopoII alpha inhibitory activities. Six compounds (four 2PNs and two 2PBFs) exhibited potent cytotoxicity with IC50 values for 72 h exposure ranging from 0.3 to above 20 mu M against MDA-MB-231, MDA-MB-435, HepG2 and PC3 cell lines. The two 2PBFs displayed comparable and even better antiproliferative as well as TopoII alpha inhibitory activities than 2PNs. Interestingly, the active 2PBFs displayed different mechanisms of TopoII alpha inhibition from that of 2PNs, suggesting that the chromophore scaffold replacement may result in a change of the binding site of inhibitors to TopoII alpha. Furthermore, the mechanisms of antiproliferation on MDA-MB-231 cells indicate that compounds 5a and 5f are promising for further development of anticancer agents. The results of this study reveal that the evolutionary strategy of medicinal chemistry through scaffold hopping is a promising strategy for structure optimization of TopoII alpha inhibitors. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Looking for new xanthine oxidase inhibitors: 3-Phenylcoumarins versus 2-phenylbenzofurans
  作者：Benedetta Era、Giovanna L. Delogu、Francesca Pintus、Antonella Fais、Gianluca Gatto、Eugenio Uriarte、Fernanda Borges、Amit Kumar、Maria J. Matos

  DOI：10.1016/j.ijbiomac.2020.06.152

  日期：2020.11

  Overproduction of uric acid in the body leads to hyperuricemia, which is also closely related to gout. Uric acid production can be lowered by xanthine oxidase (XO) inhibitors. Inhibition of XO has also been proposed as a mechanism for improving cardiovascular health. Therefore, the search for new efficient XO inhibitors is an interesting topic in drug discovery. 3-Phenylcoumarins and 2-phenylbenzofurans

  体内尿酸的过度产生会导致高尿酸血症，这也与痛风密切相关。黄嘌呤氧化酶（XO）抑制剂可降低尿酸的产生。还已经提出抑制XO作为改善心血管健康的机制。因此，寻找新的有效XO抑制剂是药物发现中一个有趣的话题。3-苯基香豆素和2-苯基苯并呋喃是药物化学中的特有支架。它们的结构相似性使其成为有趣的分子以进行比较研究。在两个支架中都引入了甲氧基和硝基取代基。当前的研究对这些分子针对该重要靶标的合成和生物学活性提供了一些见识。对于该系列中最好的化合物，3-（4-甲氧基苯基）-6-硝基香豆素（4），确定IC 50值，抑制类型，对B16F10细胞的细胞毒性和ADME理论性质。还进行了对接研究，以更好地了解该分子与XO结合口袋的相互作用。这项工作是初步筛选，以进一步设计和合成新的非嘌呤能衍生物，作为潜在的参与炎症抑制的化合物，特别是与痛风有关。