4-(苯并呋喃-2-基)苯酚 | 26870-36-0

• 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
• 中文名称: 4-(苯并呋喃-2-基)苯酚
• 英文名称: 2-(4-hydroxyphenyl)benzofuran
• 英文别名: 4-(benzofuran-2-yl)phenol；2-(4-Hydroxy-phenyl)-cumaron；4-(1-Benzofuran-2-yl)phenol
• CAS: 26870-36-0
• 化学式: C₁₄H₁₀O₂
• 分子量: 210.232
• InChiKey: YTEKHDAKURIPLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  4-(苯并呋喃-2-基)苯酚 在 四氯化锡 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 44.0h， 生成 [2-(4-{7-[(3-hydroxybenzyl)-N-methylamino]heptyloxy}phenyl)benzofuran-3-yl]-p-tolylmethanone
  参考文献：
  名称：

  2-Arylbenzofuran-based molecules as multipotent Alzheimer's disease modifying agents

  摘要：

  The complex etiology of Alzheimer's disease prompts scientists to develop multi-target strategies to combat causes and symptoms. In line with this modern paradigm and as a follow-up to our previous studies, we designed and synthesized a focused collection of new 2-arylbenzofurans and evaluated their biological properties towards specific targets involved in AD, namely human AChE and human BuChE, and A beta fibril formation. Selected compounds were also tested for their ability to inhibit A beta neurotoxicity in terms of neuronal viability loss, and to prevent A beta peptide-binding to cell membrane and intracellular reactive oxygen species (ROS) formation. The different modifications introduced in the structure of our lead compound led to an increase in activity towards one or more of the selected targets: the anticholinesterase activity of some compounds was found to be significantly higher than previously obtained related molecules, and the compounds also proved to possess A beta anti-aggregating properties and neuroprotective effects. The most interesting multi-target compounds were 18, and 1. Interestingly, 1 also showed good selectivity and moderate affinity for CB1 receptor, opening new perspectives in the field of research on AD, since cannabinoid ligands have been widely reported to have neuroprotective properties. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.045
• 作为产物：
  描述：

  水杨醇 在 氢溴酸 、 氢碘酸 、 乙酸酐 、 溶剂黄146 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 4-(苯并呋喃-2-基)苯酚
  参考文献：
  名称：

  2-苯基苯并呋喃衍生物作为丁酰胆碱酯酶抑制剂：合成，生物活性和分子模型。

  摘要：

  设计，合成和评估了一系列2-苯基苯并呋喃化合物作为胆碱酯酶抑制剂。生物学测定实验表明，大多数化合物对丁酰胆碱酯酶（BChE）表现出明显的选择性抑制作用，而对乙酰胆碱酯酶（AChE）的作用却微弱或没有。在这些苯并呋喃衍生物中，化合物16表现出最高的BChE抑制作用，IC50值为30.3μM。通过动力学分析确定该化合物为混合型抑制剂。此外，分子动力学模拟显示化合物16与BChE的催化阴离子位点（CAS）和外围阴离子位点（PAS）都结合，并且显示出最佳的相互作用能值，与我们的实验数据一致。

  DOI：

  10.1016/j.bmcl.2016.03.039

文献信息

• Substituted benzofurans and benzothiophenes
  申请人：SmithKline Corporation

  公开号：US04001426A1

  公开（公告）日：1977-01-04

  The compounds are benzoyl benzofurans and benzothiophenes having pharmacological activity, in particular, coronary vasodilator activity useful for the treatment of angina pectoris and intermediates for the preparation thereof.

  这些化合物是具有药理活性的苯甲酰苯并呋喃和苯并噻吩，特别是对治疗心绞痛有用的冠状血管扩张剂活性，以及其制备的中间体。
• Efficient Synthesis of Benzofurans Utilizing [3,3]-Sigmatropic Rearrangement Triggered byN-Trifluoroacetylation of Oxime Ethers: Short Synthesis of Natural 2-Arylbenzofurans
  作者：Norihiko Takeda、Okiko Miyata、Takeaki Naito

  DOI：10.1002/ejoc.200601001

  日期：2007.3

  synthetic method for the preparation of benzofurans has been developed. The key step of this method is the [3,3]-sigmatropic rearrangement of N-trifluoroacetyl-ene-hydroxylamines, which was triggered by acylation of oxime ethers. TFAA has been proved to be the best reagent to induce [3,3]-sigmatropic rearrangement for the synthesis of cyclic oracyclic dihydrobenzofurans. On the other hand, the TFAT-DMAP

  开发了一种制备苯并呋喃的新合成方法。该方法的关键步骤是由肟醚的酰化引发的 N-三氟乙炔-羟胺的 [3,3]-σ 重排。TFAA 已被证明是诱导 [3,3]-sigmatropic 重排合成环甲环二氢苯并呋喃的最佳试剂。另一方面，发现 TFAT-DMAP 系统对于构建各种苯并呋喃是最有效的。该反应的合成效用通过没有羟基保护的天然苯并呋喃的短合成来证明。Stemofuran A 的合成是通过酮与芳氧基胺的缩合以及随后与 TFAT-DMAP 在四步合成中的反应来完成的，总产率为 72%。相似地，Eupomatenoid 6 和 Coumestan 通过肟醚与 TFAT-DMAP 的反应合成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• A Genomic DNA Reporter Screen Identifies Squalene Synthase Inhibitors That Act Cooperatively with Statins to Upregulate the Low-Density Lipoprotein Receptor
  作者：Alastair G. Kerr、Lawrence C. S. Tam、Ashley B. Hale、Milena Cioroch、Gillian Douglas、Sarina Agkatsev、Olivia Hibbitt、Joseph Mason、James Holt-Martyn、Carole J. R. Bataille、Graham M. Wynne、Keith M. Channon、Angela J. Russell、Richard Wade-Martins

  DOI：10.1124/jpet.116.239574

  日期：2017.6

  profile and showed in vivo efficacy. Compounds OX03050 and OX03771 were found to inhibit squalene synthase, the first committed step in cholesterol biosynthesis. These squalene synthase inhibitors were shown to act cooperatively with statins to increase LDLR expression in vitro. Overall, we demonstrated here a novel series of small molecules with the potential to be further developed to treat patients

  高胆固醇血症仍然是心血管疾病发展的主要危险因素之一。许多大型双盲研究表明，使用他汀类药物降低低密度脂蛋白（LDL）胆固醇可将发生心血管事件的风险降低约30％。然而，尽管他汀类药物获得了成功，但由于依从性或效力问题，一些患者人群仍无法降低其LDL胆固醇以满足目标脂质水平。对于患有杂合性家族性高胆固醇血症的患者尤其如此，他们可能需要额外上调低密度脂蛋白受体（LDLR）才能将LDL胆固醇水平降低到最大剂量他汀类药物可达到的水平。在这里，我们从基因组DNA报告分子筛选中鉴定出一系列小分子，它们以纳摩尔效价（EC50 = 39 nM）上调了小鼠和人肝细胞系中的LDLR。对铅化合物OX03771 [（E）-N，N-二甲基-3-（4-苯乙烯基苯氧基）丙-1-胺]进行的构效关系研究导致鉴定了化合物OX03050 [（E）- 3-（4-苯乙烯基苯氧基）丙-1-醇]，具有相似的效价（EC50 = 26 nM）
• Acid-mediated intermolecular C–F/C–H cross-coupling of 2-fluorobenzofurans with arenes: synthesis of 2-arylbenzofurans
  作者：Takeshi Fujita、Ryutaro Morioka、Takuya Fukuda、Naoto Suzuki、Junji Ichikawa

  DOI：10.1039/d1cc03453g

  日期：——

  Transition-metal-free acid-promoted biaryl construction was achieved via intermolecular C–F/C–H cross-coupling. By treating 2-fluorobenzofurans with arenes and AlCl₃, 2-arylbenzofurans including a bioactive natural product were obtained.

  通过无过渡金属酸促进的分子间C-F/C-H交叉偶联实现了双芳基的构建。将2-氟苯并呋喃与芳烃和AlCl3处理后，得到了包括一种生物活性天然产物在内的2-芳基苯并呋喃。
• Synthesis of 2-Phenylbenzofuran Derivatives and Selective Binding Activities on Estrogen Receptor
  作者：Ping Zhang、Yewei Yang、Xiaoliang Zheng、Wenhai Huang、Zhen Ma、Zhengrong Shen

  DOI：10.1248/cpb.60.270

  日期：——

  An improved chemical reaction protocol with short time and easy work-up was described here for 2-phenylbenzofuran derivatives. The final purified products, 2-phenylbenzofuran derivatives 5a—g and the intermediate diols 4a—g, were evaluated for their estrogen receptor (ER) binding affinity and selective activity in vitro. Among these fourteen tested compounds, 4g and 5g showed higher binding affinity on ER subtypes, ERα and ERβ. Compound 4g exhibited preferable ERα binding, while 5g was more estrogen selective for ERβ. The molecular docking was also performed to explore the detailed interactive interface between ER and the compounds.

  这里描述了一种改进的化学反应协议，适用于2-苯基苯并呋喃衍生物，具有反应时间短和后处理简单的特点。最终纯化的产品，包括2-苯基苯并呋喃衍生物5a—g和中间体二醇4a—g，经过评估其体外雌激素受体（ER）结合亲和力和选择性活性。在这十四个测试化合物中，4g和5g在ER亚型ERα和ERβ上表现出更高的结合亲和力。化合物4g表现出对ERα的优良结合，而5g则对ERβ更具选择性。还进行了分子对接研究，以探索ER与这些化合物之间的详细相互作用界面。