2-bromo-5-methoxybenzofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-bromo-5-methoxybenzofuran
• 英文别名: 2-Bromo-5-methoxy-1-benzofuran
• 化学式: C₉H₇BrO₂
• 分子量: 227.057
• InChiKey: BNGYLDVNNLUTEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-5-methoxybenzofuran 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 、 三溴化硼 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-(4-hydroxyphenyl)benzofuran-5-ol
  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-(2,2-dibromovinyl)-4-methoxyphenol 在 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-bromo-5-methoxybenzofuran
  参考文献：
  名称：

  An efficient tandem elimination–cyclization–desulfitative arylation of 2-(gem-dibromovinyl)phenols(thiophenols) with sodium arylsulfinates

  摘要：

  开发了一种高效的串联去除、环化和去亚磺酰化芳基化反应，利用2-(gem-二溴乙烯基)酚（硫酚）与芳基亚磺酸钠反应。在TBAF–PdCl2–Cu(OAc)2–NEt3的催化下，该反应在无配体条件下以一锅法生成了产率良好的2-芳基苯并呋喃（硫烯）。

  DOI：

  10.1039/c2ob27232f

文献信息

• An efficient tandem elimination–cyclization–desulfitative arylation of 2-(gem-dibromovinyl)phenols(thiophenols) with sodium arylsulfinates
  作者：Wei Chen、Pinhua Li、Tao Miao、Ling-Guo Meng、Lei Wang

  DOI：10.1039/c2ob27232f

  日期：——

  An efficient tandem elimination–cyclization–desulfitative arylation of 2-(gem-dibromovinyl)phenols(thiophenols) with sodium arylsulfinates has been developed. In the presence of TBAF–PdCl2–Cu(OAc)2–NEt3, the reactions generated 2-arylbenzofurans(thiophenes) with good yields in one-pot under ligand-free conditions.

  开发了一种高效的串联去除、环化和去亚磺酰化芳基化反应，利用2-(gem-二溴乙烯基)酚（硫酚）与芳基亚磺酸钠反应。在TBAF–PdCl2–Cu(OAc)2–NEt3的催化下，该反应在无配体条件下以一锅法生成了产率良好的2-芳基苯并呋喃（硫烯）。
• A highly efficient one-pot reaction of 2-(gem-dibromovinyl)phenols(thiophenols) with K4Fe(CN)6 to 2-cyanobenzofurans(thiophenes)
  作者：Wei Zhou、Wei Chen、Lei Wang

  DOI：10.1039/c2ob25356a

  日期：——

  2-Cyanobenzofurans and 2-cyanobenzothiophenes were prepared through an efficient one-pot Ullmann-reaction/cyanation reaction. In the presence of CuI/Na2CO3–Pd(OAc)2/PPh3 in DMF, the reaction of 2-(gem-dibromovinyl)phenols and 2-(gem-dibromovinyl)thiophenols with K4Fe(CN)6, as non-toxic and user-friendly cyanating reagent, proceeded smoothly to generate the corresponding 2-cyanobenzofurans and 2-cyanobenzothiophenes

  通过有效的一锅Ullmann反应/氰化反应制备2-氰基苯并呋喃和2-氰基苯并噻吩。在DMF中CuI / Na 2 CO 3 -Pd（OAc）2 / PPh 3的存在下，2-（宝石-二溴乙烯基）苯酚和2-（宝石-二溴乙烯基）苯硫酚与K 4 Fe（CN）6的反应作为无毒且对用户友好的氰化试剂，该试剂可顺利进行，以高收率生成相应的2-氰基苯并呋喃和2-氰基苯并噻吩。
• Pyrrolidinyl benzofurans and benzodioxanes: Selective α4β2 nicotinic acetylcholine receptor ligands with different activity profiles at the two receptor stoichiometries
  作者：Rebecca Appiani、Marco Pallavicini、Ayman K. Hamouda、Cristiano Bolchi

  DOI：10.1016/j.bmcl.2022.128701

  日期：2022.6

  5-amino benzodioxane analogues 3 and 4, which are all α4β2 nAChR partial agonists, and 2-(N-methyl-2-pyrrolidinyl)-6-hydroxybenzofuran (12) were selected for functional characterization at the two α4β2 stoichiometries, the high sensitivity (α4)2(β2)3 and the low sensitivity (α4)3(β2)2. The benzene pattern substitution, which had previously been found to control α4β2 partial agonist activity and α4β2 vs

  已经合成了一系列在 C(2) 或 C(3) 处带有N-甲基-2-吡咯烷基残基的外消旋苯并呋喃，并测试了对 α4β2 和 α3β4 尼古丁乙酰胆碱受体 (nAChRs) 的亲和力。如先前报道的基于苯并二恶烷的类似物，苯环适当位置的羟基化导致高 α4β2 nAChR 亲和力和 α4β2 对 α3β4 nAChR 选择性。7-Hydroxy- N -methyl-2-pyrrolidinyl-1,4-benzodioxane ( 2 ) 及其 7- 和 5- 氨基苯并二恶烷类似物3和4，它们都是 α4β2 nAChR 部分激动剂，以及 2-( N -methyl- 2-吡咯烷基)-6-羟基苯并呋喃 ( 12) 被选择用于两种 α4β2 化学计量的功能表征，即高灵敏度 (α4) 2 (β2) 3和低灵敏度 (α4) 3 (β2) 2。先前发现苯模式取代可控制 α4β2 部分激动剂活性和 α4β2 对
• 2-ETHYLAMINE SUBSTITUTED BENZOFURAN AND BENZOTHIOPHENE COMPOSITIONS FOR MENTAL DISORDERS OR ENHANCEMENT
  申请人：[en]TACTOGEN INC

  公开号：WO2024108179A2

  公开（公告）日：2024-05-23

  Pharmaceutically active 2-ethylamine substituted benzofuran and benzothiophene compositions are provided for the treatment of mental disorders or for mental enhancement, including for entactogenic therapy. The present invention also includes 2-ethylamine substituted benzofuran and benzothiophene compounds, compositions, and methods for generally modulating central nervous system activity and treating central nervous system disorders.
• 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.