4,6-dimethoxy-3-phenylbenzofuran | 108838-36-4

• 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: 4,6-dimethoxy-3-phenylbenzofuran
• 英文别名: 4,6-Dimethoxy-3-phenyl-1-benzofuran
• CAS: 108838-36-4
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: HXXIXJDDDOBIBJ-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 沸点：
  404.6±45.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-dimethoxy-3-phenylbenzofuran 以 二氯甲烷 、 水 为溶剂， 生成 N-methyl-2-(4',6'-dimethoxy-3'-phenylbenzofuran-2'-yl)glyoxylamide
  参考文献：
  名称：

  活化的苯并呋喃喃甲醇的酸催化反应：杯苯并呋喃的形成

  摘要：

  3-取代的4，6-二甲氧基苯并呋喃的亲电取代的区域化学很大程度上受C3上的取代基控制。在优选形成3-芳基的存在导致2-取代苯并呋喃衍生物而笨重叔3-丁基丁基取代基占7-取代产物的主导地位。2-羟甲基苯并呋喃的酸催化反应主要产生不对称连接的杯[3]苯并呋喃。但是，对7-羟甲基苯并呋喃进行酸处理只能以高收率得到对称连接的杯[3]苯并呋喃。苯并呋喃基乙醛酰胺，乙醛酸酯和酮可以高收率获得，其相应的醇还原产物的酸催化反应通常可产生中等至高收率的对称连接的杯[3]苯并呋喃以及少量的杯[4]。苯并呋喃。

  DOI：

  10.1016/s0040-4020(02)00472-6
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium acetate 、 乙酸酐 作用下， 生成 4,6-dimethoxy-3-phenylbenzofuran
  参考文献：
  名称：

  Motylewski, Chemische Berichte, 1909, vol. 42, p. 3149

  摘要：

  DOI：

文献信息

• Cationic Palladium(II)-Catalyzed Addition of Arylboronic Acids to Nitriles. One-Step Synthesis of Benzofurans from Phenoxyacetonitriles
  作者：Baowei Zhao、Xiyan Lu

  DOI：10.1021/ol062438v

  日期：2006.12.1

  text] A cationic palladium complex catalyzed addition of arylboronic acids to nitriles to yield aryl ketones with moderate to good yields was developed. A one-step synthesis of benzofurans from phenoxyacetonitriles under the catalysis of [(bpy)Pd+(micro-OH)]2(-OTf)2 or [(bpy)Pd2+(H2O)2](-OTf)2 was developed which showed that the cationic palladium catalyst is highly active for these addition reactions

  [结构：见正文]开发了一种阳离子钯络合物，可将芳基硼酸加成至腈中，从而制得中等至良好收率的芳基酮。研究表明，在[（bpy）Pd +（micro-OH）] 2（-OTf）2或[（bpy）Pd2 +（H2O）2]（-OTf）2的催化下，由苯氧基乙腈一步合成苯并呋喃阳离子钯催化剂对这些加成反应具有很高的活性。
• Preparation of activated benzofurans and their reactions with aldehydes
  作者：David St.C. Black、Donald C. Craig、Naresh Kumar、Robert Rezie

  DOI：10.1016/s0040-4020(99)00152-0

  日期：1999.4

  Reactions of 3-substituted 4,6-dimethoxybenzofurans with formaldehyde and aryl aldeydes in the presence of acetic acid and phosphoryl chloride respectively give new macrocyclic calix[3]benzofurans, predominantly with an unsymmetrical linkage pattern. Incorporation of a t-butyl substituent at the 3-position, however, leads to the formation of only a trimer with a symmetrical linkage pattern.

  在乙酸和磷酰氯的存在下，3-取代的4,6-二甲氧基苯并呋喃与甲醛和芳基醛的反应分别产生新的大环杯[3]苯并呋喃，主要具有不对称的键合模式。然而，在3-位引入叔丁基取代基导致仅形成具有对称连接图案的三聚体。
• Modified Vilsmeier reactions of activated benzofurans with indolines: Synthesis of benzofuran-fused benzocarbazoles
  作者：David St.C. Black、Robert Rezaie

  DOI：10.1016/s0040-4039(99)00699-1

  日期：1999.5

  Regioselective reactions of 3-substituted 4,6-dimethoxybenzofurans with indolin-2-ones and triflic anhydride afforded 7- and/or 2-substituted indolo-benzofurans and the latter were cyclised to previously unknown benzofuran-fused benzocarbazoles using palladium (II) acetate in heated acetic acid.

  3-取代的4,6-二甲氧基苯并呋喃与吲哚-2-酮和三氟甲磺酸的区域选择性反应得到7和/或2-取代的吲哚-苯并呋喃，并使用乙酸钯（II）将后者环化成以前未知的苯并呋喃稠合的苯并咔唑。在加热的乙酸中。
• Synthesis and biological activity of novel mono-indole and mono-benzofuran inhibitors of bacterial transcription initiation complex formation
  作者：Marcin Mielczarek、Ruth V. Thomas、Cong Ma、Hakan Kandemir、Xiao Yang、Mohan Bhadbhade、David StC. Black、Renate Griffith、Peter J. Lewis、Naresh Kumar

  DOI：10.1016/j.bmc.2015.02.037

  日期：2015.4

  Our ongoing research focused on targeting transcription initiation in bacteria has resulted in synthesis of several classes of mono-indole and mono-benzofuran inhibitors that targeted the essential protein-protein interaction between RNA polymerase core and sigma(70)/sigma(A) factors in bacteria. In this study, the reaction of indole-2-, indole-3-, indole-7- and benzofuran-2-glyoxyloyl chlorides with amines and hydrazines afforded a variety of glyoxyloylamides and glyoxyloylhydrazides. Similarly, condensation of 2- and 7-trichloroacetylindoles with amines and hydrazines delivered amides and hydrazides. The novel molecules were found to inhibit the RNA polymerase-sigma(70)/sigma(A) interaction as measured by ELISA, and also inhibited the growth of both Gram-positive and Gram-negative bacteria in culture. Structure-activity relationship (SAR) studies of the mono-indole and mono-benzofuran inhibitors suggested that the hydrophilic-hydrophobic balance is an important determinant of biological activity. (C) 2015 Elsevier Ltd. All rights reserved.
• Discovery of 4,6-bis(benzyloxy)-3-phenylbenzofuran as a novel Pin1 inhibitor to suppress hepatocellular carcinoma via upregulating microRNA biogenesis
  作者：Xin Fan、Huaiyu He、Jiao Li、Guoyong Luo、Yuanyuan Zheng、Jian-Kang Zhou、Juan He、Wenchen Pu、Yun Zhao

  DOI：10.1016/j.bmc.2019.04.028

  日期：2019.6

  Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1) participates in diverse cancer-associated signaling pathways, playing an oncogenic role in multiple human cancers, including hepatocellular carcinoma (HCC). Our recent works clarify that Pin1 modulates miRNAs biogenesis by interacting with ERK-phosphorylated exportin-5 (XPO5) and changing XPO5 conformation, giving a potential target for HCC treatment. Herein, we discover 4,6-bis(benzyloxy)-3-phenylbenzofuran (TAB29) as a novel Pin1 inhibitor that targets Pin1 PPIase domain. TAB29 potently inhibits Pin1 activity with the IC50 value of 874 nM and displays an excellent selectivity toward Pin1 in vitro. Cell-based biological evaluation reveals that TAB29 significantly suppresses cell proliferation of HCC cells through restoring the nucleus-to-cytoplasm export of XPO5 and upregulating mature miRNAs expression. Collectively, this work provides a promising small molecule lead compound for Pin1 inhibition, highlighting the therapeutic potential of miRNA-based treatment for human cancers.