(3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propanal) | 1027369-30-7

• 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: (3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propanal)
• 英文别名: 3-[2-(1,3-Benzodioxol-5-yl)-7-methoxy-benzofuran-5-yl]propanal；3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propanal
• CAS: 1027369-30-7
• 化学式: C₁₉H₁₆O₅
• 分子量: 324.333
• InChiKey: KBPANQBDOBDTQX-UHFFFAOYSA-N

物化性质

• 沸点：
  490.1±45.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propanal) 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以95.7%的产率得到3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propanal oxime
  参考文献：
  名称：

  Synthesis of egonol derivatives and their antimicrobial activities

  摘要：

  Eighteen derivatives of egonol (A-R) were synthesized and evaluated for their antimicrobial activities against Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC 6633, Candida albicans ATCC 10231 and Escherichia coli ATCC 8739 microorganisms comparing with egonol. The obtained data reported that compound B exhibited improved activities against all tested bacteria than egonol, others have shown different range of activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.044
• 作为产物：
  描述：

  egonol-9(Z),12(Z)-linoleate 在 乙醇 、 戴斯-马丁氧化剂 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 (3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propanal)
  参考文献：
  名称：

  Benzofurans from Styrax agrestis As Acetylcholinesterase Inhibitors: Structure–Activity Relationships and Molecular Modeling Studies

  摘要：

  An extract of Styrax agrestis fruits, collected in Vietnam, significantly inhibited acetylcholinesterase (AChE) in vitro. Bioassay-guided fractionation revealed three new egonol-type benzofurans: egonol-9(Z),12(Z) linoleate (1), 7-demethoxy-egonol-9(Z),12(Z) linoleate (2), and 7-demethoxyegonol oleate (4). Ten known egonol-type benzofurans were also isolated (3, 5, 6-13). In order to better understand structure activity relationships in this series, egonol derivatives 14-19 were prepared by chemical modifications and evaluated for their inhibition of AChE, butyrylcholinesterase (BChE), and AChE-induced A beta aggregation. Compounds 1-4 were the most potent inhibitors of the series, which exhibited inhibitory activity against AChE (IC50 1.4-3.1 mu M) and, for 1, A beta aggregation (77.6%). Molecular docking studies were also performed to investigate interaction of these compounds with the active site of AChE.

  DOI：

  10.1021/np200308j

文献信息

• 2-Phenylbenzo[ b ]furans: Synthesis and promoting activity on estrogen biosynthesis
  作者：Wenchen Pu、Yun Yuan、Danfeng Lu、Xin Wang、Hanwei Liu、Chun Wang、Fei Wang、Guolin Zhang

  DOI：10.1016/j.bmcl.2016.10.013

  日期：2016.11

  2-phenylbenzo[b]furan glycosides could promote estrogen biosynthesis. To find high active 2-phenylbenzo[b]furans, fifty-four 2-phenylbenzo[b]furans were prepared via four strategies according to corresponding substrate scopes. Biological evaluation in HEK293A cells showed that some compounds exhibited promotive activity on estrogen biosynthesis. 2-(4-Chlorophenyl)-7-methoxybenzo[b]furan possessed the

  雌激素的生物合成对人类的许多生理过程至关重要。雌激素水平异常与多种疾病密切相关，包括乳腺癌和骨质疏松症。以前我们发现2-苯基苯并[b]呋喃糖苷可以促进雌激素的生物合成。为了找到高活性的2-苯基苯并[b]呋喃，根据相应的底物范围，通过四种策略制备了五十四种2-苯基苯并[b]呋喃。HEK293A细胞的生物学评估表明，某些化合物对雌激素的生物合成具有促进作用。2-（4-氯苯基）-7-甲氧基苯并[b]呋喃具有最高的活性，EC50值为14.68μM。此外，这些化合物不会影响HEK292A细胞中的芳香化酶表达，
• Synthesis and antibacterial activity of egonol derivatives
  作者：Safiye Emirdağ Öztürk、Yurdanur Akgül、Hüseyin Anıl

  DOI：10.1016/j.bmc.2008.02.057

  日期：2008.4

  4'methylenedioxyphenyl)benzofuran was isolated from seeds of Styrax officinalis L. The structural elucidication of these compounds (1-11) was established using 1D ((1)H, (13)C), 2D NMR (HMBC, HMQC, COSY) and LCMS spectroscopic data. While egonol and some synthesised new compounds show similar antibacterial activity and MIC values against S. aureus, B. subtilis, C. albicans and E. coli, other new derivatives show

  3-苯并二恶唑-5-基）-7-甲氧基-1-苯并呋喃-5-基]丙基苯甲酸酯10，5- [3''-羟丙基] -7-甲氧基-3-硝基-2-（3'，4'报道了-亚甲基二氧苯基）苯并呋喃11及其对金黄色葡萄球菌，枯草芽孢杆菌，白色念珠菌和大肠杆菌的抗菌活性。从麦草的种子中分离出原料烯醇5- [3''-（羟基）丙基] -7-甲氧基-2-（3'，4'亚甲基二氧苯基）苯并呋喃。这些化合物的结构解析（1-使用1D（（1）H，（13）C），2D NMR（HMBC，HMQC，COSY）和LCMS光谱数据建立11）。蛋黄酚和一些合成的新化合物对金黄色葡萄球菌，枯草芽孢杆菌，白色念珠菌和大肠杆菌显示相似的抗菌活性和MIC值，而其他新衍生物对金黄色葡萄球菌，枯草芽孢杆菌，C。显示出不同的活性。
• Spectroscopic and biological studies of new mononuclear metal complexes of a bidentate NN and NO hydrazone–oxime ligand derived from egonol
  作者：Ilknur Babahan、Safiye Emirdağ-Öztürk、Esin Poyrazoğlu-Çoban

  DOI：10.1016/j.saa.2014.12.074

  日期：2015.4

  N4 donor groups of the ligands to NiII, CuII, CoII and ZnII ions. The detection of H-bonding (OH⋯O) in the [M(LH)2] metal complexes by IR spectra supported the square–planar MN4 coordination of Ni(II), Cu(II) and Co(II) complexes. The antimicrobial activities of compounds LH2 and their Ni(II), Cu(II), Co(II) and Zn(II) complexes were evaluated using the disc diffusion method against 16 bacteria and

  合成了一种新颖的配体，邻位二肟配体（例如，烯醇-乙二肟）（LH 2），并使用1 H NMR，13 C NMR，MS，AAS，红外光谱和磁化率测量对其进行了表征。还合成了LH 2的金属：配体比率为1：2的单核镍（II），铜（II）和钴（II）配合物。Zn（II）形成金属对配体比例为1：1的络合物[Zn（LH）Cl 2 ]。红外光谱表明该配体以双齿方式起作用，并且将配体的N 4个供体基团配位为Ni II，Cu II，Co II和Zn II离子。H键的检测（O[M（LH）2 ]金属配合物中的H⋯O）的红外光谱支持Ni（II），Cu（II）和Co（II）配合物的方形平面MN 4配位。 使用圆盘扩散法评估了化合物LH 2及其Ni（II），Cu（II），Co（II）和Zn（II）配合物对16种细菌和5种酵母的抗菌活性。还确定了对所有细菌和酵母菌的最小抑制浓度（MIC）。在尝试的测试化合物中，显示所有化合物（L，LH
• A new hybrid ligand and its metal complexes from a natural plant ( <scp> <i>Styrax officinalis</i> </scp> ) bearing egonol, thiosemicarbazone and oxime units, and their anti‐cancer activities
  作者：Ilknur Babahan‐Bircan、Safiye Emirdağ、Ali Özmen、Mürüvvet Abbak、Oguejiofo T. Ujam、Ilke Demirkaya、M. Emin Günay

  DOI：10.1002/aoc.6784

  日期：2022.9

  (1 μM). The results displayed that the compounds obtained in this study were effective in the concentration range of 5–40 μM in prostate and breast cancer cell lines. It can be said that the compounds (egonol, its derivatives, hybrid ligand, and its metal complexes) are mostly more effective in PC-3 migration lines. Consequently, the cytotoxic efficiencies of [Cu3(ETO)2·4Cl], 5.27 μM for MCF-7 and 13

  一种新的杂合配体，一种维克-二肟配体 ( ETO)，含有来自天然植物 ( Styrax officinalis ) 的氨基硫脲和egonol部分) 及其三核 [Ni(II)、Cu(II)、Co(II) 和 Fe(II)] 和单核 [Pd(II) 和 Zn(II)] 配合物已被合成和表征。通过常规光谱技术（IR、NMR 和 MS）对配体、复合物和天然成分进行表征，并针对两种人类癌细胞系（MCF-7 和 PC-3）进行评估，以确定它们的抗增殖和凋亡特性。使用 Hoechst/碘化丙啶双染法在两种癌细胞系中检测到凋亡或坏死效应。紫杉醇用作阳性对照（1 μM）。结果表明，本研究中获得的化合物在 5-40 μM 浓度范围内对前列腺和乳腺癌细胞系有效。可以说化合物（egonol、其衍生物、杂化配体、及其金属配合物）在 PC-3 迁移线中大多更有效。因此，细胞毒效率[Cu 3 (ETO) 2 ·4Cl]，MCF-7
• Benzofurans from <i>Styrax agrestis</i> As Acetylcholinesterase Inhibitors: Structure–Activity Relationships and Molecular Modeling Studies
  作者：Jiawei Liu、Vincent Dumontet、Anne-Laure Simonin、Bogdan I. Iorga、Vincent Guerineau、Marc Litaudon、Van Hung Nguyen、Françoise Gueritte

  DOI：10.1021/np200308j

  日期：2011.10.28

  An extract of Styrax agrestis fruits, collected in Vietnam, significantly inhibited acetylcholinesterase (AChE) in vitro. Bioassay-guided fractionation revealed three new egonol-type benzofurans: egonol-9(Z),12(Z) linoleate (1), 7-demethoxy-egonol-9(Z),12(Z) linoleate (2), and 7-demethoxyegonol oleate (4). Ten known egonol-type benzofurans were also isolated (3, 5, 6-13). In order to better understand structure activity relationships in this series, egonol derivatives 14-19 were prepared by chemical modifications and evaluated for their inhibition of AChE, butyrylcholinesterase (BChE), and AChE-induced A beta aggregation. Compounds 1-4 were the most potent inhibitors of the series, which exhibited inhibitory activity against AChE (IC50 1.4-3.1 mu M) and, for 1, A beta aggregation (77.6%). Molecular docking studies were also performed to investigate interaction of these compounds with the active site of AChE.