methyl ester of 6-acetyl-5-hydroxy-2-methylbenzo[b]furan-3-carboxylic acid | 63529-84-0

• 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: methyl ester of 6-acetyl-5-hydroxy-2-methylbenzo[b]furan-3-carboxylic acid
• 英文别名: 6-acetyl-5-hydroxy-2-methylbenzo[b]furane-3-carboxylic acid methyl ester；6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylic acid methyl ester；methyl 6-acetyl-5-hydroxy-2-methyl-1-benzofuran-3-carboxylate；methyl 6-acetyl-5-hydroxy-2-methylbenzofuran-3-carboxylate；6-acetyl-5-hydroxy-2-methyl-benzofuran-3-carboxylic acid methyl ester
• CAS: 63529-84-0
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: VGEWPEKBZZZVMN-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C(Solv: methanol (67-56-1))
• 沸点：
  373.8±37.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl ester of 6-acetyl-5-hydroxy-2-methylbenzo[b]furan-3-carboxylic acid 在 溴 作用下， 以 氯仿 为溶剂， 反应 8.5h， 以77%的产率得到methyl 4-bromo-6-(dibromoacetyl)-5-hydroxy-2-methyl-1-benzofuran-3-carboxylate
  参考文献：
  名称：

  Synthesis and Preliminary Evaluation of the Antimicrobial Activity of Selected 3-Benzofurancarboxylic Acid Derivatives

  摘要：

  以 6-乙酰基-5-羟基-2-甲基-3-苯并呋喃羧酸为起始原料，制备了特定 3-苯并呋喃羧酸的卤素衍生物。所有合成结构都获得了 1H-NMR 光谱，化合物 VI 还获得了 X 射线晶体结构。测试了所有衍生物对部分革兰氏阳性球菌、革兰氏阴性杆菌和酵母菌的抗菌活性。三种化合物 III、IV 和 VI 对革兰氏阳性细菌具有抗菌活性（MIC 50 至 200 mg/mL）。化合物 VI 和 III 对白色念珠菌菌株 C. albicans 和 C. parapsilosis 具有抗真菌活性（MIC - 100 mg/mL）。

  DOI：

  10.3390/molecules15074737
• 作为产物：
  描述：

  6-acetyl-5-hydroxy-2-methyl-1-benzofuran-3-carboxylic acid 、 甲醇 在 硫酸 作用下， 以95%的产率得到methyl ester of 6-acetyl-5-hydroxy-2-methylbenzo[b]furan-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and structural characterization of derivatives of 2- and 3-benzo[b]furan carboxylic acids with potential cytotoxic activity

  摘要：

  Derivatives of 2- and 3-benzo[b]furancarboxylic acids were prepared and evaluated for their cytotoxic potential in the National Cancer Institute, Bethesda, USA. Six compounds: 7-acetyl-6-hydroxy-3-methyl-2-benzofurancarboxylic acid (2), 6-hydroxy-7-(p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylic acid (4), 5-bromo-7-hydroxy-6-methoxy-2-benzofurancarboxylic acid methyl ester (6a), 6-acetyl-5-(O-ethyl-2'-diethylamino)-2-methyl-3-benzofurancarboxylic acid methyl ester (1f), 6-(O-ethyl-2'-diethylamino)-7-p-methoxycinnamoyl)-3-methyl-2-benzofurancarboxylic acid methyl ester hydrochloride (4b), 5-bromo-7-(O-ethyl-2'-diethylamino)-6-methoxy-2-benzofurancarboxylic acid methyl ester (6b) showed significant cytotoxic activities against human cancer cell lines. In addition the crystal structures of 7-methoxy-2-benzofurancarboxylic acid methyl ester (7a) has been solved by X-ray structure analysis of single crystals.

  DOI：

  10.1016/j.farmac.2005.05.005

文献信息

• Synthesis of New Derivatives of Benzofuran as Potential Anticancer Agents
  作者：Mariola Napiórkowska、Marcin Cieślak、Julia Kaźmierczak-Barańska、Karolina Królewska-Golińska、Barbara Nawrot

  DOI：10.3390/molecules24081529

  日期：——

  our previous research indicated that some derivatives of benzofurans, particularly halogeno-derivatives, are selectively toxic towards human leukemia cells. Continuing our work with this group of compounds we here report new data on the synthesis as well as regarding the physico-chemical and biological characterization of fourteen new derivatives of benzofurans, including six brominated compounds. The

  我们之前的研究结果表明，苯并呋喃的一些衍生物，特别是卤代衍生物，对人类白血病细胞具有选择性毒性。继续我们对这组化合物的研究，我们在此报告了关于 14 种苯并呋喃新衍生物（包括 6 种溴化化合物）的合成以及物理化学和生物表征的新数据。所有新化合物的结构均通过光谱方法（1H-和 13C-NMR、ESI MS）和元素分析确定。它们对 K562（白血病）、MOLT-4（白血病）、HeLa（宫颈癌）和正常细胞（HUVEC）的细胞毒性进行了评估。五种化合物（1c、1e、2d、3a、3d）显示出对所有测试细胞系的显着细胞毒活性和对癌细胞系的选择性。
• Microwave-assisted preparation and antimicrobial activity of O-alkylamino benzofurancarboxylates
  作者：Kinga Ostrowska、Elżbieta Hejchman、Irena Wolska、Hanna Kruszewska、Dorota Maciejewska

  DOI：10.1007/s00706-013-1067-7

  日期：2013.11

  A series of derivatives of 2 and 3-benzofurancarboxylates were synthesized under microwave-assisted conditions. Their in-vitro antimicrobial properties were assessed. Inhibition by the compounds of the growth of antibiotic-susceptible standards and clinically isolated strains of Gram-positive and Gram-negative bacteria, yeasts, and a human fungal pathogen was moderate to significant. Methyl 5-bromo-7-[2-(N,N-diethylamino)ethoxy]-6-methoxy-2-benzofurancarboxylate hydrochloride was identified as the most active compound (MIC 3-12 x 10(-3) mu mol/cm(3) against Gram-positive bacteria; MIC 9.4 x 10(-2) mu mol/cm(3) against Candida and Aspergillus brasiliensis). The molecular and crystal structures of 2-(N,N-diethylamino)ethyl 6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate were established by single-crystal X-ray diffraction..
• Synthesis and structural studies of novel Cu(II) complexes with hydroxy derivatives of benzo[b]furan and coumarin
  作者：Aleksandra Drzewiecka、Anna E. Koziol、Marcin T. Klepka、Anna Wolska、Hanka Przybylinska、Sonia B. Jimenez-Pulido、Kinga Ostrowska、Marta Struga、Jerzy Kossakowski、Tadeusz Lis

  DOI：10.1016/j.poly.2012.05.042

  日期：2012.8

  A series of new Cu(II) complexes with the hydroxy derivatives of benzo[b]furan and coumarin have been electrochemically synthesized. The geometry of the metal-ligand interaction has been described using the single crystal X-ray diffraction method and X-ray absorption spectroscopy. Two ligands are bonded to the metal cation via the acetyl and deprotonated hydroxyl O atoms. The centrosymmetric coordination polyhedron of Cu(II) exhibits a square-planar geometry (CuO4), with both ligands coordinating in the chelating mode. (C) 2012 Elsevier Ltd. All rights reserved.
• ZAWADOWSKI T.; KOSSAKOWSKI J.; RECHOWICZ P., ROCZ. CHEM. <ROCH-AC>, 1977, 51, NO 1, 159-162
  作者：ZAWADOWSKI T.、 KOSSAKOWSKI J.、 RECHOWICZ P.

  DOI：——

  日期：——
• Halogen derivatives of benzo[b]furans useful as anti-neoplastic or anti-proliferative drugs
  申请人：Centrum Badan Molekularnych I Makromolekularnych Pan

  公开号：EP2631232B1

  公开（公告）日：2015-09-16