1-(4,6,7-trimethoxybenzofuran-5-yl)ethan-1-one | 40512-23-0

• 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: 1-(4,6,7-trimethoxybenzofuran-5-yl)ethan-1-one
• 英文别名: khellinone methyl ether；4,6,7-trimethoxy-5-acetylbenzofuran；1-(4,6,7-trimethoxy-1-benzofuran-5-yl)ethanone
• CAS: 40512-23-0
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: MDUIZONRWCPMAD-UHFFFAOYSA-N

物化性质

• 沸点：
  138-140 °C(Press: 0.1 Torr)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  1-(4,6,7-trimethoxybenzofuran-5-yl)ethan-1-one 在 盐酸 、 sodium acetate 、 sodium 、 sodium nitrite 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 4,6,7-trimethoxy-5-benzofurylglyoxal-ω-phenylhydrazone
  参考文献：
  名称：

  Hishmat, Orchidee H.; Zohair, Madiha M. Y.; Miky, Jehane A. A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 6, p. 460 - 462

  摘要：

  DOI：
• 作为产物：
  描述：

  凯林 在 盐酸 、 硫酸 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 生成 1-(4,6,7-trimethoxybenzofuran-5-yl)ethan-1-one
  参考文献：
  名称：

  新型喹喔啉，嘧啶和吡唑呋喃色酮衍生物的合成作为细胞毒剂

  摘要：

  摘要首次合成了一系列新颖的喹喔啉，嘧啶和吡唑呋喃色酮衍生物。这些衍生物是在温和条件下使用逐步有效的方法制备的。发达的方案导致合成了呋喃苯醌衍生物，产率中等至良好（60-75％）。使用多种光谱技术（包括IR，NMR和质谱）鉴定了制备的衍生物的结构。使用体外艾氏腹水试验评估合成衍生物的细胞毒活性。吡唑并苯并呋喃显示出最有效的作用，表明吡唑核对于细胞毒性活性的重要性。 图形概要

  DOI：

  10.1007/s00706-017-1960-6

文献信息

• Metal-Free Activation of C(sp³ )-H Bond, and a Practical and Rapid Synthesis of Privileged 1-Substituted 1,2,3,4-Tetrahydroisoquinolines
  作者：Santosh Kumar Choudhury、Pragati Rout、Bibhuti Bhusan Parida、Jean-Claude Florent、Ludger Johannes、Ganngam Phaomei、Emmanuel Bertounesque、Laxmidhar Rout

  DOI：10.1002/ejoc.201700471

  日期：2017.9.25

  reaction of cotarnine and acyl/aryl ketones in green solvents provides an efficient approach to an array of privileged 1,2,3,4-tetrahydroisoquinolines in excellent yields by metal free Activaion of C(SP3)-H bonds. This one-pot procedure takes place under base-free conditions at room temperature, and tolerates a wide range of functionalities. The reaction is highly chemo-selective, scalable in multi-gram

  Cotarnine 和酰基/芳基酮在绿色溶剂中的反应提供了一种有效的方法，通过 C(SP3)-H 键的无金属激活，以优异的收率获得一系列特权 1,2,3,4-四氢异喹啉。这种一锅程序在室温下无碱条件下进行，并具有广泛的功能。该反应具有高度化学选择性，可在多克规模上进行扩展，并且通过简单过滤分离出纯产物，无需后处理。有趣的是，从可塔宁卤化物盐的补充两步程序以良好的收率提供了曼尼希产品。范围详细说明了 9-溴可豆碱盐，以获取 9-溴香豆素启发的多种类似物。
• Benzofuranyl-pyran-2-ones, -pyridazines, and -pyridones from naturally occurring furochromones (visnagin and khellin)
  作者：Eman M. Keshk

  DOI：10.1002/hc.10219

  日期：——

  The novel and versatile enaminones 2a,b were synthesized by treatment of visnaginone methyl ether 1a or khellinone methyl ether 1b with N,N-dimethylformamide dimethylacetal. They were reacted with hippuric acid or N-acetylglycine to yield benzofuran-5-yl-2H-pyran-2-ones 3a–d. The reaction of 2a,b with cyanoacetamide and malononitrile dimer in sodium ethoxide gave benzofuran-5-yl-pyridones 4a,b and

  通过用 N,N-二甲基甲酰胺二甲基乙缩醛处理 visnaginone 甲醚 1a 或 khellinone 甲醚 1b 合成了新型多功能烯胺酮 2a、b。它们与马尿酸或 N-乙酰甘氨酸反应生成苯并呋喃-5-基-2H-吡喃-2-酮 3a-d。2a,b 与氰基乙酰胺和丙二腈二聚体在乙醇钠中的反应分别得到苯并呋喃-5-基-吡啶酮 4a,b 和 [苯并呋喃-5-基-1H-吡啶-2-亚基]丙二腈 5a。用水合肼或羟胺回流 2a,b，分别得到苯并呋喃-5-基-1H-吡唑 6a,b 和苯并呋喃-5-基-异恶唑 7a,b。此外，2a,b 在氢氧化钠存在下与芳基重氮盐偶联，生成 3-(benzofuran-5-yl)-2-aryl-hydrazono-3-oxo-propanals 8a,b，它们是合成 3-(benzofuran-5-yl)-2-aryl-hydrazono-3-oxo-propanals
• Synthetic routes to benzofurans and benzothiophenes and intermediates
  申请人：The Upjohn Company

  公开号：US04609739A1

  公开（公告）日：1986-09-02

  The present invention provides novel compositions of matter and processes for their preparation. More particularly, the present invention consists of novel chemical intermediates and associated processes for the preparation of khellin and other furochromone analogues, which have demonstrated antiatherosclerotic activity. These novel intermediates and processes can also be used for the preparation of benzofurans and benzothiophenes which inhibit the synthesis of leukotriene and/or lipoxygenase.

  本发明提供了新颖的物质组合和其制备方法。更具体地说，本发明涉及新型化学中间体及其制备过程，用于制备赤花素和其他呋喃酮类似物，这些化合物已经表现出抗动脉粥样硬化活性。这些新型中间体和制备过程还可用于制备苯并呋喃和苯并噻吩，这些化合物可抑制白三烯和/或脂氧化酶的合成。
• Synthesis and Bioactivity Assessment of Novel Spiro Pyrazole-Oxindole Congeners Exhibiting Potent and Selective in vitro Anticancer Effects
  作者：Heba M. Abo-Salem、Amr Nassrallah、Ahmed A.F. Soliman、Manal S. Ebied、Mohamed E. Elawady、Sayeda A. Abdelhamid、Eslam R. El-Sawy、Yazeed A. Al-Sheikh、Mourad A. M. Aboul-Soud

  DOI：10.3390/molecules25051124

  日期：——

  The present work aims to design and synthesize novel series of spiro pyrazole-3,3’-oxindoles analogues and investigate their bioactivity as antioxidant and antimicrobial agents, as well as antiproliferative potency against selected human cancerous cell lines (i.e., breast, MCF-7; colon, HCT-116 and liver, HepG-2) relative to healthy noncancerous control skin fibroblast cells (BJ-1). The mechanism of their cytotoxic activity has been also examined by immunoassaying the levels of key anti- and proapoptotic protein markers. The analytical and spectral data of the all synthesized target congeners were compatible with their structures. Synthesized compounds showed diverse moderate to powerful antimicrobial and antioxidant activities. Results of MTT assay revealed that seven synthesized compounds (i.e., 11a, 11b, 12a, 12b, 13b, 13c and 13h) particularly exhibited significant cytotoxicity against the three cancerous cell lines under investigation. Ranges of IC50 values obtained were 5.7–21.3 and 5.8–37.4 µg/mL against HCT-116 and MCF-7, respectively; which is 3.8 and 6.5-fold (based on the least IC50 values) more significant relative to the reference chemotherapeutic drug doxorubicin. In HepG-2 cells, the analogue 13h exhibited the highest cytotoxicity with IC50 value of 19.2µg/mL relative to doxorubicin (IC50 = 21.6µg/mL). The observed cytotoxicity was specific to cancerous cells, as evidenced by the minimal toxicity in the noncancerous control skin-fibroblast cells. ELISA results indicated that the observed antiproliferative effect against examined cancer cell lines is mediated via engaging the activation of apoptosis as illustrated by the significant increase in proapoptotic protein markers (p53, bax and caspase-3) and reduction in the antiapoptotic marker bcl-2. Taken together, results of the present study emphasize the potential of spiro pyrazole-oxindole analogues as valuable candidate anticancer agents against human cancer cells.

  本研究旨在设计和合成新型的螺环吡唑-3,3'-氧化吲哚类似物系列，并研究它们作为抗氧化剂和抗微生物剂的生物活性，以及相对于健康的非癌细胞控制皮肤成纤维细胞（BJ-1）对选定的人类癌细胞系（即乳腺癌MCF-7、结肠癌HCT-116和肝癌HepG-2）的抗增殖效力。通过免疫测定关键的抗凋亡和促凋亡蛋白标记物水平，也对它们的细胞毒活性机制进行了研究。所有合成目标同系物的分析和光谱数据与它们的结构相符。合成的化合物表现出多样的中等至强大的抗微生物和抗氧化活性。MTT实验结果显示，七种合成的化合物（即11a、11b、12a、12b、13b、13c和13h）特别对所研究的三种癌细胞系表现出显著的细胞毒性。获得的IC50值范围分别为5.7-21.3和5.8-37.4µg/mL，相对于健康的非癌化疗药物多柔比星，这分别是3.8和6.5倍（基于最小IC50值）更显著的。在HepG-2细胞中，类似物13h表现出最高的细胞毒性，IC50值为19.2µg/mL，相对于多柔比星（IC50=21.6µg/mL）。观察到的细胞毒性是特异性的，证明在非癌细胞控制皮肤成纤维细胞中毒性极小。ELISA结果表明，针对检测的癌细胞系的观察到的抗增殖效果是通过促进凋亡的激活介导的，如显著增加的促凋亡蛋白标记物（p53、bax和caspase-3）和减少的抗凋亡标记物bcl-2所示。综合以上结果，本研究结果强调了螺环吡唑-氧化吲哚类似物作为针对人类癌细胞的有价值的候选抗癌剂的潜力。
• Efficient Synthesis of New Benzofuran-based Thiazoles and Investigation of their Cytotoxic Activity Against Human Breast Carcinoma Cell Lines
  作者：Sobhi M. Gomha、Abdou O. Abdelhamid、Nadia A. Abdelrehem、Sahar M. Kandeel

  DOI：10.1002/jhet.3131

  日期：2018.4

  A new series of 1,3‐thiazole‐benzofuran derivatives was synthesized via heterocyclization of 2‐(1‐(6‐alkoxy‐4,7‐dimethoxybenzofuran‐5‐yl)ethylidene)‐2‐methyl‐2l4‐diazane‐1‐carbothioamides with hydrazonoyl halides. Also, 1‐(4,7‐dimethoxybenzofuran‐5‐yl)‐3‐phenylprop‐2‐en‐1‐one derivatives were used for synthesis of another series of 1,3‐thiazole‐pyrazole‐benzofuran. The structure of the newly synthesized

  通过2-（1-（1-（6-烷氧基-4,7-二甲氧基苯并呋喃-5-基）亚乙基）-2-甲基-2-14-二氮杂-1-基的杂环化反应合成了一系列新的1,3-噻唑-苯并呋喃衍生物。硫代酰胺与卤代酰卤化物。同样，使用1-（4,7-二甲氧基苯并呋喃-5基）-3-苯基丙-2-烯-1-酮衍生物合成另一系列的1,3-噻唑-吡唑-苯并呋喃。尽可能通过元素分析，光谱数据和替代途径阐明了新合成产物的结构。与阿霉素药物相比，评估了七个新化合物对人乳腺癌（MCF-7）细胞系的抗癌活性。结果表明，一些新化合物显示出有希望的抗癌活性。