4-((3-methoxyphenyl)amino)furan-2(5H)-one | 1221715-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-((3-methoxyphenyl)amino)furan-2(5H)-one
• 英文别名: 4-(3-Methoxyanilino)-2(5H)-furanone；3-(3-methoxyanilino)-2H-furan-5-one
• CAS: 1221715-76-9
• 化学式: C₁₁H₁₁NO₃
• mdl: MFCD23703696
• 分子量: 205.213
• InChiKey: LUORIJMDTOOFBN-UHFFFAOYSA-N

物化性质

• 沸点：
  390.8±42.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((3-methoxyphenyl)amino)furan-2(5H)-one 在 四氯苯醌 、 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 反应 27.0h， 生成 6-methoxy-9-(3,4,5-trimethoxyphenyl)-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one
  参考文献：
  名称：

  Synthesis and comparative evaluation of 4-oxa- and 4-aza-podophyllotoxins as antiproliferative microtubule destabilizing agents

  摘要：

  A series of novel 4-oxa-podophyllotoxin derivatives 7 featuring the intact lactone ring D and various substituents in rings B and E has been synthesized and evaluated in a phenotypic sea urchin embryo assay along with the representative 4-aza-analogs 5 for their antimitotic and microtubule destabilizing activity. The most active compounds exhibited myristicin-derived or a 3',5'-dimethoxy substitution pattern in the ring E and a 6-methoxy moiety replacing the methylenedioxy ring A. Compounds 5xb, 5xe, 5yb, 7xa, 7xb, and 7xc showed potent antiproliferative effects in the NCI60 cytotoxicity screen. Notably, growth of the multi-drug resistant NCI/ADR-RES cells was more affected by these agents than the parent OVCAR-8 cell line. Although generally 4-oxa-podophyllotoxins were less potent than the respective 4-aza-derivatives in these assays, stability of the former series towards oxidation may prove to be of interest for the development of anticancer agents with in vivo activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.128
• 作为产物：
  描述：

  4-羟乙酰乙酸内酯 、 间氨基苯甲醚 以 乙腈 为溶剂， 反应 0.67h， 以74%的产率得到4-((3-methoxyphenyl)amino)furan-2(5H)-one
  参考文献：
  名称：

  Synthesis of 4-azo-butenolides

  摘要：

  An efficient, catalyst-free, microwave-assisted approach has been developed for the synthesis of 4-azo-butyenolides derivatives by condensing tetronic acid with various anilines. This approach exhibited good functional group compatibility and produced the desired products in good to excellent yields in just 30-40min. This approach can be seen as a better alternative to protocols with long reaction times used for the synthesis of these compounds, which are synthons for the obtaining of quinolines.[GRAPHICS].

  DOI：

  10.1080/00397911.2017.1354380

文献信息

• Polyalkoxybenzenes from Plants. 5. Parsley Seed Extract in Synthesis of Azapodophyllotoxins Featuring Strong Tubulin Destabilizing Activity in the Sea Urchin Embryo and Cell Culture Assays
  作者：Marina N. Semenova、Alex S. Kiselyov、Dmitry V. Tsyganov、Leonid D. Konyushkin、Sergei I. Firgang、Roman V. Semenov、Oleg R. Malyshev、Mikhail M. Raihstat、Fabian Fuchs、Anne Stielow、Margareta Lantow、Alex A. Philchenkov、Michael P. Zavelevich、Nikolay S. Zefirov、Sergei A. Kuznetsov、Victor V. Semenov

  DOI：10.1021/jm200737s

  日期：2011.10.27

  targeted molecules were evaluated in vivo in a phenotypic sea urchin embryo assay for antimitotic and tubulin destabilizing activity. The most active compounds identified by the in vivo sea urchin embryo assay featured myristicin-derived ring E (4e, 6e, and 8e). These molecules were determined to be more potent than podophyllotoxin. Cytotoxic effects of selected molecules were further confirmed and evaluated

  使用欧芹种子油中的烯丙基聚烷氧基苯合成了一系列带有修饰的环B和E的4-氮杂鬼臼毒素衍生物。在表型海胆胚胎试验中体内评估了靶向分子的抗有丝分裂和微管蛋白去稳定活性。通过体内海胆胚胎测定法鉴定出的最具活性的化合物的特征是肉豆蔻酸衍生的环E（4e，6e和8e）。确定这些分子比鬼臼毒素更有效。通过使用A549和Jurkat人类白血病T细胞系的常规测定法进一步证实和评估了所选分子的细胞毒性作用，包括细胞生长抑制，细胞周期停滞，细胞微管破坏和凋亡诱导。B环的修饰产生6-OMe取代的分子8e，其为最具活性的化合物。最后，在Jurkat细胞中，化合物8e诱导了由顶端caspases-2和-9而不是caspase-8介导的caspase依赖性凋亡，这暗示了caspase-9依赖性内在凋亡途径的参与。
• Microwave‐Assisted Three‐Component Synthesis of Novel <i>N</i> ‐Arylated‐Dihydrobenzo[ <i>g</i> ]quinoline‐5,10‐Diones and Their Potential Cytotoxic Activity
  作者：Ha Thanh Nguyen、Giang Le‐Nhat‐Thuy、Phuong Hoang Thi、Quynh Giang Nguyen Thi、Tuan Anh Nguyen、Thu Ha Nguyen Thi、Tuyet Anh Dang Thi、Tuyen Van Nguyen

  DOI：10.1002/cbdv.202200359

  日期：2022.8

  A convenient three-component synthetic approach was developed en route to new and significative N-arylated-dihydrobenzo[g]quinoline-5,10-diones using 2-hydroxy-1,4-naphthoquinone, a variety of aromatic aldehydes, and 4-(arylamino)furan-2(5H)-ones. A sequence of steps including Knoevenagel condensation, Michael addition, [1,3]-hydrogen shift, intramolecular cyclization and dehydration led to the formation

  在使用 2-羟基-1,4-萘醌、多种芳香醛和4- (芳基氨基)furan-2(5 H )-ones。包括 Knoevenagel 缩合、迈克尔加成、[1,3]-氢位移、分子内环化和脱水在内的一系列步骤导致产物的形成。所有产品均通过光谱技术进行结构表征，并根据它们对四种癌细胞系（KB、HepG2、A549 和 MCF7）和人胚胎肾 (Hek-293) 细胞系的细胞毒性进行评估。
• Synthesis of 4-azo-butenolides
  作者：Ana Paula da Rocha Pissurno、Rosangela da Silva de Laurentiz

  DOI：10.1080/00397911.2017.1354380

  日期：2017.10.18

  An efficient, catalyst-free, microwave-assisted approach has been developed for the synthesis of 4-azo-butyenolides derivatives by condensing tetronic acid with various anilines. This approach exhibited good functional group compatibility and produced the desired products in good to excellent yields in just 30-40min. This approach can be seen as a better alternative to protocols with long reaction times used for the synthesis of these compounds, which are synthons for the obtaining of quinolines.[GRAPHICS].
• Synthesis and comparative evaluation of 4-oxa- and 4-aza-podophyllotoxins as antiproliferative microtubule destabilizing agents
  作者：Natalia B. Chernysheva、Dmitry V. Tsyganov、Alex A. Philchenkov、Michael P. Zavelevich、Alex S. Kiselyov、Roman V. Semenov、Marina N. Semenova、Victor V. Semenov

  DOI：10.1016/j.bmcl.2012.01.128

  日期：2012.4

  A series of novel 4-oxa-podophyllotoxin derivatives 7 featuring the intact lactone ring D and various substituents in rings B and E has been synthesized and evaluated in a phenotypic sea urchin embryo assay along with the representative 4-aza-analogs 5 for their antimitotic and microtubule destabilizing activity. The most active compounds exhibited myristicin-derived or a 3',5'-dimethoxy substitution pattern in the ring E and a 6-methoxy moiety replacing the methylenedioxy ring A. Compounds 5xb, 5xe, 5yb, 7xa, 7xb, and 7xc showed potent antiproliferative effects in the NCI60 cytotoxicity screen. Notably, growth of the multi-drug resistant NCI/ADR-RES cells was more affected by these agents than the parent OVCAR-8 cell line. Although generally 4-oxa-podophyllotoxins were less potent than the respective 4-aza-derivatives in these assays, stability of the former series towards oxidation may prove to be of interest for the development of anticancer agents with in vivo activity. (C) 2012 Elsevier Ltd. All rights reserved.