2-(4-Methoxybenzoyl)-1-benzofuran-3-amine | 223788-34-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-Methoxybenzoyl)-1-benzofuran-3-amine
• 英文别名: (3-Amino-1-benzofuran-2-yl)(4-methoxyphenyl)methanone；(3-amino-1-benzofuran-2-yl)-(4-methoxyphenyl)methanone
• CAS: 223788-34-9
• 化学式: C₁₆H₁₃NO₃
• mdl: MFCD03011621
• 分子量: 267.284
• InChiKey: BLZJBFVSORKWST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-(4-Methoxybenzoyl)-1-benzofuran-3-amine 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Benzofuro[3,2-b]pyridines as mixed and selective ETB endothelin receptor antagonists

  摘要：

  The discovery, synthesis and structure-activity relationships of a series of novel benzofuro[3,2-b]pyridines as non-selective endothelin ETA/ETB as well as selective ETB receptor antagonists are described. The most potent non-selective inhibitor 7s displayed an IC50 of 21 nM and 41 nM for ETA and ETB receptors, respectively, whereas 7ee merely showed affinity for the ETB receptor (IC50 = 3.6 nM). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00040-2
• 作为产物：
  描述：

  2-[2-(4-Methoxyphenyl)-2-oxoethoxy]benzonitrile 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以33%的产率得到2-(4-Methoxybenzoyl)-1-benzofuran-3-amine
  参考文献：
  名称：

  Synthesis and Analgesic Activity of Some Substituted 1-Benzofurans and 1-Benzothiophenes

  摘要：

  2-苯甲酰基和2-(吡啶甲酰基)-1-苯并呋喃-3-胺是由2-羟基苯甲腈和相应的溴乙酮衍生物制备而成的。类似地，2-苯甲酰基和2-(吡啶甲酰基)-1-苯并噻吩-3-胺是由2-硫代基苯甲腈制备而成的。用乙酸酐或氯甲酸乙酯处理2-苯甲酰基-1-苯并呋喃-3-胺可得到相应的N-乙酰基或N-乙氧羰基衍生物。这些N-活化化合物与溴乙酸乙酯烷基化，得到乙基N-乙酰基-N-(2-苯甲酰基-1-苯并呋喃-3-基)甘氨酸酯和乙基N-(2-苯甲酰基-1-苯并呋喃-3-基)-N-乙氧羰基甘氨酸酯。它们经轻度水解得到相应的甘氨酸衍生物。乙基N-(2-苯甲酰基-1-苯并呋喃-3-基)氨基甲酸酯的甲基化得到相应的N-甲基氨基甲酸酯，后者水解为N-甲基-(2-苯甲酰基-1-苯并呋喃-3-基)胺。2-苯甲酰基-7-甲氧基-1-苯并呋喃-3-胺和2-(4-甲氧基苯甲酰基)-1-苯并呋喃-3-胺经三溴化硼去甲基化得到相应的羟基衍生物；它们与溴乙酸乙酯的O-烷基化反应得到乙基[(3-氨基-2-苯甲酰基-1-苯并呋喃-7-基)氧基]乙酸酯和乙基{4-[(3-氨基-1-苯并呋喃-2-基)羰基]苯氧基}乙酸酯，分别。这些酯的轻度水解得到相应的酸。类似地，羟基衍生物与(二甲氨基)丙基氯化物烷基化得到相应的(二甲氨基)丙氧基衍生物。2-羟基苯甲腈与2-溴-1-(2-, 3- 或 4-吡啶基)乙酮反应得到相应的2-(吡啶甲酰基)-1-苯并呋喃-3-胺。类似地，2-(吡啶甲酰基)-1-苯并噻吩-3-胺是由2-硫代基苯甲腈类似地制备而成的。2-苯甲酰基-3-(溴甲基)-1-苯并呋喃与二甲胺、1-甲基哌嗪和硫代-1-甲基哌嗪钠盐反应得到相应的烷基化产物。发现几种化合物具有显著的镇痛活性。

  DOI：

  10.1135/cccc20001093

文献信息

• Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents
  作者：Jörg Habermann、Steven V. Ley、René Smits

  DOI：10.1039/a904384e

  日期：——

  achieved by the bromination of acetophenones to α-bromoacetophenones by polymer-supported pyridinium bromide perbromide (PSPBP). The subsequent clean substitution of the obtained bromides by phenols using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD-P) and cyclodehydration of the resulting α-phenoxyacetophenones using Amberlyst 15, affords pure products without the need for any chromatographic purification

  通过用聚合物负载的溴化吡啶鎓过溴化物（PSPBP）将苯乙酮溴化为α-溴苯乙酮，可以实现一种有效的组合方法，以取代3-苯基苯并呋喃。随后使用1,5,7-三氮杂双环[4.4.0]癸-5-烯（TBD-P）将所得的溴化物彻底替换为苯酚，并使用Amberlyst 15将所得的α-苯氧基乙酰苯酮环化脱水，得到的纯产品不含需要任何色谱纯化步骤。
• Synthesis and biological evaluation of benzofuran-based 3,4,5-trimethoxybenzamide derivatives as novel tubulin polymerization inhibitors
  作者：Qiu Li、Xie-Er Jian、Zhi-Ru Chen、Lin Chen、Xian-Sen Huo、Zi-Hua Li、Wen-Wei You、Jin-Jun Rao、Pei-Liang Zhao

  DOI：10.1016/j.bioorg.2020.104076

  日期：2020.9

  A new series of derivatives characterized by the presence of the 3,4,5-trimethoxylbenzamide substituted benzofurans were synthesized and evaluated for antiproliferative activity against four cancer cell lines and one normal human cell line. Among them, derivative 6g with greatest cytotoxicity significantly inhibited the growth of MDA-MB-231, HCT-116, HT-29 and HeLa cell lines with IC50 values of 3

  合成了以3,4,5-三甲氧基苯甲酰胺取代的苯并呋喃为特征的一系列新衍生物，并评估了其对四种癌细胞系和一种正常人细胞系的抗增殖活性。其中，具有最大细胞毒性的衍生物6g显着抑制MDA-MB-231，HCT-116，HT-29和HeLa细胞系的生长，IC 50值分别为3.01、5.20、9.13和11.09μM。重要的是，6g对非肿瘤细胞系HEK-293具有优异的选择性（IC 50  > 30μM）。而且，机理研究表明6g诱导的HeLa细胞以浓度依赖的方式停滞在G2 / M期，并通过与CA-4一致的方式抑制微管蛋白的聚合。通常，这些观察结果表明6g是有前途的抗癌药物，值得进一步研究以产生潜在的抗肿瘤药。
• Endothelin receptor antagonists
  申请人：MERCK PATENT GmbH

  公开号：EP0755934A1

  公开（公告）日：1997-01-29

  Novel compounds of the formula I in which -Y-Z-, R1,R2,R3,R4,R5 and X have the meaning indicated in Patent Claim 1, and their salts show endothelin receptor-antagonistic properties.

  式 I 的新型化合物 其中 -Y-Z-、R1,R2,R3,R4,R5 和 X 具有专利权利要求 1 中所示的含义，以及它们的盐类 具有内皮素受体拮抗特性。
• Novel iodoacetamido benzoheterocyclic derivatives with potent antileukemic activity are inhibitors of STAT5 phosphorylation
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Filippo Prencipe、Carlota Lopez-Cara、Riccardo Rondanin、Daniele Simoni、Ernest Hamel、Stefania Grimaudo、Rosaria Maria Pipitone、Maria Meli、Manlio Tolomeo

  DOI：10.1016/j.ejmech.2015.11.022

  日期：2016.1

  Signal Transducer and Activator of Transcription 5 (STAT5) protein, a component of the STAT family of signaling proteins, is considered to be an attractive therapeutic target because of its involvement in the progression of acute myeloid leukemia. In an effort to discover potent molecules able to inhibit the phosphorylation-activation of STAT5, twenty-two compounds were synthesized and evaluated on the basis of our knowledge of the activity of 2-(3',4',5'-trimethoxybenzoyl)-3-iodoacetamido-6-methoxy benzo[b]furan derivative I as a potent STAT5 inhibitor. Most of these molecules, structurally related to compound 1, were characterized by the presence of a common 3',4',5'-trimethoxybenzoyl moiety at the 2-position of different benzoheterocycles such as benzo[b]furan, benzo[b]thiophene, indole and N-methylindole. Effects on biological activity of the iodoacetamido group and of different moieties (methyl and methoxy) at the C-3 to C-7 positions were examined. In the series of benzo[b]furan derivatives, moving the iodoacetylamino group from the C-4 to the C-5 or C-6 positions did not significantly affect antiproliferative activity. Compounds 4, 15, 20 and 23 blocked STAT5 signals and induced apoptosis of K562 BCR-ABL positive cells. For compound 23, the trimethoxybenzoyl moiety at the 2-position of the benzo[b]furan core was not essential for potent inhibition of STAT5 activation. (C) 2015 Elsevier Masson SAS. All rights reserved.
• US5700807A
  申请人：——

  公开号：US5700807A

  公开（公告）日：1997-12-23