2,2-dimethyl-3-(4-nitrophenylamino)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione | 1037059-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 2,2-dimethyl-3-(4-nitrophenylamino)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
• 英文别名: 2,2-dimethyl-3-(4-nitroanilino)-3H-benzo[g][1]benzofuran-4,5-dione
• CAS: 1037059-39-4
• 化学式: C₂₀H₁₆N₂O₅
• 分子量: 364.357
• InChiKey: XOXKVAOVWLVYET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-bromo-2,2-dimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione 、 4-硝基苯胺 以 二氯甲烷 、 氯仿 为溶剂， 生成 2,2-dimethyl-3-(4-nitrophenylamino)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
  参考文献：
  名称：

  3-芳氨基和 3-烷氧基-nor-β-拉帕酮衍生物：合成和对癌细胞系的细胞毒性

  摘要：

  以中等至高产率合成了几种 3-芳基氨基和 3-烷氧基-去甲-β-拉帕酮衍生物，发现对癌细胞 SF295（中枢神经系统）、HCT8（结肠）、MDA-MB435（黑色素瘤）、和 HL60（白血病），IC 50低于 2 μM。芳氨基对硝基和 2,4-二甲氧基取代的萘醌表现出最好的细胞毒性，而邻硝基和 2,4-二甲氧基取代的萘醌比多柔比星更具选择性，并且与前体拉帕酮相似，因此很有前景。抗癌药物开发中的新先导化合物。

  DOI：

  10.1021/jm900865m

文献信息

• [EN] LAPACHONE DERIVATIVES CONTAINING TWO REDOX CENTERS AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS DE LAPACHONE CONTENANT DEUX CENTRES REDOX ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：UNIV TEXAS

  公开号：WO2017070012A1

  公开（公告）日：2017-04-27

  Provided herein are compounds containing two redox centers including a chalcogen redox center of the formula: wherein: R1, R2, X1, X2, Y1, and m are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.

  本文提供了含有两个氧化还原中心的化合物，其中包括一个硫属氧化还原中心，其化学式如下：其中：R1、R2、X1、X2、Y1和m如本文所定义。本文还提供了所述化合物的药物组合物以及使用这些化合物进行治疗的方法，包括它们在癌症治疗中的应用。
• Synthesis and anti-Trypanosoma cruzi activity of derivatives from nor-lapachones and lapachones
  作者：Eufrânio N. da Silva Júnior、Maria Cecília B.V. de Souza、Michelle C. Fernandes、Rubem F.S. Menna-Barreto、Maria do Carmo F.R. Pinto、Francisco de Assis Lopes、Carlos Alberto de Simone、Carlos Kleber Z. Andrade、Antônio V. Pinto、Vitor F. Ferreira、Solange L. de Castro

  DOI：10.1016/j.bmc.2008.03.032

  日期：2008.5

  New naphthoquinone derivatives were synthesized and assayed against bloodstream trypomastigote forms of Trypanosoma cruzi, the etiological agent of Chagas' disease. The compounds were rationalized based on hybrid drugs and appear as important compounds against this parasite. From nor-lapachol were prepared five substituted ortho-naphthofuranquinones, a non-substituted para-naphthofuranquinone, a new oxyrane and an azide and from alpha-lapachone a new non-substituted para-naphthofuranquinone. Other five substituted ortho-naphthofuranquinones recently designed as cytotoxic, were also evaluated. The most active compounds were the ortho naphthofuranquinones 3-(4-methoxyphenylamino)-2,3-dihydro-2,2-dimethylnaphtho[1,2-b]furan-4,5-dione and 3-(3-nitrophenylamino)-2,3-dihydro-2,2-dimethylnaphtho[1,2-b]furan-4,5-dione with trypanocidal activity higher than that of benznidazole, the standard drug. The compounds were rationalized based on hybrid drugs and appear as important compounds against T. cruzi. The trypanocidal activity of these substances endowed with redox properties representing a good starting point for a medicinal chemistry program aiming the chemotherapy of Chagas' disease. (c) 2008 Elsevier Ltd. All rights reserved.