3-(4-methoxyanilino)-2,2-dimethyl-3H-benzo[g][1]benzofuran-4,5-dione | 1037059-40-7

• 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: 3-(4-methoxyanilino)-2,2-dimethyl-3H-benzo[g][1]benzofuran-4,5-dione
• CAS: 1037059-40-7
• 化学式: C₂₁H₁₉NO₄
• 分子量: 349.386
• InChiKey: ULSOSJFIPXSKPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

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 、 甲氧苯胺 以 二氯甲烷 、 氯仿 为溶剂， 生成 3-(4-methoxyanilino)-2,2-dimethyl-3H-benzo[g][1]benzofuran-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

• 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.
• A new approach for the synthesis of 3-substituted cytotoxic nor-β-lapachones
  作者：Mariana F. C. Cardoso、Illana M. C. B. da Silva、Helvécio M. dos Santos Júnior、David R. Rocha、Ana Jérsia Araújo、Claudia Pessoa、Manoel O. de Moraes、Letícia V. C. Lotufo、Fernando de C. da Silva、Wilson C. Santos、Vitor F. Ferreira

  DOI：10.1590/s0103-50532013000100003

  日期：——

  Several studies have demonstrated the cytotoxic potential of nor-beta-lapachone derivative against cancer cells. Considering nor-beta-lapachone as an important prototype, a set of new 3-substituted nor-beta-lapachones was synthesized by a new synthetic route that involves the use of synthetic intermediate generated for coupling with several nucleophiles containing the carbohydrate and 2H-pyrazole substituent moieties. All the compounds were screened against four tumor cell lines. Two of the compounds showed moderate cytotoxicity, while the other compounds strongly inhibit all tested cancer cell lines.
• 3-Arylamino and 3-Alkoxy-nor-β-lapachone Derivatives: Synthesis and Cytotoxicity against Cancer Cell Lines
  作者：Eufrânio N. da Silva Júnior、Clara F. de Deus、Bruno C. Cavalcanti、Cláudia Pessoa、Letícia V. Costa-Lotufo、Raquel C. Montenegro、Manoel O. de Moraes、Maria do Carmo F. R. Pinto、Carlos A. de Simone、Vitor F. Ferreira、Marilia O. F. Goulart、Carlos Kleber Z. Andrade、Antônio V. Pinto

  DOI：10.1021/jm900865m

  日期：2010.1.14

  Several 3-arylamino and 3-alkoxy-nor-β-lapachone derivatives were synthesized in moderate to high yields and found to be highly potent against cancer cells SF295 (central nervous system), HCT8 (colon), MDA-MB435 (melanoma), and HL60 (leukemia), with IC50 below 2 μM. The arylamino para-nitro and the 2,4-dimethoxy substituted naphthoquinones showed the best cytoxicity profile, while the ortho-nitro and

  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。