4-Anilino-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione | 1037059-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 4-Anilino-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
• CAS: 1037059-41-8
• 化学式: C₂₁H₁₉NO₃
• 分子量: 333.387
• InChiKey: IWKRKOQJCPFXGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-bromo-α-lapachone 、 苯胺 反应 0.5h， 以70%的产率得到4-Anilino-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
  参考文献：
  名称：

  Synthesis and anti-Trypanosoma cruzi activity of derivatives from nor-lapachones and lapachones

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.03.032

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.