10-ethyl-7-hydroxy-3-methyl-10H-pyrido[2,3-b]carbazole-5,11-dione | 459452-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 10-ethyl-7-hydroxy-3-methyl-10H-pyrido[2,3-b]carbazole-5,11-dione
• 英文别名: 10-ethyl-7-hydroxy-3-methylpyrido[2,3-b]carbazole-5,11-dione
• CAS: 459452-41-6
• 化学式: C₁₈H₁₄N₂O₃
• 分子量: 306.321
• InChiKey: HGTSVAYGPZJULK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 10-ethyl-7-hydroxy-3-methyl-10H-pyrido[2,3-b]carbazole-5,11-dione 在 sodium acetate 、 锌 作用下， 反应 0.75h， 以55%的产率得到5,7,11-triacetoxy-10-ethyl-3-methyl-10H-pyrido[2,3-b]carbazole
  参考文献：
  名称：

  Synthesis of Carbazolequinone Derivatives as Inhibitors ofToxoplasma gondii Purine Nucleoside Phosphorylase

  摘要：

  9-Ethyl-6-hydroxycarbazolequinone (9) was synthesized and submitted to a hetero Diels-Alder reaction towards azadienes 10a or 10b to afford the hydroxypyridocarbazole-5,11-diones 11 or 12a,b, A Bracher cyclization applied to compound 12b led to the 9-hydroxyquinoneimine 15 admixed with its 9-methyl ether 16. These compounds as well as other carbazolequinone derivatives were evaluated towards a purine nucleoside phosphorylase isolated from two strains of Toxoplasma gondii (a virulent strain RH and a cystic strain ME 49). The carbazolequinones 1a, 1b, 1d, 9 and pyridocarbazolequinones 2a, 4 and 5 have shown inhibitory activities similar or better than those observed with the reference compound 8-aminoguanosine. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200206)2002:11<1834::aid-ejoc1834>3.0.co;2-k
• 作为产物：
  描述：

  2,2'-二羟基联苯 在 potassium nitrososulfonate 作用下， 以 乙醇 、 氯仿 、 水 、 丙酮 为溶剂， 反应 5.0h， 生成 10-ethyl-7-hydroxy-3-methyl-10H-pyrido[2,3-b]carbazole-5,11-dione
  参考文献：
  名称：

  Synthesis of Carbazolequinone Derivatives as Inhibitors ofToxoplasma gondii Purine Nucleoside Phosphorylase

  摘要：

  9-Ethyl-6-hydroxycarbazolequinone (9) was synthesized and submitted to a hetero Diels-Alder reaction towards azadienes 10a or 10b to afford the hydroxypyridocarbazole-5,11-diones 11 or 12a,b, A Bracher cyclization applied to compound 12b led to the 9-hydroxyquinoneimine 15 admixed with its 9-methyl ether 16. These compounds as well as other carbazolequinone derivatives were evaluated towards a purine nucleoside phosphorylase isolated from two strains of Toxoplasma gondii (a virulent strain RH and a cystic strain ME 49). The carbazolequinones 1a, 1b, 1d, 9 and pyridocarbazolequinones 2a, 4 and 5 have shown inhibitory activities similar or better than those observed with the reference compound 8-aminoguanosine. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200206)2002:11<1834::aid-ejoc1834>3.0.co;2-k

文献信息

• Synthesis of Carbazolequinone Derivatives as Inhibitors ofToxoplasma gondii Purine Nucleoside Phosphorylase
  作者：Zouhair Bouaziz、Arnaud Ghérardi、François Régnier、Marie-Elizabeth Sarciron、Xavier Bertheau、Bernard Fenet、Nadia Walchshofer、Houda Fillion

  DOI：10.1002/1099-0690(200206)2002:11<1834::aid-ejoc1834>3.0.co;2-k

  日期：2002.6

  9-Ethyl-6-hydroxycarbazolequinone (9) was synthesized and submitted to a hetero Diels-Alder reaction towards azadienes 10a or 10b to afford the hydroxypyridocarbazole-5,11-diones 11 or 12a,b, A Bracher cyclization applied to compound 12b led to the 9-hydroxyquinoneimine 15 admixed with its 9-methyl ether 16. These compounds as well as other carbazolequinone derivatives were evaluated towards a purine nucleoside phosphorylase isolated from two strains of Toxoplasma gondii (a virulent strain RH and a cystic strain ME 49). The carbazolequinones 1a, 1b, 1d, 9 and pyridocarbazolequinones 2a, 4 and 5 have shown inhibitory activities similar or better than those observed with the reference compound 8-aminoguanosine. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.