9-ethyl-6-hydroxy-1,4-dihydrocarbazole-1,4(9H)-dione | 459452-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-ethyl-6-hydroxy-1,4-dihydrocarbazole-1,4(9H)-dione
• 英文别名: 9-Ethyl-6-hydroxy-carbazole-1,4-dione；9-ethyl-6-hydroxycarbazole-1,4-dione
• CAS: 459452-40-5
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: PWDJTYBLOJUANO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-ethyl-6-hydroxy-1,4-dihydrocarbazole-1,4(9H)-dione 在 sodium acetate 、 锌 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 5,7,11-triacetoxy-10-ethyl-4-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 高氯酸 、 lead dioxide 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 1.5h， 生成 9-ethyl-6-hydroxy-1,4-dihydrocarbazole-1,4(9H)-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 and antifungal evaluation of 6-hydroxy-1H-carbazole-1,4(9H)-diones
  作者：Chung-Kyu Ryu、Seung-Yon Lee、Na Young Kim、Jung An Hong、Joo Hee Yoon、Aram Kim

  DOI：10.1016/j.bmcl.2010.10.124

  日期：2011.1

  6-Hydroxy-1-carbazole-1,4(9)-diones were synthesized and tested for in vitro antifungal activity against fungi. Many of these tested compounds exhibited potent antifungal activity.

  合成了 6-羟基-1-咔唑-1,4(9)-二酮并测试了其体外抗真菌活性。许多这些测试的化合物表现出有效的抗真菌活性。
• PHOSPHAPHENANTHRENE-CARBAZOLE-BASED ORGANIC LIGHT-EMITTING COMPOUND, AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME
  申请人：Chung Kwang Choon

  公开号：US20130161603A1

  公开（公告）日：2013-06-27

  Provided are a phosphaphenanthrene-carbazole-based organic light-emitting compound having superior light emitting properties, and an organic light-emitting device including the same.

  提供了一种基于磷酸苯并咔唑的有优越发光性能的有机发光化合物，以及包括该化合物的有机发光装置。
• US9431616B2
  申请人：——

  公开号：US9431616B2

  公开（公告）日：2016-08-30
• 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.