4,6-dimethyl-1,8-diaza-2,9,10-anthracenetrione | 143726-24-3

• 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: 4,6-dimethyl-1,8-diaza-2,9,10-anthracenetrione
• 英文别名: 4,6-dimethyl-1H-1,8-diazaanthracen-2,9,10-trione；Pyrido[3,2-g]quinoline-2,5,10(1H)-trione, 4,7-dimethyl-；4,7-dimethyl-1H-pyrido[3,2-g]quinoline-2,5,10-trione
• CAS: 143726-24-3
• 化学式: C₁₄H₁₀N₂O₃
• 分子量: 254.245
• InChiKey: YPCWBICNZDPPGK-UHFFFAOYSA-N

物化性质

• 沸点：
  562.1±50.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6-dimethyl-1,8-diaza-2,9,10-anthracenetrione 在 urea hydrogen peroxide 作用下， 以 三氟乙酸 为溶剂， 反应 24.0h， 以87%的产率得到3,5-dimethyl-8H-1,8-diazaanthracene-7,9,10-trione-1-oxide
  参考文献：
  名称：

  N-Oxides of azaanthraquinones

  摘要：

  A procedure is described for the efficient N-oxidation of heterocyclic quinones, which represents a considerable improvement over previous, multi-step methods.

  DOI：

  10.1016/s0040-4020(01)85524-1
• 作为产物：
  描述：

  4-methyl-2,5,8(1H)-quinolinetrione 、 3,4-Dimethyl-1H-quinoline-2,5,8-trione 在 silica gel 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以88%的产率得到4,6-dimethyl-1,8-diaza-2,9,10-anthracenetrione
  参考文献：
  名称：

  硅胶支持的喹啉三酮杂Diels-Alder反应

  摘要：

  当2,5,8（1 H）-喹啉三酮负载在硅胶上并用过量的1-二甲基氨基-1-氮杂二烯处理后，进行快速色谱分离，得到相应的5,8-二氢-1,8-二氮杂蒽2通常以优异的产率获得了9，10-三酮或1，8-二氮杂蒽-2，9，10-三酮。该方法最小化或完全防止了向起始醌中添加二甲胺，该问题在过去已严重地限制了1-二甲基氨基-1-氮杂二烯作为醌的杂二烯的用途。

  DOI：

  10.1016/0040-4039(96)01526-2

文献信息

• Anthraquinonic derivatives having an antitumor activity and applications
  申请人：Universidad Complutense De Madrid

  公开号：US05716963A1

  公开（公告）日：1998-02-10

  Said derivatives have the general formula (I) and are: ##STR1## (I-A) 4,6,7-trimethyl-5,8,8a,10a-tetrahydro-1H-1-azaanthracen-2,9,10-trione; (I-B) 2-ethoxy-3-methyl-1-azaanthracen-9,10-dione; (I-C) 3-ethyl-1,8-dihydro-1H-1,8-diazaanthracen-2,7,9,10-tetraone; (I-d) 2-acethoxy-3-methyl-1,8-diazaanthracen-2,9,10-trione; (I-e) 6-fluor-4-methyl-1H-1,8-diazaanthracen-2,9,10-trione; (I-f) 6-dimethylamino-4-methyl-1H-1,8-diazaanthracen-2,9,10-trione; (I-g) 4-methyl-5-(2-nitrophenyl)-5,8-dihydro-1H-1,8-diazaanthracen-2,9,10-trione ; (I-h) 3,5-dimethyl-1,8-dihydro-1,8-diazaanthracen-2,7,9,10-tetraone; (I-i) 3,6-difluor-1,8-diazaanthracen-9,10-dione; (I-j) 6-methyl-3-phenyl-1H-1,8-diazaanthracen-2,9,10-trione; (I-k) 3-fluor-4-methyl-1-dihydro-1-azaanthracen-9,10-dione; 3-fluor-1-azaanthracen-1,10-dione. Application as antitumor agents.

  所述衍生物具有通式（I），即：4,6,7-三甲基-5,8,8a,10a-四氢-1H-1-氮杂蒽-2,9,10-三酮（I-A）；2-乙氧基-3-甲基-1-氮杂蒽-9,10-二酮（I-B）；3-乙基-1,8-二氢-1H-1,8-二氮杂蒽-2,7,9,10-四酮（I-C）；2-乙酰氧基-3-甲基-1,8-二氮杂蒽-2,9,10-三酮（I-d）；6-氟-4-甲基-1H-1,8-二氮杂蒽-2,9,10-三酮（I-e）；6-二甲胺基-4-甲基-1H-1,8-二氮杂蒽-2,9,10-三酮（I-f）；4-甲基-5-(2-硝基苯基)-5,8-二氢-1H-1,8-二氮杂蒽-2,9,10-三酮（I-g）；3,5-二甲基-1,8-二氢-1,8-二氮杂蒽-2,7,9,10-四酮（I-h）；3,6-二氟-1,8-二氮杂蒽-9,10-二酮（I-i）；6-甲基-3-苯基-1H-1,8-二氮杂蒽-2,9,10-三酮（I-j）；3-氟-4-甲基-1-二氢-1-氮杂蒽-9,10-二酮（I-k）；3-氟-1-氮杂蒽-1,10-二酮。用作抗肿瘤剂。
• Synthesis and Biological Activity of New 1,8-Diaza-2,9,10-anthracenetrione Derivatives
  作者：Cristina Gesto、Elena de la Cuesta、Carmen Avendaño、F. Emling

  DOI：10.1002/jps.2600810819

  日期：1992.8

  8-quinolinetriones and 1-azadienes afford 1,8-diaza-2,9,10-anthracenetriones, which are simple analogues of the antitumoral antibiotic diazaquinomicin A. Cytotoxicity in this series and antitumor activity of the lead compound, 6-methyl-1,8-diaza-2,9,10-anthracenetrione, are reported.

  2,5,8-喹啉三酮和1-氮杂二烯的Diels-Alder杂环加成反应可得到1,8-diaza-2,9,10-蒽蒽酮，它们是抗肿瘤抗生素diazaquinomicin A的简单类似物。该系列药物的细胞毒性和抗肿瘤活性据报道，前导化合物6-甲基-1,8-二氮杂-2,9,10-蒽酮。
• Structure-Antitumor Activity Relationships of Aza- and Diaza-Anthracene-2,9,10-Triones and Their Partially Saturated Derivatives
  作者：Carmen Avendaño、Pilar López-Alvarado、José María Pérez、Miguel Ángel Alonso、Eva Pascual-Alfonso、Miriam Ruiz-Serrano、J. Carlos Menéndez

  DOI：10.3390/molecules29020489

  日期：——

  relationships. From the results obtained, we conclude that some representatives of the 1,8-diazaanthracene-2,9,10-trione framework show potent and selective cytotoxicity against solid tumors. Similar findings were made for the related 1-azaanthracene-2,9,10-trione derivatives, structurally similar to the marcanine natural products, which showed improved activity over their natural counterparts. An enantioselective

  1,8-二氮杂蒽-2,9,10-三酮，它们的 5,8-二氢衍生物和 1,8-二氮杂蒽-2,7,9,10-四酮，在结构上与二氮杂喹啉菌素家族天然产物相关，采用 Diels-Alder 策略以区域选择性方式合成。研究了这些文库在各种人类癌细胞系中的细胞毒性，以建立结构-活性关系。从获得的结果中，我们得出结论，1,8-二氮杂蒽-2,9,10-三酮框架的一些代表对实体瘤显示出有效的选择性细胞毒性。相关的 1-氮杂蒽-2,9,10-三酮衍生物也发现了类似的结果，它们在结构上与 marcanine 天然产物相似，其活性优于天然产物。针对手性 5 取代的 1,8-二杂蒽-2,9,10-三酮的情况开发了一种基于使用 SAMP 相关手性衍生的对映选择性方案，并表明它们的细胞毒性不是对映特异性的。
• NEW ANTHRAQUINONIC DERIVATIVES HAVING AN ANTITUMOR ACTIVITY, AND APPLICATIONS THEREOF
  申请人：UNIVERSIDAD COMPLUTENSE DE MADRID

  公开号：EP0695752A1

  公开（公告）日：1996-02-07

  Said derivatives have the general formula (I) and are: (I-A) 4,6,7-trimethyl-5,8,8a,10a-tetrahydro-1H-1-azaanthracen-2,9,10-trione; (I-B) 2-ethoxy-3-methyl-1-azaanthracen-9,10-dione; (I-C) 3-ethyl-1,8-dihydro-1H-1,8-diazaanthracen-2,7,9,10-tetraone; (I-d) 2-acethoxy-3-methyl-1,8-diazaanthracen-2,9,10-trione; (I-e) 6-fluor-4-methyl-1H-1,8-diazaanthracen-2,9,10-trione; (I-f) 6-dimethylamino-4-methyl-1H-1,8-diazaanthracen-2,9,10-trione; (I-g) 4-methyl-5-(2-nitrophenyl)-5,8-dihydro-1H-1,8-diazaanthracen-2,9,10-trione; (I-h) 3,5-dimethyl-1,8-dihydro-1,8-diazaanthracen-2,7,9,10-tetraone; (I-i) 3,6-difluor-1,8-diazaanthracen-9,10-dione; (I-j) 6-methyl-3-phenyl-1H-1,8-diazaanthracen-2,9,10-trione; (I-k) 3-fluor-4-methyl-1,4-dihydro-1-azaanthracen-9,10-dione; (I-l) 3-fluor-1-azaanthracen-1,10-dione. Application as antitumor agents.

  上述衍生物具有通式(I)，它们是(I-A) 4,6,7-trimethyl-5,8,8a,10a-tetrahydro-1H-1-azaanthracen-2,9,10-trione; (I-B) 2-ethoxy-3-methyl-1-azaanthracen-9,10-dione; (I-C) 3-ethyl-1,8-dihydro-1H-1,8-diazaanthracen-2,7,9,10-tetraone;(I-d) 2-乙氧基-3-甲基-1,8-二氮杂蒽-2,9,10-三酮； (I-e) 6-氟-4-甲基-1H-1,8-二氮杂蒽-2,9,10-三酮； (I-f) 6-二甲基氨基-4-甲基-1H-1,8-二氮杂蒽-2,9,10-三酮；(I-g) 4-methyl-5-(2-nitrophenyl)-5,8-dihydro-1H-1,8-diazaanthracen-2,9,10-trione; (I-h) 3,5-dimethyl-1,8-dihydro-1,8-diazaanthracen-2,7,9,10-tetraone; (I-i) 3,6-difluor-1,8-diazaanthracen-9,10-dione;(I-j) 6-methyl-3-phenyl-1H-1,8-diazaanthracen-2,9,10-trione; (I-k) 3-fluor-4-methyl-1,4-dihydro-1-azaanthracen-9,10-dione; (I-l) 3-fluor-1-azaanthracen-1,10-dione.作为抗肿瘤药物的应用。
• 1-Acylamino-1-azadienes as an alternative to 1-dimethylamino-1-azadienes in the preparation of 1,8-diazaanthracene-2,9,10-triones.
  作者：JoséMaría Pérez、Carmen Avendaño、J. Carlos Menéndez

  DOI：10.1016/0040-4020(95)00295-j

  日期：1995.6

  Acetylhydrazones of alpha,beta-saturated aldehydes behave as 1-azadienes in their reaction with 2,5,8(1H)-quinolinetriones, affording 1,8-diazaanthracene-2,9,10-triones, while die corresponding N-methyl derivatives are unreactive. In comparison with N,N-dimethylhydrazones, acetylhydrazones are less reactive bur me yields obtained are similar or higher because of the suppression of side products formed by addition of dimethylamine to the starting quinone.