3-methyl-1,8-diaza-9,10-anthraquinone | 90381-67-2

• 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: 3-methyl-1,8-diaza-9,10-anthraquinone
• 英文别名: 3-Methylpyrido[3,2-g]quinoline-5,10-dione
• CAS: 90381-67-2
• 化学式: C₁₃H₈N₂O₂
• 分子量: 224.219
• InChiKey: XVXWDZYWGRHSJR-UHFFFAOYSA-N

物化性质

• 熔点：
  290-300 °C (decomp)
• 沸点：
  469.0±45.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-1,8-diaza-9,10-anthraquinone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 3-acetoxymethyl-1,8-diazaanthracene-9,10-dione
  参考文献：
  名称：

  Synthesis and in vitro evaluation of 1,8-diazaanthraquinones bearing 3-dialkylaminomethyl or 3-(N-alkyl- or N-aryl)carbamoyloxymethyl substituent

  摘要：

  A series of 1,8-diazaanthraquinone derivatives carrying a 3-dialkylaminomethyl or a 3-(N-alkyl or aryl)carbamoyloxymethyl substituent was synthesised and their in vitro cytotoxic activities were evaluated against eight human cancer cell lines (HOP62, SK-OV-3, HCT-15, SF295, MCF7, SNU-354, KB-3-1 and KB-V-1). A number of compounds including 8c, 8d and 11c showed cytotoxic activity comparable to that of doxorubicin against all human cancer cell lines tested. The compounds 8c and 8d were 2100 times more potent than doxorubicin against HCT-15, MCF7 and SNU-354 cancer cell lines. Furthermore, these compounds retained considerable cytotoxic activity against the doxorubicin-resistant cell line KB-V-1, implying their therapeutic potential to treat doxorubicin-resistant tumours. These compounds inhibited topoisomerase II-mediated DNA relaxation in vitro, suggesting that this inhibitory effect be attributable to their cytotoxicity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00118-1
• 作为产物：
  描述：

  5,8-喹啉二酮 以 乙醇 、 苯 为溶剂， 反应 26.0h， 生成 3-methyl-1,8-diaza-9,10-anthraquinone
  参考文献：
  名称：

  Cycloaddition routes to azaanthraquinone derivatives. 2. Use of azadienes

  摘要：

  DOI：

  10.1021/jo00387a032

文献信息

• Hetero Diels–Alder Reactions of 1-Acetylamino- and 1-Dimethylamino-1-azadienes with Benzoquinones
  作者：José Marı́a Pérez、Pilar López-Alvarado、Carmen Avendaño、J.Carlos Menéndez

  DOI：10.1016/s0040-4020(00)00058-2

  日期：2000.3

  Treatment of bromobenzoquinone with 2 equiv. of a 1-dimethylamino-1-azadiene afforded mixtures of the corresponding 1,8-diaza-9,10-anthraquinone and 1,5-diaza-9,10-anthraquinone. Double hetero Diels–Alder reactions between 1-dimethylamino-1-azadienes and 2,6-dibromobenzoquinone afford symmetrically substituted 1,8-diaza-9,10-anthraquinone derivatives in excellent yields. 3-Substituted 1-azadienes afford

  2当量的溴苯醌处理。制备1-二甲基氨基-1-氮杂二烯，得到相应的1，8-二氮杂-9，10-蒽醌和1，5-二氮杂-9，10-蒽醌的混合物。双杂Diels – 1-二甲基氨基-1-氮杂二烯与2,6-二溴苯醌之间的Alder反应以极好的收率得到对称取代的1,8-二氮杂-9,10-蒽醌衍生物。3-取代的1-azadienes提供芳族衍生物，而4-取代的或3,4-二取代的1-azadienes导致1,8-双-（二甲基氨基）-1,4,5,8-四氢-1,8-二氮杂-9,10-蒽醌，在热条件下被芳香化。还可以控制杂Diels-Alder反应，得​​到孤立的7-溴5,8-喹啉醌，将其与第二氮杂二烯处理可以制备不对称的1,8-二氮杂9,10-蒽醌。
• Ultrasound assisted Diels-Alder reactions of 1-azadienes with “normal” electronic demand.
  作者：Mercedes Villacampa、Jose' María Pérez、Carmen Avendaño、J.Carlos Menéndez

  DOI：10.1016/s0040-4020(01)89620-4

  日期：1994.1

  irradiation accelerates hetero Diels-Alder reactions between 1-dimethylamino-1-azadienes and electron-defficient dienophiles. Besides the lower reaction times and increased yields, other advantages of the sonicated reactions are the possibility of isolating previously unknown adducts due to the milder reaction conditions and, in some cases, the decrease in side reactions.

  超声辐射加速了1-二甲基氨基-1-氮杂二烯与电子效率低的亲二烯体之间的杂Diels-Alder反应。除了缩短反应时间和提高产率外，超声反应的其他优点是由于反应条件温和以及在某些情况下副反应的减少，可以分离出以前未知的加合物。
• Regiochemical control in Diels–Alder routes to aza-anthraquinone derivatives
  作者：Kevin T. Potts、Debkumar Bhattacharjee、Eileen B. Walsh

  DOI：10.1039/c39840000114

  日期：——

  Quinoline- and isoquinoline-5,8-diones react with 1-methoxycyclohexa-1,3-diene at 80 °C, the former giving 8-methoxy-1-aza-anthraquinone regiospecifically and the latter 5-methoxy-2-aza-anthraquinone regioselectively; in similar cycloadditions, substituted naphtho- and azanaphtho-quinones react with 1-dimethylamino-3-methyl-1-azabuta-1,3-diene at room temperature forming substituted mono- and di-aza-anthraquinones

  喹啉和异喹啉-5,8-二烯与1-甲氧基环己-1,3-二烯在80°C下反应，前者在区域特异性地产生8-甲氧基-1-氮杂-蒽醌，后者5-甲氧基-2-氮杂-蒽醌区域选择性；在类似的环加成反应中，取代的萘醌和氮杂萘醌在室温下与1-二甲基氨基-3-甲基-1-氮杂-1，3-二烯反应，以高收率和高选择性形成取代的单-和二-氮杂-蒽醌。
• Synthesis and in vitro cytotoxicity of 3-substituted-1,8-diazaanthraquinones produced by Lewis-acid catalyzed hetero diels-alder reaction
  作者：Heesoon Lee、Seung-Il Lee、Sung-Il Yang

  DOI：10.1016/s0960-894x(98)00543-5

  日期：1998.11

  A hetero Diels-Alder reaction of quinoline-5,8-dione with 1-(N,N-dimethylamino)-3-methyl-1-aza-1,3-butadiene proceeded to give 3-methyl-1,8-diazaanthraquinone (100% regioselectivity) in the presence of Lewis-acid catalyst (ZnCl(2) or ZnBr(2)). Subsequent functionalizations of the benzylic methyl group resulted in the 1,8-diazaanthraquinone analogues as potential antitumor agents. The most active compound, 8, exhibited in vitro cytotoxic activity comparable to that of doxorubicin. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of diaza-anthraquinones by hetero diels-alder cycloaddition reactions
  作者：C. Gesto、E. de la Cuesta、C. Avendaño*

  DOI：10.1016/s0040-4020(01)89083-9

  日期：——