3-methyl-1-azaanthracene-9,10-dione-1-oxide | 154410-15-8

• 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-azaanthracene-9,10-dione-1-oxide
• 英文别名: 3-methyl-1-azaanthracen-9,10-dione 1-oxide；3-methyl-1-azaanthracenequinone-1-oxide；3-Methylbenzo[g]quinoline-5,10-dione 1-oxide；3-methyl-1-oxidobenzo[g]quinolin-1-ium-5,10-dione
• CAS: 154410-15-8
• 化学式: C₁₄H₉NO₃
• 分子量: 239.23
• InChiKey: QXXHZZZCZPQNEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-1-azaanthracene-9,10-dione-1-oxide 在 水 、 对甲苯磺酰氯 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以65%的产率得到3-methyl-1H-1-azaanthracene-2,9,10-trione
  参考文献：
  名称：

  Reactions of aza- and diazaanthraquinone N-oxides

  摘要：

  1-Azaanthracene-2,5,8-triones and 1,8-diazaanthracene-2,7,8,10-tetraones, Which are structurally related to diazaquinomycin, are prepared by functionalization of azaanthraquinone N-oxides. The complete procedure implies a Diels-Alder reaction as a key step, followed by N-oxidation and treatment of the N-oxides with benzoyl or tosyl chlorides in the presence of water.

  DOI：

  10.1016/0040-4020(94)01003-i
• 作为产物：
  描述：

  3-methylbenzo[g]quinoline-5,10-dione 在 urea hydrogen peroxide 作用下， 以 三氟乙酸 为溶剂， 反应 24.0h， 以70%的产率得到3-methyl-1-azaanthracene-9,10-dione-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

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。
• Antitumoral aza- and diazaanthracenes
  申请人：UNIVERSIDAD COMPLUTENSE DE MADRID

  公开号：EP0574195A1

  公开（公告）日：1993-12-15

  Azaanthracene-triones of the formula: (in which: R¹, R², R⁴ and R⁵ are the same or are different and each is a hydrogen atom or a lower alkyl group;    R³ is a hydrogen atom, a lower alkyl group, a phenyl group or an amino-substituted phenyl gro up; and    X is a -CH-, =N- or -NH-, whereby the ring containing the group X is a benzene, pyridine or dihydropyridene ring) have antitumoral activity.

  式中的氮杂蒽三酮： 其中R¹、R²、R⁴和R⁵相同或不同，且各自为氢原子或低级烷基； R³ 是氢原子、低级烷基、苯基或氨基取代的苯基；以及 X是-CH-、=N-或-NH-，其中含有基团X的环是苯、吡啶或二氢吡啶环）。 具有抗肿瘤活性。
• 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。
• Diaz-Guerra, Luis M.; Ocana, Blanca; Perez, Jose Maria, Bulletin des Societes Chimiques Belges, 1995, vol. 104, # 12, p. 683 - 690
  作者：Diaz-Guerra, Luis M.、Ocana, Blanca、Perez, Jose Maria、Avendano, Carmen、Espada, Modesta、et al.

  DOI：——

  日期：——
• Ocana Blanca, Espada Modesta, Avendano Carmen, Tetrahedron, 50 (1994) N 31, S 9505-9510
  作者：Ocana Blanca, Espada Modesta, Avendano Carmen

  DOI：——

  日期：——