2,3-dimethylquinoxaline-5,8-dione | 2768-63-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dimethylquinoxaline-5,8-dione
• 英文别名: 2,3-dimethylquinoxaline-5,8-quinone；2,3-dimethylquinaxoline-5,8-dione；5,8-Dihydro-5,8-dioxoquinoxaline；2,3-Dimethylquinoxalinedione；2,3-dimethyl-quinoxaline-5,8-dione；2.3-Dimethyl-5.8-dioxo-5H.8H-chinoxalin；2,3-Dimethyl-5,8-quinoxalinedione
• CAS: 2768-63-0
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: HCYDPFOIMPYWPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2,3-dimethylquinoxaline-5,8-dione 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙醇 、 三氟乙酸 为溶剂， 反应 0.83h， 生成 5,6,7,8,9,10-hexahydro-2,3-dimethylpyrido<2,3-g>quinoxaline-5,10-dione-9-spiro-1'-cyclohexa-3',5'-dien-2'-one
  参考文献：
  名称：

  An Intramolecular Cyclization of Phenol Derivatives Bearing Aminoquinones Using a Hypervalent Iodine Reagent

  摘要：

  The hypervalent iodine oxidation of phenol derivatives bearing aminoquinones at the ortho (9) or meta positions (19) in 2,2,2-trifluoroethanol was investigated with the aim of preparing novel antitumor compounds. Azacarbocyclic spirodienone derivatives (13) or phenol derivatives containing the 2,3-dihydro-1H-azepine systems (17, 20) were selectively obtained by the reaction of these phenol derivatives and the hypervalent io dine reagent, phenyliodine(III) bis(trifluoro acetate). The application of this reaction to phenol derivatives bearing aminoquinones (10-12) is also described.

  DOI：

  10.1021/jo951439q
• 作为产物：
  描述：

  1,4-二甲氧基-2,3-二硝基苯 在 ammonium cerium (IV) nitrate 、 palladium on activated charcoal 、 氢气 作用下， 反应 7.5h， 生成 2,3-dimethylquinoxaline-5,8-dione
  参考文献：
  名称：

  通过酚的高效氧化鉴定邻萘醌为抗AML剂。

  摘要：

  使用容易获得的钴-席夫碱钴配合物鉴定了一种简单的合成邻萘醌的方法。将苯酚有效氧化为邻萘醌可用于获得具有有效生物学活性的化合物，用于治疗急性髓细胞性白血病（AML）。在这些化合物中，化合物4h在体外有效抑制了不同AML细胞系的增殖。进一步的体内抗肿瘤研究表明，在MV4-11异种移植模型中，以40 mg / kg / d服用4h导致肿瘤消退，导致肿瘤消退，而无明显毒性。发现钴-席夫碱配合物是苯酚向邻醌转化的有效催化剂，化合物4h代表了一种潜在支架，可优化AML治疗药物的生产。

  DOI：

  10.1016/j.bioorg.2019.01.025

文献信息

• Synthetic anthracyclines: Total synthesis of D-ring pyridine and pyrazine analogues of 11-deoxydaunomycin.
  作者：Yasuyuki KITA、Masayuki KIRIHARA、Yuji FUJII、Ryuichi OKUNAKA、Shuji AKAI、Hiroshi MAEDA、Yasumitsu TAMURA、Kin-o SHIMOOKA、Hirofumi OHISHI、Toshimasa ISHIDA

  DOI：10.1248/cpb.39.857

  日期：——

  Treatment of sodium salts generated from tetrahydrohomophthalic anhydrides (6a, b) with 5, 8-dihydro-5, 8-dioxoquinoline (9) gave cycloadducts (7 and 8), regioselectively. These adducts were converted to the D-ring pyridine analogue (21) of 11-deoxydaunomycin. The D-ring pyrazine analogue (27) of 11-deoxydaunomycin was also prepared by a similar method.

  四氢同苯甲酸酐（6a，b）生成的钠盐与5, 8-二氢-5, 8-二氧喹啉（9）反应， regioselectively 生成了环加成物（7和8）。这些加成物被转化为11-脱氧多柔比星的D环吡啶类似物（21）。11-脱氧多柔比星的D环噁唑类似物（27）也通过类似的方法制备。
• Oxidation of phenols to quinones by bis(trifluoroacetoxy)iodobenzene.
  作者：R. Barret、M. Daudon

  DOI：10.1016/s0040-4039(00)97755-4

  日期：1990.1

  Bis (trifluoroacetoxy) iodobenzene oxidizes phenols into quinones in good yield.

  双（三氟乙酰氧基）碘苯可将苯酚氧化成醌，收率很高。
• The aza-analogues of 1,4-naphthoquinones are potent substrates and inhibitors of plasmodial thioredoxin and glutathione reductases and of human erythrocyte glutathione reductase
  作者：Christophe Morin、Tatiana Besset、Jean-Claude Moutet、Martine Fayolle、Margit Brückner、Danièle Limosin、Katja Becker、Elisabeth Davioud-Charvet

  DOI：10.1039/b802649c

  日期：——

  Various aza-analogues of 1,4-naphthoquinone and menadione were prepared and tested as inhibitors and substrates of the plasmodial thioredoxin and glutathione reductases as well as the human glutathione reductase. The replacement of one to two carbons at the phenyl ring of the 1,4-naphthoquinone core by one to two nitrogen atoms led to an increased oxidant character of the molecules in accordance with both the redox potential values and the substrate efficiencies. Compared to the 1,4-naphthoquinone and menadione, the quinoline-5,8-dione 1 and both quinoxaline-5,8-diones 5 and 6 behaved as the most efficient subversive substrates of the three NADPH-dependent disulfide reductases tested. Modulation of these parameters was observed by alkylation of the aza-naphthoquinone core.

  制备并测试了 1,4萘醌和甲萘醌的各种杂环类似物，并将其作为质体硫氧还蛋白酶和谷胱甘肽还原酶以及人类谷胱甘肽还原酶的抑制剂和底物。根据氧化还原电位值和底物效率，将 1,4-萘醌核心苯基环上的一到两个碳原子替换为一到两个氮原子可增加分子的氧化特性。与 1,4-萘醌和甲萘醌相比，喹啉-5,8-二酮 1 以及喹喔啉-5,8-二酮 5 和 6 是所测试的三种 NADPH 依赖性二硫还原酶最有效的颠覆性底物。通过对氮杂萘醌核心进行烷基化，可以观察到这些参数的变化。
• 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。
• Cycloaddition routes to azaanthraquinone derivatives. 1. Use of azadienophiles
  作者：kevin T. Potts、Debkumar Bhattacharjee、Eileen B. Walsh

  DOI：10.1021/jo00361a014

  日期：1986.5