2,5-二甲基-3,6-二氮杂环丙烷基-1,4-苯醌 | 18735-47-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,5-二甲基-3,6-二氮杂环丙烷基-1,4-苯醌
• 英文名称: MEDZQ
• 英文别名: 2,5-bis(1-aziridinyl)-3,5-dimethyl-1,4-bemzoquinone；2,5-bis(1-aziridinyl)-3,6-dimethyl-1,4-benzoquinone；2,5-dimethyl-3,6-di(aziridin-1-yl)-1,4-benzoquinone；2,5-diaziridinyl-3,6-dimethyl-1,4-benzoquinone；2,5-dimethyl-3,6-diaziridinyl-1,4-benzoquinone；2,5-bis(aziridin-1-yl)-3,6-dimethylcyclohexa-2,5-diene-1,4-dione
• CAS: 18735-47-2
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: IWVCOLOPRNYONP-UHFFFAOYSA-N

物化性质

• 熔点：
  212 °C
• 沸点：
  352.4±42.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2,5-二甲基-3,6-二氮杂环丙烷基-1,4-苯醌 在 1,4-dihydronicotinamide adenine dinucleotide 、 human recombinant NAD(P)H:quinone oxidoreductase 、 三羟甲基氨基甲烷盐酸盐 作用下， 以 水 为溶剂， 生成 2,5-二(氮丙啶-1-基)-3,6-二甲基苯-1,4-二醇
  参考文献：
  名称：

  Beall, Howard D.; Murphy, Aileene M.; Siegel, David, Molecular Pharmacology, 1995, vol. 48, # 3, p. 499 - 504

  摘要：

  DOI：

文献信息

• Quinone Compounds And Their Uses For The Treatment of Cancer
  申请人：Onco-NX Limited

  公开号：US20150210639A1

  公开（公告）日：2015-07-30

  Quinone Compounds and Their Uses for the Treatment of Cancer Quinone compounds having useful therapeutic activity such as anticancer activity, and compositions comprising such compounds, are described. The use of such compounds and compositions in the treatment of cancer is also described.

  醌化合物及其在癌症治疗中的用途 醌化合物具有有用的治疗活性，如抗癌活性，并描述了包含这些化合物的组合物。还描述了这些化合物和组合物在癌症治疗中的应用。
• The stability of carboquone in alcohols. II. Kinetics and mechanisms of degradation of carboquone in methanol.
  作者：AKIRA KUSAI、SEIGO UEDA

  DOI：10.1248/cpb.34.1299

  日期：——

  The kinetics and mechanisms of the degradation of carboquone (CQ) in methanol were investigated.Eight peaks were observed as degradation products of CQ in high performance liquid chromatography, suggesting that the degradation process of CQ in methanol is rather complicated. However, conducting the reaction in proton-rich methanol and methylate-rich methanol made it clear that CQ is degraded in methanol through a combination of two mechanisms : methanolysis of the aziridine ring, which cleaved to a (2-methoxyethyl)amino group, and substitution of the aziridine ring by methylate. Further, some of the degradation products were obtained in pure form by this procedure.Due to the asymmetric structure of CQ, two kinds of mono aziridinyl-mono methoxyethyl-amino compounds and two kinds of mono aziridinyl-mono methoxy compounds are produced. Kinetic studies of these four compounds and 2, 5-bis(1-aziridinyl)-3, 6-dimethyl-1, 4-benzoquinone made it possible to assign their chemical structures. Their deduced structures were confirmed by mass spectroscopy and proton nuclear magnetic resonance spectroscopy.

  对卡巴醌(CQ)在甲醇中的降解动力学和机制进行了研究。 高效液相色谱检测到CQ的降解产物有8个峰, 表明CQ在甲醇中的降解过程相当复杂。 但在质子丰富的甲醇和甲氧基阴离子丰富的甲醇中进行反应, 发现CQ是通过以下两种机制的组合在甲醇中降解的: 环氧化物环的甲醇解生成(2-甲氧基乙基)氨基,以及环氧化物环被甲氧基阴离子取代。 进而, 通过这种方法获得了一些纯的降解产物, 由于CQ的不对称结构, 生成了两种单环氧化物-单甲氧基乙氨基化合物和两种单环氧化物-单甲氧基化合物。 对这四种化合物和2, 5-双(1-环氧化物)吡啶-3, 6-二甲基-1, 4-苯醌的动力学研究使得可以指定它们的化学结构。 通过质谱和氢核磁共振谱验证了这些推导结构。
• Ring opening of aziridin-1-yl-quinones
  作者：I. Baxter、D. W. Cameron、R. G. F. Giles

  DOI：10.1039/j39690001325

  日期：——

  Certain aziridin-1-yl-quinones are converted by the action of sodium iodide and aluminium halides into 2-halogenoethylamino-quinones. The behaviour of the latter on catalytic reduction has been studied. The reaction of 3,6-diaziridin-1-yl-p-xyloquinone with concentrated sulphuric acid is reported.

  某些叠氮基-1-基醌通过碘化钠和卤化铝的作用转化为2-卤代乙基氨基醌。已经研究了后者在催化还原上的行为。据报道3，6-二氮杂环丁烷-1-基-对-二甲苯醌与浓硫酸的反应。
• The stability of carboquone in aqueous solution. II. Kinetics and mechanisms of degradation of 2,5-bis(1-aziridinyl)-3,6-dimethyl-1,4-benzoquinone and 2,5-bis-(1-aziridinyl)-3,6-diisopropyl-1,4-benzoquinone in aqueous solution.
  作者：AKIRA KUSAI、SEIJI TANAKA、SEIGO UEDA

  DOI：10.1248/cpb.30.2534

  日期：——

  The kinetics and mechanisms of the degradation of 2, 5-bis (1-aziridinyl)-3, 6-dimethyl-1, 4-benzoquinone (MEB) and 2, 5-bis (1-aziridinyl)-3, 6-diisopropyl-1, 4-benzoquinone (IPEB) were investigated and compared with those of 2, 5-bis (1-aziridinyl)-1, 4-benzoquinone (EB) investigated previously. The degradation of MEB and IPEB follows pseudo first-order kinetics in the same way as that of EB. The pH-rate profiles showed slopes of -1 on the acidic side and +1 on the basic side, as did that of EB. Thus, the degradation of MEB and IPEB is subject to specific acid-base catalysis. The apparent activation energies for MEB degradation at pH 4 and pH 11 were 16 and 24 kcal/mol, and those for IPEB degradation were 17 and 23 kcal/mol, respectively. In basic aqueous solution, MEB and IPEB are degraded to dihydroxybenzoquinones with monohydroxy-mono (1-aziridinyl) benzoquinones as intermediates in the same way as EB. On the other hand, in acidic aqueous solution, (2-hydroxyethylamino) benzoquinones are produced from MEB and IPEB, as in the case of EB, but they are further degraded to hydroxybenzoquinones. This was not practically observed in the case of EB. This phenomenon can be explained as follows : the alkyl groups at the 3 and 6 positions of benzoquinone increase the relative hydrolysis rate of 2-hydroxyethylamino groups derived from the hydrolytic cleavage of aziridine rings at the 2 and 5 positions of benzoquinone, making it comparable to the ring cleavage rate of aziridinyl groups.

  研究了 2，5-双（1-氮丙啶基）-3，6-二甲基-1，4-苯醌（MEB）和 2，5-双（1-氮丙啶基）-3，6-二异丙基-1，4-苯醌（IPEB）的降解动力学和机理，并与之前研究的 2，5-双（1-氮丙啶基）-1，4-苯醌（EB）的降解动力学和机理进行了比较。MEB 和 IPEB 的降解遵循与 EB 相同的伪一阶动力学。与 EB 一样，pH-速率曲线在酸性侧的斜率为-1，在碱性侧的斜率为+1。因此，MEB 和 IPEB 的降解受特定酸碱催化作用的影响。在 pH 值为 4 和 11 时，MEB 降解的表观活化能分别为 16 和 24 kcal/mol，IPEB 降解的表观活化能分别为 17 和 23 kcal/mol。在碱性水溶液中，MEB 和 IPEB 降解为二羟基苯醌，中间产物为单羟基-单（1-氮丙啶基）苯醌，降解方式与 EB 相同。另一方面，在酸性水溶液中，与 EB 的情况一样，MEB 和 IPEB 会生成（2-羟乙氨基）苯醌，但它们会进一步降解为羟基苯醌。而在 EB 的情况下，实际上并没有观察到这种现象。这种现象可以解释如下：苯醌 3 和 6 位上的烷基提高了苯醌 2 和 5 位上的氮丙啶环水解裂解产生的 2-羟乙氨基的相对水解速度，使其与氮丙啶基的裂环速度相当。
• DKAT CELL LINE, A MODEL FOR HUMAN TRIPLE-NEGATIVE BREAST CANCER
  申请人：Seewaldt Victoria L.

  公开号：US20110085982A1

  公开（公告）日：2011-04-14

  The present invention provides a human triple-negative breast cancer cell line designated DKAT. The DKAT cell line has a marker profile of high expression of Snail-1 and Snail-2 (Slug); and a p53 mutation in exon 8 at codon 273 (CGT>CAT). The present invention further provides methods of using the DKAT cell line.