9-acetyl-7,8,9,10-tetrahydro-6,9,11-trihydroxy-4-methoxy-7-oxonaphthacene-5,12-quinone | 32469-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 9-acetyl-7,8,9,10-tetrahydro-6,9,11-trihydroxy-4-methoxy-7-oxonaphthacene-5,12-quinone
• 英文别名: 7-deoxy-7-ketodaunomycinone；7-Desoxy-7-keto-dauno-mycinon；(S)-3-Acetyl-3,5,12-trihydroxy-10-methoxy-3,4-dihydrotetracene-1,6,11(2H)-trione；(3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-2,4-dihydrotetracene-1,6,11-trione
• CAS: 32469-41-3
• 化学式: C₂₁H₁₆O₈
• 分子量: 396.353
• InChiKey: MXWGWQIBIUNUNE-NRFANRHFSA-N

物化性质

• 沸点：
  745.9±60.0 °C(Predicted)
• 密度：
  1.585±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-acetyl-7,8,9,10-tetrahydro-6,9,11-trihydroxy-4-methoxy-7-oxonaphthacene-5,12-quinone 在 sodium hydroxide 、 氢溴酸 、 溶剂黄146 作用下， 生成 8-Acetyl-1,6-10,11-tetrahydroxy-5,12-naphtacen-chinon
  参考文献：
  名称：

  Arcamone,F. et al., Gazzetta Chimica Italiana, 1970, vol. 100, p. 949 - 989

  摘要：

  DOI：
• 作为产物：
  描述：

  道诺霉素 在 盐酸 、 重铬酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 9-acetyl-7,8,9,10-tetrahydro-6,9,11-trihydroxy-4-methoxy-7-oxonaphthacene-5,12-quinone
  参考文献：
  名称：

  Signal Transduction Inhibitors, Hibarimicins A, B, C, D and G Produced by Microbispora. II. Structural Studies.

  摘要：

  利用光谱学技术确定了作为酪氨酸特异性蛋白激酶抑制剂的 Hibarimicins A、B、C、D 和 G 的结构。本报告中描述的 Hibarimicins 由一个常见的苷元和六个脱氧己糖组成。苷元含有一个高度氧化的萘醌作为发色团。其中，hibarimicin B 与 Angelmicin B

  DOI：

  10.7164/antibiotics.51.402

文献信息

• Gaudiano, Giorgio; Koch, Tad H., Journal of the American Chemical Society, 1990, vol. 112, # 25, p. 9423 - 9425
  作者：Gaudiano, Giorgio、Koch, Tad H.

  DOI：——

  日期：——
• Leucodaunomycins, new intermediates in the redox chemistry of daunomycin
  作者：Donald M. Bird、Giorgio Gaudiano、Tad H. Koch

  DOI：10.1021/ja00001a044

  日期：1991.1

  The reduction of daunomycin (1a) to the hydroquinone state has been described in the literature as leading either to elimination of the sugar daunosamine with formation of of 7-deoxydaunomycinone (5) under anaerobic conditions or to subsequent oxidation by molecular oxygen, yielding reactive oxygen species under aerobic conditions. The conditions under which the hydroquinone of 1a (7) tautomerizes, producing an isolable reduced form of 1a, referred to as leucodaunomycin, (8S)-cis-8-acetyl-10-[(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosy)oxy]-6a,7,8,9,10,10a-hexahydro-5,8,12-trihydroxy-1-methoxy-6,11-naphthacenedione (3), are described here. The synthesis and characterization of the the four disastereomers, A-D, of 3, along with studies of aerobic and anaerobic chemistry of two isomers, A and C, are reported. Under aerobic conditions, the isomers of 3 react with oxygen to form 1a, 5, 7-epidaunomycinone (8), 7-deoxy-7-ketodaunomycinone (9), 7-deoxy-7,13-epidioxy-daunomycinol (10) and daunomycinone (6), and the rate constant is a function of ph and stereochemistry and varies from 3.0 x 10(-4) to 2.6 x 10(-2) s-1 at pH 7.4. Under anaerobic conditions at pH 7.4 and 25-degrees-C, an aqueous solution of isomer A of 3 forms at 97:3 ratio of 5 to 6, and the reaction follows consecutive first-order kinetics with a k1 of 1.0 x 10-(-2) S-1 for the tautomerization of 3 to hydroquinone 7 and a k2 of 3.3 x 10(-2) S-1 for the tauntomerization of quinone methide 2 to 5. Under identical conditions, isomer C of 3 forms a 96.4 ratio of 5 to 6, and the reaction follows first-order kinetics with a k of 1.2 x 10(-3) S-1 for tautomerization of 3 to 7. Finally, the ability of 3 to react with N-acetyl-L-cysteine and participate in an autocatalytic cycle in the presence of 1a to form 7-[(N-acetyl-L-cysteinyl)thio]-7-deoxydaunomycinone (11) is described.
• PANDEY, RAMECH C.;TOUSSAINT, MARGARET W.;MCGUIRE, JEFFREY C.;THOMAS, MONI+, J. ANTIBIOTICS, 42,(1989) N1, C. 1567-1577
  作者：PANDEY, RAMECH C.、TOUSSAINT, MARGARET W.、MCGUIRE, JEFFREY C.、THOMAS, MONI+

  DOI：——

  日期：——
• GAUDIANO, GIORGIO;KOCH, TAD H., J. AMER. CHEM. SOC., 112,(1990) N5, C. 9423-9425
  作者：GAUDIANO, GIORGIO、KOCH, TAD H.

  DOI：——

  日期：——
• BIRD, DONALD M.;GAUDIANO, GIORGIO;KOCH, TAD H., J. AMER. CHEM. SOC., 113,(1991) N, C. 308-315
  作者：BIRD, DONALD M.、GAUDIANO, GIORGIO、KOCH, TAD H.

  DOI：——

  日期：——