1,8-dihydroxy-2-hydroxymethylanthracene-9,10-dione | 56670-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-dihydroxy-2-hydroxymethylanthracene-9,10-dione
• 英文别名: ω-Hydroxyisochrysophanol；1.8-Dihydroxy-2-(hydroxymethyl)anthrachinon；1,8-Dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione
• CAS: 56670-70-3
• 化学式: C₁₅H₁₀O₅
• 分子量: 270.241
• InChiKey: DFYYOMRVRCBFKM-UHFFFAOYSA-N

物化性质

• 熔点：
  244-246 °C (decomp)
• 沸点：
  527.9±19.0 °C(Predicted)
• 密度：
  1.592±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,8-dihydroxy-2-hydroxymethylanthracene-9,10-dione 在 sodium hydroxide 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 8.0h， 生成 1,8-dihydroxy-2-<(2-deoxy-2-amino-β-D-glucosyloxy)methyl>-9,10-dihydro-9,10-anthracenedione
  参考文献：
  名称：

  Synthesis of anthraquinonyl glucosaminosides and studies on the influence of aglycone hydroxyl substitution on superoxide generation, DNA binding, and antimicrobial properties

  摘要：

  A series of anthraquinonyl glucosaminosides (10a-e) were synthesized by Koenigs-Knorr glycosidation of the corresponding aglycones (11a-e) with bromo sugar 12 followed by saponification. These glycosides were intended to serve as models to study the role played by the hydroxyl substituents on the aglycone portion of the antitumor anthracycline antibiotics. Superoxide generation as measured in rat heart sarcosomes was found to increase with the addition of successive hydroxyl groups to the anthraquinone nucleus. The 1,8-dihydroxy pattern was determined to generate significantly less superoxide than the 1,4-dihydroxy pattern. Hydroxyl substitution was also observed to stabilize the complex formed between the anthraquinones and DNA and was required for antibacterial activity against a number of Gram-positive organisms.

  DOI：

  10.1021/jm00159a024
• 作为产物：
  描述：

  2-bromomethyl-1,8-dimethoxy-9,10-anthracenedione 在 sodium dithionite 、 氢溴酸 作用下， 以 氯仿 、 水 、 溶剂黄146 、 乙腈 为溶剂， 生成 1,8-dihydroxy-2-hydroxymethylanthracene-9,10-dione
  参考文献：
  名称：

  Substituent effects upon the peak potentials and reductive cleavage rate constants of hydroxy- and methoxy-substituted 9,10-anthraquinones in 50% aqueous CH3CN: do they correlate?

  摘要：

  A variety of hydroxy- and methoxy-substituted 2-(acetoxymethyl)-9,10-anthraquinones (2a-7a) were reduced electrochemically and with dithionite (S2O-4(2-)) in 50% aqueous CH3CN buffers over a wide pH range. Good to excellent yields of their corresponding reductive cleavage products, the substituted 2-methyl-9,10-anthraquinones 2b-7b, were obtained from most of these anthraquinone acetates, but only at higher pH. Rate constants for the reaction of 2-(acetoxymethyl)-9,10-anthraquinone (1a) with excess dithionite ranged from 1.0 x 10(-4) S-1 at pH values less than 7 to 4.0 x 10(-4) S-1 at a pH of 10, demonstrating that loss of acetate occurs in the rate-determining step and that cleavage occurs slower via the anthrahydroquinone of 1a than the conjugate base of the anthrahydroquinone. Substituent effects upon the reductive cleavage process were determined by measuring rate constants for those acetates that react cleanly with dithionite at pH 8. These effects, which are rationalized on the basis of resonance theory and intramolecular H bonding, correlate fairly well with the peak potentials (E(p)) of the reductive cleavage products of these acetates. Thus, electron-donating substituents on an anthraquinone acetate not only make it more difficult to reduce resulting in a more negative E(p) but also enhance the rate of acetate cleavage in the corresponding anthrahydroquinone.

  DOI：

  10.1021/jo00004a049

文献信息

• Synthesis and Bioactivities of Naturally Occurring Anthraquinones: Isochrysophanol, Isozyganein, ω-Hydroxyisochrysophanol and Morindaparvin
  作者：Javed H. Zaidi、Fazal Naeem、Rashid Iqbal、Mohammed Iqbal Choudhary、Khalid Mohammed Khan、Shahnaz Perveen、Syed T. Ali Shah、Safdar Hayat、Wolfgang Voelter

  DOI：10.1515/znb-2001-0717

  日期：2001.7.1

  Isochrysophanol, isozyganein, ω-hydroxyisochrysophanol, and morindaparvin are naturally occurring substituted anthraquinones. We report the synthesis of these compounds as well as selected biological activities.

  异黄酚、isozyganein、ω-羟基异黄酚和morindaparvin 是天然存在的取代蒽醌。我们报告了这些化合物的合成以及选定的生物活性。
• Synthesis of anthraquinonyl glucosaminosides and studies on the influence of aglycone hydroxyl substitution on superoxide generation, DNA binding, and antimicrobial properties
  作者：Hanley N. Abramson、Jon W. Banning、Joseph P. Nachtman、Edward T. Roginski、Maniklal Sardessai、Henry C. Wormser、Jender Wu、Ziad Nagia、Ronald R. Schroeder、Maria Margarida Bernardo

  DOI：10.1021/jm00159a024

  日期：1986.9

  A series of anthraquinonyl glucosaminosides (10a-e) were synthesized by Koenigs-Knorr glycosidation of the corresponding aglycones (11a-e) with bromo sugar 12 followed by saponification. These glycosides were intended to serve as models to study the role played by the hydroxyl substituents on the aglycone portion of the antitumor anthracycline antibiotics. Superoxide generation as measured in rat heart sarcosomes was found to increase with the addition of successive hydroxyl groups to the anthraquinone nucleus. The 1,8-dihydroxy pattern was determined to generate significantly less superoxide than the 1,4-dihydroxy pattern. Hydroxyl substitution was also observed to stabilize the complex formed between the anthraquinones and DNA and was required for antibacterial activity against a number of Gram-positive organisms.
• Substituent effects upon the peak potentials and reductive cleavage rate constants of hydroxy- and methoxy-substituted 9,10-anthraquinones in 50% aqueous CH3CN: do they correlate?
  作者：Ronald L. Blankespoor、Elise L. Kosters、Alan J. Post、Derek P. Van Meurs

  DOI：10.1021/jo00004a049

  日期：1991.2

  A variety of hydroxy- and methoxy-substituted 2-(acetoxymethyl)-9,10-anthraquinones (2a-7a) were reduced electrochemically and with dithionite (S2O-4(2-)) in 50% aqueous CH3CN buffers over a wide pH range. Good to excellent yields of their corresponding reductive cleavage products, the substituted 2-methyl-9,10-anthraquinones 2b-7b, were obtained from most of these anthraquinone acetates, but only at higher pH. Rate constants for the reaction of 2-(acetoxymethyl)-9,10-anthraquinone (1a) with excess dithionite ranged from 1.0 x 10(-4) S-1 at pH values less than 7 to 4.0 x 10(-4) S-1 at a pH of 10, demonstrating that loss of acetate occurs in the rate-determining step and that cleavage occurs slower via the anthrahydroquinone of 1a than the conjugate base of the anthrahydroquinone. Substituent effects upon the reductive cleavage process were determined by measuring rate constants for those acetates that react cleanly with dithionite at pH 8. These effects, which are rationalized on the basis of resonance theory and intramolecular H bonding, correlate fairly well with the peak potentials (E(p)) of the reductive cleavage products of these acetates. Thus, electron-donating substituents on an anthraquinone acetate not only make it more difficult to reduce resulting in a more negative E(p) but also enhance the rate of acetate cleavage in the corresponding anthrahydroquinone.