1-hydroxy-8-methoxy-2-methyl-9,10-anthracenedione | 51996-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-hydroxy-8-methoxy-2-methyl-9,10-anthracenedione
• 英文别名: 1-Hydroxy-8-methoxy-2-methylanthracene-9,10-dione
• CAS: 51996-00-0
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: NGMVQANAAHWVBH-UHFFFAOYSA-N

物化性质

• 沸点：
  502.2±50.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-hydroxy-8-methoxy-2-methyl-9,10-anthracenedione 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以87%的产率得到1,8-二羟基-2-甲基-9,10-蒽醌
  参考文献：
  名称：

  Novel anthraquinone inhibitors of human leukocyte elastase and cathepsin G

  摘要：

  A large series of variously substituted anthraquinones has been synthesized and assayed for inhibitory capacity against human leukocyte elastase (HLE) and cathepsin G (CatG), two serine proteinases implicated in diseases characterized by the abnormal degradation of connective tissue, such as pulmonary emphysema and rheumatoid arthritis. It was found that 2-alkyl-1,8-dihydroxyanthraquinone analogues are competitive inhibitors of HLE with IC50 values ranging from 4 to 10-mu-M, and also inhibit CatG with IC50 values ranging from 25 to 55-mu-M. Consequently, analogues containing the 2-alkyl-1-hydroxy-8-methoxyanthraquinone substitution pattern inhibit HLE to the same magnitude as for the compounds above, but show very little inhibition of CatG. Anthraquinones containing long, hydrophobic n-butyl carbonate moieties in the 1- and 8-positions in conjunction with a third hydrophobic substituent in the 2- or 3-position are highly selective for HLE, with K(i) values in the range of 10(-7) M. All of the inhibitors described are completely reversible, with no evidence of acyl-enzyme formation detected.

  DOI：

  10.1021/jm00087a014
• 作为产物：
  描述：

  1,8-二羟基蒽醌 在 boron trioxide 、 sodium hydroxide 、 sodium dithionite 、 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 、 硫酸 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 28.0h， 生成 1-hydroxy-8-methoxy-2-methyl-9,10-anthracenedione
  参考文献：
  名称：

  蒽醌分子内添加碳负离子

  摘要：

  源自β-酮二酯15a和15b的碳负离子的分子内迈克尔加成产生萘并苯醌20a和20b。相反，二甲醚11环化成苯并[α]蒽醌17。1,8-二羟基蒽醌（5a）的对苯二酚与丙烯酸酯反应生成异常的蒽酮衍生物12b和12c。

  DOI：

  10.1002/jlac.198419840213

文献信息

• Regiospecific addition of monooxygenated dienes to halo quinones
  作者：Louise Boisvert、Paul Brassard

  DOI：10.1021/jo00252a031

  日期：1988.8
• Simple Analogues of Anthralin:  Unusual Specificity of Structure and Antiproliferative Activity
  作者：Klaus Müller、Helge Prinz、Ingo Gawlik、Klaus Ziereis、Hsu-Shan Huang

  DOI：10.1021/jm970292n

  日期：1997.11.1

  Fifty-nine simple analogues of the antipsoriatic agent, anthralin, have been prepared by modifying the positions of the 1,8-hydroxyl groups, replacement of the hydroxyl groups, substitution at the oxygen functions, introduction of additional functional groups into various positions of the anthracenone nucleus, or removal of particular structural elements. The compounds were evaluated for their antiproliferative action against human keratinocytes and inhibition of the generation of leukotriene B-4 in polymorphonuclear leukocytes, which may be useful to resolve the proliferative and inflammatory aspects of psoriasis, respectively. Even though many anthracenones were more potent inhibitors of leukotriene biosynthesis than anthralin, none of the compounds was substantially more effective as this drug in suppressing keratinocyte cell growth. There is an absolute requirement for two hydroxyl groups peri to a hydrogen bond acceptor such as a keto or an imino group for high potency. Ln addition to further delineating the nature of the pharmacophore for this class of compounds, also naphthalenedione with a peri hydroxyl group was identified as a pharmacophore with antiproliferative activity against keratinocyte growth.
• KROHN, K.;MUELLER, U.;PRIYONO, W.;SARSTEDT, B.;STOFFREGEN, A., LIEBIGS ANN. CHEM., 1984, N 2, 306-318
  作者：KROHN, K.、MUELLER, U.、PRIYONO, W.、SARSTEDT, B.、STOFFREGEN, A.

  DOI：——

  日期：——
• BOISVERT, LOUISE;BRASSARD, PAUL, J. ORG. CHEM., 53,(1988) N 17, C. 4052-4059
  作者：BOISVERT, LOUISE、BRASSARD, PAUL

  DOI：——

  日期：——
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.