4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
• 英文别名: 4,5-Dimethoxy-9,10-dioxoanthracene-2-carbaldehyde
• 化学式: C₁₇H₁₂O₅
• 分子量: 296.279
• InChiKey: NTOKRQNZZADXMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 在 硫酸 、 溴 作用下， 生成 大黄酸
  参考文献：
  名称：

  Rani, Meena, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 12, p. 1314 - 1315

  摘要：

  DOI：
• 作为产物：
  描述：

  芦荟大黄素 在 阻聚剂701 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 72.5h， 生成 4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
  参考文献：
  名称：

  芦荟大黄素偶联磺酰腙通过多方面协同作用作为新型抗菌调节剂对金黄色葡萄球菌25923

  摘要：

  芦荟大黄素偶联磺酰腙被设计合成为新型抗菌调节剂。芦荟大黄素苯磺酰腙5a (AEBH- 5a ) 在治疗金黄色葡萄球菌25923 (MIC = 0.5 μg/mL) 方面优于诺氟沙星，并且在细菌膜和哺乳动物膜之间表现出高选择性。特别是 AEBH- 5a可以消除形成的生物膜，缓解金黄色葡萄球菌25923 耐药性的发展。AEBH- 5a从细胞外到细胞内的抗菌机制说明AEBH- 5a会破坏细菌膜的完​​整性，导致蛋白质和核酸的泄漏。此外，AEBH- 5a不仅可以与DNA相互作用并诱导氧化应激，还可以抑制乳酸脱氢酶（LDH）的活性以及使代谢失活。计算机ADME 研究对 AEBH- 5a的预测揭示了有利的生物利用度评分和显着的药物相似性特征。该研究表明，由芦荟大黄素偶联磺酰腙引发的多方面协同作用是对抗威胁性细菌感染的合理有效策略。

  DOI：

  10.1016/j.bioorg.2022.106035

文献信息

• Pharmaceutical compounds
  申请人：Lilly Industries Limited

  公开号：US05480873A1

  公开（公告）日：1996-01-02

  Pharmaceutical compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, hydroxyl, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acyloxy, --O-glucoside, optionally substituted phenyl or optionally substituted phenyl-C.sub.1-4 alkoxy; R.sup.3 is tetrazolyl, or and R.sup.4 and R.sup.5 are each hydrogen, hydroxy, acyloxy, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halo, optionally substituted phenyl, --SO.sub.3 H or --NR'R" where R' and R" are each hydrogen or C.sub.1-4 alkyl; provided that when R.sup.3 is --CR'R".CHR'"CO.sub.2 H or tetrazolyl, R.sup.1 and R.sup.2 are each hydroxyl, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acyloxy, --O-glucoside, optionally substituted phenyl or optionally substituted phenyl C.sub.1-4 alkoxy; and or a pharmaceutically acceptable salt or ester thereof.

  公式为##STR1##的药物化合物，其中R.sup.1和R.sup.2分别为氢、羟基、卤素、C.sub.1-4烷基、C.sub.1-4烷氧基、酰氧基、-O-葡萄糖苷、可选择取代的苯基或可选择取代的苯基-C.sub.1-4烷氧基；R.sup.3为四唑基，或者R.sup.4和R.sup.5分别为氢、羟基、酰氧基、硝基、C.sub.1-4烷基、C.sub.1-4烷氧基、卤素、可选择取代的苯基、-SO.sub.3 H或-NR'R"，其中R'和R"分别为氢或C.sub.1-4烷基；但是当R.sup.3为--CR'R".CHR'"CO.sub.2 H或四唑基时，R.sup.1和R.sup.2分别为羟基、卤素、C.sub.1-4烷基、C.sub.1-4烷氧基、酰氧基、-O-葡萄糖苷、可选择取代的苯基或可选择取代的苯基-C.sub.1-4烷氧基；或其药学上可接受的盐或酯。
• Synthesis, biological evaluation and molecular modeling of aloe-emodin derivatives as new acetylcholinesterase inhibitors
  作者：Da-Hua Shi、Wei Huang、Chao Li、Ling-Ting Wang、Shi-Fan Wang

  DOI：10.1016/j.bmc.2013.01.015

  日期：2013.3

  A series of aloe-emodin derivatives were designed, synthesized and evaluated as acetylcholinesterase inhibitors. Most of the new prepared compounds showed remarkable acetylcholinesterase inhibitory activities. Among them, the compound 1-((4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl) methyl) pyridin-1-ium chloride (C3) which has a pyridinium substituent possessed the best inhibitory activity

  设计，合成和评估了一系列芦荟大黄素衍生物，作为乙酰胆碱酯酶抑制剂。大多数新制备的化合物显示出显着的乙酰胆碱酯酶抑制活性。其中，具有吡啶鎓取代基的化合物1-（（4,5-二羟基-9,10-二氧杂-9,10-二氢蒽-2-基）甲基）吡啶-1-氯（C3）具有最好的乙酰胆碱酯酶的抑制活性（IC 50  = 0.09μM）。用AUTODOCK进行的对接研究表明C3可以与乙酰胆碱酯酶的催化活性位点（CAS）和外围阴离子位点（PAS）相互作用。
• Anthraquinone derivatives, process for their preparation and their use as medicaments
  申请人：LILLY INDUSTRIES LIMITED

  公开号：EP0570091A1

  公开（公告）日：1993-11-18

  Pharmaceutical compounds of the formula in which R¹ and R² are each hydrogen, hydroxyl, halo, C₁₋₄ alkyl, C₁₋₄ alkoxy, acyloxy, -O-glucoside, optionally substituted phenyl or optionally substituted phenyl-C₁₋₄ alkoxy; R³ is CO₂H, NR'SO₂R'' where R' is hydrogen or C₁₋₄ alkyl and R'' is hydroxyl, C₁₋₄ alkyl or optionally substituted phenyl, CONR'R'' where R' and R'' are each hydrogen, C₁₋₄ alkyl, acyl or optionally substituted phenyl, CONR'OR'' where R' is C₁₋₄ alkyl or optionally substituted phenyl and R'' is C₁₋₄ alkyl or benzyl, CR'R''.CR‴ (NHR'''')CO₂H where R' and R'' are each hydrogen, C₁₋₄ alkyl or optionally substituted phenyl, R‴ is hydrogen, CO₂H or -C₁₋₄ alkylene-CO₂H, and R'''' is hydrogen or acyl, CR'R''.CHR‴CO₂H where R' and R'' are each hydrogen or C₁₋₄ alkyl and R‴ is optionally substituted phenyl, CR'R''S(O)nR‴ where R' and R'' are each hydrogen or C₁₋₄ alkyl, R‴ is optionally substituted phenyl and n is 0,1 or 2, PO₃R'R'' where R' and R'' are each hydrogen, C₁₋₄ alkyl or optionally substituted phenyl, CR'R''-PO₃R‴R'''' where R', R'', R‴ and R'''' are each hydrogen, C₁₋₄ alkyl or optionally substituted phenyl, CH=CH-PO₃R'R'' where R' and R'' are each hydrogen, C₁₋₄ alkyl or optionally substituted phenyl, CH=C-PO₃R'R''    \ PO₃R‴R''''    where R', R'', R‴ and R'''' are each hydrogen, C₁₋₄ alkyl or optionally substituted phenyl, CH₂CH-PO₃R'R''    \ PO₃R‴R''''    where R', R'', R‴ and R'''' are each hydrogen, C₁₋₄ alkyl or optionally substituted phenyl, CH=CHR' where R' is -CO₂H, nitrile, tetrazolyl, optionally substituted benzimidazol-2-yl, optionally substituted N-C₁₋₄ alkyl benzimidazol-2-yl, optionally substituted oxazol-5-yl, optionally substituted thiazol-5-yl, optionally substituted isoxazol-5-yl, optionally substituted isothiazol-5-yl or optionally substituted oxadiazol-2-yl, tetrazolyl, or pyridyl, optionally substituted benzimidazol-2-yl, optionally substituted N-C₁₋₄ alkyl benzimidazol-2-yl, optionally substituted oxazol-5-yl, optionally substituted thiazol-5-yl, optionally substituted isoxazol-5-yl, optionally substituted isothiazol-5-yl or optionally substituted oxadiazol-2-yl; and R⁴ and R⁵ are each hydrogen, hydroxy, acyloxy, nitro, C₁₋₄ alkyl, C₁₋₄ alkoxy, halo, optionally substituted phenyl, -SO₃H or -NR'R'' where R' and R'' are each hydrogen or C₁₋₄ alkyl; or a pharmaceutically acceptable salt or ester thereof.

  式中的药物化合物 其中 R¹ 和 R² 分别是氢、羟基、卤代、C₁₋₄ 烷基、C₁₋₄ 烷氧基、酰氧基、-O-葡糖苷、任选取代的苯基或任选取代的苯基-C₁₋₄ 烷氧基； R³ 是 CO₂H NR'SO₂R'' 其中 R' 是氢或 C₁₋₄ 烷基，R'' 是羟基、C₁₋₄ 烷基或任选取代的苯基、 CONR'R'' 其中 R' 和 R'' 分别为氢、C₁₋₄ 烷基、酰基或任选取代的苯基、 CONR'OR'' 其中 R' 是 C₁₋₄ 烷基或任选取代的苯基，R'' 是 C₁₋₄ 烷基或苄基、 CR'R''.CR‴ (NHR'''')CO₂H 其中 R' 和 R'' 分别是氢、C₁₋₄ 烷基或任选取代的苯基，R‴ 是氢、CO₂H 或 -C₁₋₄ 烷基-CO₂H，R'''' 是氢或酰基、 CR'R''.CHR‴CO₂H 其中 R' 和 R'' 分别是氢或 C₁₋₄ 烷基，R‴ 是任选取代的苯基、 CR'R''S(O)nR‴ 其中 R' 和 R''各自为氢或 C₁₋₄烷基，R‴为任选取代的苯基，n 为 0、1 或 2、 PO₃R'R'' 其中 R' 和 R'' 分别为氢、C₁₋₄ 烷基或任选取代的苯基、 CR'R''-PO₃R‴R'''' 其中 R'、R''、R‴ 和 R'''' 分别为氢、C₁₋₄ 烷基或任选取代的苯基、 CH=CH-PO₃R'R'' 其中 R' 和 R'' 分别为氢、C₁₋₄ 烷基或任选取代的苯基、 CH=C-PO₃R'R'' \ PO₃R‴R'''' 其中 R'、R''、R‴ 和 R'''' 各为氢、C₁₋₄ 烷基或任选取代的苯基、 CH₂CH-PO₃R'R'' \ PO₃R‴R'''' 其中 R'、R''、R‴ 和 R'''' 各为氢、C₁₋₄ 烷基或任选取代的苯基、 CH=CHR' 其中 R' 是-CO₂H、腈、四唑基、任选取代的苯并咪唑-2-基、任选取代的 N-C₁₋₄ 烷基苯并咪唑-2-基、任选取代的噁唑-5-基、任选取代的噻唑-5-基、任选取代的异噁唑-5-基、任选取代的异噻唑-5-基或任选取代的噁二唑-2-基、 四唑基，或 吡啶基、任选取代的苯并咪唑-2-基、任选取代的 N-C₁₋₄ 烷基苯并咪唑-2-基、任选取代的恶唑-5-基、任选取代的噻唑-5-基、任选取代的异恶唑-5-基、任选取代的异噻唑-5-基或任选取代的噁二唑-2-基；以及 R⁴ 和 R⁵ 分别是氢、羟基、酰氧基、硝基、C₁₋₄ 烷基、C₁₋₄ 烷氧基、卤代、任选取代的苯基、-SO₃H 或-NR'R''，其中 R' 和 R'' 分别是氢或 C₁₋₄烷基； 或其药学上可接受的盐或酯。
• New Z-chalcones obtained from aloe-emodin: Synthesis, characterization and photophysical properties
  作者：Nieves Canudas、Manuel Moreno、Sara Pekerar、Carlos Gámez、Estefania Sucre、José E Villamizar

  DOI：10.1177/1747519819841822

  日期：2019.3

  Three new Z-chalcone derivatives were synthesized under stereoselective conditions by condensation between an aldehyde derivative (prepared from aloe-emodin) and an acetophenone, using potassium hydroxide in dimethyl sulfoxide/H2O at room temperature. The Z configuration of the chalcone derivatives was established by nuclear magnetic resonance (NMR) studies. Photophysical properties related to the

  三种新的 Z-查尔酮衍生物在立体选择性条件下通过醛衍生物（从芦荟大黄素制备）和苯乙酮之间的缩合合成，使用氢氧化钾在二甲基亚砜/H2O 中室温。查耳酮衍生物的 Z 构型是通过核磁共振 (NMR) 研究确定的。测定了与不同溶剂中的 UV-Vis 吸收/发射光谱和摩尔消光系数 (ε) 相关的光物理特性。
• Design, synthesis and molecular modeling of aloe-emodin derivatives as potent xanthine oxidase inhibitors
  作者：Da-Hua Shi、Wei Huang、Chao Li、Yu-Wei Liu、Shi-Fan Wang

  DOI：10.1016/j.ejmech.2014.01.058

  日期：2014.3

  A series of aloe-emodin derivatives were synthesized and evaluated as xanthine oxidase inhibitors. Among them, four aloe-emodin derivatives showed significant inhibitory activities against xanthine oxidase. The compound 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde (A1) possessed the best xanthine oxidase inhibitory activity with IC50 of 2.79 mu M. Lineweaver-Burk plot analysis revealed that A1 acted as a mixed-type inhibitor for xanthine oxidase. The docking study revealed that the molecule A1 had strong interactions with the active site of xanthine oxidase and this result was in agreement with kinetic study. Consequently, compound A1 is a new-type candidate for further development for the treatment of gout. (C) 2014 Elsevier Masson SAS. All rights reserved.