3-hydroxyacridone | 20168-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-hydroxyacridone
• 英文别名: 3-Hydroxyacridon；3-hydroxy-10H-acridin-9-one
• CAS: 20168-55-2
• 化学式: C₁₃H₉NO₂
• 分子量: 211.22
• InChiKey: PTZZBZSWOOEBIN-UHFFFAOYSA-N

物化性质

• 熔点：
  190-192 °C
• 沸点：
  398.4±21.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxyacridone 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 52.0h， 生成 3.3.12-Trimethyl-7-oxo-1.2-dihydro-3H-pyrano<2,3-c>acridin
  参考文献：
  名称：

  Govindachari,T.R. et al., Indian Journal of Chemistry, 1968, vol. 6, p. 179 - 180

  摘要：

  DOI：
• 作为产物：
  描述：

  乳化剂MOA-3，7，9，15，20 在 氢溴酸 作用下， 反应 10.0h， 生成 3-hydroxyacridone
  参考文献：
  名称：

  Structure–activity relationship studies of acridones as potential antipsoriatic agents. 1. Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth

  摘要：

  A series of N-unsubstituted hydroxy-10H-acridin-9-ones were synthesized and evaluated for inhibitory action against HaCaT keratinocyte growth, in order to explore their potential as antipsoriatic agents. For structure activity relationship studies, the number and position of the hydroxyl groups were modified, the oxygen functions substituted or replaced, or additional functional groups were introduced into the acridone scaffold. 1,8-Dihydroxy-10H-acridin-9-one (4), which is an aza-analogue of the antipsoriatic anthralin, was only marginally active. However, 1,3-dihydroxy-substituted 5ee was the most potent acridone within this series and inhibited keratinocyte growth with an IC(50) value comparable to that of anthralin. In contrast to anthralin, nearly all members of the acridone series were devoid of radical generating properties, which were determined by their capability to interact with the free radical 2,2-diphenyl-1-picrylhydrazyl. Structures with a phenolic hydroxyl or an aromatic amine arranged ortho or para to the acridone NH group were exceptions. Also in contrast to anthralin, membrane-damaging effects as documented by the release of lactate dehydrogenase into the culture medium were not observed for acridones. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.013

文献信息

• Discovery and Structural Optimization of Acridones as Broad-Spectrum Antimalarials
  作者：Rozalia A. Dodean、Papireddy Kancharla、Yuexin Li、Victor Melendez、Lisa Read、Charles E. Bane、Brian Vesely、Mara Kreishman-Deitrick、Chad Black、Qigui Li、Richard J. Sciotti、Raul Olmeda、Thu-Lan Luong、Heather Gaona、Brittney Potter、Jason Sousa、Sean Marcsisin、Diana Caridha、Lisa Xie、Chau Vuong、Qiang Zeng、Jing Zhang、Ping Zhang、Hsiuling Lin、Kirk Butler、Norma Roncal、Lacy Gaynor-Ohnstad、Susan E. Leed、Christina Nolan、Stephanie J. Huezo、Stephanie A. Rasmussen、Melissa T. Stephens、John C. Tan、Roland A. Cooper、Martin J. Smilkstein、Sovitj Pou、Rolf W. Winter、Michael K. Riscoe、Jane X. Kelly

  DOI：10.1021/acs.jmedchem.8b01961

  日期：2019.4.11

  antimalarials are needed to support the renewed eradication agenda. We have discovered a novel antimalarial acridone chemotype with dual-stage activity against both liver-stage and blood-stage malaria. Several lead compounds generated from structural optimization of a large library of novel acridones exhibit efficacy in the following systems: (1) picomolar inhibition of in vitro Plasmodium falciparum blood-stage

  疟疾仍然是当今世界上最致命的疾病之一。需要新的化学预防和化学抗疟药来支持新的根除议程。我们发现了一种新型的抗疟疾cri啶酮化学型，具有针对肝和血液阶段疟疾的双重阶段活性。从新的a啶酮的大型文库的结构优化产生的几种先导化合物在以下系统中显示出功效：（1）皮摩尔抑制体外恶性疟原虫血液阶段生长对多药耐药性寄生虫的抑制；（2）在约氏红细胞疟原虫鼠疟疾模型中口服后的疗效；（3）预防伯氏疟原虫子孢子体外诱导的人肝细胞发育；（4）保护小鼠体内由伯氏疟原虫子孢子诱导的感染。这项研究首次提出了cri啶酮化学型肝阶段抗疟活性。本文介绍了设计，化学，结构-活性关系，安全性，代谢/药代动力学研究和机理研究的详细信息。
• Tricyclic heterocyclic derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0471516A1

  公开（公告）日：1992-02-19

  The invention relates to tricyclic heterocyclic derivatives, or pharmaceutically-acceptable salts or in vivo hydrolysable esters thereof, which possess anti-cancer activity. The invention also relates to processes for the manufacture of said tricyclic heterocyclic derivatives, to novel pharmaceutical compositions containing them and to the use of said tricyclic heterocyclic derivatives in the manufacture of a medicament for the production of an anti-cancer effect. The invention provides an optionally substituted tricyclic heterocyclic derivative of the formula I wherein A together with the adjacent vinylene group of the 4-oxo-1,4-dihydropyrid-1-yl ring completes a benzene or pyridine ring;    R¹ and R², which may be the same or different, each is (1-4C)alkyl or (1-4C)alkoxy;    and R³ is hydrogen, (1-4C)alkyl or (1-4C)alkoxy;    or a pharmaceutically-acceptable salt or in vivo hydrolysable ester thereof.

  该发明涉及三环杂环衍生物，或其药用盐或体内可水解酯，具有抗癌活性。该发明还涉及制备所述三环杂环衍生物的方法，含有它们的新型药物组合物以及利用所述三环杂环衍生物制造抗癌药物以产生抗癌效果的用途。该发明提供了公式I的可选择取代的三环杂环衍生物，其中A与4-氧代-1,4-二氢吡啶-1-基环的相邻乙烯基团共同形成苯环或吡啶环；R¹和R²，可以相同也可以不同，分别是(1-4C)烷基或(1-4C)烷氧基；R³是氢，(1-4C)烷基或(1-4C)烷氧基；或其药用盐或体内可水解酯。
• Acridone-Pterocarpan Conjugate: A Hybrid Molecular Probe for Recognition of Nucleic Acids
  作者：Shital K. Chattopadhyay、Ratnava Maitra、Indranil Kundu、Manoranjan Jana、Sushil K. Mandal、Anisur Rahman Khuda-Bukhsh

  DOI：10.1002/ejoc.201301007

  日期：2013.12

  binding ligands. Competitive binding assay in the presence of a classical minor groove binder shows the possibility of DNA minor groove binding by the ligand 4a. High cell viability of the prepared molecular probes was of utility for nuclear staining as well as cell cycle analysis through fluorescence-activated cell sorting (FACS).

  通过热诱导级联 sigmatropic 重排，天然存在的药效团 (pterocarpan) 与荧光团 (吖啶酮) 的化学融合导致形成结构不同的一类 DNA 结合配体。在经典小沟结合剂存在下的竞争性结合测定显示了配体 4a 与 DNA 小沟结合的可能性。制备的分子探针的高细胞活力可用于核染色以及通过荧光激活细胞分选 (FACS) 进行的细胞周期分析。
• Synthesis and antibacterial evaluation of alkaloid-like phenylfuroacridones
  作者：T. A. Kudryavtsev、T. N. Kudryavtseva、V. E. Melnichenko、A. Yu. Lamanov、L. G. Klimova

  DOI：10.1007/s11172-023-3985-9

  日期：2023.8

  ridones, which, in turn, were obtained by O-alkylation of the corresponding 2-, 3-, 4-hydroxyacridones with phenacyl bromide. Biological studies showed that phenylfuroacridones exhibited a low antibacterial activity against the test strain Candida albicans.

  通过2-, 3-, 4-(2-氧代-2-苯基乙氧基)吖啶酮在多磷酸中环化合成了许多新的类生物碱苯基呋喃吖啶酮，而这些吖啶酮又通过相应的2- , 3-, 4-(2-氧代-2-苯基乙氧基)吖啶酮的O-烷基化得到。 -, 3-, 4-羟基吖啶酮与苯甲酰溴。生物学研究表明，苯基呋喃吖啶酮对测试菌株白色念珠菌表现出较低的抗菌活性。
• Multi-target strategy to address Alzheimer’s disease: Design, synthesis and biological evaluation of new tacrine-based dimers
  作者：Stefano Rizzo、Alessandra Bisi、Manuela Bartolini、Francesca Mancini、Federica Belluti、Silvia Gobbi、Vincenza Andrisano、Angela Rampa

  DOI：10.1016/j.ejmech.2011.07.004

  日期：2011.9

  The multifactorial nature of Alzheimer's disease (AD) offers us a textbook example where parental compounds, mostly marketed, are modified with the aim of improving and/or conferring two or even more biological activities to contrast or less frequently revert the disease's symptoms. This is the case of tacrine and its dimeric derivative bis(7)-tacrine which, for instance, paved the way for the development of a broad collection of very interesting homo- and heterodimeric structures, conceived in light of the emerging multi-target approach for AD-related drug discovery. As a contribution to the topic, we report here the design, synthesis and biological evaluation of 12 compounds referable to bis(7)-tacrine. In addition to the cholinesterase activity, some of the selected compounds (7-9 and 12) were capable of inhibiting the non-enzymatic function of AChE and/or showed a remarkable activity against BACE1. Thus, the present study outlines a series of newly synthesized molecules, structurally related to bis(7)-tacrine, endowed with extended biological profile in agreement with the emerging multi-target paradigm. (C) 2011 Elsevier Masson SAS. All rights reserved.