9,10-dihydro-9-oxoacridine-2-acetic acid | 85468-39-9

• 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: 9,10-dihydro-9-oxoacridine-2-acetic acid
• 英文别名: acridanone-2-acetic acid；(2-acridonyl)acetic acid；9,10-Dihydro-9-oxo-2-acridineacetic acid；2-(9-oxo-10H-acridin-2-yl)acetic acid
• CAS: 85468-39-9
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: LGKBIIYMLFXBGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-9-oxoacridine-2-acetic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 生成 (9-Oxo-9,10-dihydro-acridin-2-yl)-acetyl chloride
  参考文献：
  名称：

  Synthesis and photophysics of acridine derivatives

  摘要：

  DOI：

  10.1007/bf02256913
• 作为产物：
  描述：

  对氨基乙酸苯甲酯 在 sodium hydroxide 、 PPA 、 铜 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 9,10-dihydro-9-oxoacridine-2-acetic acid
  参考文献：
  名称：

  Chemico-enzymatic synthesis of a new fluorescent-labeled DNA by PCR with a thymidine nucleotide analogue bearing an acridone derivative

  摘要：

  Triphosphate of a thymidine analogue bearing acridone was prepared and incorporated as a substrate for P using KOD Dash DNA polymerase forming a new fluorescent-labeled DNA that is useful as a DNA probe. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.072

文献信息

• Synthesis and Structure–Activity Relationships of Anti-inflammatory 9,lO-Dihydro-9-oxo-2-Acridine-alkanoic Acids and 4-(2-Carboxyphenyl)aminobenzenealkanoic Acids
  作者：Irach B. Taraporewala、Joel M. Kauffman

  DOI：10.1002/jps.2600790219

  日期：1990.2

  prepared as potential anti-inflammatory agents and evaluated by the rat hindpaw carrageenan-induced edema assay. The compounds, isosteric with known anti-inflammatory and antiallergic cyclo-oxygenase and lipoxygenase inhibitors, are 10-methyl-9,10-dihydro-9-oxo-2-acridinealkanoic acids, 9,10-dihydro-9-oxo-2-acridinealkanoic acids, and 4-(2-carboxyphenyl)aminobenzenealkanoic acids. Compounds within each

  制备了三个化学系列的18种测试化合物作为潜在的抗炎药，并通过大鼠后足角叉菜胶诱导的水肿试验进行了评估。具有已知消炎和抗过敏性环加氧酶和脂氧合酶抑制剂的等排化合物是10-甲基-9,10-二氢-9-氧代-2-ac啶烷酸，9,10-二氢-9-氧代-2-酸cr啶链烷酸和4-（2-羧基苯基）氨基苯链烷酸。这些系列中的每一个中的化合物的链烷酸侧链结构均不同。含有乙酸和支链2-丙酸侧链的化合物显示出角叉菜胶诱导的水肿的抑制作用。具有这些侧链的化合物的活性，以及​​与羧基，氧乙酸，硫代乙酸，3-丙酸侧链与Appleton和Brown提出的模板模型有关的环加氧酶的活性位点相一致，而不是由Gund和Shen提出的替代活性位点模型。一种化合物（+-）-2- [N-（2-羧基苯基）-4-氨基苯基]丙酸（3c）在50 mg / kg po时表现出水肿抑制作用，其等效剂量水平为（+ ）萘普生。含有羧酸侧链的化合物4a
• Kauffman, Joel M.; Taraporewala, Irach B., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1557 - 1559
  作者：Kauffman, Joel M.、Taraporewala, Irach B.

  DOI：——

  日期：——
• Acridone-tagged DNA as a new probe for DNA detection by fluorescence resonance energy transfer and for mismatch DNA recognition
  作者：Yasuhisa Hagiwara、Tomoya Hasegawa、Atushi Shoji、Masayasu Kuwahara、Hiroaki Ozaki、Hiroaki Sawai

  DOI：10.1016/j.bmc.2008.05.050

  日期：2008.7

  Acridone is highly fluorescent and stable against photodegradation, oxidation, and heat. It is also a small molecule with no charge, making it a promising fluorescent agent for use in a DNA probe. Thus, we have prepared 5'-terminal acridone-labeled DNAs by post-modification, and have examined their photophysical properties and their use as donors for a fluorescence resonance energy transfer ( FRET) system in combination with a 3'-terminal dabcyl-tagged DNA as an acceptor, which can detect the target DNA by emission-quenching caused by FRET. The FRET with an acridone and dabcyl pair has been found to complement that with fluorescence and dabcyl and other fluorescence-quencher pairs. Significant amounts of quenching of the acridone emissions by guanine in the DNA were observed when guanine was close to acridone, which can be applied as a quencher-free probe for the detection of special sequence of DNA. The DNA bearing acridone at the C5 position of inner thymidine could discriminate the opposite T-T base mismatch, although enhancement of discrimination ability is needed for the practical use of SNP typing. (c) 2008 Elsevier Ltd. All rights reserved.
• TARAPOREWALA, IRACH B.;KAUFFMAN, JOEL M., J. PHARM. SCI., 79,(1990) N, C. 173-178
  作者：TARAPOREWALA, IRACH B.、KAUFFMAN, JOEL M.

  DOI：——

  日期：——
• KAUFFMAN, J. M.;TARAPOREWALA, I. B., J. HETEROCYCL. CHEM., 1982, 19, N 6, 1557-1559
  作者：KAUFFMAN, J. M.、TARAPOREWALA, I. B.

  DOI：——

  日期：——