9-[ethyl (2-cyano)-acrylate]-acridine | 440367-55-5

• 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-[ethyl (2-cyano)-acrylate]-acridine
• 英文别名: 3-acridin-9-yl-2-cyano-acrylic acid ethyl ester；2-cyanoacridine-9-ylacrylate ethyl ester；2-cyano-(acridin-9-yl)-acrylic acid ethyl ester；Ethyl 3-(acridin-9-YL)-2-cyanoprop-2-enoate；ethyl 3-acridin-9-yl-2-cyanoprop-2-enoate
• CAS: 440367-55-5
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: DQRHRTFTKBWRQW-UHFFFAOYSA-N

物化性质

• 沸点：
  523.1±35.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-硫代乙内酰脲 、 9-[ethyl (2-cyano)-acrylate]-acridine 在 哌啶 作用下， 以 乙醇 为溶剂， 以75%的产率得到5-acridin-9-ylmethylidene-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  噻唑吖啶和咪唑吖啶衍生物的合成、DNA 结合和拓扑异构酶 I 抑制活性。

  摘要：

  噻唑吖啶和咪唑吖啶衍生物在某些癌细胞系中作为肿瘤抑制因子已显示出有希望的结果。为了更好地了解这些化合物的作用机制，对 5-acridin-9-ylmethylidene-3-amino-2-thioxo-thiazolidin-4-one, 5-acridin-9-ylmethylidene-2-thioxo- 的结合研究thiazolidin-4-one、5-acridin-9-ylmethylidene-2-thioxo-imidazolidin-4-one 和 3-acridin-9-ylmethyl-thiazolidin-2,4-dione 与小牛胸腺 DNA (ctDNA) 通过电子吸收和进行荧光光谱和圆二色光谱。结合常数范围从 1.46 × 10(4) 到 6.01 × 10(4) M(-1)。UV-Vis、荧光和圆二色性测量表明，这些化合物通过嵌入或外部结合与 ctDNA 有效相互作用。除了

  DOI：

  10.3390/molecules181215035
• 作为产物：
  描述：

  9-甲基吖啶 在 三乙胺 、 pyridinium chlorochromate 作用下， 生成 9-[ethyl (2-cyano)-acrylate]-acridine
  参考文献：
  名称：

  噻唑吖啶和咪唑吖啶衍生物的合成、DNA 结合和拓扑异构酶 I 抑制活性。

  摘要：

  噻唑吖啶和咪唑吖啶衍生物在某些癌细胞系中作为肿瘤抑制因子已显示出有希望的结果。为了更好地了解这些化合物的作用机制，对 5-acridin-9-ylmethylidene-3-amino-2-thioxo-thiazolidin-4-one, 5-acridin-9-ylmethylidene-2-thioxo- 的结合研究thiazolidin-4-one、5-acridin-9-ylmethylidene-2-thioxo-imidazolidin-4-one 和 3-acridin-9-ylmethyl-thiazolidin-2,4-dione 与小牛胸腺 DNA (ctDNA) 通过电子吸收和进行荧光光谱和圆二色光谱。结合常数范围从 1.46 × 10(4) 到 6.01 × 10(4) M(-1)。UV-Vis、荧光和圆二色性测量表明，这些化合物通过嵌入或外部结合与 ctDNA 有效相互作用。除了

  DOI：

  10.3390/molecules181215035

文献信息

• WO2007/109871
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and cytotoxic activity of new acridine-thiazolidine derivatives
  作者：Francisco W.A. Barros、Teresinha Gonçalves Silva、Marina Galdino da Rocha Pitta、Daniel P. Bezerra、Letícia V. Costa-Lotufo、Manoel Odorico de Moraes、Cláudia Pessoa、Maria Aline F.B. de Moura、Fabiane C. de Abreu、Maria do Carmo Alves de Lima、Suely Lins Galdino、Ivan da Rocha Pitta、Marilia O.F. Goulart

  DOI：10.1016/j.bmc.2012.04.007

  日期：2012.6

  Although their exact role in controlling tumour growth and apoptosis in humans remains undefined, acridine and thiazolidine compounds have been shown to act as tumour suppressors in most cancers. Based on this finding, a series of novel hybrid 5-acridin-9-ylmethylene-3-benzyl-thiazolidine-2,4-diones were synthesised via N-alkylation and Michael reaction. The cell viability was analysed using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, and DNA interaction assays were performed using electrochemical techniques. (C) 2012 Elsevier Ltd. All rights reserved.
• Albuquerque; Silva; Pitta, Pharmazie, 2005, vol. 60, # 1, p. 13 - 17
  作者：Albuquerque、Silva、Pitta、Silva、Silva、Malagueno、Santana、Wanderley、Lima、Galdino、Barbe、Pitta, Ivan Rocha

  DOI：——

  日期：——
• Synthesis and in vitro anticancer activity of novel thiazacridine derivatives
  作者：Marina Galdino da Rocha Pitta、Érika Silva Souza、Francisco Washington Araújo Barros、Manoel Odorico Moraes Filho、Cláudia O. Pessoa、Marcelo Zaldini Hernandes、Maria do Carmo Alves de Lima、Suely Lins Galdino、Ivan da Rocha Pitta

  DOI：10.1007/s00044-012-0236-2

  日期：2013.5

  Acridine derivatives represent a well-known class of anticancer agents that generally interfere with DNA synthesis and inhibit topoisomerase II. A series of eight new 3-acridin-9-ylmethyl-thiazolidine-2,4-dione and 3-acridin-9-ylmethyl-5-arylidene-thiazolidine-2,4-dione derivatives were synthesized. All the compounds were evaluated for their cell antiproliferation activity with the 3-(4,5-dimethyl-2-thiozolyl)-2,5-diphenyl-2H-tetrazolium bromide, MTT assay. The antiproliferative effects of the synthesized compounds were tested against several tumoral cell lines, namely SF-295 (central nervous system), HCT-8 (colon carcinoma), and MDA-MB-435 (melanoma) cells using doxorubicin as a positive control. Among the synthesized compounds, 3-acridin-9-ylmethyl-5-acridin-9-ylmethylene-thiazolidine-2,4-dione, 3-acridin-9-ylmethyl-5-(4-methoxy-benzylidene)-thiazolidine-2,4-dione, and 3-acridin-9-ylmethyl-5-(4-bromo-benzylidene)-thiazolidine-2,4-dione exhibited the most potent anticancer activity against the HCT-8 and MDA-MB-435 cell lines. After a detailed analysis of the structure of the thiazacridine molecules, we revealed the main possible interactions using the compound 3-acridin-9-ylmethyl-5-acridin-9-ylmethylene-thiazolidine-2,4-dione as an example. The benefits of these compounds, regardless of the pharmacological target are the presence of two aromatic rings (pi systems), significant planarity (intercalating ability) and the presence of three hydrogen-bond acceptors, two of which are stronger (oxygen atoms) than the other (sulfur atom).
• Synthesis, DNA Binding and Topoisomerase I Inhibition Activity of Thiazacridine and Imidazacridine Derivatives
  作者：Elizabeth Lafayette、Sinara Vitalino de Almeida、Marina da Rocha Pitta、Eduardo Carneiro Beltrão、Teresinha Gonçalves da Silva、Ricardo Olímpio de Moura、Ivan da Rocha Pitta、Luiz de Carvalho、Maria do Carmo Alves de Lima

  DOI：10.3390/molecules181215035

  日期：——

  suppressors in some cancer cell lines. For a better understanding of the mechanism of action of these compounds, binding studies of 5-acridin-9-ylmethylidene-3-amino-2-thioxo-thiazolidin-4-one, 5-acridin-9-ylmethylidene-2-thioxo-thiazolidin-4-one, 5-acridin-9-ylmethylidene-2-thioxo-imidazolidin-4-one and 3-acridin-9-ylmethyl-thiazolidin-2,4-dione with calf thymus DNA (ctDNA) by electronic absorption and fluorescence

  噻唑吖啶和咪唑吖啶衍生物在某些癌细胞系中作为肿瘤抑制因子已显示出有希望的结果。为了更好地了解这些化合物的作用机制，对 5-acridin-9-ylmethylidene-3-amino-2-thioxo-thiazolidin-4-one, 5-acridin-9-ylmethylidene-2-thioxo- 的结合研究thiazolidin-4-one、5-acridin-9-ylmethylidene-2-thioxo-imidazolidin-4-one 和 3-acridin-9-ylmethyl-thiazolidin-2,4-dione 与小牛胸腺 DNA (ctDNA) 通过电子吸收和进行荧光光谱和圆二色光谱。结合常数范围从 1.46 × 10(4) 到 6.01 × 10(4) M(-1)。UV-Vis、荧光和圆二色性测量表明，这些化合物通过嵌入或外部结合与 ctDNA 有效相互作用。除了