3-(acridin-9-ylmethyl)thiazolidine-2,4-dione | 1402724-43-9

• 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: 3-(acridin-9-ylmethyl)thiazolidine-2,4-dione
• 英文别名: 3-Acridin-9-ylmethyl-thiazolidine-2,4-dione；3-(acridin-9-ylmethyl)-1,3-thiazolidine-2,4-dione
• CAS: 1402724-43-9
• 化学式: C₁₇H₁₂N₂O₂S
• 分子量: 308.36
• InChiKey: OZEFDKWLKHNKBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  75.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(acridin-9-ylmethyl)thiazolidine-2,4-dione 、 ethyl 2-cyano-3-(4-cyanophenyl)acrylate 在 吗啉 作用下， 以 乙醇 为溶剂， 以77%的产率得到4-((3-(acridin-9-ylmethyl)-2,4-dioxothiazolidin-5-ylidene)methyl)benzonitrile
  参考文献：
  名称：

  七种新型噻唑烷衍生物的合成，抗肿瘤活性和分子对接研究。

  摘要：

  目的和目标：在过去的几十年中，癌症已成为全球公共卫生的主要问题。近年来，嵌合化学结构已经确立为药物化学的重要趋势。噻唑烷是由噻唑烷和a啶核组成的杂合分子，这两种药效团均作用于癌症的重要生物学靶标。由于它是一种严重疾病，因此合成了七个新的3-acridin-9-ylmethyl-thiazolidine-2,4-dione衍生物，对其进行了表征，计算机模拟分析并在肿瘤细胞中进行了测试。为了找出这些化合物是否具有治疗潜力。 材料与方法：通过Michael加成和Knoevenagel缩合策略合成了七个新的3-acridin-9-ylmethyl-thiazolidine-2,4-dione衍生物。通过NMR和红外光谱技术进行表征。关于生物学活性，测试了噻唑烷对实体和造血肿瘤细胞系，即Jurkat（急性T细胞白血病）的抵抗力。HL-60（急性早幼粒细胞白血病）；DU 145（前列腺癌）; MOLT

  DOI：

  10.2174/1386207323666200319105239
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 9-溴甲基丫啶 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 7.17h， 以51%的产率得到3-(acridin-9-ylmethyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  七种新型噻唑烷衍生物的合成，抗肿瘤活性和分子对接研究。

  摘要：

  目的和目标：在过去的几十年中，癌症已成为全球公共卫生的主要问题。近年来，嵌合化学结构已经确立为药物化学的重要趋势。噻唑烷是由噻唑烷和a啶核组成的杂合分子，这两种药效团均作用于癌症的重要生物学靶标。由于它是一种严重疾病，因此合成了七个新的3-acridin-9-ylmethyl-thiazolidine-2,4-dione衍生物，对其进行了表征，计算机模拟分析并在肿瘤细胞中进行了测试。为了找出这些化合物是否具有治疗潜力。 材料与方法：通过Michael加成和Knoevenagel缩合策略合成了七个新的3-acridin-9-ylmethyl-thiazolidine-2,4-dione衍生物。通过NMR和红外光谱技术进行表征。关于生物学活性，测试了噻唑烷对实体和造血肿瘤细胞系，即Jurkat（急性T细胞白血病）的抵抗力。HL-60（急性早幼粒细胞白血病）；DU 145（前列腺癌）; MOLT

  DOI：

  10.2174/1386207323666200319105239

文献信息

• Pharmaceutical compositions of hydrophobic camptothecin derivatives
  申请人：Taiwan Liposome Company, Ltd.

  公开号：US10980798B2

  公开（公告）日：2021-04-20

  Provide is a method of using a topoisomerase I inhibitor in treatment of cancer to reduce bone marrow suppression. The method includes administering to a subject in need thereof an effective amount of a pharmaceutical composition. The composition has at least one hydrophobic topoisomerase I inhibitor or a pharmaceutically acceptable salt thereof, and at least one polyethylene glycol (PEG) conjugated phospholipid, wherein the molar ratio of said PEG conjugated phospholipid to said hydrophobic topoisomerase I inhibitor or said pharmaceutically acceptable salt of said hydrophobic topoisomerase I inhibitor is about 0.45:1 to about 1.05:1.

  提供一种在癌症治疗中使用拓扑异构酶 I 抑制剂以减少骨髓抑制的方法。该方法包括向有需要的受试者施用有效量的药物组合物。该组合物具有至少一种疏水性拓扑异构酶I抑制剂或其药学上可接受的盐，以及至少一种聚乙二醇(PEG)共轭磷脂，其中所述PEG共轭磷脂与所述疏水性拓扑异构酶I抑制剂或所述疏水性拓扑异构酶I抑制剂的药学上可接受的盐的摩尔比约为0.45:1至约1.05:1。
• 10.3390/molecules29143387
  作者：Garberová, Monika、Kudličková, Zuzana、Michalková, Radka、Tvrdoňová, Monika、Sabolová, Danica、Bekešová, Slávka、Gramblička, Michal、Mojžiš, Ján、Vilková, Mária

  DOI：10.3390/molecules29143387

  日期：——

  This study focuses on the synthesis and structural characterization of new compounds that integrate thiazolidine-2,4-dione, acridine moiety, and an acetamide linker, aiming to leverage the synergistic effects of these pharmacophores for enhanced therapeutic potential. The newly designed molecules were efficiently synthesized through a multi-step process and subsequently transformed into their hydrochloride

  本研究重点关注整合了噻唑烷-2,4-二酮、吖啶部分和乙酰胺连接体的新化合物的合成和结构表征，旨在利用这些药效团的协同作用来增强治疗潜力。新设计的分子通过多步过程有效合成，随后转化为盐酸盐。采用综合光谱技术，包括核磁共振（NMR）、高分辨率质谱（HRMS）、红外（IR）光谱和元素分析，来确定合成化合物的分子结构。进行生物学评价以评估新化合物的治疗潜力。评估了这些衍生物对各种癌细胞系代谢活性的影响，并通过 MTT 测定确定了 IC50 值。对构效关系（SAR）的深入分析揭示了对其细胞毒性特征的有趣见解。具有吸电子基团的化合物通常表现出较低的IC50值，表明较高的效力。连接苯环上甲氧基的存在调节了化合物的效力和选择性。噻唑烷-2,4-二酮核心氮原子处吖啶核心的变化显着影响了针对癌细胞系的活性，吖啶-9-基取代基增强了化合物的抗增殖活性。此外，与游离碱形式相比，盐酸盐形式的化合物表现出更好的抗癌细胞系活性。化合物
• 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).
• PHARMACEUTICAL COMPOSITIONS OF HYDROPHOBIC CAMPTOTHECIN DERIVATIVES
  申请人：Taiwan Liposome Company, Ltd.

  公开号：US20190321356A1

  公开（公告）日：2019-10-24

  Provide is a method of using a topoisomerase I inhibitor in treatment of cancer to reduce bone marrow suppression. The method includes administering to a subject in need thereof an effective amount of a pharmaceutical composition. The composition has at least one hydrophobic topoisomerase I inhibitor or a pharmaceutically acceptable salt thereof, and at least one polyethylene glycol (PEG) conjugated phospholipid, wherein the molar ratio of said PEG conjugated phospholipid to said hydrophobic topoisomerase I inhibitor or said pharmaceutically acceptable salt of said hydrophobic topoisomerase I inhibitor is about 0.45:1 to about 1.05:1.
• Synthesis, Antitumor Activity and Molecular Docking Studies on Seven Novel Thiazacridine Derivatives
  作者：Marcel L. Almeida、Douglas C.F. Viana、Valécia C.M. da Costa、Flaviana A. dos Santos、Michelly C. Pereira、Maira G.R. Pitta、Moacyr J.B. de Melo Rêgo、Ivan R. Pitta、Marina G.R. Pitta

  DOI：10.2174/1386207323666200319105239

  日期：2020.7.9

  find out if the compounds have therapeutic potential. Materials and Methods: Seven new 3-acridin-9-ylmethyl-thiazolidine-2,4-dione derivatives were synthesized through Michael addition and Knoevenagel condensation strategies. Characterization was performed by NMR and Infrared spectroscopy techniques. Regarding biological activity, thiazacridines were tested against solid and hematopoietic tumoral cell

  目的和目标：在过去的几十年中，癌症已成为全球公共卫生的主要问题。近年来，嵌合化学结构已经确立为药物化学的重要趋势。噻唑烷是由噻唑烷和a啶核组成的杂合分子，这两种药效团均作用于癌症的重要生物学靶标。由于它是一种严重疾病，因此合成了七个新的3-acridin-9-ylmethyl-thiazolidine-2,4-dione衍生物，对其进行了表征，计算机模拟分析并在肿瘤细胞中进行了测试。为了找出这些化合物是否具有治疗潜力。 材料与方法：通过Michael加成和Knoevenagel缩合策略合成了七个新的3-acridin-9-ylmethyl-thiazolidine-2,4-dione衍生物。通过NMR和红外光谱技术进行表征。关于生物学活性，测试了噻唑烷对实体和造血肿瘤细胞系，即Jurkat（急性T细胞白血病）的抵抗力。HL-60（急性早幼粒细胞白血病）；DU 145（前列腺癌）; MOLT