(Z)-5-(quinolin-2-ylmethylene)-2-thioxothiazolidin-4-one | 99420-16-3

• 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: (Z)-5-(quinolin-2-ylmethylene)-2-thioxothiazolidin-4-one
• 英文别名: 5-[2]quinolylmethylene-2-thioxo-thiazolidin-4-one；5-[2]Chinolylmethylen-2-thioxo-thiazolidin-4-on；(5Z)-5-(quinolin-2-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 99420-16-3
• 化学式: C₁₃H₈N₂OS₂
• 分子量: 272.351
• InChiKey: YVCFTDKLUAYRDD-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  罗丹宁 、 喹啉-2-甲醛 生成 (Z)-5-(quinolin-2-ylmethylene)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  Notes - Condensation of Rhodanine with Pyridine and Quinoline Aldehydes

  摘要：

  DOI：

  10.1021/jo01095a618

文献信息

• Condensation Reactions of Cinchoninaldehyde and Quinaldaldehyde with Some Heterocyclic Methylene Compounds. I
  作者：Arthur P. Phillips

  DOI：10.1021/ja01221a015

  日期：1945.5
• Notes - Condensation of Rhodanine with Pyridine and Quinoline Aldehydes
  作者：Frederick Allan、G. Allan、James Thomson

  DOI：10.1021/jo01095a618

  日期：1958.1
• Thiazolidine derivatives as potent and selective inhibitors of the PIM kinase family
  作者：Carole J.R. Bataille、Méabh B. Brennan、Simon Byrne、Stephen G. Davies、Matthew Durbin、Oleg Fedorov、Kilian V.M. Huber、Alan M. Jones、Stefan Knapp、Gu Liu、Anna Nadali、Camilo E. Quevedo、Angela J. Russell、Roderick G. Walker、Robert Westwood、Graham M. Wynne

  DOI：10.1016/j.bmc.2017.02.056

  日期：2017.5

  The PIM family of serine/threonine kinases have become an attractive target for anti-cancer drug development, particularly for certain hematological malignancies. Here, we describe the discovery of a series of inhibitors of the PIM kinase family using a high throughput screening strategy. Through a combination of molecular modeling and optimization studies, the intrinsic potencies and molecular properties of this series of compounds was significantly improved. An excellent pan-PIM isoform inhibition profile was observed across the series, while optimized examples show good selectivity over other kinases. Two PIM-expressing leukemic cancer cell lines, MV4-11 and 1(562, were employed to evaluate the in vitro anti-proliferative effects of selected inhibitors. Encouraging activities were observed for many examples, with the best example (44) giving an IC55 of 0.75 mu M against the K562 cell line. These data provide a promising starting point for further development of this series as a new cancer therapy through PIM kinase inhibition. (C) 2017 Elsevier Ltd. All rights reserved.