(Z)-5-(benzofuran-2-ylmethylene)-2-thioxothiazolidin-4-one | 181765-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (Z)-5-(benzofuran-2-ylmethylene)-2-thioxothiazolidin-4-one
• 英文别名: (5Z)-5-(1-benzofuran-2-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 181765-62-8
• 化学式: C₁₂H₇NO₂S₂
• 分子量: 261.325
• InChiKey: MCIXPJLOMAXCER-POHAHGRESA-N

物化性质

• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 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：
  99.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-5-(benzofuran-2-ylmethylene)-2-thioxothiazolidin-4-one 在 sodium hydroxide 、 水 、 溴 作用下， 反应 2.0h， 生成 Thieno[3,2-b]benzofuran-2-carboxylic acid
  参考文献：
  名称：

  Thieno[3,2-b]benzofuran - Synthesis and Reactions

  摘要：

  噻吩[3,2-b]苯并呋喃是从苯并[b]呋喃-3(2H)-酮或苯并[b]呋喃-2-甲醛开始合成的。亲电取代反应，如溴化、甲酰化、乙酰化或硝化，发生在位置2。位置2处的电子给体基团将进一步的亲电取代引向位置3和6，而位置2处带有电子受体的化合物则仅在位置6上发生取代。丁基锂的金属化反应发生在位置2。该标题化合物的¹H和¹³C NMR信号已完全被指定。

  DOI：

  10.1135/cccc19971468
• 作为产物：
  描述：

  罗丹宁 、 苯并[b]呋喃-2-甲醛 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 0.75h， 以90%的产率得到(Z)-5-(benzofuran-2-ylmethylene)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  Thieno[3,2-b]benzofuran - Synthesis and Reactions

  摘要：

  噻吩[3,2-b]苯并呋喃是从苯并[b]呋喃-3(2H)-酮或苯并[b]呋喃-2-甲醛开始合成的。亲电取代反应，如溴化、甲酰化、乙酰化或硝化，发生在位置2。位置2处的电子给体基团将进一步的亲电取代引向位置3和6，而位置2处带有电子受体的化合物则仅在位置6上发生取代。丁基锂的金属化反应发生在位置2。该标题化合物的¹H和¹³C NMR信号已完全被指定。

  DOI：

  10.1135/cccc19971468

文献信息

• PREMATURE-TERMINATION-CODONS READTHROUGH COMPOUNDS
  申请人：GATTI Richard A.

  公开号：US20130274283A1

  公开（公告）日：2013-10-17

  Premature termination codons readthrough compounds, composition thereof, and methods of making and using the same are provided.

  提供了关于早期终止密码子读穿化合物、其组合物以及制备和使用方法的信息。
• Synthesis and evaluation of compounds that induce readthrough of premature termination codons
  作者：Michael E. Jung、Jin-Mo Ku、Liutao Du、Hailiang Hu、Richard A. Gatti

  DOI：10.1016/j.bmcl.2011.07.107

  日期：2011.10

  A structure-activity relationship (SAR) study was carried out to identify novel, small molecular weight compounds which induce readthrough of premature termination codons. In particular, analogs of RTC13, 1, were evaluated. In addition, hypothesizing that these compounds exhibit their activity by binding to the ribosome, we prepared the hybrid analogs 13 containing pyrimidine bases and these also showed good readthrough activity. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.
• US9255088B2
  申请人：——

  公开号：US9255088B2

  公开（公告）日：2016-02-09
• US9598395B2
  申请人：——

  公开号：US9598395B2

  公开（公告）日：2017-03-21