5-isopropylidiene-3-ethyl-2-thio-2,4-oxazolidinedione | 1256477-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-isopropylidiene-3-ethyl-2-thio-2,4-oxazolidinedione
• 英文别名: 4-Oxazolidinone, 3-ethyl-5-(1-methylethylidene)-2-thioxo-；3-ethyl-5-propan-2-ylidene-2-sulfanylidene-1,3-oxazolidin-4-one
• CAS: 1256477-64-1
• 化学式: C₈H₁₁NO₂S
• 分子量: 185.247
• InChiKey: LDECQECVSFMDKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-乙基-2-硫代-4-噁唑烷酮 、 丙酮 在 ammonium acetate 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 60.0h， 以76%的产率得到5-isopropylidiene-3-ethyl-2-thio-2,4-oxazolidinedione
  参考文献：
  名称：

  Novel rhodanine derivatives induce growth inhibition followed by apoptosis

  摘要：

  We have designed and synthesized three novel compounds, 5-isopropylidiene derivatives of 3-dimethyl-2-thio-hydantoin (ITH-1), 3-ethyl-2-thio-2,4-oxazolidinedione (ITO-1), and 5-benzilidene-3-ethyl rhodanine (BTR-1), and have tested their chemotherapeutic properties. Our results showed that all three compounds induced cytotoxicity in a time-and concentration-dependent manner on leukemic cell line, CEM. Among the compounds tested, BTR-1 was 5- to 7-fold more potent than ITH-1 and ITO-1 when compared by trypan blue and MTT assays. IC(50) value of BTR-1 was estimated to be <10 mu M. Both cell cycle analysis and tritiated thymidine assays revealed that BTR-1 affects DNA replication by inducing a block at S phase. BTR-1 treatment led to increased level of ROS production and DNA strand breaks suggesting activation of apoptosis for induction of cell death. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.084

文献信息

• Novel rhodanine derivatives induce growth inhibition followed by apoptosis
  作者：Balaji T. Moorthy、Subban Ravi、Mrinal Srivastava、Kishore K. Chiruvella、H. Hemlal、Omana Joy、Sathees C. Raghavan

  DOI：10.1016/j.bmcl.2010.08.084

  日期：2010.11

  We have designed and synthesized three novel compounds, 5-isopropylidiene derivatives of 3-dimethyl-2-thio-hydantoin (ITH-1), 3-ethyl-2-thio-2,4-oxazolidinedione (ITO-1), and 5-benzilidene-3-ethyl rhodanine (BTR-1), and have tested their chemotherapeutic properties. Our results showed that all three compounds induced cytotoxicity in a time-and concentration-dependent manner on leukemic cell line, CEM. Among the compounds tested, BTR-1 was 5- to 7-fold more potent than ITH-1 and ITO-1 when compared by trypan blue and MTT assays. IC(50) value of BTR-1 was estimated to be <10 mu M. Both cell cycle analysis and tritiated thymidine assays revealed that BTR-1 affects DNA replication by inducing a block at S phase. BTR-1 treatment led to increased level of ROS production and DNA strand breaks suggesting activation of apoptosis for induction of cell death. (C) 2010 Elsevier Ltd. All rights reserved.