5-(5-bromo-thiophen-2-ylmethylene)-2-thioxo-thiazolidin-4-one | 127378-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-(5-bromo-thiophen-2-ylmethylene)-2-thioxo-thiazolidin-4-one
• 英文别名: 5-(5-bromo-[2]thienylmethylene)-2-thioxo-thiazolidin-4-one；5-(5-Brom-[2]thienylmethylen)-2-thioxo-thiazolidin-4-on；5-[(5-Bromo-2-thienyl)methylene]-2-thioxo-4-thiazolidinone；5-[(5-bromothiophen-2-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 127378-37-4
• 化学式: C₈H₄BrNOS₃
• 分子量: 306.228
• InChiKey: FXJZQFCLIBCBAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(5-bromo-thiophen-2-ylmethylene)-2-thioxo-thiazolidin-4-one 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Combination of 4-anilinoquinazoline and rhodanine as novel epidermal growth factor receptor tyrosine kinase inhibitors

  摘要：

  A type of novel rhodanine-based 4-anilinoquinazoline, which designed the combination between quinazoline as the backbone and various substituted biological rhodanine groups as the side chain, have been synthesized, and their antiproliferative activities were also evaluated firstly. These compounds displayed good antiproliferative activity and EGFR-TK inhibitory activity. Among them, compound 8d showed good inhibitory activity (IC50 = 2.7 mu M for Hep G2, IC50 = 3.1 mu M for A549) and molecular docking of 8d into EGFR TK active site was also performed, this inhibitor well fitting the active site might well explain its excellent inhibitory activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.065
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 罗丹宁 在 sodium acetate 、 溶剂黄146 作用下， 反应 24.0h， 生成 5-(5-bromo-thiophen-2-ylmethylene)-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  Combination of 4-anilinoquinazoline and rhodanine as novel epidermal growth factor receptor tyrosine kinase inhibitors

  摘要：

  A type of novel rhodanine-based 4-anilinoquinazoline, which designed the combination between quinazoline as the backbone and various substituted biological rhodanine groups as the side chain, have been synthesized, and their antiproliferative activities were also evaluated firstly. These compounds displayed good antiproliferative activity and EGFR-TK inhibitory activity. Among them, compound 8d showed good inhibitory activity (IC50 = 2.7 mu M for Hep G2, IC50 = 3.1 mu M for A549) and molecular docking of 8d into EGFR TK active site was also performed, this inhibitor well fitting the active site might well explain its excellent inhibitory activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.065

文献信息

• N-Glucopyranosyl-5-aralkylidenerhodanines: Synthesis and Antibacterial and Antiviral Activities
  作者：William O. Foye、Phichai Tovivich

  DOI：10.1002/jps.2600661126

  日期：1977.11

  N-glycoside formation. A number of the rhodanine derivatives, especially those with nitro or chloro groups in the aromatic ring, showed antibacterial activity. N-beta-D-Glucopyranosyl-5-(4-nitrobenzylidene) rhodanine showed antiviral activity by inhibition of viral RNA synthesis. Some effect on blood sugar levels also was observed with several rhodanines.

  合成了一系列的N-（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）-5-芳烷基亚乙基金丹宁，并且除去了乙酰基基团，得到了N-β-D-吡喃葡萄糖基-5-芳烷基亚芳基但不通过酸水解裂解若丹宁环。在甲醇中用氨水进行碱水解会裂解为N-葡萄糖基硫脲，为N-糖苷的形成提供了证据。许多若丹宁衍生物，特别是在芳族环中具有硝基或氯基的那些，均显示出抗菌活性。N-β-D-Glucopyranosyl-5-（4-硝基亚苄基）若丹宁通过抑制病毒RNA合成表现出抗病毒活性。几种罗丹宁对血糖水平也有一定影响。
• Combination of 4-anilinoquinazoline and rhodanine as novel epidermal growth factor receptor tyrosine kinase inhibitors
  作者：Si-Ning Li、Yun-Yun Xu、Jia-Yu Gao、Hong-ran Yin、Shi-Lei Zhang、Huan-Qiu Li

  DOI：10.1016/j.bmc.2015.04.065

  日期：2015.7

  A type of novel rhodanine-based 4-anilinoquinazoline, which designed the combination between quinazoline as the backbone and various substituted biological rhodanine groups as the side chain, have been synthesized, and their antiproliferative activities were also evaluated firstly. These compounds displayed good antiproliferative activity and EGFR-TK inhibitory activity. Among them, compound 8d showed good inhibitory activity (IC50 = 2.7 mu M for Hep G2, IC50 = 3.1 mu M for A549) and molecular docking of 8d into EGFR TK active site was also performed, this inhibitor well fitting the active site might well explain its excellent inhibitory activity. (C) 2015 Elsevier Ltd. All rights reserved.