3-(4-bromophenyl)-2-(4-(dimethylamino)phenyl)thiazolidin-4-one | 1402049-23-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(4-bromophenyl)-2-(4-(dimethylamino)phenyl)thiazolidin-4-one
• 英文别名: 3-(4-Bromophenyl)-2-(4-(dimethylamino) phenyl)thiazolidin-4-one；3-(4-bromophenyl)-2-[4-(dimethylamino)phenyl]-1,3-thiazolidin-4-one
• CAS: 1402049-23-3
• 化学式: C₁₇H₁₇BrN₂OS
• 分子量: 377.305
• InChiKey: AYYXWVFJMMNUAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  巯基乙酸 、 4-(二甲氨基)苄醇 、 4-溴苯胺 在 1-丙基磷酸酐 作用下， 以 二甲基亚砜 、 乙酸乙酯 为溶剂， 以88%的产率得到3-(4-bromophenyl)-2-(4-(dimethylamino)phenyl)thiazolidin-4-one
  参考文献：
  名称：

  T3P®-DMSO介导的一锅级联方案，用于从醇类合成4-噻唑烷酮

  摘要：

  据报道，丙基膦酸酐（T3P®）-DMSO介导的醇氧化为羰基化合物，随后将其与芳基/杂芳基胺和巯基乙酸环化，得到4-噻唑烷酮。首次直接从醇类合成4-噻唑烷酮。温和的反应条件，宽泛的官能团耐受性，简便的后处理和良好的收率是该方案的显着特征。

  DOI：

  10.1016/j.tetlet.2012.08.020

文献信息

• T3P®-DMSO mediated one pot cascade protocol for the synthesis of 4-thiazolidinones from alcohols
  作者：Kothanahally S. Sharath Kumar、Toreshettahally R. Swaroop、Kachigere B. Harsha、Kereyagalahally H. Narasimhamurthy、Kanchugarakoppal S. Rangappa

  DOI：10.1016/j.tetlet.2012.08.020

  日期：2012.10

  Propylphosphonic anhydride (T3P®)-DMSO mediated oxidation of alcohols to carbonyl compounds and their subsequent cyclization with aryl/hetero aryl amines and thioglycolic acid to afford 4-thiazolidinones has been reported. Synthesis of 4-thiazolidinones directly from alcohols has been carried out for the first time. Mild reaction conditions, wide functional group tolerance, ease of work-up, and good

  据报道，丙基膦酸酐（T3P®）-DMSO介导的醇氧化为羰基化合物，随后将其与芳基/杂芳基胺和巯基乙酸环化，得到4-噻唑烷酮。首次直接从醇类合成4-噻唑烷酮。温和的反应条件，宽泛的官能团耐受性，简便的后处理和良好的收率是该方案的显着特征。
• Antiproliferative and tumor inhibitory studies of 2,3 disubstituted 4-thiazolidinone derivatives
  作者：Kothanahally S. Sharath Kumar、Ananda Hanumappa、Maruthai Vetrivel、Mahesh Hegde、Yarabhally R. Girish、Thinnali R. Byregowda、Suguna Rao、Sathees C. Raghavan、Kanchugarakoppal S. Rangappa

  DOI：10.1016/j.bmcl.2015.06.069

  日期：2015.9

  4-Thiazolidinone derivatives were synthesized using T3P (R)-DMSO media as a cyclodehydrating agent. All the molecules were tested for their cytotoxicity against leukemic cell lines. The compound 3-(4-bromophenyl)-2-(4-(dimethylamino)phenyl)thiazolidin-4-one (4e) with electron donating substituent at para position of phenyl ring displayed considerable cytotoxicity against Reh and Nalm6 cells with an IC50 value of 11.9 and 13.5 mu M, respectively. Furthermore, the compound 4e tested for tumor regression studies induced by EAC in Swiss albino mouse. Both in vitro and in vivo results suggested significant antiproliferative activity of compound 4e in Reh cells and mouse tumor tissue treated with compound 4e showed multifocal areas of necrosis and numerous number of apoptotic cells. (C) 2015 Elsevier Ltd. All rights reserved.