tert-butyl 4-(6-(2-(2-methoxy-4-(methoxycarbonyl)phenyl)-4-oxothiazolidin-3-yl)pyridin-3-yl)piperazine-1-carboxylate | 1402049-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl 4-(6-(2-(2-methoxy-4-(methoxycarbonyl)phenyl)-4-oxothiazolidin-3-yl)pyridin-3-yl)piperazine-1-carboxylate
• 英文别名: Tert-butyl 4-[6-[2-(2-methoxy-4-methoxycarbonylphenyl)-4-oxo-1,3-thiazolidin-3-yl]pyridin-3-yl]piperazine-1-carboxylate；tert-butyl 4-[6-[2-(2-methoxy-4-methoxycarbonylphenyl)-4-oxo-1,3-thiazolidin-3-yl]pyridin-3-yl]piperazine-1-carboxylate
• CAS: 1402049-25-5
• 化学式: C₂₆H₃₂N₄O₆S
• 分子量: 528.629
• InChiKey: PMJLHEIHNGXAFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(6-(2-(2-methoxy-4-(methoxycarbonyl)phenyl)-4-oxothiazolidin-3-yl)pyridin-3-yl)piperazine-1-carboxylate 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl 3-methoxy-4-(3-(5-(4-(4-methoxyphenylsulfonyl)piperazin-1-yl)pyridin-2-yl)-4-oxothiazolidin-2-yl)benzoate
  参考文献：
  名称：

  Synthesis and antiproliferative effect of novel 4-thiazolidinone-, pyridine- and piperazine-based conjugates on human leukemic cells

  摘要：

  The present work reveals the synthesis and antiproliferative effect of a series of 2, 3 disubstituted 4-thiazolidinone analogues on human leukemic cells. The chemical structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR and mass spectral analysis. Compound methyl 3-methoxy-4-(4-oxo-3-(5-(piperazin-1-yl)pyridin-2-yl)thiazolidin-2-yl)benzoate (5) displayed potent activity (IC50 9.71, 15.24 and 19.29 mu M) against Nalm6, K562, Jurkat cells. Cell cycle analysis and mitochondrial membrane potential further confirmed that compound 5 is cytotoxic and able to induce cell death. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.009
• 作为产物：
  描述：

  N-Boc-哌嗪 在 palladium 10% on activated carbon 、 氢气 、 1-丙基磷酸酐 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 乙酸乙酯 为溶剂， 反应 8.0h， 生成 tert-butyl 4-(6-(2-(2-methoxy-4-(methoxycarbonyl)phenyl)-4-oxothiazolidin-3-yl)pyridin-3-yl)piperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis and antiproliferative effect of novel 4-thiazolidinone-, pyridine- and piperazine-based conjugates on human leukemic cells

  摘要：

  The present work reveals the synthesis and antiproliferative effect of a series of 2, 3 disubstituted 4-thiazolidinone analogues on human leukemic cells. The chemical structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR and mass spectral analysis. Compound methyl 3-methoxy-4-(4-oxo-3-(5-(piperazin-1-yl)pyridin-2-yl)thiazolidin-2-yl)benzoate (5) displayed potent activity (IC50 9.71, 15.24 and 19.29 mu M) against Nalm6, K562, Jurkat cells. Cell cycle analysis and mitochondrial membrane potential further confirmed that compound 5 is cytotoxic and able to induce cell death. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.009

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。