2-(4-chloro-2-formylphenoxy)-N-(4-methoxyphenyl)acetamide | 1023383-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-chloro-2-formylphenoxy)-N-(4-methoxyphenyl)acetamide
• CAS: 1023383-19-8
• 化学式: C₁₆H₁₄ClNO₄
• 分子量: 319.744
• InChiKey: UHIUKLXZGBBUMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-2-formylphenoxy)-N-(4-methoxyphenyl)acetamide 、 2-(6-methylbenzothiazol-2-ylimino)thiazolidin-4-one 在 sodium acetate 、 溶剂黄146 作用下， 反应 3.0h， 以75%的产率得到2-(4-chloro-2-[(1Z)-2-(6-methylbenzothiazol-2-ylimino)-4-oxothiazolidin-5-ylidenemethyl]-phenoxy)-N-(4-methoxyphenyl)acetamide
  参考文献：
  名称：

  含苯并噻唑部分的4-噻唑烷酮的合成及抗癌活性评估

  摘要：

  已经进行了几种具有苯并噻唑部分的新颖的4-噻唑烷酮的抗肿瘤筛选。（苯并噻唑-2-基）肼与三硫代羰基二乙醇酸或6-甲基-2-氨基苯并噻唑与2-乙氧基甲硫基-2-噻唑啉-4-酮的反应产生了起始的3-（1）或2-取代的（11）4这已经在Knoevenagel缩合随后被用于获取一系列5-亚芳基衍生物的-thiazolidinones 2-10，12-16。或者，根据2-氯-N-（6-甲基苯并噻唑-2-基）-乙酰胺与硫氰酸铵的反应，通过反合成方法得到化合物11。化合物的结构由1 H确定，13 C NMR，IR和X射线分析。体外合成的化合物的抗癌活性是由美国国家癌症研究所和两个（测试6，16）的他们已经揭示于白血病，黑色素瘤，肺癌，结肠癌，中枢神经系统癌，卵巢癌，肾癌，前列腺癌和乳腺癌细胞系中的抗癌活性。在测试的化合物中，2- {2- [3-（苯并噻唑-2-基氨基）-4-氧代-2-硫代噻唑烷啶-5-亚甲基甲基]

  DOI：

  10.1016/j.ejmech.2010.08.008

文献信息

• Bradykinin antagonists and thiazolidinone derivatives as new potential anti-cancer compounds
  作者：Stanislav Avdieiev、Lajos Gera、Dmytro Havrylyuk、Robert S. Hodges、Roman Lesyk、Vincent Ribrag、Yegor Vassetzky、Vadym Kavsan

  DOI：10.1016/j.bmc.2014.06.046

  日期：2014.8

  Glioblastoma (GB), the most aggressive brain tumour, and mantle cell lymphoma (MCL), a rare but very aggressive type of lymphoma, are highly resistant to chemotherapy. GB and MCL chemotherapy gives very modest results, the vast majority of patients experience recurrent disease. To find out the new treatment modality for drug-resistant GB and MCL cells, combining of bradykinin (BK) antagonists with conventional temozolomide (TMZ) treatment, and screening of thiazolidinones derivatives were the main objectives of this work. As it was revealed here, BKM-570 was the lead compound among BK antagonists under investigation (IC50 was 3.3 mu M) in human GB cells. It strongly suppressed extracellular signal-regulated kinases 1/2 (ERK1/2) and protein kinase B (AKT) phosphorylation. BK antagonists did not decrease the viability of MCL cells, thus showing the cell-specific mode, while thiazolidinone derivatives, a novel group of promising anti-tumour compounds inhibited proliferation of MCL cells: IC50 of ID 4526 and ID 4527 compounds were 0.27 mu M and 0.16 mu M, correspondingly. However, single agents are often not effective in clinic due to activation of collateral pathways in tumour cells. We demonstrated a strong synergistic effect after combinatorial treatment by BKM-570 together with TMZ that drastically increased cytotoxic action of this drug in rat and human glioma cells. Small proportion of cells was still viable after such treatment that could be explained by presence of TMZ-resistant cells in the population.It is possible to expect that the combined therapy aimed simultaneously at different elements of tumourigenesis will be more effective with lower drug concentrations than the first-line drug temozolomide used alone in clinics. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and anticancer activity evaluation of 4-thiazolidinones containing benzothiazole moiety
  作者：Dmytro Havrylyuk、Ludmyla Mosula、Borys Zimenkovsky、Olexandr Vasylenko、Andrzej Gzella、Roman Lesyk

  DOI：10.1016/j.ejmech.2010.08.008

  日期：2010.11

  alternatively by a counter synthesis method based on the reaction of 2-chloro-N-(6-methylbenzothiazol-2-yl)-acetamide and ammonium thiocyanate. The structures of compounds have been determined by 1H, 13C NMR, IR and X-ray analysis. In vitro anticancer activity of the synthesized compounds was tested by the National Cancer Institute and two (6, 16) of them has revealed the anticancer activity on leukemia, melanoma

  已经进行了几种具有苯并噻唑部分的新颖的4-噻唑烷酮的抗肿瘤筛选。（苯并噻唑-2-基）肼与三硫代羰基二乙醇酸或6-甲基-2-氨基苯并噻唑与2-乙氧基甲硫基-2-噻唑啉-4-酮的反应产生了起始的3-（1）或2-取代的（11）4这已经在Knoevenagel缩合随后被用于获取一系列5-亚芳基衍生物的-thiazolidinones 2-10，12-16。或者，根据2-氯-N-（6-甲基苯并噻唑-2-基）-乙酰胺与硫氰酸铵的反应，通过反合成方法得到化合物11。化合物的结构由1 H确定，13 C NMR，IR和X射线分析。体外合成的化合物的抗癌活性是由美国国家癌症研究所和两个（测试6，16）的他们已经揭示于白血病，黑色素瘤，肺癌，结肠癌，中枢神经系统癌，卵巢癌，肾癌，前列腺癌和乳腺癌细胞系中的抗癌活性。在测试的化合物中，2- 2- [3-（苯并噻唑-2-基氨基）-4-氧代-2-硫代噻唑烷啶-5-亚甲基甲基]