methyl 2-hydroxy-5-[(5-(2-methoxybenzylidene)-4(H)-oxo-1,3-thiazol-2-yl)-amino]benzoate

• 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: methyl 2-hydroxy-5-[(5-(2-methoxybenzylidene)-4(H)-oxo-1,3-thiazol-2-yl)-amino]benzoate
• 英文别名: methyl 2-hydroxy-5-[[(5Z)-5-[(2-methoxyphenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoate
• 化学式: C₁₉H₁₆N₂O₅S
• 分子量: 384.412
• InChiKey: ALYZSISDPJZBNX-SXGWCWSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-氨基水杨酸甲酯 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 苯 为溶剂， 反应 32.0h， 生成 methyl 2-hydroxy-5-[(5-(2-methoxybenzylidene)-4(H)-oxo-1,3-thiazol-2-yl)-amino]benzoate
  参考文献：
  名称：

  Design and synthesis of novel 5-aminosalicylate (5-ASA)–4-thiazolinone hybrid derivatives with promising antiproliferative activity

  摘要：

  Two privileged pharmacophores were assembled in one molecular frame involving 5-aminosalicylate and 4-thiazolinones that can be found in different stereochemical features. The compounds were fully characterized and evaluated for antiproliferative activity against four human cancer cell lines and some are equipotent to doxorubicin with lower cytotoxicity to normal cells. The most interesting finding relates to compound 10, which shows an IC50 value of 70 nM against MCF-7 cells, while the IC50 against human fibroblasts is 10 mu M. The results of this study indicate that the new compounds are optimal anti-cancer leading compounds and merit further studies to optimize their structure, detect their biotargets and in vivo activity. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.02.073

文献信息

• Design and synthesis of novel 5-aminosalicylate (5-ASA)–4-thiazolinone hybrid derivatives with promising antiproliferative activity
  作者：Hajjaj H.M. Abdu-Allah、Samia G. Abdel-Moty、Raafat El-Awady、Abdel-Nasser A. El-Shorbagi

  DOI：10.1016/j.bmcl.2016.02.073

  日期：2016.4

  Two privileged pharmacophores were assembled in one molecular frame involving 5-aminosalicylate and 4-thiazolinones that can be found in different stereochemical features. The compounds were fully characterized and evaluated for antiproliferative activity against four human cancer cell lines and some are equipotent to doxorubicin with lower cytotoxicity to normal cells. The most interesting finding relates to compound 10, which shows an IC50 value of 70 nM against MCF-7 cells, while the IC50 against human fibroblasts is 10 mu M. The results of this study indicate that the new compounds are optimal anti-cancer leading compounds and merit further studies to optimize their structure, detect their biotargets and in vivo activity. (C) 2016 Elsevier Ltd. All rights reserved.