phenyl 6-(morpholinomethyl)benzo[d]thiazol-2-ylcarbamate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: phenyl 6-(morpholinomethyl)benzo[d]thiazol-2-ylcarbamate
• 英文别名: phenyl N-[6-(morpholin-4-ylmethyl)-1,3-benzothiazol-2-yl]carbamate
• 化学式: C₁₉H₁₉N₃O₃S
• 分子量: 369.444
• InChiKey: OFBIVUWCLAUKIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 6-(morpholinomethyl)benzo[d]thiazol-2-ylcarbamate 在 一水合肼 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以80.8%的产率得到N-(6-(morpholinomethyl)benzo[d]thiazol-2-yl)hydrazinecarboxamide
  参考文献：
  名称：

  新型氨基咪唑骨架偶联的苯并噻唑衍生物的设计，合成及抗增殖活性。

  摘要：

  通过基于结构的分子杂交策略，设计并合成了两类新颖的结合了半脲酮骨架的苯并噻唑衍生物。通过标准MTT测定法评估了所有目标化合物在体外对三种癌细胞系（HT-29，MKN-45和H460）的细胞毒性。药理结果表明，与参考药物索拉非尼和PAC-1相比，七种化合物（17h-n）表现出可比甚至更好的抗增殖活性。尤其是，化合物17i对测试的三种癌细胞系表现出显着的细胞毒性，IC50值分别为0.84、0.06和0.52 µM，分别比索拉非尼强4.3倍，36.6倍，4.2倍，并且比索拉非尼高1.2倍，13.7倍，6.9倍分别比PAC-1活跃。

  DOI：

  10.2174/1573406412666160107113343
• 作为产物：
  描述：

  4-吗啉甲基苯胺 在 吡啶 、 溴 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 phenyl 6-(morpholinomethyl)benzo[d]thiazol-2-ylcarbamate
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety as potent antitumor agents

  摘要：

  A series of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety were designed and synthesized and their cytotoxic activities against five cancer cell lines (NCI-H226, SK-N-SH, HT29, MKN45, and MDA-MB-231) were screened in vitro. Most of them showed moderate to excellent activity against all the tested cell lines. Among them, compounds 15g (procaspase-3 EC50 = 1.42 mu M) and 16b (procaspase-3 EC50 = 0.25 mu M) exhibited excellent antitumor activity with IC50 values ranging from 0.14 mu M to 0.98 mu M against all cancer cell lines, which were 1.8-8.7 times more active than the first procaspase activating compound (PAC-1) (procaspase-3 EC50 = 4.08 mu M). The structure activity relationship (SAR) analyses indicated that the introduction of a lipophilic group (a benzyloxy or heteroaryloxy group) at the 4-position of the 2-hydroxy phenyl ring was beneficial to antitumor activity, and the presence of substituents containing nitrogen that are positively charged at physiological pH could also improve antitumor activity. It was also confirmed that the steric effect of the 4-position substituent of the benzyloxy group had a significant influence on cytotoxic activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.058