tert-butyl 6-((2,6-dimethylphenyl)carbamoyl)benzo[d]thiazol-2-yl-carbamate

• 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: tert-butyl 6-((2,6-dimethylphenyl)carbamoyl)benzo[d]thiazol-2-yl-carbamate
• 英文别名: [6-[[(2,6-Dimethylphenyl)amino]carbonyl]-2-benzothiazolyl]carbamic acid, 1,1-dimethylethyl ester；[6-[[(2,6-Dimethylphenyl)amino]carbonyl]-2-benzothiazolyl]carbamic acid,1,1-dimethylethyl ester；[6-(2,6-Dimethyl-phenylcarbamoyl)-benzothiazol-2-yl]-carbamic acid tert-butyl ester；tert-butyl N-[6-[(2,6-dimethylphenyl)carbamoyl]-1,3-benzothiazol-2-yl]carbamate
• 化学式: C₂₁H₂₃N₃O₃S
• 分子量: 397.498
• InChiKey: PASLDQCIZPUMJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 6-((2,6-dimethylphenyl)carbamoyl)benzo[d]thiazol-2-yl-carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到2-amino-N-(2,6-dimethylphenyl)benzo[d]thiazole-6-carboxamide
  参考文献：
  名称：

  Design and synthesis of novel 4-benzothiazole amino quinazolines Dasatinib derivatives as potential anti-tumor agents

  摘要：

  Three series of novel 4-benzothiazole amino quinazolines Dasatinib derivatives have been designed and synthesized. The entire target compounds were investigated for their in vitro cytotoxic activity by the MTT-based assay against 6 human cancer cell lines. Compared with the parental Dasatinib, most of the new compounds, especially 2, 4, 6-trimethylaniline series (3), demonstrated significant inhibitory activities against six cell lines. Furthermore, the target compounds were screened for Src and Abl kinase inhibitory activity. Among them, 1a, 1f and 3a-3f are more potential dual Src/Abl kinase inhibitors. Thus they may be promising lead compounds to be developed as an alternative for current Dasatinib therapy or for Imatinib-resistant patients, potentially via simultaneously blocking multiple RTK signaling pathways. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.013
• 作为产物：
  描述：

  2-氨基苯并噻唑-6-羧酸乙酯 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 tert-butyl 6-((2,6-dimethylphenyl)carbamoyl)benzo[d]thiazol-2-yl-carbamate
  参考文献：
  名称：

  Design and synthesis of novel 4-benzothiazole amino quinazolines Dasatinib derivatives as potential anti-tumor agents

  摘要：

  Three series of novel 4-benzothiazole amino quinazolines Dasatinib derivatives have been designed and synthesized. The entire target compounds were investigated for their in vitro cytotoxic activity by the MTT-based assay against 6 human cancer cell lines. Compared with the parental Dasatinib, most of the new compounds, especially 2, 4, 6-trimethylaniline series (3), demonstrated significant inhibitory activities against six cell lines. Furthermore, the target compounds were screened for Src and Abl kinase inhibitory activity. Among them, 1a, 1f and 3a-3f are more potential dual Src/Abl kinase inhibitors. Thus they may be promising lead compounds to be developed as an alternative for current Dasatinib therapy or for Imatinib-resistant patients, potentially via simultaneously blocking multiple RTK signaling pathways. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.013

文献信息

• Molecular design, synthesis, and structure–Activity relationships leading to the potent and selective p56lck inhibitor BMS-243117
  作者：Jagabandhu Das、James Lin、Robert V. Moquin、Zhongqi Shen、Steven H. Spergel、John Wityak、Arthur M. Doweyko、Henry F. DeFex、Qiong Fang、Suhong Pang、Sidney Pitt、Ding Ren Shen、Gary L. Schieven、Joel C. Barrish

  DOI：10.1016/s0960-894x(03)00380-9

  日期：2003.7

  A series of structurally novel benzothiazole based small molecule inhibitors of p56(lck) were prepared to elucidate their structure-activity relationships (SARs), selectivity and cell activity in the T-cell proliferation assay. BMS-243117 (compound 2) is identified as a potent, and selective Lck inhibitor with good cellular activity (IC50 = 1.1 muM) against T-cell proliferation. (C) 2003 Elsevier Science Ltd. All rights reserved.