2-amino-N-mesitylbenzo[d]thiazole-6-carboxamide | 225520-11-6

• 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-amino-N-mesitylbenzo[d]thiazole-6-carboxamide
• 英文别名: 2-Amino-N-(2,4,6-trimethylphenyl)-1,3-benzothiazole-6-carboxamide
• CAS: 225520-11-6
• 化学式: C₁₇H₁₇N₃OS
• 分子量: 311.407
• InChiKey: UCCHJCMVURCTBK-UHFFFAOYSA-N

物化性质

• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-N-mesitylbenzo[d]thiazole-6-carboxamide 在 2-甲基-2-硝基丙烷 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 生成 2-Bromo-benzothiazole-6-carboxylic acid (2,4,6-trimethyl-phenyl)-amide
  参考文献：
  名称：

  Discovery of 2-amino-heteroaryl-benzothiazole-6-anilides as potent p56lck inhibitors

  摘要：

  A series of structurally novel benzothiazole based small molecule inhibitors of p56(lck) was prepared to elucidate their structure-activity relationships (SAR), selectivity and cell activity in the T-cell proliferation assay. BMS-350751 (2) and BMS-358233 (3) are identified as potent Lck inhibitors with excellent cellular activities against T-cell proliferation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00511-0
• 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 、 sodium hydroxide 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-amino-N-mesitylbenzo[d]thiazole-6-carboxamide
  参考文献：
  名称：

  Molecular design, synthesis, and structure–Activity relationships leading to the potent and selective p56lck inhibitor BMS-243117

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(03)00380-9

文献信息

• Benzothiazole protein trosine kinase inhibitors
  申请人：——

  公开号：US20020123484A1

  公开（公告）日：2002-09-05

  Novel benzothiazoles and salts thereof, pharmaceutical compositions containing such compounds, and methods of using such compounds in the treatment of protein tyrosine kinase-associated disorders such as immunologic disorders.

  新型苯并噻唑及其盐，含有这类化合物的药物组合物，以及使用这类化合物治疗蛋白酪氨酸激酶相关疾病（如免疫性疾病）的方法。
• [EN] BENZOTHIAZOLE PROTEIN TYROSINE KINASE INHIBITORS<br/>[FR] COMPOSES DE BENZOTHIAZOLE UTILISES COMME INHIBITEURS DE LA PROTEINE TYROSINE-KINASE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO1999024035A1

  公开（公告）日：1999-05-20

  (EN) Novel benzothiazoles and salts thereof, pharmaceutical compositions containing such compounds, and methods of using such compounds in the treatment of protein tyrosine kinase-associated disorders such as immunologic disorders.(FR) L'invention concerne de nouveaux composés de benzothiazole et des sels desdits composés, des compositions pharmaceutiques contenant ces composés, et des procédés mettant en oeuvre ces composés pour le traitement d'affections, telles que la réaction d'hypersensibilité immédiate, associées à la protéine tyrosine-kinase.

  (中) 本发明涉及新型苯并噻唑化合物及其盐、含有这些化合物的制药组合物，以及使用这些化合物治疗蛋白酪氨酸激酶相关疾病，如免疫疾病的方法。
• Design and synthesis of novel 4-benzothiazole amino quinazolines Dasatinib derivatives as potential anti-tumor agents
  作者：Jin Cai、Min Sun、Xiaoqing Wu、Junqing Chen、Peng Wang、Xi Zong、Min Ji

  DOI：10.1016/j.ejmech.2013.03.013

  日期：2013.5

  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.
• BENZOTHIAZOLE PROTEIN TYROSINE KINASE INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1037632A1

  公开（公告）日：2000-09-27
• EP1037632A4
  申请人：——

  公开号：EP1037632A4

  公开（公告）日：2002-08-21