N-(2-amino-4-methoxy-1,3-benzothiazol-7-yl)-N-ethylacetamide | 1026174-66-2

• 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: N-(2-amino-4-methoxy-1,3-benzothiazol-7-yl)-N-ethylacetamide
• CAS: 1026174-66-2
• 化学式: C₁₂H₁₅N₃O₂S
• 分子量: 265.336
• InChiKey: LTGIHGILHYKCAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  96.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-amino-4-methoxy-1,3-benzothiazol-7-yl)-N-ethylacetamide 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-(7-(N-ethylacetamido)-4-methoxybenzo[d]thiazol-2-yl)-4-hydroxy-4-(3-(trifluoromethyl)phenyl)piperidine-1-carboxamide
  参考文献：
  名称：

  Discovery of benzothiazole-based adenosine A2B receptor antagonists with improved A2A selectivity

  摘要：

  The highly potent but modestly selective N-(2-amino-4-methoxy-benzothiazol-7-yl)-N-ethyl-acetamide derivative 2 was selected as the starting point for the design of novel selective A(2B) antagonists, due to its excellent potency, and good drug-like properties. A series of compounds containing nonaromatic amides or ureas of five- or six-membered rings, and also bearing an m-trifluoromethyl-phenyl group (shown to impart superior potency) were prepared and evaluated for their selectivity against the A(2A) and A(1) receptors. This work resulted in the identification of compound 30, with excellent potency and high selectivity against both A(2A) and A(1) receptors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.053
• 作为产物：
  描述：

  N-[7-(acetyl-ethyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide 在 甲醇 、 水 、 sodium hydroxide 作用下， 以70%的产率得到N-(2-amino-4-methoxy-1,3-benzothiazol-7-yl)-N-ethylacetamide
  参考文献：
  名称：

  4-Substituted-7-N-alkyl-N-acetyl 2-aminobenzothiazole amides: Drug-like and non-xanthine based A2B adenosine receptor antagonists

  摘要：

  7-N-Acetamide-4-methoxy-2-aminobenzothiazole 4-fluorobenzamide (compound 1) was chosen as a drug-like and non-xanthine based starting point for the discovery of A(2B) receptor antagonists because of its slight selectivity against A(1) and A(2A) receptors and modest A(2B) potency. SAR exploration of compound 1 described herein included modi. cations to the 7-N-acetamide group, substitution of the 4-methoxy group by halogens as well as replacement of the p-flouro-benzamide side chain. This work culminated in the identification of compound 37 with excellent A(2B) potency, modest selectivity versus A(2A) and A(1) receptors, and good rodent PK properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.056