N-[7-(acetyl-ethyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide | 554420-57-4

• 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: N-[7-(acetyl-ethyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide
• 英文别名: N-[7-[acetyl(ethyl)amino]-4-methoxy-1,3-benzothiazol-2-yl]-4-fluorobenzamide
• CAS: 554420-57-4
• 化学式: C₁₉H₁₈FN₃O₃S
• 分子量: 387.435
• InChiKey: HHAUAECIUWZNID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  99.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  7-N-acetamide-4-methoxy-2-aminobenzothiazole 4-fluorobenzamide 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[7-(acetyl-ethyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide
  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

文献信息

• 7-Amino-benzothiazole derivatives
  申请人：——

  公开号：US20030153566A1

  公开（公告）日：2003-08-14

  The present invention relates to compounds of the formula 1 wherein R 1 , R 2 and R 3 are as described herewithin. The compounds of formula I have been found to be adenosine receptor ligands. Specifically, the compounds of the present invention have a good affinity to the A 2A -receptor and they are therefore useful in the treatment of diseases, related to this receptor.

  本发明涉及式1的化合物，其中R1、R2和R3如本文所述。发现本发明的化合物具有腺苷受体配体的特性。具体来说，本发明的化合物对A2A受体具有良好的亲和力，因此在治疗与该受体相关的疾病方面是有用的。
• 7-AMINO-BENZOTHIAZOLE DERIVATIVES AS ADENOSINE RECEPTOR LIGANDS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1456188A1

  公开（公告）日：2004-09-15
• US6713499B2
  申请人：——

  公开号：US6713499B2

  公开（公告）日：2004-03-30
• [EN] 7-AMINO-BENZOTHIAZOLE DERIVATIVES AS ADENOSINE RECEPTOR LIGANDS<br/>[FR] DERIVES DE 7-AMINO-BENZOTHIAZOLE UTILISES COMME LIGANDS DE RECEPTEUR D'ADENOSINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2003053946A1

  公开（公告）日：2003-07-03

  The present invention relates to the compounds of the general formula (I). It has been found that the compounds of general formula (I) are adenosine receptor ligands. Secifically, the compounds of the present invention have a good affinity to the A2A-receptor and they are therefore useful in the treatment of diseases, related to this receptor.