3-(2-Methylimidazol-1-yl-acetyl)-benzonitrile | 431040-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-Methylimidazol-1-yl-acetyl)-benzonitrile
• 英文别名: 3-(2-(2-Methyl-1H-imidazol-1-YL)acetyl)benzonitrile；3-[2-(2-methylimidazol-1-yl)acetyl]benzonitrile
• CAS: 431040-28-7
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: JDWWEBGWIHBPOD-UHFFFAOYSA-N

物化性质

• 沸点：
  465.2±30.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-Methylimidazol-1-yl-acetyl)-benzonitrile 、 吡嗪-2-基-硫代脲 在 吡啶 、 碘 作用下， 生成 3-[5-(2-methylimidazol-1-yl)-2-(pyrazin-2-ylamino)thiazol-4-yl]benzonitrile
  参考文献：
  名称：

  A new orally bioavailable dual adenosine A2B/A3 receptor antagonist with therapeutic potential

  摘要：

  The synthesis and SAR of 5 -heterocycle- substituted aminothiazole adenosine receptor antagonists is described. Several compounds show high affinity and selectivity for the A(2B) and A(3) receptors. One compound (5f) shows good ADME properties in the rat and as such may be an important new compound in testing the current hypotheses proposing a therapeutic role for a dual A(2B)/A(3) antagonist in allergic diseases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.021
• 作为产物：
  描述：

  3-乙酰苯腈 在 溴 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 1.5h， 生成 3-(2-Methylimidazol-1-yl-acetyl)-benzonitrile
  参考文献：
  名称：

  A new orally bioavailable dual adenosine A2B/A3 receptor antagonist with therapeutic potential

  摘要：

  The synthesis and SAR of 5 -heterocycle- substituted aminothiazole adenosine receptor antagonists is described. Several compounds show high affinity and selectivity for the A(2B) and A(3) receptors. One compound (5f) shows good ADME properties in the rat and as such may be an important new compound in testing the current hypotheses proposing a therapeutic role for a dual A(2B)/A(3) antagonist in allergic diseases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.021

文献信息

• Aminothaizoles and their use as adenosine receptor antagonists
  申请人：——

  公开号：US20040053982A1

  公开（公告）日：2004-03-18

  Compounds of formula (I) in free or salt form, where A is a C 6 -C 15 monovalent aromatic group. R 1 is hydrogen, phenyl optionally substituted by one or more substituents selected from halogen, cyano, hydroxy, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl or acyloxy, or a 5- or 6-membered monovalent heterocyclic group, R 2 is hydrogen, C 1 -C 8 -alkyl, acyl or CON(R 3 )R 4 , provided that R 2 is C 1 -C 8 -alkyl, acyl or CON(R 3 )R 4 when R 1 is hydrogen, R 3 and R 4 are each independently hydrogen, or C 1 -C 8 -alkyl, together with the nitrogen atom to which they are attached denote a 5- or 6-membered heterocyclic group, and Z l , Z 2 , Z 3 and Z 4 are each independently N or CR 5 , at least one of them being CR 5 , and R 5 is hydrogen, C 1 -C 8 -alkyl or C 1 -C 8 -alkoxy. The compounds are useful as adenosine receptor antagonists, particularly in the treatment of inflammatory or obstrucive airways diseases. 1

  公式（I）的化合物，以自由形式或盐形式存在，其中A是C6-C15单价芳香基团。R1是氢，苯基可选地由卤素，氰基，羟基，C1-C8烷基，C1-C8卤代烷基，C1-C8烷氧基，C1-C8烷氧基-C1-C8烷基或酰氧基中的一个或多个取代基取代，或是5-或6-成员单价杂环基团，R2是氢，C1-C8烷基，酰基或CON（R3）R4，前提是当R1是氢时，R2是C1-C8烷基，酰基或CON（R3）R4，R3和R4分别独立地是氢或C1-C8烷基，与它们连接的氮原子一起表示5-或6-成员杂环基团，Z1，Z2，Z3和Z4是独立的N或CR5，其中至少一个是CR5，R5是氢，C1-C8烷基或C1-C8烷氧基。这些化合物在腺苷受体拮抗剂中有用，特别是在治疗炎症或阻塞性呼吸道疾病中。
• AMINOTHIAZOLES AND THEIR USE AS ADENOSINE RECEPTOR ANTAGONISTS
  申请人：Novartis AG

  公开号：EP1339711A1

  公开（公告）日：2003-09-03
• US7109202B2
  申请人：——

  公开号：US7109202B2

  公开（公告）日：2006-09-19
• [EN] AMINOTHIAZOLES AND THEIR USE AS ADENOSINE RECEPTOR ANTAGONISTS<br/>[FR] AMINOTHIAZOLES ET UTILISATION DE CEUX-CI COMME ANTAGONISTES DU RECEPTEUR DE L'ADENOSINE
  申请人：NOVARTIS AG

  公开号：WO2002042298A1

  公开（公告）日：2002-05-30

  Compounds of formula (I) in free or salt form, where A is a C6-C15 monovalent aromatic group. R1 is hydrogen, phenyl optionally substituted by one or more substituents selected from halogen, cyano, hydroxy, C¿1?-C8-alkyl, C1-C8-haloalkyl, C1-C8-alkoxy, C1-C8-alkoxy-C1-C8-alkyl or acyloxy, or a 5- or 6- membered monovalent heterocyclic group, R?2¿ is hydrogen, C¿1-?C8-alkyl, acyl or CON(R?3)R4¿, provided that R2 is C1-C8-alkyl, acyl or CON(R?3)R4 when R1¿ is hydrogen, R?3 and R4¿ are each independently hydrogen, or C¿1?-C8-alkyl, together with the nitrogen atom to which they are attached denote a 5- or 6- membered heterocyclic group, and Z?1, Z2, Z3 and Z4¿ are each independently N or CR5, at least one of them being CR?5, and R5¿ is hydrogen, C¿1?-C8-alkyl or C1-C8-alkoxy. The compounds are useful as adenosine receptor antagonists, particularly in the treatment of inflammatory or obstrucive airways diseases.
• WO2023/139132
  申请人：——

  公开号：——

  公开（公告）日：——