N-benzyl-2-naphthalen-1-ylimidazo[1,2-a]pyrazin-3-amine | 1401520-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-benzyl-2-naphthalen-1-ylimidazo[1,2-a]pyrazin-3-amine
• CAS: 1401520-27-1
• 化学式: C₂₃H₁₈N₄
• 分子量: 350.423
• InChiKey: QSWGNRILCYNYAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氨基吡嗪 、 苄异腈 、 1-萘甲醛 在 盐酸 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 0.33h， 以14%的产率得到N-benzyl-2-naphthalen-1-ylimidazo[1,2-a]pyrazin-3-amine
  参考文献：
  名称：

  Antibacterial activities of Groebke–Blackburn–Bienaymé-derived imidazo[1,2-a]pyridin-3-amines

  摘要：

  We sought to explore the imidazo[1,2-a]pyridin-3-amines for TLR7 (or 8)-modulatory activities. This chemotype, readily accessed via the Groebke-Blackburn-Bienayme multi-component reaction, resulted in compounds that were TLR7/8-inactive, but exhibited bacteriostatic activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). To investigate the mechanism of antibacterial activity of this new chemotype, a resistant strain of S. aureus was generated by serially passaging the organism in escalating doses of the most active analogue. A comparison of minimum inhibitory concentrations (MICs) of known bacteriostatic agents in wild-type and resistant strains indicates a novel mechanism of action. Structure-activity relationship studies have led to the identification of positions on the scaffold for additional structural modifications that should allow for the introduction of probes designed to examine cognate binding partners and molecular targets, while not significantly compromising antibacterial potency. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.052

文献信息

• Antibacterial activities of Groebke–Blackburn–Bienaymé-derived imidazo[1,2-a]pyridin-3-amines
  作者：Nikunj M. Shukla、Deepak B. Salunke、Euna Yoo、Cole A. Mutz、Rajalakshmi Balakrishna、Sunil A. David

  DOI：10.1016/j.bmc.2012.07.052

  日期：2012.10

  We sought to explore the imidazo[1,2-a]pyridin-3-amines for TLR7 (or 8)-modulatory activities. This chemotype, readily accessed via the Groebke-Blackburn-Bienayme multi-component reaction, resulted in compounds that were TLR7/8-inactive, but exhibited bacteriostatic activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). To investigate the mechanism of antibacterial activity of this new chemotype, a resistant strain of S. aureus was generated by serially passaging the organism in escalating doses of the most active analogue. A comparison of minimum inhibitory concentrations (MICs) of known bacteriostatic agents in wild-type and resistant strains indicates a novel mechanism of action. Structure-activity relationship studies have led to the identification of positions on the scaffold for additional structural modifications that should allow for the introduction of probes designed to examine cognate binding partners and molecular targets, while not significantly compromising antibacterial potency. (C) 2012 Elsevier Ltd. All rights reserved.