N-benzyl-2-phenylimidazo[1,2-a]pyrazin-3-amine | 209907-33-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-benzyl-2-phenylimidazo[1,2-a]pyrazin-3-amine
• CAS: 209907-33-5
• 化学式: C₁₉H₁₆N₄
• 分子量: 300.363
• InChiKey: PPNMXFUYWPPOTA-UHFFFAOYSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 N-benzyl-2-phenylimidazo[1,2-a]pyrazin-3-amine 在 PS-Trisamine scavenger reagent 、 polimer supported morpholine resin 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  新的三组分缩合反应并行合成3-氨基咪唑并[1,2-a]吡啶和吡嗪

  摘要：

  三氟甲磺酸scan催化2-氨基吡啶，醛和异腈之间的三组分缩合反应，得到3-氨基咪唑并[1,2-a]吡啶的衍生物。氨基吡嗪反应类似。通过在离子交换树脂上平行合成和纯化以高收率制备的杂环库在氨基上进行进一步反应。

  DOI：

  10.1016/s0040-4039(98)00653-4
• 作为产物：
  描述：

  氨基吡嗪 、 苄异腈 、 苯甲醛 以 neat (no solvent) 为溶剂， 反应 3.0h， 以90%的产率得到N-benzyl-2-phenylimidazo[1,2-a]pyrazin-3-amine
  参考文献：
  名称：

  Visible-light-activated C–C and C–N bond formation in the synthesis of imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles under catalyst and solvent-free conditions

  摘要：

  通过Groebke-Blackburn-Bienaymé反应，在无催化剂和溶剂的条件下，利用普遍可获得的能源合成3-氨基咪唑融合杂环化合物。

  DOI：

  10.1039/c8nj03339k

文献信息

• Quinazolone derivatives as alpha 1A/B adrenergic receptor antagonists
  申请人：——

  公开号：US20030069230A1

  公开（公告）日：2003-04-10

  This invention relates to compounds which are generally alpha-1A/B adrenoceptor antagonists and which are represented by Formula I: 1 wherein Z is —C(O)— or —S(O) 2 —, X is carbon or nitrogen, Y is carbon, and X-Y considered together are two adjoining atoms of the ring A, said ring being a fused aromatic ring of five to six atoms per ring optionally incorporating one to two heteroatoms per ring, chosen from N, O, or S; and the other substituents are as defined in the specification; or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, methods for their use as therapeutic agents, and methods of preparation thereof.

  这项发明涉及一般为α-1A/B肾上腺素受体拮抗剂的化合物，其由式I表示： 1 其中Z为—C(O)—或—S(O) 2 —，X为碳或氮，Y为碳，X-Y一起被视为环A的两个相邻原子，所述环是一个由每个环中的一个到两个异原子（选自N、O或S）的五到六个原子的融合芳香环；其他取代基如规范中所定义；或其单体异构体、消旋或非消旋异构体混合物，或其药学上可接受的盐或溶剂化合物。该发明还涉及含有这种化合物的药物组合物，以及它们作为治疗剂的使用方法和制备方法。
• Visible-light-activated C–C and C–N bond formation in the synthesis of imidazo[1,2-<i>a</i>]pyridines and imidazo[2,1-<i>b</i>]thiazoles under catalyst and solvent-free conditions
  作者：Km Neha Shivhare、Manish K. Jaiswal、Anushree Srivastava、Saurabh K. Tiwari、I. R. Siddiqui

  DOI：10.1039/c8nj03339k

  日期：——

  Synthesis of 3-aminoimidazo-fused heterocycles via the Groebke–Blackburn–Bienaymé reaction using a universally available energy source under catalyst and solvent-free conditions.

  通过Groebke-Blackburn-Bienaymé反应，在无催化剂和溶剂的条件下，利用普遍可获得的能源合成3-氨基咪唑融合杂环化合物。
• Structure–Activity Relationships in Human Toll-like Receptor 8-Active 2,3-Diamino-furo[2,3-<i>c</i>]pyridines
  作者：Deepak B. Salunke、Euna Yoo、Nikunj M. Shukla、Rajalakshmi Balakrishna、Subbalakshmi S. Malladi、Katelyn J. Serafin、Victor W. Day、Xinkun Wang、Sunil A. David

  DOI：10.1021/jm301066h

  日期：2012.9.27

  hypothesized that the imidazo[1,2-a]pyrazines, readily accessible via the Groebke–Blackburn–Bienaymé multicomponent reaction, would possess sufficient structural similarity with TLR7/8-agonistic imidazoquinolines. With pyridoxal as the aldehyde component, furo[2,3-c]pyridines, rather than the expected imidazo[1,2-a]pyridines, were obtained, which were characterized by NMR spectroscopy and crystallography. Several

  在我们不断寻找新的和合成上更简单的候选疫苗佐剂的过程中，我们假设咪唑并[1,2- a ]吡嗪可通过 Groebke-Blackburn-Bienaymé 多组分反应轻松获得，与 TLR7/8- 具有足够的结构相似性。激动剂咪唑并喹啉。以吡哆醛为醛组分，得到呋喃[2,3- c ]吡啶，而不是预期的咪唑并[1,2- a ]吡啶，通过NMR光谱和晶体学对其进行表征。发现几种类似物可激活 TLR8 依赖性 NF-κB 信号传导。在一个聚焦的呋喃 [2,3- c ] 吡啶库中，观察到不同的 C2 取代基具有明显的 SAR。在人类 PBMC 中，没有 furo[2,3-c ]吡啶显示任何促炎细胞因子诱导但上调几个趋化因子配体基因。在兔子的免疫研究中，活性最强的化合物显示出显着的辅助作用。完全缺乏促炎细胞因子诱导，加上新型呋喃 [2,3- c ] 吡啶的强佐剂活性，使这种迄今未知的化学型成为有吸引力的一类化合物，预计没有局部或全身反应原性。
• Microwave-accelerated three-component condensation reaction on clay: solvent-free synthesis of imidazo[1,2-a] annulated pyridines, pyrazines and pyrimidines
  作者：Rajender S. Varma、Dalip Kumar

  DOI：10.1016/s0040-4039(99)01585-3

  日期：1999.10

  A rapid one-pot synthesis of imidazo[1,2-a] annulated pyridines, pyrazines and pyrimidines is described that occurs in the presence of recyclable montmorillonite K 10 clay under solvent-free conditions using microwave irradiation.

  描述了咪唑并[1,2- a ]环化吡啶，吡嗪和嘧啶的快速一锅合成，该反应在可回收的蒙脱土K 10粘土存在下，无溶剂条件下使用微波辐射进行。
• 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.