6-氟-咪唑并[1,2-a]吡啶-3-甲醛 | 1019020-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 6-氟-咪唑并[1,2-a]吡啶-3-甲醛
• 英文名称: 6-fluoroimidazo[1,2-a]pyridine-3-carbaldehyde
• CAS: 1019020-06-4
• 化学式: C₈H₅FN₂O
• mdl: MFCD09994347
• 分子量: 164.139
• InChiKey: IDZDHTZYPZABPB-UHFFFAOYSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-氟-咪唑并[1,2-a]吡啶-3-甲醛 在 碘 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 20.0h， 生成 1-(4-chlorophenyl)-3-(5-(6-fluoroimidazo[1,2-a]pyridin-3-yl)-1,3,4-oxadiazol-2-yl)thiourea
  参考文献：
  名称：

  咪唑并吡啶衍生的恶二唑基硫脲衍生物作为潜在抗糖尿病药物的发现：合成、体外抗氧化剂筛选和计算机分子建模方法

  摘要：

  设计并合成了一系列新型咪唑并吡啶基恶二唑衍生物( 5a-l )。它们的结构通过光谱数据得到确认，然后进行体外评估，包括α-葡萄糖苷酶、α-淀粉酶抑制、2-二苯基-1-三硝基苯肼（DDPH）和2,2'-偶氮双（3-乙基苯并噻唑啉-6-磺酸）（ABTS）自由基清除活性。抑制活性结果表明，与标准阿卡波糖的IC 50 值相比，所有合成的类似物均表现出显着的α-葡萄糖苷酶和α-淀粉酶抑制作用，IC 50 值分别为0.90 ± 0.10至18.10 ± 0.20 μM（对于α-葡萄糖苷酶）和1.10 ± 0.10至19.70 ± 0.20 μM（对于α-淀粉酶） 11.50 ± 0.30μM（α-葡萄糖苷酶）和 12.20 ± 0.30 μM（对于 α-淀粉酶）。合成的类似物还表现出显着的 DPPH 和 ABTS 自由基清除活性，IC 50值范围为 1.05 ± 0.05 至 4.56 ± 3.12 μM

  DOI：

  10.1016/j.molstruc.2023.136185
• 作为产物：
  描述：

  2-溴丙二醛 、 2-氨基-5-氟吡啶 以 乙醇 为溶剂， 反应 18.0h， 生成 6-氟-咪唑并[1,2-a]吡啶-3-甲醛
  参考文献：
  名称：

  Synthesis and biological evaluation of sulfonylhydrazone-substituted imidazo[1,2-a]pyridines as novel PI3 kinase p110α inhibitors

  摘要：

  We have previously reported the imidazo[1,2-a]pyridine derivative 4 as a novel p110 alpha inhibitor; however, although 4 is a potent inhibitor of p110 alpha enzymatic activity and tumor cell proliferation in vitro, it is unstable in solution and ineffective in vivo. To increase stability the pyrazole of 4 was replaced with a hydrazone and a moderately potent p110 alpha inhibitor 7a was obtained. Subsequent optimization of 7a afforded exceptionally potent p110 alpha inhibitors, including 8c and 8h, with IC(50) values of 0.30 nM and 0.26 nM, respectively; to the best of our knowledge, these compounds are the most potent PI3K p110 alpha inhibitors reported to date. Compound 8c was also stable in solution and exhibited significant anti-tumor effectiveness in vivo. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.070

文献信息

• New adenosine receptor ligands and uses thereof
  申请人：Domain Therapeutics

  公开号：EP2210891A1

  公开（公告）日：2010-07-28

  The present invention provides new compounds with high affinity for adenosine A2A receptors. It also provides antagonists of adenosine A2A receptors and their use as medicaments for the treatment and/or prophylaxis of diseases and disorders where the partial or total inactivation of adenosine A2A receptors signalling pathways could be beneficial such as Alzheimer's disease, Parkinson's disease, attention deficit and hyperactivity disorders (ADHD), Huntington's disease, neuroprotection, schizophrenia, anxiety and pain. The present invention further relates to pharmaceutical compositions containing such new compounds with high affinity for adenosine A2A receptors and their use for the treatment and/or prophylaxis of diseases and disorders where the partial or total inactivation of adenosine A2A receptors could be beneficial.

  本发明提供了对腺苷A2A受体具有高亲和力的新化合物。它还提供了腺苷A2A受体的拮抗剂，以及它们作为药物用于治疗和/或预防部分或完全失活腺苷A2A受体信号通路可能有益的疾病和疾病，如阿尔茨海默病、帕金森病、注意力缺陷和多动症（ADHD）、亨廷顿病、神经保护、精神分裂症、焦虑和疼痛。本发明还涉及含有对腺苷A2A受体具有高亲和力的新化合物的药物组合物，以及它们用于治疗和/或预防部分或完全失活腺苷A2A受体可能有益的疾病和疾病。
• Imidazopyridine-Based Thiazole Derivatives as Potential Antidiabetic Agents: Synthesis, In Vitro Bioactivity, and In Silico Molecular Modeling Approach
  作者：Rafaqat Hussain、Wajid Rehman、Shoaib Khan、Aneela Maalik、Mohamed Hefnawy、Ashwag S. Alanazi、Yousaf Khan、Liaqat Rasheed

  DOI：10.3390/ph16091288

  日期：——

  A new series of thiazole derivatives (4a-p) incorporating imidazopyridine moiety was synthesized and assessed for their in vitro potential α-glucosidase potency using acarbose as a reference drug. The obtained results suggested that compounds 4a (docking score = −13.45), 4g (docking score = −12.87), 4o (docking score = −12.15), and 4p (docking score = −11.25) remarkably showed superior activity against

  合成了一系列新的包含咪唑并吡啶部分的噻唑衍生物 (4a-p)，并使用阿卡波糖作为参考药物评估了其体外潜在的 α-葡萄糖苷酶效力。获得的结果表明，化合物4a（对接分数= -13.45）、4g（对接分数= -12.87）、4o（对接分数= -12.15）和4p（对接分数= -11.25）针对目标α显着表现出优异的活性-葡萄糖苷酶，IC50值分别为5.57±3.45、8.85±2.18、7.16±1.40和10.48±2.20。通过进一步研究最活跃的支架与α-葡萄糖苷酶活性位点相互作用的结合模式，完成对接分析以探索α-葡萄糖苷酶的活性空腔。结果的解释清楚地表明，支架 4a 和 4o 成为最有效的 α-葡萄糖苷酶抑制剂，有望与 α-葡萄糖苷酶的活性位点具有优异的结合相互作用。此外，利用各种光谱方法，如1H-NMR、13C-NMR和HREI-MS，确定了合成支架的精确结构。
• NEW ADENOSINE RECEPTOR LIGANDS AND USES THEREOF
  申请人：Domain Therapeutics

  公开号：EP2391625A1

  公开（公告）日：2011-12-07
• [EN] NEW ADENOSINE RECEPTOR LIGANDS AND USES THEREOF<br/>[FR] NOUVEAUX LIGANDS DES RÉCEPTEURS D'ADÉNOSINE ET LEURS APPLICATIONS
  申请人：DOMAIN THERAPEUTICS

  公开号：WO2010084425A1

  公开（公告）日：2010-07-29

  The present invention provides new compounds with high affinity for adenosine A2A receptors. It also provides antagonists of adenosine A2A receptors and their use as medicaments for the treatment and/or prophylaxis of diseases and disorders where the partial or total inactivation of adenosine A2A receptors signalling pathways could be beneficial such as Alzheimer's disease, Parkinson's disease, attention deficit and hyperactivity disorders (ADHD), Huntington's disease, neuroprotection, schizophrenia, anxiety and pain. The present invention further relates to pharmaceutical compositions containing such new compounds with high affinity for adenosine A2A receptors and their use for the treatment and/or prophylaxis of diseases and disorders where the partial or total inactivation of adenosine A2A receptors could be beneficial.
• Correlation between in vitro anti-urease activity and in silico molecular modeling approach of novel imidazopyridine–oxadiazole hybrids derivatives
  作者：Shoaib Khan、Rafaqat Hussain、Yousaf Khan、Tayyiaba Iqbal、Tariq Aziz、Metab Alharbi

  DOI：10.1515/chem-2023-0210

  日期：2024.3.27

  In the current era, a potent drug is still needed on the market for the treatment of various diseases worldwide. Researchers mainly focus on those enzymes that cause these diseases. One of the major diseases is caused by an enzyme called urease, which increases the concentration of ammonia in the body upon hydrolysis. Researchers across the globe have keen interest to synthesize the potent inhibitor for this conversion. From this perspective, hybrid analogs of imidazopyridine and oxadiazole (1–20) were designed and efficiently synthesized followed by characterizing them through varied spectroscopic methods (1HNMR, 13CNMR, and HREI-MS). In addition, in vitro analyses of the synthesized compounds were conducted to evaluate their anti-urease potency. There was significant potential in most compounds analyzed, but analogs 15, 16, and 17 (IC50 = 2.20 ± 0.10 μM, IC50 = 2.50 ± 0.10 μM, and IC50 = 2.30 ± 2.10 μM, respectively) performed exceptionally well in comparison with thiourea (IC50 = 22.30 ± 0.44 μM). The selected candidates were further investigated under a molecular docking study to confirm protein ligand interactions. In addition, energy gap (E gap) of the HOMO–LUMO was explored via density functional theory studies.