2-(4-fluorophenyl)-6-methylimidazo[1,2-a]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-fluorophenyl)-6-methylimidazo[1,2-a]pyridine
• 化学式: C₁₄H₁₁FN₂
• mdl: MFCD01456299
• 分子量: 226.253
• InChiKey: WLMPCCSMVOBMIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-6-methylimidazo[1,2-a]pyridine 在 三溴化磷 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 1.75h， 生成 2-(2-(4-fluorophenyl)-6-methylimidazo[1,2-a]pyridin-3-yl)-N,N-dimethylethanamide
  参考文献：
  名称：

  利用微波辅助化学三步快速组装唑吡坦及其氟化类似物的研究

  摘要：

  我们开发了唑吡坦及其氟化类似物 1-3 的高效微波辅助三步合成。该程序依赖于易于获得且价格低廉的起始材料的利用。与传统加热系统相比，我们的协议在产品的产量和纯度方面表现出卓越的性能。值得注意的是，与油浴加热系统相比，完成反应所需的总时间要短得多。最后，我们对唑吡坦酒石酸盐 I 的制备进行了详细研究，并使用偏光显微镜评估了其粒径。我们的目标是选择合适的方法来产生可接受的粒度，因为固体大小直接影响生物流体中的溶解度和进一步的生物利用度。

  DOI：

  10.3390/molecules25143161
• 作为产物：
  描述：

  2-氨基-5-甲基吡啶 、 2-氯代-4'-氟苯乙酮 以 乙醇 为溶剂， 生成 2-(4-fluorophenyl)-6-methylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Discovery of new leads against Mycobacterium tuberculosis using scaffold hopping and shape based similarity

  摘要：

  BM212 [1,5-diaryl-2-methyl-3-(4-methylpiperazin-1-yl)-methyl-pyrrole] is a pyrrole derivative with strong inhibitory activity against drug resistant Mycobacterium tuberculosis and mycobacteria residing in macrophages. However, it was not pursued because of its poor pharmacokinetics and toxicity profile. Our goal was to design and synthesize new antimycobacterial BM212 analogs with lower toxicity and better pharmacokinetic profile. Using the scaffold hopping approach, three structurally diverse heterocycles - 2,3-disubstituted imidazopyridines, 2,3-disubstituted benzimidazoles and 1,2,4-trisubstituted imidazoles emerged as promising antitubercular agents. All compounds were synthesized through easy and convenient methods and their structures confirmed by IR, H-1 NMR, C-11 NMR and MS. In-vitro cytotoxicity studies on normal kidney monkey cell lines and HepG2 cell lines, as well as metabolic stability studies on rat liver microsomes for some of the most active compounds, established that these compounds have negligible cytotoxicity and are metabolically stable. Interestingly the benzimidazole compound (4a) is as potent as the parent molecule BM212 (MIC 2.3 mu g/ml vs 0.7-1.5 mu g/ml), but is devoid of the toxicity against HepG2 cell lines (IC50 203.10 mu M vs 7.8 mu M). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.034

文献信息

• [EN] IMIDAZOPYRIDINE COMPOUNDS<br/>[FR] COMPOSÉS IMIDAZOPYRIDINES
  申请人：PROXIMAGEN LTD

  公开号：WO2010064020A1

  公开（公告）日：2010-06-10

  The invention relates to compounds of formula (I): and their pharmaceutically acceptable salts and solvates, which are inhibitors of SSAO activity. The invention further relates to pharmaceutical compositions comprising these compounds and to the use of these compounds for the treatment or prevention of medical conditions wherein inhibition of SSAO activity is beneficial, such as inflammatory diseases and immune disorders.

  这项发明涉及式(I)的化合物及其药学上可接受的盐和溶剂化合物，这些化合物是SSAO活性的抑制剂。该发明还涉及包含这些化合物的药物组合物，以及利用这些化合物治疗或预防抑制SSAO活性有益的医疗状况，如炎症性疾病和免疫紊乱。
• A selenium-coordinated palladium(<scp>ii</scp>) <i>trans</i>-dichloride molecular rotor as a catalyst for site-selective annulation of 2-arylimidazo[1,2-<i>a</i>]pyridines
  作者：Neha Meena、Shobha Sharma、Ramprasad Bhatt、Vikki N. Shinde、Anurag Prakash Sunda、Nattamai Bhuvanesh、Anil Kumar、Hemant Joshi

  DOI：10.1039/d0cc03599h

  日期：——

  ΔG‡298K/ΔG‡350K values of 15.5 and 17.2 kcal mol−1 for a roughly 4.5 Å-long rotor. The molecular rotor showed excellent catalytic activity with reverse regioselectivity for annulation of 2-arylimidazo[1,2-a]pyridines (yields: ∼53–78%) with only 1.5 mol% catalyst loading.

  该报告描述了一种新型的由次级相互作用（SeCH⋯Cl）控制的分子转子的合成，该分子转子具有连接在Se–Pd–Se轴上的Cl–Pd–Cl转子辐条。对于大约4.5埃长的转子，在各种温度下获得的NMR数据确定ΔG ‡ 298K / ΔG ‡ 350K的值分别为15.5和17.2 kcal mol -1。分子转子对2-芳基咪唑并[1,2- a ]吡啶的环化反应具有优异的催化活性和反向区域选择性（产率：约53–78％），催化剂负载量仅为1.5 mol％。
• A simple and efficient route to 2‐arylimidazo[1,2‐a]pyridines and zolimidine using automated grindstone chemistry
  作者：Dharmendra Das、Zigmee T. Bhutia、Padmini C. Panjikar、Amrita Chatterjee、Mainak Banerjee

  DOI：10.1002/jhet.4106

  日期：2020.11

  A green and efficient mechanochemical method for the synthesis of a series of 2‐arylimidazo[1,2‐a]pyridines was developed using an electrical grinder. I2 catalyzed mechanochemical grinding facilitates the cyclocondensation reaction between various aryl methyl ketones and 2‐aminopyridines to afford 2‐arylimidazo[1,2‐a]pyridines in good yields at ambient temperature. The method was successfully used

  使用电动研磨机开发了一种绿色高效的机械化学方法，用于合成一系列2-芳基咪唑并[1,2-a]吡啶。I 2催化的机械化学研磨促进了各种芳基甲基酮与2-氨基吡啶之间的环缩合反应，从而在室温下以高收率得到2-芳基咪唑并[1,2-a]吡啶。该方法已成功用于市售药物zolimidine的克级合成。这种环境可持续协议的显着优势包括条件温和，仪器简单，催化剂便宜，原子经济，反应时间短等。
• A visible-light-promoted cross-dehydrogenative-coupling reaction of N -arylglycine esters with imidazo[1,2- a ]pyridines
  作者：Zhi-Qiang Zhu、Li-Jin Xiao、Chun-Cheng Zhou、Han-Lin Song、Zong-Bo Xie、Zhang-Gao Le

  DOI：10.1016/j.tetlet.2018.07.047

  日期：2018.8

  cross-dehydrogenative-coupling reaction between N-arylglycine esters and imidazo[1,2-a]pyridines for the construction of CC bond was developed. A range of N-arylglycine esters and imidazo[1,2-a]pyridines were able to undergo the CDC reaction readily to afford α-heteroaryl substituted α-amino acid derivatives in good to excellent yields. A tentative mechanism for the photoredox reaction was also proposed. Importantly

  N-芳基甘氨酸酯与咪唑并[1,2- a ]吡啶之间温和方便的可见光促进的交叉脱氢偶联反应被用于构建C C键。一系列的N-芳基甘氨酸酯和咪唑并[1,2- a ]吡啶能够很容易地进行CDC反应，从而以良好或优异的收率得到α-杂芳基取代的α-氨基酸衍生物。还提出了光氧化还原反应的初步机制。重要的是，在这种可见光促进的转化中使用铜（II）盐作为唯一催化剂使该反应可持续且实用。
• Direct thiocarbamation of imidazoheterocycles <i>via</i> dual C–H sulfurization
  作者：Jian-Chao Deng、Jun-Rong Zhang、Ming-Hua Li、Jie-Cheng Huang、Zhi-Sheng Lai、Xin-Yu Tong、Zi-Ning Cui、Ri-Yuan Tang

  DOI：10.1039/c9ob01403a

  日期：——

  Direct thiocarbamation via dual C–H sulfurization.

  直接通过双重C-H硫化的硫酰化。