2-(3,4-difluorophenyl)imidazo[1,2-a]pyridine | 849628-12-2

• 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-(3,4-difluorophenyl)imidazo[1,2-a]pyridine
• CAS: 849628-12-2
• 化学式: C₁₃H₈F₂N₂
• mdl: MFCD24862174
• 分子量: 230.217
• InChiKey: IOYYEZFNNIRFPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-difluorophenyl)imidazo[1,2-a]pyridine 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以55%的产率得到2-(3,4-difluorophenyl)-3-iodoimidazo[1,2-a]pyridine
  参考文献：
  名称：

  2,3-Diarylimidazo[1,2-a]pyridines as potential inhibitors of UV-induced keratinocytes apoptosis: synthesis, pharmacological properties and interactions with model membranes and oligonucleotides by NMR

  摘要：

  Four 2,3-diarylimidazo[1,2-alpha]pyridines (I, 1a-c) were synthesized as inhibitors of UV-induced apoptosis and showed quite different properties. First, only the pyridinyl derivative I showed protection in molt cells. From the supposed intracellular target, phospholipid membrane models were studied by H-1, H-2 and P-31 NMR spectroscopy. All these molecules can incorporate the membrane bilayer of small unilamellar vesicles of lecithin (SUV). However, I is clearly closed to the external polar head of the lipids, and is relatively mobile in the layer. Conversely, the other molecules are strongly immobilized in the deep part of the external layer. P-31 solid-state NMR spectra recorded on phospholipid dispersions (multilayers vesicles (MLV)) completely excluded any detergent effect or any modification of temperature transition. The only structural or dynamic effect observed was a homogeneous, but limited, reduction in the chemical shift anisotropy in the presence of 1, in agreement with its superficial location. H-2 NMR experiment performed on the same model using perdeuterated phospholipids showed no significant fluidity reduction at the level of terminal CD3 groups in the presence of la-c, according to their deep location. Finaly, their interactions with synthetic oligonucleotide, d(CGATCG)(2) was studied showing non specific interactions of la on the external GC pair, while no interaction was observed with the other derivatives. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2004.10.009
• 作为产物：
  描述：

  3',4'-二氟苯乙酮 在 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.27h， 生成 2-(3,4-difluorophenyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  咪唑并[1,2-a]吡啶衍生物的微波辅助合成和发光活性

  摘要：

  在这项工作中，合成了一系列苯甲酰溴衍生物，并用作合成取代的咪唑并[1,2- a ]吡啶的关键中间体。首先，在微波辐射的辅助下，通过苯乙酮的溴化反应获得苯甲酰溴分子，在15分钟的反应中获得产物4a-v，产率在50％至99％之间。随后，这些分子与2-氨基吡啶共轭，产生了咪唑并[1,2- a ]吡啶衍生物（7a-v）在60秒的反应中产率为24％至99％。相对于通过更繁琐的方法（如热辅助和机械辅助路线）获得的产量，确定了更高的产量。根据取代基的性质，在紫外线激发下观察到电磁光谱的紫色和蓝色区域中的强烈发光发射。这种对环境友好的方法有望构成一类重要的有机化合物，用于开发生物标志物，光化学传感器和医学应用。

  DOI：

  10.1002/jhet.3950

文献信息

• Transition-metal-free, visible-light-mediated regioselective C–H trifluoromethylation of imidazo[1,2-a]pyridines
  作者：Qiguang Zhou、Song Xu、Ronghua Zhang

  DOI：10.1016/j.tetlet.2019.02.003

  日期：2019.3

  trifluoromethylation of imidazo[1,2-a]pyridines has been developed at mild conditions by employing cheap and commercially available anthraquinone-2-carboxylic acid (AQN-2-CO2H) as the photo-organocatalyst, and Langlois reagent as the trifluoromethylating reagent. A series of 3-(trifluoromethyl)imidazo[1,2-a]pyridine derivatives with broad functionalities could be conveniently and efficiently obtained by direct regioselective

  咪唑并[1,2- a ]吡啶的无过渡金属，可见光诱导的三氟甲基化反应已在温和条件下通过使用廉价且可商购的蒽醌-2-羧酸（AQN-2-CO 2 H）来开发作为光有机催化剂，和Langlois试剂作为三氟甲基化试剂。通过直接区域选择性官能化可以方便而有效地获得一系列具有广泛功能的3-（三氟甲基）咪唑并[1,2- a ]吡啶衍生物。
• Synthesis and Structure−Activity Relationships of Imidazopyridine/Pyrimidine‐ and Furopyridine‐Based Anti‐infective Agents against Trypanosomiases
  作者：Daniel G. Silva、Anna Junker、Shaiani M. G. Melo、Fernando Fumagalli、J. Robert Gillespie、Nora Molasky、Frederick S. Buckner、An Matheeussen、Guy Caljon、Louis Maes、Flavio S. Emery

  DOI：10.1002/cmdc.202000616

  日期：2021.3.18

  could be defined as active against Trypanosoma cruzi and T. brucei brucei, respectively (antitrypanosomal activities <10 μM). The present work discusses the structure−activity relationships of new fused‐ring scaffolds based on imidazopyridine/pyrimidine and furopyridine cores. This library of compounds shows significant potential for anti‐trypanosomiases drug discovery.

  被忽视的热带病仍然是非洲和南美洲最严重的公共卫生问题之一。对这些疾病的药物治疗是有限的，这总是导致死亡病例。因此，迫切需要新的抗锥虫药物。为了解决这个问题，制备了大量不同的杂环化合物。简单的合成方法可以容忍预功能化的结构，从而产生一组结构多样的类似物。我们报告了一组 57 种对动质体寄生虫具有选择性活性潜力的杂环化合物。一般而言，总组中的 29 和 19 种化合物可被定义为对克氏锥虫和布氏锥虫具有活性，分别（抗锥虫活性<10 μM）。目前的工作讨论了基于咪唑并吡啶/嘧啶和呋喃吡啶核心的新型稠环支架的构效关系。该化合物库显示出抗锥虫病药物发现的巨大潜力。
• Design, Synthesis and Biological Evaluation of Imidazo[1,2-a]pyridine Derivatives as Novel DPP-4 Inhibitors
  作者：Qing Li、Muxing Zhou、Li Han、Qing Cao、Xinning Wang、LeiLei Zhao、Jinpei Zhou、Huibin Zhang

  DOI：10.1111/cbdd.12560

  日期：2015.10

  A new series of DPP‐4 inhibitors with imidazo[1,2‐a]pyridine scaffold were designed by exploiting scaffold hopping strategy and docking study. Based on docking binding model, structural modifications of 2‐benzene ring and pyridine moieties of compound 5a led to the identification of compound 5d with 2, 4‐dichlorophenyl group at the 2‐position as a potent (IC50 = 0.13 μm), selective (DPP‐8/DPP‐4 = 215 and DPP‐9/DPP‐4 = 192) and in vivo efficacious DPP‐4 inhibitor. Further, molecular docking revealed that compound 5d could retain key binding features of DPP‐4 with the pyridine moiety of imidazo[1,2‐a]pyridine ring providing an additional π−π interaction with Phe357 of DPP‐4. Compound 5d might be a promising lead for further development of novel DPP‐4 inhibitor treating T2DM.
• [EN] TAU-PROTEIN TARGETING COMPOUNDS AND ASSOCIATED METHODS OF USE<br/>[FR] COMPOSÉS CIBLANT LA PROTÉINE TAU ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：ARVINAS OPERATIONS INC

  公开号：WO2021011913A1

  公开（公告）日：2021-01-21

  The present disclosure relates to bifunctional compounds, which find utility as modulators of tan protein. In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a VHL or cereblon ligand which binds to the E3 ubiquitin ligase and on the other end a moiety which binds tan protein, such that tan protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of tan. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of tan protein. Diseases or disorders that result from aggregation or accumulation of tan protein are treated or prevented with compounds and compositions of the present disclosure.