6-methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine | 842-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine
• CAS: 842-73-9
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: PCHSIVKWNPZZPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine 在 sodium sulfide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 Methyl-[4-(6-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amine
  参考文献：
  名称：

  Structure−Activity Relationship of Imidazo[1,2-a]pyridines as Ligands for Detecting β-Amyloid Plaques in the Brain

  摘要：

  A series of novel beta-amyloid (Abeta) aggregate-specific ligands, 2-(4'-dimethylaminophenyl)-6-iodoimidazo[1,2-alpha]pyridine, (IMPY), and its related derivatives were prepared. An in vitro binding study with preformed Abeta aggregates showed that 16(IMPY) and its bromo derivative competed with binding of 2-(4'-dimethylaminophenyl)-6-iodobenzothiazole, [I-125]7(TZDM), a known ligand for Abeta aggregates, with high binding affinities (K-i = 15 and 10 nM, respectively). In vitro autoradiography of brain sections of a transgenic mouse (Tg2576) with [I-125]16(IMPY) displayed high selective binding to amyloid-like structures, comparable to that observed by staining with thioflavin-S visualized under fluorescence. In vivo biodistribution after an intravenous injection of [I-125]16(IMPY) in normal mice showed a high initial brain uptake and fast washout, indicating a low background activity associated with this iodinated ligand. Taken together, the data suggests that [I-123]16(IMPY) may be useful for imaging Abeta aggregates in patients with Alzheimer's disease.

  DOI：

  10.1021/jm020351j
• 作为产物：
  描述：

  2-氨基-5-甲基吡啶 、 对硝基苯乙酮 在 copper(l) iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以91%的产率得到6-methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  铜催化氧化串联C-H的胺化/环化反应：向咪唑并[1,2-A]吡啶的直接访问†

  摘要：

  描述了一种简单方便的策略，该方法可通过廉价的铜催化串联亚胺形成和分子内好氧氧化C–H键胺化/环化反应合成咪唑并[1,2-a]吡啶。通过容易获得的苯乙酮和2-氨基吡啶的反应，可以制备出一系列咪唑并[1,2-a]吡啶，并具有良好至优异的收率（48-92％）。该方法的范围已通过以下步骤的一步合成验证唑来idine，一种用于消化性溃疡的药物，收率为61％。

  DOI：

  10.1039/c3ra43889a

文献信息

• 3-(acylaminomethyl)imidazo[1,2-a]pyridine derivatives and pharmaceutical
  申请人：Synthelabo

  公开号：US04767755A1

  公开（公告）日：1988-08-30

  A compound which is a 3-(acylaminomethyl)imidazo[1,2-a]pyridine derivative of formula (I) ##STR1## or a pharmacologically acceptable acid addition salt is useful in therapy.

  一种化合物，其为式(I)的3-(酰胺甲基)咪唑[1,2-a]吡啶衍生物，或其药理学上可接受的酸盐加合物，在治疗中是有用的。
• TEMPO-Mediated Cross-Dehydrogenative Coupling of Indoles and Imidazo[1,2-<i>a</i>]pyridines with Fluorinated Alcohols
  作者：Dhananjay S. Nipate、Sonam Jaspal、Vikki N. Shinde、Krishnan Rangan、Anil Kumar

  DOI：10.1021/acs.orglett.1c00031

  日期：2021.2.19

  A simple and highly efficient metal-free method has been developed for hydroxyfluoroalkylation of indoles and imidazo[1,2-a]pyridines via TEMPO-mediated C(sp3)–H and C(sp2)–H bond cross-dehydrogenative coupling of fluorinated alcohols and indoles. The protocol showed broad substrate scope, afforded good yields of hydroxyfluoroalkylated products, and was amenable for scale-up. Mechanistic investigation

  已经开发了一种简单高效的无金属方法，用于通过TEMPO介导的C（sp 3）–H和C（sp 2）–H键交叉脱氢偶联将吲哚和咪唑并[1,2- a ]吡啶进行羟基氟烷基化氟化醇和吲哚。该方案显示出广泛的底物范围，提供了良好的羟基氟烷基化产物收率，并且适合规模扩大。机理研究表明该自由基途径的参与。
• Metal-free synthesis of aminomethylated imidazoheterocycles: dual role of <i>tert</i>-butyl hydroperoxide as both an oxidant and a methylene source
  作者：Om P. S. Patel、Nitesh Kumar Nandwana、Ajay Kumar Sah、Anil Kumar

  DOI：10.1039/c8ob02432d

  日期：——

  A metal-free method is developed for the aminomethylation of imidazoheterocycles with 2/4-aminoheterocycles using TBHP as a carbon source as well as an oxidant.

  以 TBHP 为碳源和氧化剂，开发了一种咪唑杂环与 2/4- 氨基杂环进行氨基甲基化的无金属方法。
• Preparation of 2-aryl and 2-aryloxymethyl imidazo[1,2-<i>a</i>]pyridines and related compounds
  作者：Richard J. Sundberg、D. J. Dahlhausen、G. Manikumar、B. Mavunkel、Atanu Biswas、V. Srinivasan、Fred King、Philip Waid

  DOI：10.1002/jhet.5570250119

  日期：1988.1

  A series of substituted 2-aryl imidazo[1,2-a]pyridines has been prepared in which a variety of substituents are introduced on the 4′-position of the phenyl ring and on the 3, 5, 6 or 7 position of the heterocyclic ring. Most examples have acetamido, bromo, cyano, or formyl substituents at the 4′-position. Analogous imidazo-[2,1-b]fhiazoles and imidazo[1,2-a]pyrimidines have also been prepared. Another

  一系列取代的2-芳基咪唑并[1,2-α]吡啶已被制备，其中多种取代基被引入在苯环的4'位和在3，5的，6或7位杂环。大多数实例在4'-位具有乙酰氨基，溴，氰基或甲酰基取代基。还已经制备了类似的咪唑并[ 2，1- b ]噻唑和咪唑并[1,2- a ]嘧啶。制备了由咪唑的4'-甲酰基苯氧基甲基衍生物，吡啶，噻唑，苯并咪唑和环取代的咪唑并[1,2- a ]吡啶的三个位置异构体组成的另一系列化合物。还制备了咪唑和咪唑并[1,2- a ]吡啶的2-（4'-甲酰基苯基乙烯基）衍生物。
• A copper-catalyzed multi-component reaction accessing fused imidazo-heterocycles via C–H functionalization
  作者：G. Santosh Kumar、S. Pushpa Ragini、A. Sanjeeva Kumar、H. M. Meshram

  DOI：10.1039/c5ra09025c

  日期：——

  An efficient synthesis of fused imidazo-heterocycles is described using Cu(OTf)₂in [bmim]BF₄by the multi-component reaction of pyridin-2(1H)-one or thiazol/benzo[d]thiazol-2(3H)-ones withO-tosylhydroxyl amine and acetophenones under microwave irradiation.

  描述了一种高效合成融合咪唑-杂环化合物的方法，使用Cu(OTf)₂在[bmim]BF₄中，通过吡啶-2(1H)-酮或噻唑/苯并[d]噻唑-2(3H)-酮与O-对甲苯磺酰羟胺和乙酰苯酮在微波辐射下的多组分反应。