6-溴-2-(4-甲基苯基)咪唑并[1,2-a]吡啶 | 858516-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 6-溴-2-(4-甲基苯基)咪唑并[1,2-a]吡啶
• 中文别名: 6-溴-2-(4-甲基苯基)咪唑并[1,2-A]吡啶
• 英文名称: 6-bromo-2-(4-methylphenyl)imidazo[1,2-a]pyridine
• 英文别名: 6-bromo-2-(p-tolyl)imidazo[1,2-a]pyridine
• CAS: 858516-70-8
• 化学式: C₁₄H₁₁BrN₂
• mdl: MFCD00444782
• 分子量: 287.159
• InChiKey: OPMUYIDHWOOLTK-UHFFFAOYSA-N

物化性质

• 密度：
  1.43

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-溴-2-(4-甲基苯基)咪唑并[1,2-a]吡啶 在 copper(l) iodide 、 sodium azide 、 硫酸 、 盐酸羟胺 、 potassium carbonate 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 6-bromo-2-p-tolyl-imidazo[1,2-a]pyridine-3-carbaldehyde-O-[1-(4-methylbenzyl)-1H-1,2,3-triazol-4-yl]methyl oxime
  参考文献：
  名称：

  Facile synthesis of new imidazo[1,2-a]pyridines carrying 1,2,3-triazoles via click chemistry and their antiepileptic studies

  摘要：

  The present article reports the synthesis and anticonvulsant studies of new 2-arylimidazo[1,2-a]pyridines carrying suitably substituted 1,2,3-triazoles as well as their intermediates. The structures of newly synthesized compounds were confirmed by various spectroscopic techniques. The anticonvulsant study was carried out by MES and scPTZ screening methods, while their toxicity study was performed following Rotarod method. The active compounds showed enhanced seizure control in scPTZ method when compared with that of MES method. Compounds 3f, 4c, 4f, 5k, 5p and 5w carrying active pharmacophores exhibited complete protection against seizure and their results were comparable with standard drug diazepam. Majority of new compounds were found to be non-toxic, while few of them showed toxicity at 100 mg/kg. The c log P values of target compounds are in the range of 3.5-5.3, which confirm their lipophilic nature. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.086
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 、 2-溴-4'-甲基苯乙酮 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 6-溴-2-(4-甲基苯基)咪唑并[1,2-a]吡啶
  参考文献：
  名称：

  sp 3-和sp 2-杂化CH键的氧化交叉偶联：咪唑并[1,2- a ]吡啶的钒催化氨甲基化

  摘要：

  已经实现了取代的2-芳基咪唑并[1,2- a ]吡啶对N-甲基吗啉氧化物的钒催化氧化偶联，N-甲基吗啉既是偶联剂又是氧化剂。该反应用于各种取代的咪唑并[1,2- a ]吡啶和吲哚底物，产率高达90％。机理研究表明该反应可以通过曼尼希型过程进行。这项工作证明了如何将氧化氨基甲基化用作将叔胺引入杂环的有用方法，从而为常规曼尼希型反应提供了另一种方法。

  DOI：

  10.1021/acs.orglett.5b02539

文献信息

• Visible-light-induced regioselective sulfenylation of imidazopyridines with thiols under transition metal-free conditions
  作者：Rajjakfur Rahaman、Shivasish Das、Pranjit Barman

  DOI：10.1039/c7gc02906c

  日期：——

  A metal-free visible-light-promoted regioselective C-3 sulfenylation of imidazo[1,2-a]pyridines and indoles using thiols has been developed via C(sp2)–H functionalization. This method provides direct access to a wide range of structurally diverse 3-sulfenylimidazopyridines of biological interest. The operational simplicity, eco-energy source, high atom efficiency, and the use of green solvents under

  通过C（sp 2）–H官能团开发了一种无金属的可见光促进的咪唑并[1,2- a ]吡啶和吲哚类吲哚类化合物的C-3区域选择性C-3亚磺酰基。该方法提供了直接接触生物感兴趣的结构上广泛的3-亚磺酰基咪唑并吡啶的途径。操作简便，生态能源，高原子效率以及在环境条件下使用绿色溶剂是该方法的一些吸引人的特征。
• 一种C-3位硫代咪唑并[1,2-a]吡啶类化合物 的制备方法
  申请人：曲阜师范大学

  公开号：CN105218540B

  公开（公告）日：2017-07-04

  本发明公开一种C‑3位硫代咪唑并[1,2‑a]吡啶类化合物的制备方法，以通咪唑并[1,2‑a]吡啶类化合物和磺酰肼类化合物为原料，叔丁基过氧化氢为氧化剂，乙腈为溶剂，含碘化合物为催化剂，反应温度为60‑120℃的条件下，进行反应得到C‑3位硫代咪唑并[1,2‑a]吡啶类化合物，与传统的合成方法相比，具有反应条件温和、环境污染小、反应气味低、产率高、官能团兼容性好及分离纯化方便等优势。
• Imidazo[1,2-<i>a</i>]pyridine Derivatives as Aldehyde Dehydrogenase Inhibitors: Novel Chemotypes to Target Glioblastoma Stem Cells
  作者：Luca Quattrini、Edoardo Luigi Maria Gelardi、Vito Coviello、Stefania Sartini、Davide Maria Ferraris、Mattia Mori、Ichiro Nakano、Silvia Garavaglia、Concettina La Motta

  DOI：10.1021/acs.jmedchem.9b01910

  日期：2020.5.14

  resist to cytotoxic treatments. As the cytosolic enzyme aldehyde dehydrogenase 1A3 turns out to be overexpressed in these kinds of cells, playing a key role for their vitality, treatments targeting this enzyme may represent a successful strategy to fight GBM. In this work, we describe a novel class of imidazo[1,2-a]pyridine derivatives as aldehyde dehydrogenase 1A3 inhibitors, reporting the evidence of

  胶质母细胞瘤（GBM）是脑肿瘤中最致命的形式。众所周知，由于存在具有干细胞样特性的细胞亚群和抗细胞毒性治疗的能力，其能够摆脱迄今为止可用的治疗选择。事实证明，胞质酶醛脱氢酶1A3在此类细胞中过表达，对其活力起着关键作用，针对这种酶的治疗可能代表了对抗GBM的成功策略。在这项工作中，我们描述了一种新型的咪唑并[1,2-a]吡啶衍生物作为醛脱氢酶1A3抑制剂，报告了它们作为治疗GBM的新型药物的重要性的证据。除了显示有趣的功能配置文件，
• Imidazo[1,2-a]pyridines and their use as pharmaceuticals
  申请人：sanofi-aventis

  公开号：EP1964840A1

  公开（公告）日：2008-09-03

  Imidazo[1,2-a]pyridines and their use as pharmaceuticals The present invention relates to derivatives of imidazo[1,2-a]pyridines of the formula (I), in which R, R1 to R4 and n have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide (NO) synthase and are valuable pharmacologically active compounds. Specifically, the compounds of the formula I upregulate the expression of the enzyme endothelial NO synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention further relates to processes for the preparation of compounds of the formula I, to pharmaceutical compositions comprising them, and to the use of compounds of the formula I for the manufacture of a medicament for the stimulation of the expression of endothelial NO synthase or for the treatment of various diseases including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency, for example.

  咪唑[1,2-a]吡啶及其作为药物的用途。本发明涉及咪唑[1,2-a]吡啶衍生物的公式(I)，其中R、R1至R4和n具有声明中指示的含义，这些衍生物调节内皮型一氧化氮(NO)合酶的转录，并且是有价值的药理活性化合物。具体来说，公式I的化合物上调内皮型NO合酶酶的表达，并可应用于需要增加该酶的表达或增加NO水平或正常化降低的NO水平的情况。该发明还涉及公式I化合物的制备方法，包括它们的药物组合物，以及公式I化合物用于制造刺激内皮型NO合酶表达或治疗各种疾病的药物，包括心血管疾病如动脉粥样硬化、血栓形成、冠状动脉疾病、高血压和心脏功能不全等。
• Vanadyl Acetylacetonate Catalyzed Methylenation of Imidazo[1,2-<i>a</i>]pyridines by Using Dimethylacetamide as a Methylene Source: Direct Access to Bis(imidazo[1,2-<i>a</i>]pyridin-3-yl)methanes
  作者：Pinku Kaswan、Nitesh Kumar Nandwana、Brenton DeBoef、Anil Kumar

  DOI：10.1002/adsc.201600225

  日期：2016.6.30

  imidazo[1,2‐a]pyridines using dimethylacetamide (DMA) as methylene source in the presence of vanadyl acetylacetonate [VO(acac)2] as the catalyst and iodobenzene diacetate as the oxidant. The reaction involves coupling of sp3‐ and sp2‐hybridized carbons and proceeds through the formation of an iminium ion. A wide variety of imidazo[1,2‐a]pyridines were converted to bis(imidazo[1,2‐a]pyridin‐3‐yl)methanes

  已经开发了一种有效的方案，用于在乙酰丙酮氧钒[VO（acac）2 ]为催化剂和碘代乙酸二苯酯为氧化剂的情况下，使用二甲基乙酰胺（DMA）作为亚甲基来源的咪唑并[1,2- a ]吡啶的甲基化。该反应涉及sp 3-和sp 2-杂化碳的偶合，并通过形成亚胺离子进行。多种咪唑并[1,2一]吡啶转化为双（咪唑并[1,2一]吡啶-3-基）甲烷在良好至优异的产量。克级反应证明了放大工艺的潜力。