6-溴-2-(4-氟-苯基)-咪唑并[1,2-a]吡啶 | 426825-66-3

• 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-氟-苯基)-咪唑并[1,2-a]吡啶
• 英文名称: 6-bromo-2-(4-fluorophenyl)imidazo[1,2-a]pyridine
• CAS: 426825-66-3
• 化学式: C₁₃H₈BrFN₂
• mdl: MFCD06641501
• 分子量: 291.122
• InChiKey: NKIQEILZYPFNFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  2

反应信息

• 作为反应物：
  描述：

  6-溴-2-(4-氟-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-(4-fluorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde-O-[1-(4-nitrobenzyl)-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：

  4-氟苯乙酮肟 在 copper dichloride 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 6-溴-2-(4-氟-苯基)-咪唑并[1,2-a]吡啶
  参考文献：
  名称：

  肟酯的CuCl 2催化的N O键裂解：咪唑杂环和呋喃[3,2- c ]苯并稠合的咪唑的方法

  摘要：

  通过用几种肟酯与一组2-氨基氮杂氮杂铜进行铜催化的氮杂环化反应，开发了一种以良好至高收率的多种咪唑杂环杂环的铰接方法。上述环化反应可能是通过单电子转移过程进行的，这体现了一种新技术，该技术为咪唑环合成生成两个新的C N键。令人欣慰的是，该化学方法的实施可以进一步扩展为通过连续的C N键形成，合成带有呋喃[3,2- c ]亚甲基部分的新型稠合咪唑，随后是C（sp 2）-H功能化/ 5-内切-乙氧基环化（CC和C在铜（II）作为π亲电Lewis酸催化剂的情况下，原位生成带有环状烯酮的稠合咪唑。

  DOI：

  10.1016/j.tetlet.2020.152147

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。
• Synthesis of Polysubstituted Imidazo[1,2-<i>a</i>]pyridines via Microwave-Assisted One-Pot Cyclization/Suzuki Coupling/Palladium-Catalyzed Heteroarylation
  作者：Jamal Koubachi、Saïd El Kazzouli、Sabine Berteina-Raboin、Abderrahim Mouaddib、Gérald Guillaumet

  DOI：10.1021/jo0712603

  日期：2007.9.1

  A new and efficient method for the synthesis of 2,3,6-trisubstituted imidazo[1,2-a]pyridine derivatives using a microwave-assisted one-pot, two-step Suzuki/heteroarylation or one-pot, three-step cyclization/Suzuki/heteroarylation was developed. Polysubstituted compounds are obtained in good yield from 2-amino-5-halogenopyridines, 2-halogenocarbonyl derivatives, boronic acids, and heteroaryl bromides

  一种新的，高效的微波辅助一锅两步铃木/杂芳基化或一锅三步环化合成2,3,6-三取代的咪唑并[1,2- a ]吡啶衍生物的方法开发了/ Suzuki /杂芳基化。从2-氨基-5-卤代吡啶，2-卤代羰基衍生物，硼酸和杂芳基溴化物以高收率获得多取代的化合物。
• [EN] NOVEL SUBSTITUTED IMIDAZOLES AS CASEIN KINASE 1 δ/&egr; INHIBITORS<br/>[FR] UTILISATION DE NOUVEAUX IMIDAZOLES SUBSTITUÉS COMME INHIBITEURS DE LA CASÉINE KINASE 1 &Dgr;/&Egr;
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2014100533A1

  公开（公告）日：2014-06-26

  The invention provides compounds of Formula (I) and pharmaceutically acceptable salts thereof. The compounds of Formula (I) inhibit protein kinase activity thereby making them useful as anticancer agents.

  这项发明提供了式（I）的化合物及其药学上可接受的盐。式（I）的化合物通过抑制蛋白激酶活性，因此可用作抗癌药物。
• Comparative Study on the Reactivity of 6-Haloimidazo[1,2-a]pyridine Derivatives towardsNegishi- andStille-Coupling Reactions
  作者：Maud Hervet、Isabelle Théry、Alain Gueiffier、Cécile Enguehard-Gueiffier

  DOI：10.1002/hlca.200390290

  日期：2003.10

  Suzuki-cross-coupling reaction of 6-haloimidazo[1,2-a]pyridines is dependent on the availability of the (hetero)arylboronic acids. Thus, with the aim to develop expanded applications of (hetero)arylations of imidazo[1,2-a]pyridines, we investigated the Negishi- and Stille-cross-coupling reactions at the 6-position. Remarkably, attempts to apply the Negishi-cross-coupling conditions to the organozinc derivative prepared

  6-卤代咪唑并[1,2- a ]吡啶的铃木交叉偶联反应的范围取决于（杂）芳基硼酸的可用性。因此，具有的目标是发展扩大的咪唑并（杂）芳基化的应用[1,2一]吡啶，我们研究了根岸-和的Stille -Cross偶联反应在6-位。值得注意的是，尝试将Negishi交叉偶联条件应用于由6-卤代咪唑并[1,2- a ]吡啶经锂锌交换制得的有机锌衍生物，导致5-苯基化合物3的产率为54％，而不是所需的6 -苯基异构体（方案1）。相反，在Stille条件下，将各种可商购的卤化的五或六元环杂环有效地偶联至6-（三烷基锡烷基）咪唑并[1,2- a ]吡啶（表2）。
• 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。