1-(3'-pyridyl)-2-methylimidazole | 837376-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(3'-pyridyl)-2-methylimidazole
• 英文别名: 3-(2-methyl-1H-imidazol-1-yl)pyridine；3-(2-methylimidazol-1-yl)pyridine
• CAS: 837376-62-2
• 化学式: C₉H₉N₃
• 分子量: 159.191
• InChiKey: MNHXJOCWNHZKLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3'-pyridyl)-2-methylimidazole 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 80.0 ℃ 、10.13 MPa 条件下， 反应 24.0h， 以81%的产率得到3-(2-methyl-1H-imidazol-1-yl)piperidine
  参考文献：
  名称：

  A Convenient Synthesis of (1H-Azol-1-yl)piperidines

  摘要：

  A convenient preparation of 3- and 4-(1H-azol-1-yl)piperidines by arylation of azoles (i.e., pyrazoles, imidazoles, and triazoles) with 3- and 4-bromopyridines and subsequent reduction of the pyridine ring was developed. The method was extended to benzo analogues of the title compounds.

  DOI：

  10.1055/s-0031-1291126
• 作为产物：
  描述：

  3-氟吡啶 、 2-甲基咪唑 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 0.5h， 以30%的产率得到1-(3'-pyridyl)-2-methylimidazole
  参考文献：
  名称：

  [EN] SYNTHETIC COMPOUNDS AND DERIVATIVES AS MODULATORS OF SMOKING OR NICOTINE INGESTION AND LUNG CANCER
  [FR] COMPOSES SYNTHETIQUES ET DERIVES DE CEUX-CI EN TANT QUE MODULATEURS DE FUMEE OU D'INGESTION DE NICOTINE ET DU CANCER DU POUMON

  摘要：

  本公开了与尼古丁相关的化合物，其选择性地抑制细胞色素P-450 2A6（CYP2A6），选择性地抑制细胞色素P-450 2A13（CYP2A13），和/或选择性地调节尼古丁型乙酰胆碱受体（nAChR）。还公开了包含本发明化合物的药物组合物，以及使用这些药物组合物治疗或预防与尼古丁摄入相关的疾病或紊乱，或者通过选择性调节nAChRs治疗的疾病或紊乱的方法。

  公开号：

  WO2005066162A1

文献信息

• Rhodium and Iridium Complexes with Chelating <i>C–C′</i>-Imidazolylidene–Pyridylidene Ligands: Systematic Approach to Normal, Abnormal, and Remote Coordination Modes
  作者：Candela Segarra、Elena Mas-Marzá、José A. Mata、Eduardo Peris

  DOI：10.1021/om3005096

  日期：2012.7.23

  been used as imidazolylidene–pyridylidene ligand precursors for the preparation of rhodium(III) and iridium(III) complexes. The relative configuration of the [Him-pyH](X)2 salts determines whether the coordination of the pyridylidene occurs through the normal, abnormal, or remote form. In order to obtain complexes with the imidazolylidene part of the ligand coordinated through the abnormal form, salts

  一系列连接的咪唑鎓-吡啶鎓盐（[Him-pyH]（X）2）已用作制备咪唑鎓（III）和铱鎓（III）配合物的咪唑啉-吡啶鎓配体前体。[Him-pyH]（X）2盐的相对构型决定了吡啶叉基的配位是否通过正常，异常或遥远形式发生。为了获得配体的咪唑基亚烷基部分通过异常形式配位的配合物，使用了由甲基保护的咪唑鎓的C2位置被甲基封闭的盐，尽管该产品是由甲基的C–H脂族活化产生的。取而代之的是C2-Me键的C-C裂解。对三种分子的晶体学研究使我们能够评估相对分子质量。反式的吡啶亚基的正常，异常和远程协作的形式和影响力还比较它由imidazolylidene提供的反式影响。
• Synthetic Compounds and Derivatives as Modulators of Smoking or Nicotine Ingestion and Lung Cancer
  申请人：Cashman John R.

  公开号：US20080188527A1

  公开（公告）日：2008-08-07

  Disclosed are nicotine-related compounds that selectively inhibit cytochrome P-450 2A6 (CYP2A6), selectively inhibit cytochrome P-450 2A13 (CYP2A13), and/or selectively modulate a nicotinic acetylcholine receptor (nAChR). Also disclosed are pharmaceutical compositions comprising a compound of the invention, as well as methods of using the pharmaceutical compositions for treating or preventing a disease or disorder associated with nicotine-ingestion, or a disease or disorder amenable to treatment by selective modulation of nAChRs.

  本发明涉及选择性抑制细胞色素P-450 2A6（CYP2A6）、选择性抑制细胞色素P-450 2A13（CYP2A13）和/或选择性调节尼古丁乙酰胆碱受体（nAChR）的尼古丁相关化合物。本发明还涉及包含本发明化合物的制药组合物，以及使用该制药组合物治疗或预防与尼古丁摄入相关的疾病或障碍，或可通过选择性调节nAChR进行治疗的疾病或障碍的方法。
• Synthetic compounds and derivatives as modulators of smoking or nicotine ingestion and lung cancer
  申请人：Cashman John R.

  公开号：US08609708B2

  公开（公告）日：2013-12-17

  Disclosed are nicotine-related compounds that selectively inhibit cytochrome P-450 2A6 (CYP2A6), selectively inhibit cytochrome P-450 2A13 (CYP2A13), and/or selectively modulate a nicotinic acetylcholine receptor (nAChR). Also disclosed are pharmaceutical compositions comprising a compound of the invention, as well as methods of using the pharmaceutical compositions for treating or preventing a disease or disorder associated with nicotine-ingestion, or a disease or disorder amenable to treatment by selective modulation of nAChRs.

  本发明揭示了一些与尼古丁相关的化合物，它们具有选择性地抑制细胞色素P-450 2A6（CYP2A6），选择性地抑制细胞色素P-450 2A13（CYP2A13），和/或选择性地调节一种尼古丁乙酰胆碱受体（nAChR）。同时，本发明还揭示了包括本发明化合物的制药组合物，以及使用该制药组合物治疗或预防与尼古丁摄入相关的疾病或障碍，或者通过选择性调节nAChRs治疗的疾病或障碍的方法。
• SYNTHETIC COMPOUNDS AND DERIVATIVES AS MODULATORS OF SMOKING OR NICOTINE INGESTION AND LUNG CANCER
  申请人：Cashman John R.

  公开号：US20100298345A1

  公开（公告）日：2010-11-25

  Disclosed are nicotine-related compounds that selectively inhibit cytochrome P-450 2A6 (CYP2A6), selectively inhibit cytochrome P-450 2A13 (CYP2A13), and/or selectively modulate a nicotinic acetylcholine receptor (nAChR). Also disclosed are pharmaceutical compositions comprising a compound of the invention, as well as methods of using the pharmaceutical compositions for treating or preventing a disease or disorder associated with nicotine-ingestion, or a disease or disorder amenable to treatment by selective modulation of nAChRs.

  本发明涉及选择性抑制细胞色素P-450 2A6（CYP2A6）的尼古丁相关化合物，选择性抑制细胞色素P-450 2A13（CYP2A13），和/或选择性调节尼古丁乙酰胆碱受体（nAChR）。本发明还涉及包含本发明化合物的制药组合物，以及使用该制药组合物治疗或预防与尼古丁摄入有关的疾病或障碍，或者通过选择性调节nAChRs进行治疗的疾病或障碍的方法。
• 5-Substituted, 6-Substituted, and Unsubstituted 3-Heteroaromatic Pyridine Analogues of Nicotine as Selective Inhibitors of Cytochrome P-450 2A6
  作者：Travis T. Denton、Xiaodong Zhang、John R. Cashman

  DOI：10.1021/jm049696n

  日期：2005.1.1

  A series of 5- and 6-substituted and unsubstituted 3-heteroaromatic analogues of nicotine were synthesized in an effort to delineate the structural requirements for selectively inhibiting human cytochrome P-450 (CYP) 2A6, the major nicotine metabolizing enzyme. Thiophene, substituted thiophene, furan, substituted furan, imidazole, substituted imidazole, pyridine, substituted pyridine, thiazole, and quinoline moieties were used to replace the N-methylpyrrolidine ring of nicotine. Bromo and methyl groups were introduced at the 5-position of the pyridine ring and fluoro, chloro, and methoxy groups were placed at the 6-position of the pyridine ring in order to explore the structure-activity relationship (SAR) of inhibition of CYP2A6. The inhibitory activity of the most potent CYP2A6 inhibitors on the functional activity of human cytochrome P450s 3A4, 2E1, 2136, 2C9, 2C19, and 2D6 was also examined to determine inhibitor selectivity. We identified 36 compounds that were more potent than nicotine at inhibition of coumarin 7-hydroxylase (CYP2A6) activity. We also found a number of compounds to be highly selective for the inhibition of human CYP2A6 versus the other human CYPs examined.