[¹¹C]4-cyanopyridine | 1220040-66-3

• 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: [¹¹C]4-cyanopyridine
• 英文别名: pyridine-4-carbonitrile
• CAS: 1220040-66-3
• 化学式: C₆H₄N₂
• 分子量: 103.1
• InChiKey: GPHQHTOMRSGBNZ-SFIIULIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [¹¹C]4-cyanopyridine 在 一水合肼 作用下， 以 水 为溶剂， 反应 0.08h， 生成 C₅⁽¹¹⁾CH₈N₄
  参考文献：
  名称：

  Radiosynthesis and Bioimaging of the Tuberculosis Chemotherapeutics Isoniazid, Rifampicin and Pyrazinamide in Baboons

  摘要：

  The front-line tuberculosis (TB) chemotherapeutics isoniazid (INH), rifampicin (RIF), and pyrazinamide (PZA) have been labeled with carbon-11 and the biodistribution of each labeled drug has been determined in baboons using positron emission tomography (PET). Each radiosynthesis and formulation has been accomplished in 1 h, using [C-11]CH3I to label RIF and [C-11]HCN to label INH and PZA. Following iv administration, INH, PZA, RIF, and/or their radiolabeled metabolites clear rapidly from many tissues; however, INH, PZA, and/or their radiolabeled metabolites accumulate in the bladder while RIF and/or its radiolabeled metabolites accumulates in the liver and gall bladder, consistent with the known routes of excretion of the drugs. In addition, the biodistribution data demonstrate that the ability of the three drugs and their radiolabeled metabolites to cross the blood brain barrier decreases in the order PZA > INH > RIF, although in all cases the estimated drug concentrations are greater than the minimum inhibitory concentration (MIC) values for inhibiting bacterial growth of Mycobacterium tuberculosis (MTB). The pharmacokinetic (PK) and drug distribution data have important implications for treatment of disseminated TB in the brain and pave the way for imaging the distribution of the pathogen in vivo.

  DOI：

  10.1021/jm901858n
• 作为产物：
  描述：

  4-碘吡啶 、 [11C]hydrogen cyanide 在 四(三苯基膦)钯 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 生成 [¹¹C]4-cyanopyridine
  参考文献：
  名称：

  Radiosynthesis and Bioimaging of the Tuberculosis Chemotherapeutics Isoniazid, Rifampicin and Pyrazinamide in Baboons

  摘要：

  The front-line tuberculosis (TB) chemotherapeutics isoniazid (INH), rifampicin (RIF), and pyrazinamide (PZA) have been labeled with carbon-11 and the biodistribution of each labeled drug has been determined in baboons using positron emission tomography (PET). Each radiosynthesis and formulation has been accomplished in 1 h, using [C-11]CH3I to label RIF and [C-11]HCN to label INH and PZA. Following iv administration, INH, PZA, RIF, and/or their radiolabeled metabolites clear rapidly from many tissues; however, INH, PZA, and/or their radiolabeled metabolites accumulate in the bladder while RIF and/or its radiolabeled metabolites accumulates in the liver and gall bladder, consistent with the known routes of excretion of the drugs. In addition, the biodistribution data demonstrate that the ability of the three drugs and their radiolabeled metabolites to cross the blood brain barrier decreases in the order PZA > INH > RIF, although in all cases the estimated drug concentrations are greater than the minimum inhibitory concentration (MIC) values for inhibiting bacterial growth of Mycobacterium tuberculosis (MTB). The pharmacokinetic (PK) and drug distribution data have important implications for treatment of disseminated TB in the brain and pave the way for imaging the distribution of the pathogen in vivo.

  DOI：

  10.1021/jm901858n

文献信息

• Copper(II)-Mediated [¹¹C]Cyanation of Arylboronic Acids and Arylstannanes
  作者：Katarina J. Makaravage、Xia Shao、Allen F. Brooks、Lingyun Yang、Melanie S. Sanford、Peter J. H. Scott

  DOI：10.1021/acs.orglett.8b00242

  日期：2018.3.16

  A copper-mediated method for the transformation of diverse arylboron compounds and arylstannanes to aryl-[11C]-nitriles is reported. This method is operationally simple, uses commercially available reagents, and is compatible with a wide variety of substituted aryl- and heteroaryl substrates. This method is applied to the automated synthesis of high specific activity [11C]perampanel in 10% nondecay-corrected

  报道了一种铜介导的方法，用于将各种芳基硼化合物和芳基锡烷转变为芳基-[ 11 C]-腈。该方法操作简单，使用可商购的试剂，并且与多种取代的芳基和杂芳基底物兼容。此方法适用于以10％未​​经衰减校正的放射化学产率（RCY）的方式自动合成高比活[ 11 C] per喃。
• Copper-Mediated Radiocyanation of Unprotected Amino Acids and Peptides
  作者：Liam S. Sharninghausen、Sean Preshlock、Stephen T. Joy、Mami Horikawa、Xia Shao、Wade P. Winton、Jenelle Stauff、Tanpreet Kaur、Robert A. Koeppe、Anna K. Mapp、Peter J. H. Scott、Melanie S. Sanford

  DOI：10.1021/jacs.2c01959

  日期：2022.4.27

  functional groups, including unprotected amino acids. As such, it enables the site-specific introduction of [11C]CN into peptides at an iodophenylalanine residue. The use of a diamine-ligated copper(I) mediator is crucial for achieving high radiochemical yield under relatively mild conditions, thus limiting racemization and competing side reactions of other amino acid side chains. The reaction has been scaled

  本报告描述了铜介导的芳基卤化物的放射氰化，适用于复杂分子。这种转化可以容忍范围极广的官能团，包括未受保护的氨基酸。因此，它能够在碘苯丙氨酸残基处将 [ 11 C]CN定点引入肽中。使用二胺连接的铜 (I) 介体对于在相对温和的条件下实现高放射化学产率至关重要，从而限制其他氨基酸侧链的外消旋化和竞争性副反应。该反应已按比例缩放并自动化以递送放射性标记的肽，包括促肾上腺皮质激素 1-27 (ACTH) 和痛敏肽 (NOP) 的类似物。例如，利用这种 Cu 介导的放射氰化作用来制备 >40 mCi 的 [ 11C]cyano-NOP 使用正电子发射断层扫描评估灵长类动物的生物分布。这项调查提供了初步证据，表明伤害感受肽穿过血脑屏障并显示所有大脑区域的摄取（注射后 60 分钟 SUV > 1），这与恒河猴大脑中 NOP 受体的已知分布一致。
• Palladium(<scp>ii</scp>)-mediated rapid ¹¹C-cyanation of (hetero)arylborons
  作者：Zhouen Zhang、Takashi Niwa、Yasuyoshi Watanabe、Takamitsu Hosoya

  DOI：10.1039/c8ob02049c

  日期：——

  A highly efficient method applicable to the synthesis of a wide range of [¹¹C]cyanoarenes, including PET tracers for aromatase imaging, has been developed by a palladium(ii)-mediated rapid ¹¹C-cyanation of (hetero)arylborons with [¹¹C]cyanides.

  一种高效的方法被开发出来，适用于合成广泛的[¹¹C]氰基芳烃，包括PET显像的芳香化酶探针，该方法是通过钯（ii）介导的快速¹¹C-氰基化反应，将(hetero)arylborons和[¹¹C]氰化物反应。
• Evaluation and improvement of CuI‐mediated ¹¹ C‐cyanation
  作者：Hideki Ishii、Tomoteru Yamasaki、Toshimitsu Okamura、Yiding Zhang、Yusuke Kurihara、Masanao Ogawa、Nobuki Nengaki、Ming‐Rong Zhang

  DOI：10.1002/jlcr.4016

  日期：2023.3

  CuI-mediated 11C-cyanation was evaluated by synthesizing [11C]perampanel ([11C]5) as a model compound and compared with previous reports. To a DMF solution with 5′-(2-bromophenyl)-1′-phenyl-[2,3′-bipyridin]-6′(1′H)-one (4) and CuI, [11C]NH4CN in a stream of ammonia/nitrogen (5:95, v/v) gas was bubbled. Subsequently, the reaction mixture was heated at 180°C for 5 min. After HPLC purification, [11C]5 was obtained in 7.2 ± 1.0% (n = 4) non-decay corrected radiochemical yield with >99% radiochemical purity and a molar activity of 98 ± 28 GBq/μmol. In vivo evaluations of [11C]5 were performed using small animals. PET scans to check the kinetics of [11C]5 in the whole body of mice suggested that [11C]5 spreads rapidly into the brain, heart, and lungs and then accumulates in the small intestine. To evaluate the performance of CuI-mediated 11C-cyanation reaction, bromobenzene (6a) was selected as the model compound; however, it failed. Therefore, optimization of the reaction conditions has been performed, and consequently, the addition of K2CO3 and prolonging the reaction time improved the radiochemical yield about double. With this improved method, CuI-mediated 11C-cyanation of various (hetero)aromatic bromides was performed to exhibit the tolerance of most functional groups and to provide 11C-cyanated products in good to moderate radiochemical yields.