2-aminobenzonitrile-[cyano-14C] | 91746-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-aminobenzonitrile-[cyano-14C]
• 英文别名: 2-amino-[cyano-(14)C]benzonitrile；2-aminobenzonitrile
• CAS: 91746-81-5
• 化学式: C₇H₆N₂
• 分子量: 120.127
• InChiKey: HLCPWBZNUKCSBN-RHRFEJLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 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：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-aminobenzonitrile-[cyano-14C] 在 potassium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 5.0h， 以86%的产率得到[carboxyl-¹⁴C]anthranilic acid
  参考文献：
  名称：

  Synthesis of a series of carbon-14 labelled 4-aminoquinazolines and quinazolin-4 (3H)-ones

  摘要：

  4-氨基喹唑啉和喹唑啉-4（3H）-酮在4位都标记有碳-14，它们分别由2-氨基苯甲腈-[氰基-14C]和2-氨基苯甲酸-[羧基-14C]或2-氨基苯甲酰胺-[羧基-14C]制备，在微波增强条件下使用快速的一锅法。版权所有 © 2009 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1658
• 作为产物：
  描述：

  2-碘苯胺 在 sodium metabisulfite 、 copper(II) sulfate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2-aminobenzonitrile-[cyano-14C]
  参考文献：
  名称：

  Biosynthesis of [ ¹⁴ C]‐11‐De‐ O ‐Methyltomaymycin, a Precursor of Radiolabelled Antibody Drug Conjugates

  摘要：

  AbstractAntibody drug conjugates (ADCs) are one of the most promising technologies to treat cancer as they combine the specificity of an antibody with the high potency of a cytotoxic molecule such as tomaymycin derivatives, which are DNA‐interactive antitumor antibiotics previously isolated from bacterial broth. The multistep chemical synthesis of some tomaymycin derivatives is complicated because their structures contain a reactive imine bond. Therefore, we turned to biosynthesis to obtain 14C radiolabelled tomaymycin derivative to support ADME studies. Following Hurley's work (J. Antibiotics 1977, 30, 349–370; Antimicrob. Agents Chemother. 1979, 15, 42–45; Acc. Chem. Res. 1980, 13, 263–269), the 14C radiolabel was incorporated efficiently in one step from radiolabelled tyrosine using the strain Streptomyces sp. FH6421. This process has been further optimized by using anthranilic acid as radiolabelled precursor, leading to one of the highest incorporation levels of radiochemical precursors published to date. This biosynthetic strategy is the fastest way to access such radiolabelled precursors.

  DOI：

  10.1002/cbic.202100080

文献信息

• Syntheses of the tricyclic cores of clozapine, dibenzo[b,f][1,4]thiazepin-11(10H)-one, and dibenzo[b,f][1,4]oxazepin-11(10H)-one in C-14 labeled form by [14C]carbonylation
  作者：Charles S. Elmore、Peter N. Dorff、J. Richard Heys

  DOI：10.1002/jlcr.1802

  日期：2010.11

  utilized [14C]carbonylation as the isotope incorporating step. While this route worked, it was not deemed superior to the previous route. However, this methodology proved quite effective in preparing C-14 labeled dibenzothiazepine and dibenzoxapine ring systems. Copyright © 2010 John Wiley & Sons, Ltd.

  已证明氯氮平因代谢激活而与蛋白质共价结合，这被认为是发生在一小部分人群中的严重副作用（包括死亡）的前兆。几个小组已经研究了氯氮平对蛋白质的共价修饰，并有充分的记录。因此，药物代谢部门希望使用 [14C] 氯氮平作为共价结合试验的阳性对照。[14C]氯氮平的制备首先使用先前报道的路线进行，然后使用利用[14C]羰基化作为同位素掺入步骤的新路线。虽然这条路线有效，但并不认为它优于之前的路线。然而，这种方法证明在制备 C-14 标记的二苯并噻嗪和二苯并沙平环系统方面非常有效。
• Fast and efficient synthesis of¹⁴C labelled benzonitriles and their corresponding acids
  作者：Søren Christian Schou

  DOI：10.1002/jlcr.1585

  日期：2009.5.15

  14C-Anthranilic acid has been prepared in a fast and efficient way in a two-step reaction in 82% overall radiochemical yield. Thus, 2-iodoaniline was transformed into 2-amino-[7-14C]-benzonitrile using a palladium catalyzed cyanation with zinc 14C-cyanide. Subsequent basic hydrolysis of the cyano group afforded [7-14C]-anthranilic acid. The method was successfully applied to a benzophenone scaffold, 4-iodophenol and 4-iodobenzoic acid producing the corresponding carboxylic acids in good to excellent radiochemical yields (62–82%) and with high specific activity (1.94–1.98 GBq/mmol). Copyright © 2009 John Wiley & Sons, Ltd.

  14C-Anthranilic acid 是通过两步反应快速高效地制备出来的，总放射化学收率为 82%。这样，2-碘苯胺在钯催化下与 14C 氰化锌发生氰化反应，转化为 2-氨基-[7-14C]-苯腈。随后氰基发生碱性水解，得到[7-14C]-anthranilic acid。该方法成功地应用于二苯甲酮支架、4-碘苯酚和 4-碘苯甲酸，产生了相应的羧酸，放射性化学收率良好至极佳（62-82%），比活度高（1.94-1.98 GBq/mmol）。Copyright © 2009 John Wiley & Sons, Ltd. All Rights Reserved.
• Biosynthesis of [ ¹⁴ C]‐11‐De‐ <i>O</i> ‐Methyltomaymycin, a Precursor of Radiolabelled Antibody Drug Conjugates
  作者：Catherine Aubert、Mélanie Lavisse、Sebastien Roy

  DOI：10.1002/cbic.202100080

  日期：2021.7.15

  AbstractAntibody drug conjugates (ADCs) are one of the most promising technologies to treat cancer as they combine the specificity of an antibody with the high potency of a cytotoxic molecule such as tomaymycin derivatives, which are DNA‐interactive antitumor antibiotics previously isolated from bacterial broth. The multistep chemical synthesis of some tomaymycin derivatives is complicated because their structures contain a reactive imine bond. Therefore, we turned to biosynthesis to obtain 14C radiolabelled tomaymycin derivative to support ADME studies. Following Hurley's work (J. Antibiotics 1977, 30, 349–370; Antimicrob. Agents Chemother. 1979, 15, 42–45; Acc. Chem. Res. 1980, 13, 263–269), the 14C radiolabel was incorporated efficiently in one step from radiolabelled tyrosine using the strain Streptomyces sp. FH6421. This process has been further optimized by using anthranilic acid as radiolabelled precursor, leading to one of the highest incorporation levels of radiochemical precursors published to date. This biosynthetic strategy is the fastest way to access such radiolabelled precursors.
• Synthesis of a series of carbon-14 labelled 4-aminoquinazolines and quinazolin-4 (3H)-ones
  作者：Nader Saemian、Omid Khalili Arjomandi、Gholamhossein Shirvani

  DOI：10.1002/jlcr.1658

  日期：2009.9.15

  4-Aminoquinazolines and quinazolin-4 (3H)-ones, both labelled with carbon-14 in the 4-position, were prepared from 2-aminobenzonitrile-[cyano-14C] and 2-aminobenzoic acid-[carboxy -14C] or 2-amino- benzamide-[carboxy -14C], respectively, using rapid, one-pot procedures under microwave enhanced conditions. Copyright © 2009 John Wiley & Sons, Ltd.

  4-氨基喹唑啉和喹唑啉-4（3H）-酮在4位都标记有碳-14，它们分别由2-氨基苯甲腈-[氰基-14C]和2-氨基苯甲酸-[羧基-14C]或2-氨基苯甲酰胺-[羧基-14C]制备，在微波增强条件下使用快速的一锅法。版权所有 © 2009 John Wiley & Sons, Ltd.