[carboxyl-¹⁴C]anthranilic acid | 5848-20-4

• 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: [carboxyl-¹⁴C]anthranilic acid
• 英文别名: 2-aminobenzoic acid
• CAS: 5848-20-4
• 化学式: C₇H₇NO₂
• 分子量: 139.127
• InChiKey: RWZYAGGXGHYGMB-WGGUOBTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [carboxyl-¹⁴C]anthranilic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 o-Aminobenzylalkohol-methylen-¹⁴C
  参考文献：
  名称：

  Synthesis of labeled ambroxol and its major metabolites

  摘要：

  氨溴索是一种用于呼吸系统疾病治疗的溶解粘液剂。在此，我们报告了碳-14标记的氨溴索的合成，其中放射性原子位于苄基碳上或均匀分布在环己烷环中，特定活度分别为59和81 mCi/mmol。我们还描述了氘标记氨溴索的制备、其氘标记的四氢喹啉代谢物（DHTQ）、碳-13标记的3,5-二溴氨基苯甲酸代谢物，以及一种未标记的O-葡萄糖苷酸结合物。版权所有 © 2009 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1694
• 作为产物：
  描述：

  2,2,2-trifluoro-N-(2-iodophenyl)acetamide 在 sodium metabisulfite 、 copper(II) sulfate 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 7.0h， 生成 [carboxyl-¹⁴C]anthranilic acid
  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

• Preparation of a carbon-14 analog of 2-[2-(4-(dibenzo[b, f][1,4]thiazepin-11-yl)piperazin-1-yl)ethoxy]ethanol
  作者：N. Saadatjoo、M. Javaheri、N. Saemian、M. Amini

  DOI：10.1134/s1066362216050131

  日期：2016.9

  2-[2-(4-(Dibenzo[b, f][1,4]thiazepin-11-yl)piperazin-1-yl)ethoxy]ethanol (Quetiapine) labeled with 14C in 11-position was synthesized in five steps from [carboxy-14C]anthranilic acid. The key precursor of the target product is [11-14C]dibenzothiazepin-11(10H)-one. The reaction is performed as one-pot process.

  在五个位置合成了以14 C标记的2- [2-（4-（二苯并[ b，f ] [1,4]噻嗪pin-11-基）哌嗪-1-基）乙氧基]乙醇（喹硫平）步骤从[羧基-14 C]邻氨基苯甲酸开始。目标产物的关键前体是[11- 14 C] dibenzothiazepin-11（10 ħ） -酮。反应以一锅法进行。
• 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.
• 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.
• Preparation of 1-fluoro-4-methyl-9H-[carbonyl-¹⁴C]thioxanthen-9-one and amine derivatives
  作者：Mohsen Javaheri、Gholamhossein Shirvani、Mohsen Amini、Nader Saemian、Naghi Saadatjoo

  DOI：10.1002/jlcr.3406

  日期：2016.6.30

  of compound and are a common heterocyclic scaffold in biologically active and medicinally significant compounds. In this paper the synthesis of 1-fluoro-4-methyl-9H-thioxanthen-9-one and some amine derivatives labeled with carboxyl-14 is described.

  9H-Thioxanthen-9-ones 是一类重要的化合物，是具有生物活性和药用意义的化合物中常见的杂环支架。本文描述了 1-fluoro-4-methyl-9H-thioxanthen-9-one 和一些用羧基-14 标记的胺衍生物的合成。
• Synthesis of a carbon-14 analog of 8-chloro-11- (4-methyl-1-piperazinyl)-11-[14C]-5H-dibenzo[b,e][1,4]diazepine (clozapine) using microwave irradiation
  作者：N. Saadatjoo、M. Javaheri、N. Saemian、M. Amini

  DOI：10.1134/s1066362216040123

  日期：2016.7

  8-Chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b, e][1,4] diazepine labeled with C-14 in 11-position was synthesized in four steps from [carboxyl-C-14]anthranilic acid using microwave irradiation with good overall radiochemical yield.