[¹⁴CO]anisic acid chloride | 111930-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [¹⁴CO]anisic acid chloride
• 英文别名: [(14)CO]-anisoyl chloride；4-methoxybenzoyl chloride
• CAS: 111930-84-8
• 化学式: C₈H₇ClO₂
• 分子量: 172.584
• InChiKey: MXMOTZIXVICDSD-PPJXEINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [¹⁴CO]anisic acid chloride 在 四氯化锡 、 boron tribromide-methyl sulfide complex 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  10th international symposium on the synthesis and applications of isotopes and isotopically labelled compounds-synthesis of compounds labelled with long-lived isotopes Session 17, Thursday, June 18, 2009

  摘要：

  本节是第一节的延续。本节介绍了一些详细描述氚化物合成的方法，以及关于多居里级氚处理方法的讨论。此外，还详细描述了多种同位素标记化合物的制备方法。版权所有 © 2010 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1773
• 作为产物：
  描述：

  4-methoxy-[α-¹⁴C]benzoic acid 、 氯化亚砜 生成 [¹⁴CO]anisic acid chloride
  参考文献：
  名称：

  JOHNSTON D.; DUNCAN D. R., J. LABELLED COMPOUNDS AND RADIOPHARM., 24,(1987) N 3, 339-342

  摘要：

  DOI：

文献信息

• The magic of small structure differences in a sodium‐glucose cotransporter drug discovery project— ¹⁴ C‐labelled drug candidates in a key‐differentiating study
  作者：Manfred Schudok、Heiner Glombik、Volker Derdau

  DOI：10.1002/jlcr.3869

  日期：2021.2

  We describe the dramatic differences in the synthesis and physiological and pharmacokinetical profiling of two sodium-glucose cotransporter (SGLT) drug candidates AVE2268 and AVE8887 with very similar chemical structures. It is a classic example of how a radioactive study was able to spare resources in preclinical development prior to entering a costly clinical program. It also demonstrated that radioactive compounds can be used to study differences between two very similar compounds in vivo.

  我们描述了两种钠-葡萄糖共转运蛋白（SGLT）候选药物AVE2268和AVE8887在合成、生理和药代动力学方面的巨大差异，这两种药物的化学结构非常相似。这是一个典型的例子，说明在进入成本高昂的临床试验项目之前，放射性研究能够节省临床前研发资源。它还表明，放射性化合物可用于研究两种非常相似的化合物在体内的差异。
• Synthesis of isotopically labelled SGLT inhibitors and their metabolites
  作者：Volker Derdau、Thorsten Fey、Jens Atzrodt

  DOI：10.1016/j.tet.2009.12.003

  日期：2010.2

  Isotopically labelled analogues of two structurally very similar SGLT inhibitors AVE2268 (1a) and AVE8887 (1b) have been synthesized by various routes. The radioactive labelled [C-14]-AVE2268 was prepared in five steps including a Friedel-Crafts acylation as the key step for the C-14-label introduction. For [C-14]-AVE8887 the same synthetic approach was not successful and therefore an alternative thiophene metallation/Weinreb amide sequence was developed. This pathway was also applied to obtain stable isotopically labelled analogues of both AVE2268 and AVE8887. Finally, the synthesis of two metabolites, sulfate 12 and glucuronide 13 were achieved by applying interesting protecting group and oxidation strategies. (C) 2009 Elsevier Ltd. All rights reserved.