266308-67-2

Upstream product

• 125770-94-7 [13C₆]acetophenone 
• 125945-98-4 benzoic-ring-¹³C₆ acid 

Downstream Products

• 1141509-99-0 1-[13C₆]-phenyl-1-propanone 
• 125945-98-4 benzoic-ring-¹³C₆ acid 
• 1025976-68-4 C₁₀⁽¹³⁾C₆H₁₄O₄ 

Relevant academic research and scientific papers

Potent and selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1 labeled with carbon-13 and carbon-14

(S)-6-(2-Hydroxy-2-methylpropyl)-3-((S)-1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (1) and (4aR,9aS)-1-(1H-benzo[d]midazole-5-carbonyl)-2,3,4,4a,9,9a-hexahydro-1-H-indeno[2,1-b]pyridine-6-carbonitrile hydrochloride (2) are potent and selective inhibitor of 11β-hydroxysteroid dehydrogenase type 1 enzyme. These 2 drug candidates developed for the treatment of type-2 diabetes were prepared labeled with carbon-13 and carbon-14 to enable drug metabolism, pharmacokinetics, bioanalytical, and other studies. In the carbon-13 synthesis, benzoic-13C6 acid was converted in 7 steps and in 16% overall yield to [13C6]-(1). Aniline-13C6 was converted in 7 steps to 1H-benzimidazole-1-2,3,4,5,6-13C6-5-carboxylic acid and then coupled to a tricyclic chiral indenopiperidine to afford [13C6]-(2) in 19% overall yield. The carbon-14 labeled (1) was prepared efficiently in 2 radioactive steps in 41% overall yield from an advanced intermediate using carbon-14 labeled methyl magnesium iodide and Suzuki-Miyaura cross coupling via in situ boronate formation. As for the synthesis of [14C]-(2), 1H-benzimidazole-5-carboxylic-14C acid was first prepared in 4 steps using potassium cyanide-14C, then coupled to the chiral indenopiperidine using amide bond formation conditions in 26% overall yield.

Economical synthesis of 13C-labeled opiates, cocaine derivatives and selected urinary metabolites by derivatization of the natural products

The illegal use of opiates and cocaine is a challenge world-wide, but some derivatives are also valuable pharmaceuticals. Reference samples of the active ingredients and their metabolites are needed both for controlling administration in the clinic and to detect drugs of abuse. Especially, 13C- labeled compounds are useful for identification and quantification purposes by mass spectroscopic techniques, potentially increasing accuracy by minimizing ion alteration/suppression effects. Thus, the synthesis of [acetyl-13C4]heroin, [acetyl-13C4-methyl-13C]heroin, [acetyl-13C2-methyl-13C]6-acetylmorphine, [N-methyl-13C-O-metyl- 13C]codeine and phenyl-13C6-labeled derivatives of cocaine, benzoylecgonine, norcocaine and cocaethylene was undertaken to provide such reference materials. The synthetic work has focused on identifying 13C atom-efficient routes towards these derivatives. Therefore, the 13C-labeled opiates and cocaine derivatives were made from the corresponding natural products.

Synthesis of [14C] - and [13C6]-labeled tipranavir and its potential hydroxyl metabolite and the glucuronide conjugate

Tipranavir or Aptivus is a non-peptidic protease inhibitor approved for the combination treatment with ritonavir of HIV infection. Tipranavir labeled with radioactive and stable isotopes of carbon was required for drug metabolism (excretion, distribution,

An efficient synthesis of 13C12-benzoyl peroxide

13C12-Benzoyl peroxide was prepared in overall yield of 78% from 13C6-benzene via acetophenone, benzoic acid and benzoyl chloride intermediates.

A simple synthesis of 13C6-labelled flavone and 5-methoxyflavone

The 13C6-labelled molecules, flavone and 5-ethoxyflavone, with the carbon-13 label at all six carbons of the aromatic B ring, have been prepared for use as internal standards in isotope dilution-mass spectrometry. The key step involv