Preparation of 1‐fluoro‐4‐methyl‐9H‐[carbonyl‐¹⁴C]thioxanthen‐9‐one and amine derivatives

Abstract

9H-Thioxanthen-9-ones are an important class 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.

Preparation of four 1,4‐dihydropyridine derivatives (DHPs) labeled with carbon‐14

“…In the following, the labeled compound 1 was converted into 2 new DHP derivatives. From reaction of 1 with [ Carboxyl ‐ 14 C] thiosalicylic acid 2 , products 3 (double labeled) and 4 (triple labeled) were obtained in 37% and 16% yields, respectively (Scheme ). Finally, using a single‐step reaction, compound 5 was obtained by reaction of [ carbonyl ‐ 14 C] benzaldehyde with ethyl phenylpropylate and aniline with 27% yield (Scheme ).…”

Synthesis of 2 carbon‐14 analogue of thioflavanones

“…Barium 14 C‐carbonate 235.9 MBq/mmol was purchased from Amersham Pharmacia Biotech UK Ltd. (Amersham Place, Little Chalfont, Buckinghamshire, England) and was converted to potassium [ 14 C]cyanide according to the standard procedure . Moreover, potassium [ 14 C]cyanide was converted to [carboxyl‐ 14 C]thiosalicylic acid according to the method previously used in multistep . IR spectra were recorded on a Bruker FT‐IR, Vector 22 instrument, and the 1 H NMR spectra were recorded on a Varian unity plus 400 spectrometer (400 MHz).…”

Recent developments in heterocycle labeling with carbon isotopes

“…Thioxanthen‐9‐one is a common scaffold present in several drugs with antiparasitic activity, such as lucanthone, a compound that exhibits anticolinergic activity in worms, in use for the treatment of schistosomiasis. In 2016, Javaheri et al described a general route to such a tricyclic core …”