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A convenient method for 14C-labeling of 2-methylthio-1-[4-N-α-ethoxycarbonylbenzyl)-amino-benzyl]-5-hydroxymethyl-2-[14C]-1H-imidazole and 1-[4-N-α-ethoxy-carbonylbenzyl)-aminobenzyl]-5-hydroxymethyl-2-[14C]-1H-imidazole as potential antihypertensives

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Abstract

The key synthetic intermediate, (2-mercapto-1-(4-nitrobenzyl)-1H-imidazol-5-yl)methanol-[2-14C], has been synthesized by using one pot procedure from potassium[14C]-thiocyanate. It was converted to two nonpeptide angiotensin II receptor antagonists, 2-methylthio-1-[4-N-α-ethoxycarbonyl benzyl)-aminobenzyl]-5-hydroxymethyl-1H-imidazole-[2-14C] and 1-[4-N-α-ethoxy-carbonylbenzyl)-aminobenzyl]-5-hydroxymethyl-1H-imidazole-[2-14C] via a 3-step sequence synthetic pathway.

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Fig. 1
Scheme 1
Scheme 2

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Acknowledgment

We gratefully acknowledge the help of Dr. R. Dowlatabadi (Tehran University of Medical Science, Faculty of Pharmacy) for 1H-NMR spectroscopy.

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Correspondence to Nader Saemian.

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Saemian, N., Shirvani, G., Oliyaee, S.S. et al. A convenient method for 14C-labeling of 2-methylthio-1-[4-N-α-ethoxycarbonylbenzyl)-amino-benzyl]-5-hydroxymethyl-2-[14C]-1H-imidazole and 1-[4-N-α-ethoxy-carbonylbenzyl)-aminobenzyl]-5-hydroxymethyl-2-[14C]-1H-imidazole as potential antihypertensives. J Radioanal Nucl Chem 292, 237–241 (2012). https://doi.org/10.1007/s10967-011-1484-1

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