Multi‐¹³ C‐labelled inhibitors of tubulin assembly: 5‐substituted methyl N‐(1H‐benzimidazol‐2‐YL)carbamates

Abstract

Eight methyl N-(lH-benzimidazol-2-yl)carbamates with1 3 various 5-substituents were synthesized, each C-enriched at carbon 2, and the carbonyl and methoxy carbons. Five were prepared by cyclization involving the appropriate 4-substituted 1,2-diaminobenzene (CgHgcO-, CH3CH2CH20-, C H~C H Z C H~S -, CgHgS-and CH3CH2CH2CH2-), and methyl-C N-[imino(methylthio)methyl-Clcarbamate-C or methyl N,N'-bis(methoxy-C-carbonyl-C)carbamimidothionate-C. The latter were prepared from commercially available and thiourea. The remaining three (5-substituents: C6H5CH(OH)-, CgHgSO-and CH3CH2CH2SO-) were prepared by side-chain reduction or oxidation. The H-and C-NMR, and the methane CI mass spectral data of the products and intermediates are presented.

Synthesis of Albendazole Metabolite: Characterization and HPLC Determination

“…We report an integrated laboratory project for undergraduate students in medicinal chemistry laboratory that focuses on organic synthesis, nuclear magnetic resonance (NMR) spectroscopy, and high-performance liquid chromatography (HPLC) analysis. The students synthesize albendazole metabolite 2 by oxidation of compound 1 using H 2 O 2 in acetic acid (7,8) (Scheme I). They use HPLC to analyze the crude reaction and determine the concentration of sulfoxide 2.…”