NMR elucidation of novel SQ109 derivatives

Abstract

The NMR elucidation of five novel SQ109 analogues including SQ109 is reported herein. These derivatives were synthesized as potential anti-tuberculosis candidates. One-dimensional NMR ( 1 H and 13 C) techniques show a series of overlapping signals from the methine and methylene groups of these compounds, thereby making it extremely difficult to assign all NMR signals. Twodimensional (2D) NMR techniques were instrumental in overcoming these challenges. This paper appears to be a rare report on the complete structure elucidation of monosubstituted adamantane moieties.

Trends in NMR Structural Elucidation Of Polycyclic Cages, Namely: Adamantane, Pentacycloundecane and Trishomocubane

“…Compounds 1-4,reported by Onajole et al 35 , have the most de-shielded proton assigned to H-2, followed by H-4b/9b, H-1/3, Makatini et al, 36 reported di-substituents of compound 7 on C-2 with peptide linkages de-shielding the resonances of the neighbouring protons (Table 2), e.g. H-1/3 have chemical shifts around 2.66-2.74 ppm as compared to 1-6.…”

Interplay of thermochemistry and Structural Chemistry, the journal (volume 21, 2010) and the discipline

“…SQ109 (N-geranyl-N 0 -(2-adamantyl)ethane-1,2-diamine) is an ethambutol cage diamine derivative and possesses excellent activity against multi-drug-resistant (MDR) strains of tuberculosis. Onajole et al [291] report in their paper NMR elucidation of SQ109 and five new analogues, which have a potential activity against tuberculosis. Twodimensional NMR techniques assisted in resolving a series of overlapping signals from the methine and methylene groups.…”