Ring I of aminoglycosides has also been replaced by heterocycles (Figure 1 and Scheme 1) [1-2]. These compounds were studied for their binding affinity toward the fragment of the targeted 16S rRNA, but compound 231 showed activity against E. coli (ATCC25922) (MIC=3 mM).
Figure 1. heterocyclic aminoglycosides
Scheme 1. Synthesis of heterocyclic aminoglycosides
Heterocyclic side chains have also been introduced at the O-2 of paromomycin (Figure 2)  affording compounds with similar activity as compared to paromomycin (Table 1).
Figure 2. Synthesis of paromomycin derivatives at 2"-O
Table 1. MIC (mg/mL) of paromomycin derivatives at 2"-O
1. Ding, Y.; Hofstadler, S. A.; Swayze, E. E.; Griffey, R. H. Org. Lett. 2001, 3, 1621–1623.
2. Ding, Y.; Hofstadler, S. A.; Swayze, E. E.; Risen, L.; Griffey, R. H. Angew. Chem. Int. Ed. 2003, 42, 3409–3412.
3. Francois, B.; Szychowski, J.; Adhikari, S. S.; Pachamuthu, K.; Swayze, E. E.; Griffey, R. H.; Migawa, M. T.; Westhof, E.; Hanessian, S. Angew. Chem. Int. Ed. 2004, 43, 6735–6738.
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