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Heterocycle-Substituted Aminoglycosides

Ring I of aminoglycosides has also been replaced by heterocycles (Figure 1 and Scheme 1) [1-2].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) [3] 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

Compounds Paromomycin 29 30 31
E. coli (ATCC 25922)
 
5 6 25 5
S. aureus (ATCC 13709)
 
3 2 3 1
Streptococcus pyogenes (ATCC 49399)
 
3 6
Proteus vulgaris (ATCC 8427)
 
1 3
Klebsiella pneumoniae (ATCC 13883) 1 3

 


1. Ding, Y.; Hofstadler, S. A.; Swayze, E. E.; Griffey, R. H. Org. Lett. 2001, 3, 16211623.

2. Ding, Y.; Hofstadler, S. A.; Swayze, E. E.; Risen, L.; Griffey, R. H. Angew. Chem. Int. Ed. 2003, 42, 34093412.

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, 67356738.

 

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