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  • Title: Synthesis and activity of butirosin derivatives with 5''-amidino and 5''-guanidino substituents.
    Author: Narita Y, Masuyoshi S, Yamasaki T, Naito T, Kawaguchi H.
    Journal: J Antibiot (Tokyo); 1991 Jan; 44(1):86-92. PubMed ID: 1705928.
    Abstract:
    The preparation and antibacterial activity of the 5''-guanidino (6) and 5''-amidino (7) derivatives of 4'-deoxybutirosin A (1) as well as the 5''-guanidino derivative (8) of butirosin A are described. The key intermediates, tetra-N-benzyloxycarbonyl-5''-azido derivatives were selectively reduced with NiCl2-NaBH4 to give the corresponding 5'-amino derivatives. Subsequent guanidination or amidination followed by deblocking afforded the final compounds 6, 7 and 8. The 5''-guanidino derivatives (6 and 8) were more active against Gram-positive and Gram-negative bacteria than the corresponding 5''-hydroxy derivatives (1 and butirosin A). Compound 6 was also active against a variety of methicillin-resistant Staphylococcus aureus (MRSA).
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