Chemical modifications of Spiramycin I at the C6 ethyl aldehyde

The macrolide antibiotics are family of natural and semi-synthetic compounds with antimicrobial activity against various infectious diseases. These compounds are composed of a large macrocyclic ring containing 12, 14, 15 or 16 atoms, a lactone moiety and one or more neutral or amino sugars that are glycosidically bonded to the ring. With the ever increasing prevalence of antibacterial resistance, there is a major need for new antibiotics to aid in the fight against infectious diseases.; Spiramycin is a 16-membered macrolide antibiotic that is known to be especially active against gram-positive, and to a lesser extent, gram-negative bacteria. This class of antibiotic exhibits activity in the treatment of infections caused by staphylococci, streptococci, pneumococci, gonococci, Treponema pallidium, Toxoplasma gondii and crytosporidium. Spiramycin offers such a broad range of activity that it is a prime candidate for derivation in the effort to obtain novel antibiotics.; We designed derivatives of the commercially available 16-membered macrolide antibiotic Spiramycin I. These structurally modified derivatives of Spiramycin I were designed based on the covalent interaction of the C6 ethyl aldehyde with the N6 of A2130. The five new compounds were fully characterized and biologically evaluated for antimicrobial and antimalarial activity. Based on the data from the biological assays, we obtained new biologically active antibiotics towards the fight against antibacterial resistance. The new semisynthetic derivatives of Spiramycin I also proved that modification at the C6 ethyl aldehyde can be achieved while maintaining antimicrobial activity.