Naslov
Initial Scale-Up and Process Improvements for the Preparation of a Lead Antibacterial Macrolone Compound

Autori
Štimac, Vlado ; Matanović-Škugor, Maja ; Palej Jakopović Ivana ; Vinter, Adrijana ; Ilijaš, Marina ; Alihodžić, Sulejman ; Mutak, Stjepan

Izvornik
Organic process research & development (1083-6160) 14 (2010), 6; 1393-1401

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
macrolide; quinolone; antimicrobial agents; scale-up process

Sažetak
Macrolones are a novel class of potent antimicrobial agents that consist of a macrolide scaffold to which a quinolone unit is tethered by various linkers to the 4′′-O-position of the cladinose sugar. In this paper is described a modified 13-step route to a lead compound in the series. Critical reaction steps in the medicinal chemistry route were modified for an initial scale-up process, and as a result, a synthetic procedure suitable for preparation of multihundred gram quantities of the final product, with 98% purity, has been developed. The new procedure does not require any purification by column chromatography for any of the reaction steps. The overall yield was increased from 5−8% in the medicinal chemistry route to 27% in the improved procedure.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA