Semisynthetic Modification of Antibiotic Lincomycin.

Lincosamide Antibiotics: Structure, Activity, and Biosynthesis

“…For example, Sztaricskai, Omura, and coworkers synthesized the 7‐azido‐ and 7‐heteroaryl‐thio‐licomycin analogues 12 – 16 (Figure 3). [10c] The azido compound 12 showed higher antibacterial activity compared to that of 1 .…”

“…It exhibits improved antimicrobial activities and pharmacokinetics compared to 1 . Based on this information, the structure‐activity relationship at the C‐7 position of lincosamides have been investigated by many groups [10c,23] . For example, Sztaricskai, Omura, and coworkers synthesized the 7‐azido‐ and 7‐heteroaryl‐thio‐licomycin analogues 12 – 16 (Figure 3).…”

Synthesis of novel lincomycin derivatives and their in vitro antibacterial activities

“…On the other hand, Lewis et al 4,5 disclosed VIC-105555 ( Figure 1) and proved that its in vitro activity against Enterococcus faecalis was much stronger than that of CLDM and its half-life in plasma was greatly improved compared with that of CLDM in a variety of animal species. As a pioneer work, Sztaricskai and Ō mura et al 6 reported introduction of a heterocycle via sulfur atom onto the LCM carbon framework (1 and 2 shown in Figure 1) with (7R)-configuration, by means of S N 2 reaction analogous to the synthesis of CLDM. All these derivatives introduced as shown in the above exhibited substantially same antibacterial spectra as those of LCM or CLDM, and there was no description about their antibacterial activities against resistant bacteria of S. pneumoniae with erm gene.…”

Squaramide Tethered Clindamycin, Chloroquine, and Mortiamide Hybrids: Design, Synthesis, and Antimalarial Activity

“…Our synthetic endeavors started with the preparation of clindamycin- and chloroquine-monosquaramide esters 7 and 10 (Scheme ). Thus, clindamycin 1 was converted into the known azide 4 following an inversion of configuration at C7 . Then, reduction of the azide furnished the corresponding amine 5 in high yield and treatment with diethyl squarate under basic conditions provided clindamycin-monosquaramide ester 7 in excellent yield .…”

“…Thus, clindamycin 1 was converted into the known azide 4 following an inversion of configuration at C7. 38 Then, reduction of the azide furnished the corresponding amine 5 in high yield 39 and treatment with diethyl squarate under basic conditions provided clindamycin-monosquaramide ester 7 in excellent yield. 40 A similar strategy was executed starting from hydroxychloroquine sulfate 2.…”