| Abstract
| - N-(Adamantyl-1)methyl, N-(adamantyl-2), and N-(ω-aminodecyl) amides of vancomycin, eremomycin, and dechloroeremomycin aglycons and their des-(N-Me-d-Leu) derivatives weresynthesized and their antibacterial and anti-HIV activities were investigated. Carboxamideswith an intact peptide core demonstrated activity against glycopeptide-susceptible and -resistantbacteria (1−32 μM). N-(Adamantyl-1)methylcarboxamide of eremomycin aglycons had goodantiretroviral activity (1.6 μM against HIV-1). Compounds with destroyed peptide core [des-(N-Me-d-Leu)-aglycon amides] were inactive against both glycopeptide-sensitive and -resistantbacteria. (Adamantyl-1)methylamide of des-(N-Me-d-Leu)-eremomycin aglycon had good antiretroviral activity (EC50 of 5.5 μM for HIV-1 and 3.5 μM for HIV-2). (Adamantyl-1)methylamides of eremomycin aglycon and its des-(N-Me-d-Leu)-derivative are the mostpromising and selective antiretroviral agents. Their ability to induce bacterial resistance toglycopeptide antibiotics during prolonged administration may be expected to be very low orabsent. This might make the use of these derivatives feasible in the prolonged therapy orprophylaxis of HIV infections.
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