334513-21-2

Upstream product

• 100-46-9 benzylamine 
• 334513-00-7 Trt-β-Ala-γ-Aba-OSu 
• 665782-46-7 4-[3-(trityl-amino)-propionylamino]-butyric acid 
• 103-49-1 dibenzylamine 
• 58995-30-5 N-trityl-β-alanine 

Downstream Products

• 132194-39-9 N¹,N⁸-bis(dihydrocaffeoyl)spermidine 
• 334513-35-8 N-(3-amino-propyl)-N'-benzyl-N-ethyl-butane-1,4-diamine 
• 334513-30-3 N-(3-amino-propyl)-N',N'-dibenzyl-butane-1,4-diamine 
• 334513-05-2 N,N-dibenzyl-N'-ethyl-N'-[3-(trityl-amino)-propyl]-butane-1,4-diamine 
• 334513-07-4 (4-dibenzylamino-butyl)-[3-(trityl-amino)-propyl]-carbamic acid tert-butyl ester 
• 334513-11-0 3-(3,4-bis-benzyloxy-phenyl)-N-{3-[3-(3,4-bis-benzyloxy-phenyl)-acryloylamino]-propyl}-N-(4-dibenzylamino-butyl)-acrylamide 
• 334513-28-9 N⁸,N⁸-dibenzyl-N¹-tritylspermidine 

Relevant academic research and scientific papers

Synthesis and antimicrobial activity of chloramphenicol-polyamine conjugates

Abstract A series of chloramphenicol (CAM) amides with polyamines (PAs), suitable for structure-activity relationship studies, were synthesized either by direct attachment of the PA chain on the 2-aminopropane-1,3-diol backbone of CAM, previously oxidized selectively at its primary hydroxyl group, or from chloramphenicol base (CLB) through acylation with succinic or phthalic anhydride and finally coupling with a PA. Conjugates 4 and 5, in which the CLB moiety was attached on N4 and N1 positions, respectively, of the N8,N8-dibenzylated spermidine through the succinate linker, were the most potent antibacterial agents. Both conjugates were internalized into Escherichia coli cells by using the spermidine-preferential uptake system and caused decrease in protein and polyamine content of the cells. Noteworthy, conjugate 4 displayed comparable activity to CAM in MRSA or wild-type strains of Staphylococcus aureus and Escherichia coli, but superior activity in E. coli strains possessing ribosomal mutations or expressing the CAM acetyltransferase (cat) gene. Lead compounds, and in particular conjugate 4, have been therefore discovered during the course of the present work with clinical potential.

Simple syntheses of N-alkylated spermidine fragments and analogues of the spermine alkaloid kukoamine A

Acylation of a variety of amines with succinimidyl N-trityl-β-alanyl-γ-aminobutyrate and N-trityl-γ-aminobutyryl-β-alaninate, readily obtained through coupling of succinimidyl N-trityl-β-alaninate with trimethylsilyl γ-aminobutyrate and of N-trityl-γ-aminobutyric acid with methyl β-alaninate, respectively, followed by LiAlH4 reduction, produced N-monoalkylated spermidine fragments and analogues of the spermine alkaloid kukoamine A. The applicability of this methodology on the solid phase was also demonstrated.