In 2016,Basak, Akash; Abouelhassan, Yasmeen; Norwood, Verrill M. IV; Bai, Fang; Nguyen, Minh Thu; Jin, Shouguang; Huigens, Robert W. III published 《Synthetically Tuning the 2-Position of Halogenated Quinolines: Optimizing Antibacterial and Biofilm Eradication Activities via Alkylation and Reductive Amination Pathways》.Chemistry – A European Journal published the findings.Synthetic Route of C6H5Br2N The information in the text is summarized as follows:
Agents capable of eradicating bacterial biofilms are of great importance to human health as biofilm-associated infections are tolerant to our current antibiotic therapies. We have recently discovered that halogenated quinoline (HQ) small mols. are: (1) capable of eradicating methicillin-resistant Staphylococcus aureus (MRSA), methicillin-resistant Staphylococcus epidermidis (MRSE) and vancomycin-resistant Enterococcus faecium (VRE) biofilms, and (2) synthetic tuning of the 2-position of the HQ scaffold has a significant impact on antibacterial and antibiofilm activities. Here, we report the chem. synthesis and biol. evaluation of 39 HQ analogs that have a high degree of structural diversity at the 2-position. We identified diverse analogs that are alkylated and aminated at the 2-position of the HQ scaffold and demonstrate potent antibacterial (MIC≤0.39 μM) and biofilm eradication (MBEC 1.0-93.8 μM) activities against drug-resistant Staphylococcus aureus, Staphylococcus epidermidis and Enterococcus faecium strains while demonstrating <5 % haemolysis activity against human red blood cells (RBCs) at 200 μM. In addition, these HQs demonstrated low cytotoxicity against HeLa cells. Halogenated quinolines are a promising class of antibiofilm agents against Gram-pos. pathogens that could lead to useful treatments against persistent bacterial infections. In the experiment, the researchers used many compounds, for example, 3,5-Dibromoaniline(cas: 626-40-4Synthetic Route of C6H5Br2N)
3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Synthetic Route of C6H5Br2N
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary