Synthesis, characterization and evaluation of 1,3,5-triazine aminobenzoic acid derivatives for their antimicrobial activity

Abstract

BackgroundReplacement of chloride ions in cyanuric chloride give several variants of 1,3,5-triazine derivatives which were investigated as biologically active small molecules. These compounds exhibit antimalarial, antimicrobial, anti-cancer and anti-viral activities, among other beneficial properties. On the other hand, treatment of bacterial infections remains a challenging therapeutic problem because of the emerging infectious diseases and the increasing number of multidrug-resistant microbial pathogens. As multidrug-resistant bacterial strains proliferate, the necessity for effective therapy has stimulated research into the design and synthesis of novel antimicrobial molecules.Results1,3,5-Triazine 4-aminobenzoic acid derivatives were prepared by conventional method or by using microwave irradiation. Using microwave irradiation gave the desired products in less time, good yield and higher purity. Esterification of the 4-aminobenzoic acid moiety afforded methyl ester analogues. The s-triazine derivatives and their methyl ester analogues were fully characterized by FT-IR, NMR (1H-NMR and 13C-NMR), mass spectra and elemental analysis. All the synthesized compounds were evaluated for their antimicrobial activity. Some tested compounds showed promising activity against Staphylococcus aureus and Escherichia coli. ConclusionsThree series of mono-, di- and trisubstituted s-triazine derivatives and their methyl ester analogues were synthesized and fully characterized. All the synthesized compounds were evaluated for their antimicrobial activity. Compounds (10), (16), (25) and (30) have antimicrobial activity against S. aureus comparable to that of ampicillin, while the activity of compound (13) is about 50% of that of ampicillin. Compounds (13) and (14) have antimicrobial activity against E. coli comparable to that of ampicillin, while the activity of compounds (9–12) and (15) is about 50% of that of ampicillin. Furthermore, minimum inhibitory concentrations values for clinical isolates of compounds (10), (13), (14), (16), (25) and (30) were measured. Compounds (10) and (13) were more active against MRSA and E. coli than ampicillin. Invitro cytotoxicity results revealed that compounds (10) and (13) were nontoxic up to 250 µg/mL (with SI = 10) and 125 µg/mL (with SI = 5), respectively.Graphical abstractThree series of mono-, di- and trisubstituted s-triazine derivatives and their methyl ester analogues were synthesized and evaluated for their antimicrobial activity. Several compounds have antimicrobial activity against S. aureus and E. coli comparable to that of ampicillin. Electronic supplementary materialThe online version of this article (doi:10.1186/s13065-017-0267-3) contains supplementary material, which is available to authorized users.

A modular approach for the installation of functionalized phosphonates to heterocycles

“…40 Therefore, an emphasis was placed on pyrimidine and pyridine scaffolds and their regioselective functionalization as seen in Figure 3. A morpholine-containing triazine, a popular scaffold in medicinal chemistry, 41 underwent the phosphonate SNAr smoothly with a non-stabilized phosphonate to provide 36 in 90% yield. Versatile pyrimidine building block 24 provided 26 in good yield with trimethyl phosphonate.…”

Recent Advances on the s‐Triazine Scaffold with Emphasis on Synthesis, Structure‐Activity and Pharmacological Aspects: A Concise Review

“…Khadijah M. Al‐Zaydi et al . in 2017, described the synthesis of s ‐triazine based aminobenzoic acid derivatives ( 77 – 78 ) and tested them against various bacterial strains [69] . The compounds 77 and 78 exhibited considerable anti‐microbial activity (Table 25) for gram‐positive and gram‐ negative bacterial strains.…”

Synthesis of Multifunctional Charge-Transfer Agents: Toward Single-Walled Carbon Nanotubes with Defined Covalent Functionality and Preserved π System

“…The last building block of our CTA probes is the bridge between the charge-transfer moieties (the methoxy-aniline derivatives) and the SWNTs. For this role we picked up cyanuric chloride, whose three chlorine atoms can be replaced one by one in a controlled way by fine-tuning the reaction conditions. − We substitute one or two of the chlorine atoms with the methoxy-aniline groups. The third chlorine provides the anchor for the CTA onto the SWNTs: we convert it into a reactive nitrene derivative, which we have shown to efficiently attach to the sidewall of SWNTs. , We chose a covalent attachment protocol to ensure long-term stability of the attachment of the CTA onto the SWNTs.…”