Synthetic Approach for Novel Fluorine Substituted <i>α</i>-Aminophosphonic Acids Containing 1,2,4-Triazin-5-One Moiety as Antioxidant Agents

Abstract

Novel fluorine substituted α-amino phosphonic acids containing 1,2,4-triazin-5-one (6a-f) have been obtained from fluoroacylation of 6-(2ʹ-amino-5ʹ-nitrophenyl)-3-thioxo-1,2,4-triazin-5(4H)-one (1) followed by ammonilysis to give the corresponding 3-amino-derivative 3. Condensation of compound 3 with nitro/halogenated aromatic aldehydes yielded the Schiff bases 4. The simple addition of diethyl phosphonate to compound 4 produced the α-amino phosphonates 5. Acidic hydrolysis of compound 5 produced the fluorine substituted α-amino acids derivatives 6. Structures of the new compounds have been established with the help of elemental analysis and spectral measurements. Also, the products evaluated as antioxidants, where the fluorinated α-amino phosphonic acids 6 are more active than the other synthesized systems.

Synthesis of some new 5-amino-3-(substituted-amino)-6-(fluoro/ nitro)aryl-1,2,4-triazine derivatives as lamotrigine analogs and their evaluation in vitro as antibacterial agents

“…TLC analyses were performed on Merck silica gel 60 F254 aluminum plates with hexane/ethyl acetate mixtures. Compounds 1 and 2 were obtained according to the reported method 9 .…”

“…Finally, the newly synthesized lamotrigine analogs (7)(8)(9)(10)(11)(12)(13)(14) were screened for their in vitro antibacterial activity against four bacterial isolated Bacillus subtilis, Streptococcus faecalis, Micrococcus luteus, and Staphylococcus aureus. The results of the study revealed that the compounds 7-14 showed significant antibacterial potency.…”

“…Also, Lamotrigine and its ammonium salt complexes used as antimicrobial activity 7 . Recently, Makki et al 8,9 reported a simple route to synthesize Lamotrigine analogs as an antiinflammatory and antioxidant agent. 1,2,4-triazine nucleus is scaffold of various biological activities, also have a significant variety of pharmaceutical properties, such as antitumor 10 , anti-HIV, antimicrobial 11 .…”

Behavior of 3-hydrazino-6-aryl-1,2,4-triazin-5-one as a strong nucleophile towards active electrophilic compounds and their antibacterial evaluation

“…1). Moreover, the interaction between compound 3 as a strong nucleophile and cyanoacetic acid as bi-electrophile in ethanol with few drops of piperidine as a catalyst, yielded 11 (8), while treatment with 2-chloroacetonitrile in DMF, afforded 12 [1,2,4]triazin-7-yl)phenyl)pivalamide (9) respectively Scheme 4.…”

“…On the other hand, phosphorusbearing 1,2,4-triazine mostly enhanced their physical, chemical, and biological properties. 7,8 Also, 3-hydrazino-6-aryl-1,2,4-triazin-5-one used to produce heterobicyclic as anti-HIV and/or molluscicidal activity against some snails. 7 As well as 3-thixio-1,2,4-traizin-5-one derivatives used as starting materials to obtain heteropolycyclic nitrogen systems as antioxidant and anti-inflammatory 9 .…”