A new synthesis of 5-deazaflavins

Design, synthesis, and antitumor efficacy of novel 5-deazaflavin derivatives backed by kinase screening, docking, and ADME studies

“…The third pathway to prepare 5-deazaisoalloxazine derivatives involves the direct reaction of these compounds with the suitable reagent to get a certain target compound. 10 , 24 As continuing our previous studies of 5-deazaflavins 1–7 , in this study, we explore the effect of different substituents at C-2 or N-10 positions on the antitumor activity of 5-deazaflavins. We illustrate the synthetic approaches utilised for the preparation of various novel 5-deazaflavin derivatives namely: 2-( N -substituted amino and heterocyclic amino)-7-(unsubstituted/substituted)-10-alkyl-2-deoxo-5-deazaflavins (4a–h) and (4k–m) , 2-Hydrazino-10-alkyl-2-deoxo-5-deazaflavins ( 4i,j ), 2,2′-(Piperazine-1,4-diyl)bis(10-alkyl-2-deoxo-5-deazaflavins), 2[(E)-2-(substituted)benzylidenehydrazino]-10-alkyl-2-deoxo-5-deazaflavins (5a–j) , 10-aryl-2-deoxo-2-thioxo-5-deazaflavins (8a–c) , and 2-(substituted amino)-10-aryl-2-deoxo-5-deazaflavins (9a–g) to afford new candidates as antitumor agents via PTK inhibition.…”

“…Synthesis of 5-deazaflavins could be achieved from suitably functionalised pyrimidine derivatives such as barbituric acid 21 , 6-( N -substituted)aminopyrimidines 1 , 2 , 18 , 19 , and 6-chloro-5-formylpyrimidines 22 , 23 . Alternatively, the appropriate quinoline derivatives provide another starting material for the synthesis of 5-deazaisoalloxazine 24 , 25 . The third pathway to prepare 5-deazaisoalloxazine derivatives involves the direct reaction of these compounds with the suitable reagent to get a certain target compound.…”

Ylidenemalononitrile Enamines as Fluorescent “Turn-On” Indicators for Primary Amines

“…Analysis by 1 H NMR spectroscopy demonstrated that 1a reacts with propylamine (∼300 min; room temperature) to yield a new species with changes to the vinyl protons (Figure a). These resonances suggested that the new product was either the isomerized cis -enamine or the acyclic amidines 2a (Scheme ).…”