1428273-83-9Relevant academic research and scientific papers
Modified 2,4-diaminopyrimidine-based dihydrofolate reductase inhibitors as potential drug scaffolds against Bacillus anthracis
Nammalwar, Baskar,Bourne, Christina R.,Wakeham, Nancy,Bourne, Philip C.,Barrow, Esther W.,Muddala, N. Prasad,Bunce, Richard A.,Berlin, K. Darrell,Barrow, William W.
, p. 203 - 211 (2015)
The current Letter describes the synthesis and biological evaluation of dihydrophthalazine-appended 2,4-diaminopyrimidine (DAP) inhibitors (1) oxidized at the methylene bridge linking the DAP ring to the central aromatic ring and (2) modified at the central ring ether groups. Structures 4a-b incorporating an oxidized methylene bridge showed a decrease in activity, while slightly larger alkyl groups (CH2CH3 vs CH3) on the central ring oxygen atoms (R2 and R3) had a minimal impact on the inhibition. Comparison of the potency data for previously reported RAB1 and BN-53 with the most potent of the new derivatives (19b and 20a-b) showed similar values for inhibition of cellular growth and direct enzymatic inhibition (MICs 0.5-2 μg/mL). Compounds 29-34 with larger ester and ether groups containing substituted aromatic rings at R3 exhibited slightly reduced activity (MICs 2-16 μg/mL). One explanation for this attenuated activity could be encroachment of the extended R3 into the neighboring NADPH co-factor. These results indicate that modest additions to the central ring oxygen atoms are well tolerated, while larger modifications have the potential to act as dual-site inhibitors of dihydrofolate reductase (DHFR).
Efficient oxidation of arylmethylene compounds using nano-MnO2
Nammalwar, Baskar,Fortenberry, Chelsea,Bunce, Richard A.,Lageshetty, Sathish Kumar,Ausman, Kevin D.
, p. 2010 - 2013 (2013/04/10)
Nano-MnO2 has been developed as an efficient and mild reagent for the high-yield oxidation of arylmethylene compounds to the corresponding aldehydes and ketones as well as benzylic ethers to esters. The reagent is conveniently prepared and shows reactivity superior to synthetic (Attenburrow) MnO2 and commercial MnO2 under both microwave and conventional conditions. Typical reactions are performed using 25 wt % of nano-MnO2 relative to the substrate, and the reagent can be recycled up to six times without significant loss of activity. The observed conversions correlate well with surface-water content in the different MnO2 samples, as determined by thermogravimetric analysis.
