194039-66-2Relevant academic research and scientific papers
NH insertion reactions catalyzed by reusable water-soluble ruthenium(II)-hm-phenyloxazoline complex
Abu-Elfotoh, Abdel-Moneim
, p. 4750 - 4754 (2017)
A water-soluble Ru(II)-hm-pheox complex was efficiently catalyzed NH insertion of EDA with a broad class of amine derivatives in water/ether biphasic medium to deliver the biologically active precursors α-aminoester products with excellent yields (up to >99%). The products were separated by decantation and the catalyst was washed and reused several times (at least 8 times) without any specific loss of its catalytic activity. The plausible mechanism of the reaction was explained. Additionally, In case of ethylene diamine, the NH insertion product could be transformed to biological active piperazinone compound in high yield. The asymmetric version of this catalytic reaction is under investigation.
Polymer-supported ruthenium(II)/phenyloxazoline complex: Reusable and highly selective catalyst for N-H insertion reactions
Abu-Elfotoh, Abdel-Moneim
, p. 349 - 352 (2017/01/24)
A group of functionalized β-amino esters were successfully synthesized in excellent yields (> 99 %) via NH-insertion of ethyldiazoacetate into various amines catalyzed by porous-polymer-supported ruthenium(II)-pheox catalyst. The catalyst was readily recovered and reused at least five times without loss of its catalytic activity.
Quinones synthesis via hydrogen peroxide oxidation of dihydroxy arenes catalyzed by homogeneous and macroporous-polymer-supported ruthenium catalysts
Abu-Elfotoh, Abdel-Moneim,Tsuzuki, Kazuyuki,Nguyen, Tram Bao,Chanthamath, Soda,Shibatomi, Kazutaka,Iwasa, Seiji
, p. 8612 - 8617 (2013/09/12)
Ruthenium(II)/dimethyl phenyloxazoline (Ru(II)/dm-Pheox) complex 2a and its macroporous-polymeric-catalyst 4 were found to be very rapid and efficient catalysts in the hydrogen peroxide oxidation of 1,2- and 1,4-dihydroxy arenes. Most of the quinone products were delivered in 99% yield. The polymeric-catalyst 4 could be reused at least five times.
Nonclassical 2,4-diamino-5-aryl-6-ethylpyrimidine antifolates: Activity as inhibitors of dihydrofolate reductase from Pneumocystis carinii and Toxoplasma gondii and as antitumor agents
Robson, Claire,Meek, Michelle A.,Grunwaldt, Jan-Dierk,Lambert, Peter A.,Queener, Sherry F.,Schmidt, Dirk,Griffin, Roger J.
, p. 3040 - 3048 (2007/10/03)
Twelve novel 2,4-diamino-5-(4'-benzylamino)- and 2,4-diamino-5-[4'-(N- methylbenzylamino)-3'-nitrophenyl]-6-ethylpyrimidines bearing 4-substituents on the benzylamino or N-methylbenzylamino aryl ring were synthesized and evaluated as nonclassical inhibitors of Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase (DHFR). Compounds were prepared by reaction of 2,4-diamino-5-(4'-chloro-3'-nitrophenyl)-(8) or 2,4-diamino-5-(4'-fluoro-3'- nitrophenyl)-6-ethylpyrimidine (15) with the appropriate 4-substituted (CO2H, CO2Me, SO2NH2, dioxolan-2-yl, CHO, dimethyloxazolin-2-yl) benzylamine or N-methylbenzylamine derivative. Compounds 25-29 were synthesized from 2,4-diamino-5-{4'-[N-(4''-carboxybenzyl)amino]-3'- nitrophenyl}-6-ethylpyrimidine (10) and the corresponding amine (NH3, MeNH2, Me2NH, piperidine, diethyl L-glutamate) via isobutyl mixed anhydride coupling; hydrolysis of the diethyl L-glutamate 29 afforded the L-glutamate analogue 30. The compounds exhibited potent inhibitory activity against T. gondii (IC50 values 0.0018-0.14 μM) and rat liver (IC50 values 0.0029- 0.27 μM) DHFR, with a 4-substituent invariably enhancing binding to both enzymes relative to the unsubstituted benzoprim (5) or methylbenzoprim (6). Modest selectivity for T. gondii enzyme was observed with several analogues, whereas all of the compounds were relatively weak inhibitors of P. carinii DHFR and exhibited no selectivity. Selected analogues were evaluated for in vivo antitumor activity against the methotrexate-resistant M5076 murine reticulosarcoma, with 2,4-diamino-5-{4'-[N-[4''-(N'- methylcarbamoyl)benzyl]-N-methylamino]-3'-nitrophenyl}-6-ethylpyrimidine (14) (K(i) for rat liver DHFR = 0.000 35 ± 0.000 29 nM) combining significant antitumor activity with minimal toxicity.
