24039-08-5Relevant academic research and scientific papers
Unexpected formation of 4-alkyl-5-(4-alkylthiosemicarbazido)-4,5-dihydro-1, 2,4-triazine-3(2H)-thiones from 1,3-dialkyl-4,5-bis-(4-alkylthiosemicarbazido) imidazolidin-2-ones in acidic medium
Gazieva, Galina A.,Poluboyarov, Pavel A.,Kolotyrkina, Natal'ya G.,Lubuzh, Elena D.,Kravchenko, Angelina N.
, p. 42 - 44 (2014/02/14)
4-Alkyl-5-(4-alkylthiosemicarbazido)-4,5-dihydro-1,2,4-triazine-3(2H) -thiones are obtained either by heating 1,3-dialkyl-4,5-bis-(4- alkylthiosemicarbazido)imidazolidin-2-ones in acidic medium or the reaction of 1,3-dialkyl-4,5-dihydroxyimidazolidin-2-on
Dehydrogenation, oxidative denitration and ring contraction of N,N-dimethyl-5-nitrouracil by a Bacillus nitroreductase Nfr-A1
Cortial, Sylvie,Chaignon, Philippe,Sergent, Didier,Dezard, Sophie,Ouazzani, Jamal
experimental part, p. 1 - 8 (2012/04/17)
Nfr-A1, a Bacillus subtilis nitroreductase, catalyzes the nitroreduction of a large panel of aromatic and heterocyclic nitro compounds, except those belonging to nitrouracil class of molecules. Besides nitroreduction, Nfr-A1 exhibits a strong NADH oxidase activity in the presence of oxygen, leading to high concentration of H2O2 (up to 200 μM). In the presence of (N,N)-dimethyl-5-nitrouracil 1 (dim-NU), Nfr-A1 achieves the reduction of dim-NU double bond to compounds 2 and 3 and in parallel the oxidation of dim-NU to the denitrated five membered derivatives 4 and 5. The reduction is catalyzed by the reduced flavin Fl-Red and resembles those catalyzed by dihydropyrimidine dehydrogenases (DPD), during the catabolism of pyrimidines. The oxidative denitration is catalyzed in part by hydrogen peroxide generated through the NADH-oxidase activity, and certainly by the peroxyflavin intermediate Fl-OOH for the other part. The mechanisms of reaction were proposed according to experimental data and literature. These findings together with our previous results on the potential biological role of Nfr-A1, confirm the large spectrum of catalysis supported by this enzyme. The oxidative denitration is sporadically reported in literature and represents a safe and green alternative for the remediation of nitro-compounds.
Cyclization of 1,3-dialkyl-4,5-bis(1-thiosemicarbazido)-imidazolidin-2- ones(thiones) with aromatic aldehydes
Gazieva, Galina A.,Vasilevskii, Sergei V.,Belyakov, Pavel A.,Nelyubina, Yulia V.,Lubuzh, Elena D.,Kravchenko, Angelina N.
scheme or table, p. 285 - 287 (2011/05/15)
Cyclization of 1,3-dialkyl-4,5-bis(1-thiosemicarbazido)imidazolidin-2- ones(thiones) with aromatic aldehydes under acidic catalysis affords 1,3-dialkyl-4-(arylideneamino)-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H) -ones and 5,7-dialkyltetrahydro-1H-imidazo[4,5-e]-1,2,4-triazine-3,6(2H,4H)- dithiones.
4,5-Dihydroxyimidazolidin-2-ones in α-ureidoalkylation of N-carboxyalkyl-, N-hydroxyalkyl-, and N-(aminoalkyl)ureas 4.* α-Ureidoalkylation of N-(2-acetylaminoethyl)ureas
Gazieva,Lozhkin,Baranov,Kravchenko,Makhova
experimental part, p. 642 - 646 (2011/02/16)
α-Ureidoalkylation of N-(2-acetylaminoethyl)ureas with various 4,5-dihydroxyimidazoli- din-2-ones was systematically studied. Novel N-(2-acetylaminoethyl)glycolurils were obtained. Their yields were found to decrease both when moving from 1,3-H2- to 1,3-Alk2-4,5- dihydroxy- imidazolidin-2-ones and when increasing the size of the substituent at the second N atom in the starting acetylaminoethylurea. The higher yields were achieved with 4,5-diphenyl-4,5- dihydroxyimidazolidin-2-one as the starting compound. 2-(2-Acetylaminoethyl)-4-methylgly- coluril exhibits nootropic activity.
4,5-Dihydroxyimidazolidin-2-ones in a-ureidoalkylation of N-carboxy-, N-hydroxy-, and N-aminoalkylureas 2. α-Ureidoalkylation of N-(hydroxyalkyl)ureas
Kravchenko,Sigachev,Belyakov,Ilyin,Lyssenko,Davankov,Lebedev,Makhova,Tartakovsky
experimental part, p. 1264 - 1269 (2010/10/04)
sThe a-ureidoalkylation of N-(hydroxyalkyl)ureas (ureido alcohols) with 1,3-H3-and 1,3-Me2-4,5-dihydroxyimidazolidin-2-ones was systematically studied. The yields of glycolurils decrease both in going from 1,3-H2-to 1,3-Me2-4,5-dihydroxyimidazolidin-2-one and with increasing length (or with branching) of the hydroxyalkyl chain in ureido alcohols. The optimal reaction time for ureido alcohols is 1 h. The X-ray diffraction study showed that 2-(2-hydroxy-1,1-dimethylethyl)glycoluril crystallizes as a conglomerate. The enantiomeric analysis of 2-(2-hydroxyethyl)glycoluril was carried out by chiral-phase HPLC. ; 2009 Springer Science+Business Media, Inc.
KINETICS AND MECHANISM OF BASE-CATALYZED CYCLIZATION OF SUBSTITUTED AMIDES AND NITRILES OF HYDANTOIC ACID
Machacek, Vladimir,Svobodova, Gabriela,Sterba, Vojeslav
, p. 140 - 155 (2007/10/02)
Rates of base-catalyzed cyclizations of 8 substituted derivatives of hydantoic acid amide type R3-NH(5)-CO(4)-NR2(3)-CH2(2)-CO(1)-NHR1 and 9 nitriles type R3-NH(5)-CO(4)-NR2(3)-CHR1(2)-CN have been measured in aqueous and methanolic media.The cyclization of the amides in aqueous medium is also accompanied by hydrolysis of the hydantoins formed.In some cases the hydrolysis rate constant is greater than the corresponding cyclization reaction rate constant.With the least reactive amides, the cyclization is also accompanied by hydrolysis of the amide group.The ra te of the cyclization reactions in water is higher than that in methanol (at the same concentration of the lyate ions) by the factor of 10 - 100.Substitution of hydrogen at 3 and 5 positions by methyl or phenyl groups causes an acceleration of the cyclization reaction, whereas a substitution in the amide group causes a considerable retardation.The greatest acceleration of the cyclization (by as much as 4 orders) is caused by introduction of phenyl group to the N(5) position, which is due to a substantial increase of concentration of the reactive anion.
