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Giniyatullin, R. Kh.; Mikhailov, A. S.; Семенов, В. Э.; Акамсин, В. Д.; Резник, В. С.; Чернова, А. В.; Doroshkina, G. M.; Nafikova, A. A.; Latypov, Shamil K.; Efremov, Yu. Ya.; Шарафутдинова, Д. Р.; Gubaidullin, А. Т.; Литвинов, И. А.

doi:10.1023/a:1025653328231

Cited by 9 publications

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References 8 publications

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“…Synthesis of Uracilophanes. We have recently reported that the interaction of 1,3-bis(ω-bromoalkyl)-6-methyluracils with 1,3-bis[ω-(ethylamino)alkyl]-6-methyluracils gives a series of isomeric bis(ethylamino)(1,3)uracilophanes with trans - and cis -arrangements of the carbonyl groups at the C(4) atoms of different uracil moieties. − In particular, coupling of dibromide 1a with diamine 2a afforded isomeric uracilophanes 3a ( trans -arrangement of C(4)O) and 3b ( cis -arrangement of C(4)O) which were separated and described in the solid state and in solution. , Herein in the same manner uracilophanes 4a and 4b are synthesized from compounds 1b and 2b (Scheme ). In this case, we did not succeed in isolating individual isomers 4a and 4b and obtained only their mixture.…”

Section: Resultsmentioning

confidence: 99%

“…Water-soluble uracilophane 5 designated as APM-1 was prepared by quaternization of N atoms in bridges of trans -isomer 3a with n -decyl bromide in CH 3 CN according to the established procedure. , The reaction of the 4a and 4b mixture with n -decyl bromide resulted in a mixture of trans- and cis -isomeric uracilophanes 6a and 6b designated as APM-2. Synthesized uracilophanes with quaternary ammonium in the spacers are shown in Scheme .…”

Section: Resultsmentioning

confidence: 99%

“…These reactions imply the formation of isomers which differ from one another by the mutual arrangement of the carbonyl and methyl groups at different pyrimidine rings: cis - and trans -isomers. Compound 2b has been prepared from the reaction of 1,3-bis(5-bromopentyl-1)-5-decyl-6-methyluracil with ethylamine according to the known protocol. , The synthesis of isomeric uracilophanes 3a and 3b and in particular the individual macrocycle 3a with a trans -arrangement of the carbonyl C(4)O group at different uracil moieties was described elsewhere. − In the case of preparation of uracilophanes 4a and 4b we did not succeed in isolating individual geometric isomers of macrocycles and obtained a mixture of macrocycles 4a and 4b with trans - and cis -arrangements of the carbonyl and methyl groups.

2 Synthesis of Uracilophanes …”

Section: Methodsmentioning

confidence: 99%

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Nanoreactors Based on Amphiphilic Uracilophanes: Self-Organization and Reactivity Study

et al. 2007

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New amphiphilic pyrimidinic macrocycles (APMs) with two (APM-1) and three (APM-2) decyl tails have been synthesized by quaternization of the bridged N. Complex examination of the APM-based systems with the help of tensiometry, conductometry, dynamic light scattering, and UV and NMR spectroscopy provides evidence for their aggregation. Calculations based on surface tension isotherms and on packing parameter considerations make it possible to assume a lamellar packing of macrocycles when aggregating. Marked differences in the aggregation behavior of APM-1 and APM-2 have been found. The additives of polyethylenimine (PEI) exert little influence on the critical micelle concentration (cmc) of APM-1, while in the APM-2/PEI systems there occurs a pronounced decrease in the cmc and also a ca. 2-fold decrease in the surface area per molecule. The APM-based assemblies are explored as nanoreactors for the hydrolysis of O-alkyl O-p-nitrophenyl (chloromethyl)phosphonates (alkyl = ethyl, hexyl). The kinetic study reveals a minor rate effect of the APM-1-based systems. In the APM-2-based systems an acceleration of the hydrolysis of both phosphonates occurs as compared to the uncatalyzed process. Within the APM-2 --> APM-2/PEI --> APM-2/PEI/La(III) series, due to the cooperative contributions of the supramolecular, polymer, and homogeneous catalysis, an increase in the catalytic effect is observed from 30 times to 3 orders of magnitude as compared to that of the basic hydrolysis of the substrates.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

2 Synthesis of Uracilophanes …”

Section: Methodsmentioning

confidence: 99%

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Nanoreactors Based on Amphiphilic Uracilophanes: Self-Organization and Reactivity Study

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“…This type of isomerism we described in suffi cient detail by an example of pyrimidinophanes containing two uracyl fragments connected with polymethylene bridges; in particular, the method of identifi cation of individual cis-and transisomers was discussed based on measuring dipole moments [11,12].…”

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Uracyl derivatives functionalized with N-, S-, O-heterocycles

et al. 2011

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Reactions of 1,3-bis(bromopentyl)-5(6)-substituted uracyls with a series of fi ve-membered heterocycles containing in the ring N, S, or O atoms and a mercapto group as a substituent at the carbon atom of the ring afforded uracyl derivatives of acyclic and macrocyclic structure with 2-thiobenzoxazole, 2-thio-5-methyl-1,3,4-thiadiazole, 2-thiobenzimidazole, and 2,5-dithio-1,3,4-thiadiazole fragments. N atoms of benzoxazole and imidazole fragments of compounds obtained undergo alkylation and quaternization with alkyl iodides and alkyl tosylates.Heterocyclic systems, in particular, fi ve-membered systems containing in the ring N, S, O atoms, exhibit a wide range of biological action. Versatile derivatives of fi ve-membered N-, S-, O-heterocycles containing diverse substituents were synthesized and their biological activity was investigated [1-6]. Compounds of three-dimensional architecture of acyclic or macrocyclic structure containing various number of heterocycles connected by some bridges are far less understood. For instance, the derivatives of nucleotide bases, in particular, of uracyls, connected with hydrocarbon bridges with N-, S-, O-heterocycles are very important. It is presumed that uracyl derivatives due to stronger binding with the biotarget may enhance the physiologic effect or even modify the biological activity of a specifi c pharmacophore connected to uracyl, in our case fi ve-membered N-, S-, O-heterocycles [7-9].This report described the synthesis of compounds consisting of 5-or 6-substituted uracyls connected by methylene chains to versatile fi ve-membered heterocycles. To obtain a uniform reaction course we used heterocycles with a mercapto group attached to a carbon atom of the ring.The choice of initial compounds included the possibility to vary the heteroatoms in the heterocycle composition (N, O, S), to have in the heterocycle composition alongside the mercapto group also another reaction center, in particular, an imide function, and to vary the number of mercapto groups in the heterocyclic fragment. As a result the following heterocycles were used: 2-mercaptobenzoxazole (I), 2-mercapto-5-methyl-1,3,4-thiadiazole (II), 2-mercaptobenzimidazole (III), and 2,5-dimercapto-1,3,4-thiadiazole (IV). The following uracyl derivatives were applied containing haloalkyl substituents: 1,3-bis(bromopentyl)-6-methyluracyl (V) and 1,3-bis(bromopentyl)-5-bromouracyl (VI). The bromine atom was inserted into the uracyl fragment aiming further to replace it by another substituent, e.g., by amino group.The use of DMF as the solvent and sodium hydride as the salt-forming reagent in the reaction of replacing bromine in the 1,3-bis(bromoalkyl)uracyls with heterocyclic fragment was an approach which had been suffi ciently successful in introducing purine derivatives into the alkylsubstituted uracyls [10].In the reaction of dibromide V with heterocycles I and II at room temperature in DMF in the presence of NaH products of substitution of both Br atoms, compounds VII and VIII, were obtained in 66 and 70% yield respecti...

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Synthesis of Pyrimidinophanes Containing Nitrogen Atoms in Polymethylene Bridges.

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2004

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Cited by 9 publications

References 8 publications

Nanoreactors Based on Amphiphilic Uracilophanes: Self-Organization and Reactivity Study

Nanoreactors Based on Amphiphilic Uracilophanes: Self-Organization and Reactivity Study

Uracyl derivatives functionalized with N-, S-, O-heterocycles

Synthesis of Pyrimidinophanes Containing Nitrogen Atoms in Polymethylene Bridges.

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