Log in

Relevant bibliographies by topics / 2,6,9-trisubstituted purine / Journal articles

To see the other types of publications on this topic, follow the link: 2,6,9-trisubstituted purine.

Journal articles on the topic '2,6,9-trisubstituted purine'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

Create a spot-on reference in APA, MLA, Chicago, Harvard, and other styles

Select a source type:

Consult the top 50 journal articles for your research on the topic '2,6,9-trisubstituted purine.'

Next to every source in the list of references, there is an 'Add to bibliography' button. Press on it, and we will generate automatically the bibliographic reference to the chosen work in the citation style you need: APA, MLA, Harvard, Chicago, Vancouver, etc.

You can also download the full text of the academic publication as pdf and read online its abstract whenever available in the metadata.

Browse journal articles on a wide variety of disciplines and organise your bibliography correctly.

1

Franěk, František, Věra Siglerová, Libor Havlíček, Miroslav Strnad, Tomáš Eckschlager, and Evžen Weigl. "Effect of the Purine Derivative Myoseverin and of Its Analogues on Cultured Hybridoma Cells." Collection of Czechoslovak Chemical Communications 67, no. 2 (2002): 257–66. http://dx.doi.org/10.1135/cccc20020257.

Full text

Abstract:

Two 2,6,9-trisubstituted purine derivatives, 9-isopropyl-2,6-bis[(4-methoxybenzyl)amino]-9H-purine (myoseverin, PMYO, 1) and 9-isopropyl-2,6-bis[(2-methoxybenzyl)amino]-9H-purine (OMYO, 2), and two 6,9-disubstituted derivatives, 9-isopropyl-6-[(4-methoxybenzyl)amino]-9H-purine (3) and 9-isopropyl-6-[(2-methoxybenzyl)amino]-9H-purine (4), were synthesized with the aim to examine their cell proliferation inhibiting activity, and possible additional effects in cultures of hybridoma cells producing monoclonal antibody. The substances were tested over a concentration range from 0.003 to 30 μmol l-1. The most active compound 1 caused a total loss of cell viability at 1 μmol l-1, while its isomer 2 showed the same effect at 10 μmol l-1 concentration. In the presence of compound 1, but not of compound 2, the character of the cell cycle phases profile changed dramatically, most cells being arrested in the G2/M phase. At intermediate concentrations of compound 2 a substantially higher viable cell concentration was observed, relative to control. These differences demonstrated the principal significance of the position of the methoxy groups on the benzene rings for the biological effect. The 6,9-disubstituted derivatives 3 and 4 were without significant effect in the whole range of concentrations tested. The enhancement of monoclonal antibody production, observed in certain concentration intervals of added substances, was of marginal character.

APA, Harvard, Vancouver, ISO, and other styles

2

Mazumdar, Pooja Anjali, Amit Kumar Das, Anne Kristin Bakkestuen, Lise-Lotte Gundersen, and Valerio Bertolasi. "9-(2-Phenylethyl)-6-(2-thienyl)-9H-purine." Acta Crystallographica Section E Structure Reports Online 57, no. 11 (October 13, 2001): o1052—o1054. http://dx.doi.org/10.1107/s1600536801016907.

Full text

APA, Harvard, Vancouver, ISO, and other styles

3

Wang, Ning-Yu, Mei Deng, Yong Xia, and Luo-Ting Yu. "6-Chloro-9-(2-nitrophenylsulfonyl)-9H-purine." Acta Crystallographica Section E Structure Reports Online 67, no. 3 (February 23, 2011): o687. http://dx.doi.org/10.1107/s1600536811003102.

Full text

APA, Harvard, Vancouver, ISO, and other styles

4

Belyakov, Sergey, Martins Ikaunieks, and Marina Madre. "9-(2-Acetoxyethoxymethyl)-2-formamido-6-(p-tolylsulfonyloxy)purine." Acta Crystallographica Section E Structure Reports Online 61, no. 10 (September 28, 2005): o3452—o3454. http://dx.doi.org/10.1107/s1600536805030175.

Full text

APA, Harvard, Vancouver, ISO, and other styles

5

Hřebabecký, Hubert, Milena Masojídková, and Antonín Holý. "Synthesis of Racemic 9-(6- and 2,6-Substituted 9H-Purin-9-yl)-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols, Novel Conformationally Locked Carbocyclic Nucleosides." Collection of Czechoslovak Chemical Communications 70, no. 1 (2005): 103–23. http://dx.doi.org/10.1135/cccc20050103.

Full text

Abstract:

(1R*,3R*,6R*,7S*,9S*)- and (1R*,3R*,6R*,7S*,9R*)-9-Amino-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols (16aand17a) were prepared from 2-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2-methanol (10) in five easy steps. The amines16aand17awere used to construct 6-chloro-9H-purine20and21, 2-amino-6-chloro-9H-purine30and31, and 6-chloro-8-methyl-9H-purine analogues34and35. Ammonolysis of these compounds led to 6-amino-9H-purine22aand23a, 2,6-diamino-9H-purine32and33, and 6-amino-8-methyl-9H-purine derivatives of 5-oxatricyclo[4.2.1.03,7]nonane-3-methanol36and37. (1R*,3R*,6R*,7S*,9S*)- and (1R*,3R*,6R*,7S*,9R*)-9-[6-(Dimethylamino)-9H-purin-9-yl]-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols (22band23b), and (1R*,3R*,6R*,7S*,9S*)- and (1R*,3R*,6R*,7S*,9R*)-9-[6-(cyclopropylamino)-9H-purin-9-yl]-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols (22cand23c) were prepared by aminolysis of20and21.

APA, Harvard, Vancouver, ISO, and other styles

6

Brændvang, Morten, and Lise-Lotte Gundersen. "2-Chloro-6-(2-furyl)-9-(4-methoxybenzyl)-9H-purine." Acta Crystallographica Section C Crystal Structure Communications 63, no. 5 (April 14, 2007): o274—o276. http://dx.doi.org/10.1107/s0108270107011596.

Full text

APA, Harvard, Vancouver, ISO, and other styles

7

Hocek, Michal, Milena Masojídková, Antonín Holý, Graciela Andrei, Robert Snoeck, Jan Balzarini, and Erik De Clercq. "Synthesis and Antiviral Activity of Acyclic Nucleotide Analogues Derived from 6-(Aminomethyl)purines and Purine-6-carboxamidines." Collection of Czechoslovak Chemical Communications 61, no. 10 (1996): 1525–37. http://dx.doi.org/10.1135/cccc19961525.

Full text

Abstract:

The synthesis of a series of 9-(2-phosphonomethoxyalkyl) derivatives of 6-(aminomethyl)purine 11, 2-amino-6-(aminomethyl)purine 12 and purine-6-carboxamidine 14 is reported. The 6-cyanopurines 1 and 2 were selectively alkylated with 2-[bis(isopropyloxy)phosphonylmethoxy]alkyl synthons 3 and 4 at the 9-position. Catalytic hydrogenation of the obtained 9-{2-[bis(isopropyloxy)phosphonylmethoxy]alkyl}-6-cyanopurines 9 and 10 followed by treatment with bromotrimethylsilane afforded the title compounds 11 and 12. Analogous acyclic nucleotides derived from purine-6-carboxamidines 14 were prepared from the cyanopurines 9a and 10a by treatment with sodium methoxide and ammonium chloride followed by deprotection. Compounds 11 and 12 exhibited moderate activity (MIC50 = 3-50 μg/ml) against herpes simplex virus type 1, varicella-zoster virus and Moloney murine sarcoma virus in vitro.

APA, Harvard, Vancouver, ISO, and other styles

8

Yi, Xiu-Guang, Chong-Bo Liu, Zi-Sheng Wu, Jun-Hui Chen, and Hui-Liang Wen. "Dimethyl 2-[2-(2-amino-6-chloropurin-9-yl)ethyl]malonate." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 7, 2007): o1113—o1114. http://dx.doi.org/10.1107/s1600536807004552.

Full text

Abstract:

In the title compound, C12H14ClN5O4, the dihedral angles between the purine plane and two methoxycarbonyl planes are 15.806 (19) and 68.818 (18)°. Intermolecular N—H...O and N—H...N hydrogen bonds link molecules into bands along the b axis; they are further aggregated via C—H...O interactions into layers parallel to the ab plane.

APA, Harvard, Vancouver, ISO, and other styles

9

Kelley, James L., and Ed W. McLean. "Synthesis of 9-(2-fluorobenzyl)-6-methylamino-9H-purine." Journal of Heterocyclic Chemistry 23, no. 4 (July 1986): 1189–93. http://dx.doi.org/10.1002/jhet.5570230445.

Full text

APA, Harvard, Vancouver, ISO, and other styles

10

Adebambo, Kassim F., Nicola M. Howarth, and Georgina M. Rosair. "Benzyl 2-amino-6-chloro-9H-purine-9-carboxylate." Acta Crystallographica Section E Structure Reports Online 61, no. 2 (January 29, 2005): o486—o488. http://dx.doi.org/10.1107/s1600536805002047.

Full text

APA, Harvard, Vancouver, ISO, and other styles

11

Štarha, Pavel, Igor Popa, Zdeněk Dvořák, and Zdeněk Trávníček. "6-(3,5-Dimethoxybenzylamino)-9-(oxan-2-yl)-9H-purine." Acta Crystallographica Section E Structure Reports Online 69, no. 4 (March 13, 2013): o533. http://dx.doi.org/10.1107/s1600536813006697.

Full text

APA, Harvard, Vancouver, ISO, and other styles

12

Hariono, Maywan, Habibah A. Wahab, Mei Lan Tan, Mohd Mustaqim Rosli, and Ibrahim Abdul Razak. "9-Benzyl-6-benzylsulfanyl-9H-purin-2-amine." Acta Crystallographica Section E Structure Reports Online 70, no. 3 (February 12, 2014): o288. http://dx.doi.org/10.1107/s1600536814001986.

Full text

Abstract:

In the title compound, C19H17N5S, the dihedral angles between the purine ring system (r.m.s. deviation = 0.009 Å) and the S-bound and methylene-bound phenyl rings are 74.67 (8) and 71.28 (7)°, respectively. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generateR22(8) loops. C—H...N interactions link the dimers into (100) sheets.

APA, Harvard, Vancouver, ISO, and other styles

13

Brændvang, Morten, and Lise-Lotte Gundersen. "6-(2-Benzofuryl)-2-chloro-9-[(4-methoxyphenyl)methyl]-9H-purine." Acta Crystallographica Section E Structure Reports Online 63, no. 6 (May 31, 2007): o3036—o3037. http://dx.doi.org/10.1107/s1600536807022647.

Full text

APA, Harvard, Vancouver, ISO, and other styles

14

Hřebabecký, Hubert, Milena Masojídková, and Antonín Holý. "Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 5,5- and 6,6-Bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol." Collection of Czechoslovak Chemical Communications 70, no. 4 (2005): 519–38. http://dx.doi.org/10.1135/cccc20050519.

Full text

Abstract:

(1R*,2R*,3R*,4S*)-3-Amino-6,6-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (13) was prepared from (bicyclo[2.2.1]hept-5-ene-2,2-diyl)dimethyl dibenzoate (7) viacis-diol8, cyclic sulfate10, and azide12. (1R*,2R*,3S*,4S*)-3-Amino-6,6-bis(hydroxymethyl)bicyclo[2.2.1]-heptan-2-ol (18) and (1R*,2S*,3S*,4S*)-3-amino-5,5-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (19) were obtained by addition of chromyl azide to double bond of7, chromatographic separation, debenzoylation and hydrogenation of resulting azides14and16. The amines13,18, and19were used to build (1R*,2R*,3R*,4S*)- (21a), (1R*,2R*,3S*,4S*)-3-(6-chloro-9H-purin-9-yl)-6,6-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (21b), and (1R*,2S*,3S*,4S*)-3-(6-chloro-9H-purin-9-yl)-5,5-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (21c), respectively. Ammonolysis of these compounds led to 6-amino-9H-purine derivatives22a-22c. 6-(Dimethylamino)-9H-purine analogues23a-23cand 6-(cyclopropylamino)-9H-purine analogues24a-24cwere prepared by aminolysis of21a-21c. Reaction of amines13,18, and19with ethylN-((2E)-3-ethoxymethacryloyl)carbamate afforded thymine derivatives28a-28c.

APA, Harvard, Vancouver, ISO, and other styles

15

Hřebabecký, Hubert, Milena Masojídková, Martin Dračínský, and Antonín Holý. "Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 3-(Hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol." Collection of Czechoslovak Chemical Communications 71, no. 6 (2006): 871–88. http://dx.doi.org/10.1135/cccc20060871.

Full text

Abstract:

(1R*,2R*,3R*,4R*,5R*,6S*)-3-Amino-5-(benzyloxy)-6-(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (18) was prepared in seven easy steps from benzyl (1R*,2S*,3S*,4S*)-3-(benzyloxy)bicyclo[2.2.1]hept-5-ene-2-carboxylate (10). Reaction of amine18with ethylN-((2E)-3-ethoxymethacryloyl)carbamate afforded 1-[(1R*,2R*,3R*,4R*,5S*,6R*)-6-(benzyloxy)-3-hydroxy-5- (hydroxymethyl)bicyclo[2.2.1]heptan-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (21) and after deprotection by transfer hydrogenation, free thymine analogue22. The thymine derivative21was converted to 2,3'-anhydronucleoside26. Treatment of the benzyl derivative18with sodium in liquid ammonia led to amine19, which was used as key intermediate for the construction of (1R*,2R*,3R*,4R*,5R*,6S*)-3-(6-chloro-9H-purin-9-yl)-6-(hydroxymethyl)-bicyclo[2.2.1]heptane-2,5-diol (28) and (1R*,2R*,3R*,4R*,5R*,6S*)-3-(2-amino-6-chloro-9H-purin-9-yl)-6-(hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol (33). Ammonolysis of28led to 6-amino-9H-purine derivative29. 6-(Dimethylamino)-9H-purine analogue30and 6-(cyclopropylamino)-9H-purine analogues31and34were prepared by aminolysis of corresponding chloropurine derivatives.

APA, Harvard, Vancouver, ISO, and other styles

16

Hocek, Michal, Dana Hocková, and Jan Štambaský. "Cytostatic 6-Arylpurine Nucleosides V. Synthesis of 8-Substituted 6-Phenylpurine Ribonucleosides." Collection of Czechoslovak Chemical Communications 68, no. 5 (2003): 837–48. http://dx.doi.org/10.1135/cccc20030837.

Full text

Abstract:

Regioselective Suzuki-Miyaura reaction of 8-bromo-6-iodo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine with phenylboronic acid gave 8-bromo-6-phenylpurine derivative that was used for cross-coupling reactions (with PhB(OH)2, Me3Al, Et3Al, BnZnCl) or nucleophilic substitutions (with NaOH, NaOMe, NH3, NHMe2 or thiourea). A series of 8-X-substituted 6-phenyl-9-(β-D-ribofuranosyl)purines (X = Ph, Me, Et, Bn, OH, OMe, NH2, NMe2, SH) was prepared in this way directly or after deprotection. None of the title nucleosides exhibited any considerable cytostatic activity.

APA, Harvard, Vancouver, ISO, and other styles

17

SORIANO-GARCÍA, Manuel, Carlos Rojas AVELLANEDA, and Gerardo AGUIRRE-HERNÁNDEZ. "Crystal Structure of 6-Benzylamino-9-[2-tetrahydropyranyl]-9H-purine." Analytical Sciences 19, no. 9 (2003): 1343–44. http://dx.doi.org/10.2116/analsci.19.1343.

Full text

APA, Harvard, Vancouver, ISO, and other styles

18

Novotná, Radka, and Zdeněk Trávníček. "2-Chloro-6-[(2,4-dimethoxybenzyl)amino]-9-isopropyl-9H-purine." Acta Crystallographica Section E Structure Reports Online 69, no. 3 (February 16, 2013): o390. http://dx.doi.org/10.1107/s1600536813004121.

Full text

APA, Harvard, Vancouver, ISO, and other styles

19

Krečmerová, Marcela, Milena Masojídková, and Antonín Holý. "Synthesis of N9- and N7-[2-Hydroxy-3-(phosphonomethoxy)propyl] Derivatives of N6-Substituted Adenines, 2,6-Diaminopurines and Related Compounds." Collection of Czechoslovak Chemical Communications 69, no. 10 (2004): 1889–913. http://dx.doi.org/10.1135/cccc20041889.

Full text

Abstract:

Base-catalyzed reactions of diethyl [(oxiranylmethoxy)methyl]phosphonate (2) with purine bases (adenine, 2,6-diaminopurine, 6-chloropurine and 2-amino-6-chloropurine) gave corresponding 9- or 7-[2-hydroxy-3-(phosphonomethoxy)propyl] purines. The adenine and 2,6-diaminopurine derivatives cyclize to cyclic phosphonates 4 and 6. The 9-[2-hydroxy-3-(phosphonomethoxy)propyl] derivatives of N6-substituted adenine and 2,6-diaminopurine (15-27) were prepared by the treatment of diethyl {[3-(6-chloropurin-9-yl)-2-hydroxypropoxy]methyl}phosphonate (11) or diethyl {[3-(2-amino-6-chloropurin-9-yl)-2-hydroxypropoxy]methyl}phosphonate (13) with primary or secondary amines. The reaction of 6-chloro- or 2-amino-6-chloropurine derivatives (11, 13) with thiourea gave the corresponding diethyl purine-6-thiol or 2-aminopurine-6-thiol phosphonates 47, 48. The guanine derivative 49 was prepared by the treatment of compound 13 with 80% acetic acid. All diethyl phosphonates were transformed to free phosphonic acids (31-43, 50-52) by the action of bromotrimethylsilane and subsequent hydrolysis.

APA, Harvard, Vancouver, ISO, and other styles

20

Lin, Xiaoyu, and Morris J. Robins. "Nucleic Acid Related Compounds. 136. Synthesis of 2-Amino- and 2,6-Diaminopurine Derivatives via Inverse-Electron-Demand Diels-Alder Reactions." Collection of Czechoslovak Chemical Communications 71, no. 7 (2006): 1029–41. http://dx.doi.org/10.1135/cccc20061029.

Full text

Abstract:

Thermal inverse-electron-demand Diels-Alder reactions of 5-aminoimidazoles and 2,4,6-tris(ethoxycarbonyl)-1,3,5-triazine (2) with spontaneous retro-Diels-Alder loss of ethyl cyanoformate and elimination of ammonia give 2,6-bis(ethoxycarbonyl)purines. A report that selective alkaline hydrolysis followed by acid-catalyzed decarboxylation gave 6-(ethoxycarbonyl)purine products was not in harmony with known reactions in purine chemistry. Our reinvestigation has shown that the 6-(ethoxycarbonyl) group undergoes preferential base-promoted hydrolysis, as expected, but regioselectivity for attack of hydroxide at the carbonyl group at C6 is not high (relative to hydrolysis of both C2 and C6 esters). The structure of 9-benzyl-2-(ethoxycarbonyl)purine was determined by X-ray crystallography and confirmed by Curtius rearrangement of the azidocarbonyl analogue to give 2-amino-6-benzylpurine. Acid-catalyzed decarboxylation of the 2,6-dicarboxylate formed during hydrolysis gave 9-benzylpurine, and Curtius rearrangement of 2,6-bis(azidocarbonyl)-9-benzylpurine gave 2,6-diamino-9-benzylpurine. Attempted applications of inverse-electron-demand Diels-Alder reactions of 2 with nucleoside derivatives were problematic.

APA, Harvard, Vancouver, ISO, and other styles

21

Gomes, Lígia R., John Nicolson Low, Diogo Magalhães e Silva, Fernando Cagide, and Fernanda Borges. "Crystal structures of five 6-mercaptopurine derivatives." Acta Crystallographica Section E Crystallographic Communications 72, no. 3 (February 10, 2016): 307–13. http://dx.doi.org/10.1107/s2056989016001833.

Full text

Abstract:

The crystal structures of five 6-mercaptopurine derivatives,viz.2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(3-methoxyphenyl)ethan-1-one (1), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-methoxyphenyl)ethan-1-one (2), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-chlorophenyl)ethan-1-one (3), C15H11ClN4O2S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-bromophenyl)ethan-1-one (4), C15H11BrN4O2S, and 1-(3-methoxyphenyl)-2-[(9H-purin-6-yl)sulfanyl]ethan-1-one (5), C14H12N4O2S. Compounds (2), (3) and (4) are isomorphous and accordingly their molecular and supramolecular structures are similar. An analysis of the dihedral angles between the purine and exocyclic phenyl rings show that the molecules of (1) and (5) are essentially planar but that in the case of the three isomorphous compounds (2), (3) and (4), these rings are twisted by a dihedral angle of approximately 38°. With the exception of (1) all molecules are linked by weak C—H...O hydrogen bonds in their crystals. There is π–π stacking in all compounds. A Cambridge Structural Database search revealed the existence of 11 deposited compounds containing the 1-phenyl-2-sulfanylethanone scaffold; of these, only eight have a cyclic ring as substituent, the majority of these being heterocycles.

APA, Harvard, Vancouver, ISO, and other styles

22

Ellsworth, Robert L., Henry T. Meriwether, and Holly E. Mertel. "Synthesis of 9-[(2-chloro-6-fluorophenyl) [14C]methyl]-9H-purine-6-amine (arprinocid) and 9-[(2,6-dichlorophenyl) [14C]methyl]-9H-purine-6-amine." Journal of Labelled Compounds and Radiopharmaceuticals 27, no. 11 (November 1989): 1229–41. http://dx.doi.org/10.1002/jlcr.2580271102.

Full text

APA, Harvard, Vancouver, ISO, and other styles

23

Balcells, J., J. A. Guada, C. Castrillo, and J. Gasa. "Urinary excretion of allantoin and allantoin precursors by sheep after different rates of purine infusion into the duodenum." Journal of Agricultural Science 116, no. 2 (April 1991): 309–17. http://dx.doi.org/10.1017/s002185960007773x.

Full text

Abstract:

SUMMARYTwo experiments were carried out to determine endogenous losses and the response of urinary purine derivatives to increased duodenal inputs of purine bases. Four ewes each fitted with a re-entrant cannula at the proximal duodenum, and conventionally fed, were subjected to full replacement of duodenal digesta followed by the administration of a solution either free of purines (Expt 1) or enriched with increasing amounts of purines, to supply 0·48–21·27 mmol/animal per day (Expt 2). Basal daily urinary excretions of allantoin, uric acid, hypoxanthine and xanthine were 11·5 ± 0·94, 9·9 ± 0·67, 6·9 ± 0·46 and 1·2 ±0·16 mg/kg W0·75. Allantoin was the only purine derivative which increased in response to incremental inputs of duodenal purines. The relationship between allantoin excretion and infused purines showed a urinary recovery of 0·8 for purines infused at > 220 μmol/kg W0·76. Lower rates of infusion did not alter allantoin excretion. The results show urinary allantoin to be a useful index to estimate duodenal input of purines when animals are fed close to or above their energy maintenance requirements.

APA, Harvard, Vancouver, ISO, and other styles

24

Hřebabecký, Hubert, Martin Dračínský, and Antonín Holý. "Synthesis of Novel Carbocyclic Nucleoside Analogues Containing Bicyclo[2.2.1]hept-2-ene-2-methanol." Collection of Czechoslovak Chemical Communications 73, no. 1 (2008): 44–58. http://dx.doi.org/10.1135/cccc20080044.

Full text

Abstract:

Starting ethyl (1R*,2R*,3R*,4S*)-3-bromobicyclo[2.2.1]hept-5-ene-2-carboxylate (9) was reduced with LiAlH4and benzoylated giving [(1R*,2R*,3R*,4S*)-3-bromobicyclo[2.2.1]hept-5-en-2-yl]methyl benzoate (11). Treatment of11with NaN3and CrO3in acetic acid afforded [(1R*,2S*,3R*,4R*,5S*,6R*)-6-azido-3-bromo-5-hydroxybicyclo[2.2.1]hept-2-yl]methyl benzoate (12a) and [(1R*,2S*,3S*,4R*,5S*,6R*)-5-azido-3-bromo-6-hydroxybicyclo[2.2.1]heptan-2-yl]-methyl benzoate (12b). These key intermediates were separated and converted in five reaction steps to (1R*,2R*,3S*,4S*)-3-[(5-amino-6-chloropyrimidin-4-yl)amino]-5-(hydroxymethyl)- bicyclo[2.2.1]hept-5-en-2-ol (17a) and (1R*,2R*,3S*,4S*)-3-[(5-amino-6-chloropyrimidin-4-yl)- amino]-6-(hydroxymethyl)bicyclo[2.2.1]hept-5-en-2-ol (17b). Ring closure with triethyl orthoformate led to (1R*,2R*,3S*,4S*)-5-(chloromethyl)-3-(6-chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-5-en-2-ol (18a) and (1R*,2R*,3S*,4S*)-6-(chloromethyl)-3-(6-chloro-9H-purin-9-yl)- bicyclo[2.2.1]hept-5-en-2-ol (18b) using hydrochloric acid as a catalyst or (1R*,2R*,3S*,4S*)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)bicyclo[2.2.1]hept-5-en-2-ol (19a) and (1R*,2R*,3S*,4S*)- 3-(6-chloro-9H-purin-9-yl)-6-(hydroxymethyl)bicyclo[2.2.1]hept-5-en-2-ol (19b) using trifluoro- acetic acid as a catalyst. From19aand19b, 6-amino- and 6-(cyclopropylamino)purine derivatives20and21were prepared.

APA, Harvard, Vancouver, ISO, and other styles

25

Šála, Michal, Hubert Hřebabecký, Milena Masojídková, and Antonín Holý. "Synthesis of Novel Racemic Conformationally Locked Carbocyclic Nucleosides Derived from 7-Substituted Bicyclo[2.2.1]hept-5-ene-2,2-dimethanols." Collection of Czechoslovak Chemical Communications 71, no. 5 (2006): 635–49. http://dx.doi.org/10.1135/cccc20060635.

Full text

Abstract:

(1R*,4R*,7S*)-7-Aminobicyclo[2.2.1]hept-5-ene-2,2-dimethanol (15) was prepared in four easy steps from bicyclo[2.2.1]hept-5-ene-2,2-dimethanol (10). Reaction of amine 15 with ethyl N-((E)-3-ethoxymethacryloyl)carbamate afforded thymine derivatives 17a. The amine 15 was used to construct 6-chloro-9H-purine derivative 19a, 2-amino-6-chloro-9H-purine derivative 22a. Ammonolysis of 19a led to the adenine derivative 20a. Treatment of 22a with trifluoroacetic acid afforded guanine nucleoside 23a. (1R*,4R*,7S*)-7-[6-(Cyclopropylamino)-9H-purin-9-yl]bicyclo[2.2.1]hept-5-ene-2,2-dimethanol (21a) and (1R*,4R*,7S*)-7-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]bicyclo[2.2.1]hept-5-ene-2,2-dimethanol (24a) were prepared by aminolysis of 19a and 22a. Saturated nucleosides 17b, 20b, 21b, 23b, 24b were obtained by hydrogenation on palladium catalyst.

APA, Harvard, Vancouver, ISO, and other styles

26

Hořejší, Kateřina, Radek Pohl, and Antonín Holý. "Tricyclic Purine Analogs Derived from 2-Amino-6-chloropurine and 2,6-Diaminopurine and Their Methylated Quaternary Salts." Collection of Czechoslovak Chemical Communications 71, no. 1 (2006): 77–90. http://dx.doi.org/10.1135/cccc20060077.

Full text

Abstract:

A novel series of tricyclic, etheno-bridged purine analogs was sythesized from 2-amino-6-(substituted amino)-9-methylpurines by cyclization with chloroacetaldehyde, with particular focus on the regioselectivity of the cyclization reaction and fluorescence properties. The analogs as well as the starting purines were alkylated with iodomethane, affording a new class of quaternary salts with potential biological activity. Neither significant fluorescence nor cytostatic effect was found.

APA, Harvard, Vancouver, ISO, and other styles

27

Herdewijn, P., A. Van Aerschot, and W. Pfleiderer. "Synthesis of 2-Amino-6-acetamidomethyl-9-(β-D-ribofuranosyl) purine." Synthesis 1989, no. 12 (1989): 961–62. http://dx.doi.org/10.1055/s-1989-27448.

Full text

APA, Harvard, Vancouver, ISO, and other styles

28

Lundvall, Fredrik, Jindrich Kania, and Lise-Lotte Gundersen. "(E)-9-(But-2-en-1-yl)-6-chloro-9H-purine." Acta Crystallographica Section E Structure Reports Online 69, no. 6 (May 11, 2013): o849. http://dx.doi.org/10.1107/s1600536813010416.

Full text

APA, Harvard, Vancouver, ISO, and other styles

29

Zhao, Guobao, Xinhua He, and Bohua Zhong. "Diisopropyl {[(R)-2-(2-amino-6-chloro-9H-purin-9-yl)-1-methylethoxy]methyl}phosphonate." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (March 3, 2012): o936. http://dx.doi.org/10.1107/s1600536812006757.

Full text

Abstract:

In the title compound, C15H25ClN5O4P, the r.m.s. deviation for the purine ring system is 0.0165 Å. The coordination about the P atom is a distorted tetrahedron [O=P—O angles = 116.70 (6) and 109.87 (6)°]. In the crystal, molecules are linked by N—H...O hydrogen bonds, generating a three-dimensional network.

APA, Harvard, Vancouver, ISO, and other styles

30

O. Salas, Cristian, Ana Maria Zarate, Vladimir Kryštof, Jaime Mella, Mario Faundez, Jose Brea, María Isabel Loza, et al. "Promising 2,6,9-Trisubstituted Purine Derivatives for Anticancer Compounds: Synthesis, 3D-QSAR, and Preliminary Biological Assays." International Journal of Molecular Sciences 21, no. 1 (December 25, 2019): 161. http://dx.doi.org/10.3390/ijms21010161.

Full text

Abstract:

We designed, synthesized, and evaluated novel 2,6,9-trisubstituted purine derivatives for their prospective role as antitumor compounds. Using simple and efficient methodologies, 31 compounds were obtained. We tested these compounds in vitro to draw conclusions about their cell toxicity on seven cancer cells lines and one non-neoplastic cell line. Structural requirements for antitumor activity on two different cancer cell lines were analyzed with SAR and 3D-QSAR. The 3D-QSAR models showed that steric properties could better explain the cytotoxicity of compounds than electronic properties (70% and 30% of contribution, respectively). From this analysis, we concluded that an arylpiperazinyl system connected at position 6 of the purine ring is beneficial for cytotoxic activity, while the use of bulky systems at position C-2 of the purine is not favorable. Compound 7h was found to be an effective potential agent when compared with a currently marketed drug, cisplatin, in four out of the seven cancer cell lines tested. Compound 7h showed the highest potency, unprecedented selectivity, and complied with all the Lipinski rules. Finally, it was demonstrated that 7h induced apoptosis and caused cell cycle arrest at the S-phase on HL-60 cells. Our study suggests that substitution in the purine core by arylpiperidine moiety is essential to obtain derivatives with potential anticancer activity.

APA, Harvard, Vancouver, ISO, and other styles

31

Kelley, James L., J. W. T. Selway, and Howard J. Schaeffer. "Purine Acyclic Nucleosides. 6-Dimethylamino-9-[(2-phenylalanylamido-1-substituted-ethoxy)methyl]purines as Candidate Antivirals." Journal of Pharmaceutical Sciences 74, no. 12 (December 1985): 1302–4. http://dx.doi.org/10.1002/jps.2600741211.

Full text

APA, Harvard, Vancouver, ISO, and other styles

32

Šála, Michal, Hubert Hřebabecký, Martin Dračínský, Milena Masojídková, Armando M. De Palma, Johan Neyts, and Antonín Holý. "Synthesis of novel racemic carbocyclic nucleosides derived from 5,6-disubstituted norbornene." Collection of Czechoslovak Chemical Communications 75, no. 1 (November 28, 2009): 1–20. http://dx.doi.org/10.1135/cccc2009116.

Full text

Abstract:

Novel class of the carbocyclic nucleosides based on bicyclo[2.2.1]heptene/heptane was prepared by two approaches. Thymine analogues were synthesized starting from methyl (1R*,4S*)-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate1by Michael addition of the thymine salt to the double bond as the key step. The yield and ratio of the isomers of this reaction depended on the used base (DBU, K2CO3). Purine nucleoside analogues were synthesized by the linear synthesis, the purine nucleobase was build-up on the amino group. The amino groups (exo/endoconfiguration) were introduced to the scaffold by the Curtius rearrangement. Norbornene analogues were converted to saturated andcis-hydroxylated nucleoside derivatives. [(1R*,2S*,3S*,4S*)-3-(6-Chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-5-en-2-yl]methanol (13a) and [(1R*,2R*,3R*,4S*)-3-(6-chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-5-en-2-yl]methanol (13b) showed moderate activity againstCoxsackievirus CVB3.

APA, Harvard, Vancouver, ISO, and other styles

33

Kelley, James L., and Francis E. Soroko. "9-(2-Fluorobenzyl)-6-(methylamino)-9H-purine hydrochloride. Synthesis and anticonvulsant activity." Journal of Medicinal Chemistry 29, no. 7 (July 1986): 1133–34. http://dx.doi.org/10.1021/jm00157a003.

Full text

APA, Harvard, Vancouver, ISO, and other styles

34

Rouchal, Michal, Marek Nečas, and Robert Vícha. "(1-Adamantyl){4-[(2-chloro-9-isopropyl-9H-purin-6-yl)aminomethyl]phenyl}methanone trichloromethane solvate." Acta Crystallographica Section E Structure Reports Online 65, no. 6 (May 14, 2009): o1268. http://dx.doi.org/10.1107/s1600536809016596.

Full text

Abstract:

In the title compound, C26H30ClN5O·CHCl3, the purine molecule consists of essentially planar benzene and purine ring systems [maximum deviation 0.010 (4) Å for both ring systems] forming a dihedral angle of 85.52 (9)°. Intermolecular N—H...N hydrogen bonds link adjacent molecules into centrosymmetric dimers. The structure also contains intermolecular C—H...O and C—H...N interactions. The benzene rings form offset face-to-face π–π stacking interactions with an interplanar distance of 3.541 (4) Å and a centroid-to-centroid distance of 4.022 (4) Å.

APA, Harvard, Vancouver, ISO, and other styles

35

Šišuļins, Andrejs, Jonas Bucevičius, Yu-Ting Tseng, Irina Novosjolova, Kaspars Traskovskis, Ērika Bizdēna, Huan-Tsung Chang, Sigitas Tumkevičius, and Māris Turks. "Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines." Beilstein Journal of Organic Chemistry 15 (February 15, 2019): 474–89. http://dx.doi.org/10.3762/bjoc.15.41.

Full text

Abstract:

The synthesis of novel fluorescent N(9)-alkylated 2-amino-6-triazolylpurine and 7-deazapurine derivatives is described. A new C(2)-regioselectivity in the nucleophilic aromatic substitution reactions of 9-alkylated-2,6-diazidopurines and 7-deazapurines with secondary amines has been disclosed. The obtained intermediates, 9-alkylated-2-amino-6-azido-(7-deaza)purines, were transformed into the title compounds by CuAAC reaction. The designed compounds belong to the push–pull systems and possess promising fluorescence properties with quantum yields in the range from 28% to 60% in acetonitrile solution. Due to electron-withdrawing properties of purine and 7-deazapurine heterocycles, which were additionally extended by triazole moieties, the compounds with electron-donating groups showed intramolecular charge transfer character (ICT/TICT) of the excited states which was proved by solvatochromic dynamics and supported by DFT calculations. In the 7-deazapurine series this led to increased fluorescence quantum yield (74%) in THF solution. The compounds exhibit low cytotoxicity and as such are useful for the cell labelling studies in the future.

APA, Harvard, Vancouver, ISO, and other styles

36

Yaseen, Ayat, Muhammad Murtaza Hassan, Edward Lee-Ruff, and Gerald F. Audette. "Crystal structures of the synthetic intermediate 3-[(6-chloro-7H-purin-7-yl)methyl]cyclobutan-1-one, and of two oxetanocin derivatives: 3-[(6-chloro-8,9-dihydro-7H-purin-7-yl)methyl]cyclobutan-1-ol and 3-[(6-chloro-9H-purin-9-yl)methyl]cyclobutan-1-ol." Acta Crystallographica Section E Crystallographic Communications 75, no. 6 (May 3, 2019): 732–37. http://dx.doi.org/10.1107/s2056989019004432.

Full text

Abstract:

The crystal structures of an intermediate, C10H9ClN4O, 3-[(6-chloro-7H-purin-7-yl)methyl]cyclobutan-1-one (I), and two N-7 and N-9 regioisomeric oxetanocin nucleoside analogs, C10H13ClN4O, 3-[(6-chloro-8,9-dihydro-7H-purin-7-yl)methyl]cyclobutan-1-ol (II) and C10H11ClN4O, 3-[(6-chloro-9H-purin-9-yl)methyl]cyclobutan-1-ol (IV), are reported. The crystal structures of the nucleoside analogs confirmed the reduction of the N-7- and N-9-substituted cyclobutanones with LiAl(OtBu)3 to occur with facial selectivity, yielding cis-nucleosides analogs similar to those found in nature. Reduction of the purine ring of the N-7 cyclobutanone to a dihydropurine was observed for compound (II) but not for the purine ring of the N-9 cyclobutanone on formation of compound (IV). In the crystal of (I), molecules are linked by a weak Cl...O interaction, forming a 21 helix along [010]. The helices are linked by offset π–π interactions [intercentroid distance = 3.498 (1) Å], forming layers parallel to (101). In the crystal of (II), molecules are linked by pairs of O—H...N hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. The dimers are linked by O—H...N hydrogen bonds, forming chains along [001], which in turn are linked by C—H...π and offset π–π interactions [intercentroid distance = 3.509 (1) Å], forming slabs parallel to the ac plane. In the crystal of (IV), molecules are linked by O—H...N hydrogen bonds, forming chains along [101]. The chains are linked by C—H...N and C—H...O hydrogen bonds and C—H...π and offset π–π interactions [intercentroid distance = 3.364 (1) Å], forming a supramolecular framework.

APA, Harvard, Vancouver, ISO, and other styles

37

Lisgarten, J. N., and R. A. Palmer. "Structure of 9-(2-fluorobenzyl)-6-methylamino-9H-purine hydrochloride, a novel anticonvulsant." Acta Crystallographica Section C Crystal Structure Communications 44, no. 4 (April 15, 1988): 654–57. http://dx.doi.org/10.1107/s0108270187012071.

Full text

APA, Harvard, Vancouver, ISO, and other styles

38

Anderson-McKay, Janet E., Gerald W. Both, and Gregory W. Simpson. "Stereoselective Synthesis of 6-Methyl-9-(2-Deoxy-β-D-Erythro-Pentofuranosyl)purine." Nucleosides and Nucleotides 15, no. 7-8 (July 1996): 1307–13. http://dx.doi.org/10.1080/07328319608002431.

Full text

APA, Harvard, Vancouver, ISO, and other styles

39

Holý, Antonín, Ivan Rosenberg, and Hana Dvořáková. "Synthesis of N-(2-phosphonylmethoxyethyl) derivatives of heterocyclic bases." Collection of Czechoslovak Chemical Communications 54, no. 8 (1989): 2190–210. http://dx.doi.org/10.1135/cccc19892190.

Full text

Abstract:

The preparation of N-(2-phosphonylmethoxyethyl) derivatives of purine and pyrimidine bases, IV, as analogs of the antiviral 9-(2-phosphonylmethoxyethyl)adenine (PMEA, I), is described. The synthesis consists in alkylation of alkali metal salts of heterocyclic bases or their N- or O-substituted derivatives with diethyl 2-p-toluenesulfonyloxyethoxymethylphosphonate (IIa), 2-chloroethoxymethylphosphonate (IIb) or 2-bromoethoxymethylphosphonate (IIc). The obtained N-(2-diethoxyphosphonylmethoxyethyl) derivatives of heterocyclic bases (III) were treated with bromotrimethylsilane to give phosphonic acids IV. Compounds IV were prepared from pyrimidines (uracil, cytosine and their 5-methyl derivatives), purines (adenine and its N6- and C(2)-substituted derivatives, hypoxanthine, guanine, 6-hydrazinopurine and 6-methylthiopurine etc.) and their analogs (3-deazaadenine etc.).

APA, Harvard, Vancouver, ISO, and other styles

40

Šimo, Ondrej, Alfonz Rybár, and Juraj Alföldi. "Synthesis of 4-Alkyl- or 4-Phenyl-7-methyl-1,2-dihydro-7H-imidazo[1,2,3-cd]purine-6,8-diones." Collection of Czechoslovak Chemical Communications 63, no. 3 (1998): 407–15. http://dx.doi.org/10.1135/cccc19980407.

Full text

Abstract:

New 4-alkyl- or 4-phenyl-7-methyl-1,2-dihydro-7H-imidazo[1,2,3-cd]purine-6,8-diones 1 were obtained by intramolecular alkylation of 8-alkyl- or 8-phenyl-9-(2-mesyloxyethyl)-1-methyl-9H-purine-2,6(1H,3H)-diones 5. The necessary compounds 5 were prepared from 6-[(2-hydroxyethyl)- amino]-3-methyl-5-nitrosopyrimidine-2,4(1H,3H)-dione (2), which was hydrogenated to 5-amino-6-[(2-hydroxyethyl)amino]-3-methyl derivative 3; consecutive reactions of the latter with an orthocarboxylate and mesyl chloride afforded 8-alkyl- or 8-phenyl-9-(2-hydroxyethyl)-1-methyl-9H-purine- 2,6(1H,3H)-diones 4 and compounds 5, respectively.

APA, Harvard, Vancouver, ISO, and other styles

41

Hoque, Kazi Mirajul, Linxi Chen, George P. H. Leung, and Chung-Ming Tse. "A purine-selective nucleobase/nucleoside transporter in PK15NTD cells." American Journal of Physiology-Regulatory, Integrative and Comparative Physiology 294, no. 6 (June 2008): R1988—R1995. http://dx.doi.org/10.1152/ajpregu.00016.2008.

Full text

Abstract:

Nucleoside and nucleobase transporters are important for salvage of purines and pyrimidines and for transport of their analog drugs into cells. However, the pathways for nucleobase translocation in mammalian cells are not well characterized. We identified an Na-independent purine-selective nucleobase/nucleoside transport system in the nucleoside transporter-deficient PK15NTD cells. This transport system has 1,000-fold higher affinity for nucleobases than nucleosides with Kmvalues of 2.5 ± 0.7 μM for [3H]adenine, 6.4 ± 0.5 μM for [3H]guanine, 1.1 ± 0.1 mM for [3H]guanosine, and 4.2 ± 0.5 mM [3H]adenosine. The uptake of [3H]guanine (0.05 μM) was inhibited by other nucleobases and nucleobase analog drugs (at 0.5–1 mM in the order of potency): 6-mercaptopurine = thioguanine = guanine > adenine >>> thymine = fluorouracil = uracil. Cytosine and methylcytosine had no effect. Nucleoside analog drugs with modification at 2′ and/or 5 positions (all at 1 mM) were more potent than adenosine in competing the uptake of [3H]guanine: 2-chloro-2′-deoxyadenosine > 2-chloroadenosine > 2′3′-dideoxyadenosine = 2′-deoxyadenosine > 5-deoxyadenosine > adenosine. 2-Chloro-2′-deoxyadenosine and 2-chloroadenosine inhibited [3H]guanine uptake with IC50values of 68 ± 5 and 99 ± 10 μM, respectively. The nucleobase/nucleoside transporter was resistant to nitrobenzylthioinosine {6-[(4-nitrobenzyl) thiol]-9-β-d-ribofuranosylpurine}, dipyridamole, and dilazep, but was inhibited by papaverine, the organic cation transporter inhibitor decynium-22 (IC50of ∼1 μM), and by acidic pH (pH = 5.5). In conclusion, we have identified a mammalian purine-selective nucleobase/nucleoside transporter with high affinity for purine nucleobases. This transporter is potentially important for transporting naturally occurring purines and purine analog drugs into cells.

APA, Harvard, Vancouver, ISO, and other styles

42

Holý, Antonín, Ivan Votruba, Eva Tloušťová, and Milena Masojídková. "Synthesis and Cytostatic Activity of N-[2-(Phosphonomethoxy)alkyl] Derivatives of N6-Substituted Adenines, 2,6-Diaminopurines and Related Compounds." Collection of Czechoslovak Chemical Communications 66, no. 10 (2001): 1545–92. http://dx.doi.org/10.1135/cccc20011545.

Full text

Abstract:

N6-Substituted adenine and 2,6-diaminopurine derivatives of 9-[2-(phosphonomethoxy)- ethyl] (PME), 9-[(R)-2-(phosphonomethoxy)propyl] [(R)-PMP] and enantiomeric (S)-PMP series were synthesized by reactions of primary or secondary amines with 6-chloro-9-{[2-(diisopropoxyphosphoryl)methoxy]alkyl}purines (26-28) or 2-amino-6-chloro-9-{[2-(diisopropoxy- phosphoryl)methoxy]alkyl}purines (29-31) followed by treatment of the diester intermediates32with bromo(trimethyl)silane and hydrolysis. Diesters32were also obtained by reaction ofN6-substituted purines with synthons23-25bearing diisopropoxyphosphoryl group. Alkylation of 2-amino-6-chloropurine (9) with diethyl [2-(2-chloroethoxy)ethyl]phosphonate (148) gave the diester149which was analogously converted toN6-substituted 2,6-diamino- 9-[2-(2-phosphonoethoxy)ethyl]purines151-153. Alkylation ofN6-substituted 2,6-diaminopurines with (R)-[(trityloxy)methyl]oxirane (155) followed by reaction of thus-obtained intermediates156with dimethylformamide dimethylacetal and condensation with diisopropyl [(tosyloxy)methyl]phosphonate (158) followed by deprotection of the intermediates159gaveN6-substituted 2,6-diamino-9-[(S)-3-hydroxy-2-(phosphonomethoxy)propyl]purines160-163. The highest cytostatic activityin vitrowas exhibited by the followingN6-derivatives of 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP): 2,2,2-trifluoroethyl (53), allyl (54), [(2-dimethylamino)ethyl] (68), cyclopropyl (75) and dimethyl (91). In CCRF-CEM cells, the cyclopropyl derivative75is deaminated to the guanine derivative PMEG (3) which is then converted to its diphosphate.

APA, Harvard, Vancouver, ISO, and other styles

43

Česnek, Michal, Milena Masojídková, Antonín Holý, Veronika Šolínová, Dušan Koval, and Václav Kašička. "Synthesis and Properties of 2-Guanidinopurines." Collection of Czechoslovak Chemical Communications 71, no. 9 (2006): 1303–19. http://dx.doi.org/10.1135/cccc20061303.

Full text

Abstract:

2-Guanidinopurines were prepared as derivatives of 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]-9H-purine (PMEDAP) (1), which shows an important antiviral activity. It completes earlier described synthesis of 6-guanidinopurine derivatives. The title compounds were obtained by the reaction of the corresponding 2-chloropurines with guanidine. 2- And 6-guanidinopurines were used as model compounds for determination of dissociation constants (pKa) of their ionogenic groups by capillary zone electrophoresis. The pKa values of ionogenic groups of the above compounds were compared with those of the corresponding aminopurines. The pKa of guanidino group at the purine moiety varies from 7.77 to 10.32. There is no protonation of N1-position in contrast to aminopurines. None of these compounds showed any antiviral activity.

APA, Harvard, Vancouver, ISO, and other styles

44

Milad, Hashemi Seyyed, Yahyazadeh Asieh, and Nami Navabeh. "Synthesis of Novel 6-Cyano-9-(aryl)-9H-purine Derivatives Via Formamidine Intermediates." E-Journal of Chemistry 9, no. 1 (2012): 219–23. http://dx.doi.org/10.1155/2012/762641.

Full text

Abstract:

Novel 9-substituted cyanopurine derivatives (4a-d) were synthesized in three steps in high yield. Diaminomaleonitrile (1) reacted with triethyl orthoformate to afford (Z)-N-[2-amino-1,2-dicyanovinyl] formimidate (2) which was converted to aryl-(Z)-N-[2-amino-1,2-dicyanovinyl] formamidines (3a-d) in the presence of a catalytic amount of anilinium chloride and aromatic amines in ethanol at room temperature under inert atmosphere (Argon). Furthermore, the reaction of (3a-d) with triethyl orthoformate afforded novel 6-cyano-9-(aryl)-9H-purine derivatives (4a-d) which can be used without further purification. All compounds have been fully characterized by spectroscopic data.

APA, Harvard, Vancouver, ISO, and other styles

45

Rhee, Hakjune, Won Kim, and Hyangdug Kim. "An Efficient Synthesis of (±)-cis-2-Amino-6-hydroxy-9-[4'-hydroxyethyl-2'-cyclopenten-1'-yl]purine." HETEROCYCLES 53, no. 1 (2000): 219. http://dx.doi.org/10.3987/com-99-8740.

Full text

APA, Harvard, Vancouver, ISO, and other styles

46

Capretta, Alfredo, Howard N. Hunter, Christopher S. Frampton, and Russell A. Bell. "Synthesis, NMR spectroscopy, and crystal structure of [9](N6,9)-6-aminopurinophane." Canadian Journal of Chemistry 71, no. 1 (January 1, 1993): 96–106. http://dx.doi.org/10.1139/v93-014.

Full text

Abstract:

[9](N6,9)-6-Aminopurinophane, 9, was synthesized by Mitsunobu coupling of 9-azidononanol, 5, and 6-chloropurine, 6. Reduction of the azide allowed for intramolecular nucleophilic displacement of chloride by the resultant amine and cyclization to the cyclophane. Variable temperature proton NMR showed the presence of two conformers below −25 °C separated by an activation barrier having a ΔGc≠ = 50.2 ± 2.5 kJ mol−1. The conformers arose from partial rotation about the C6—N6 bond, with the anti conformation assigned to the major isomer, 9a, and the syn conformation to the minor, 9b. The crystal structure of the [9](N6,9)-6-aminopurinophane, C14H21N5, was determined at 173 K. The crystals are monoclinic, of space group P21/n, with a = 16.941(3) Å, b = 8.512(2) Å, c = 19.300(2) Å, β = 95.90(1)°, V = 2769(1) Å3,Dc = 1.24 g cm−3 Dm = 1.27 g cm−3, for Z = 8, λ(CuKα) = 1.540598 Å. R1 = 0.0364, R2 = 0.0395 for 2846 reflections, ((R1) = 0.0319, R2 = 0.0365 for 2556 reflections with 1 > 2.5σ(I)). The purine ring shows small but significant distortions from planarity. The N(1)—C(6)—N(6)—C(1′) fragment adopts an anti conformation, which is twisted by approximately 35° from the plane of the purine ring, and the exocyclic 6-nitrogen is partially pyramidalized. Such pyramidalization is consistent with the Bader–Wiberg theory of barriers to rotation about bonds.

APA, Harvard, Vancouver, ISO, and other styles

47

Trávníček, Zdeněk, and Pavel Štarha. "trans-Dichloridobis{2-chloro-6-[(3-fluorobenzyl)amino]-9-isopropyl-9H-purine-κN7}platinum(II)." Acta Crystallographica Section E Structure Reports Online 69, no. 6 (May 18, 2013): m331. http://dx.doi.org/10.1107/s1600536813013202.

Full text

APA, Harvard, Vancouver, ISO, and other styles

48

ANDERSON-MCKAY, J. E., G. W. BOTH, and G. W. SIMPSON. "ChemInform Abstract: Stereoselective Synthesis of 6-Methyl-9-(2-deoxy-β-D-erythro- pentofuranosyl)purine." ChemInform 27, no. 47 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199647238.

Full text

APA, Harvard, Vancouver, ISO, and other styles

49

Hřebabecký, Hubert, Milena Masojídková, and Antonín Holý. "Synthesis of Purine Nucleoside Analogues Derived from Carbocyclic 5-C-(Hydroxymethyl)hexopyranoses." Collection of Czechoslovak Chemical Communications 69, no. 2 (2004): 435–52. http://dx.doi.org/10.1135/cccc20040435.

Full text

Abstract:

(1R,2R,3R,4S)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol (1) was converted to (3aS,4R,5S,7aR)-4-(benzyloxy)-2-oxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ4-1,3,2-benzodioxathiol-5-ol (3) and subsequently to (3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ4-1,3,2-benzodioxathiol-5-yl benzoate (4). Treatment of sulfate 4 with adenine and DBU afforded, after deprotection, 7 and 22 in low yields. Reaction of sulfite 3 with lithium azide gave (1R,2R,3S,6S)-6-azido-2-(benzyloxy)-4,4-bis[(trityloxy)methyl]-cyclohexane-1,3-diol (10) and (1S,4R,5S,6S)-5-azido-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]-cyclohexane-1,4-diol (11) which were, after separation, reduced with LAH to (1R,2R,3S,6S)-6-amino-2-(benzyloxy)-4,4-bis[(trityloxy)methyl]cyclohexane-1,3-diol (9) and (1S,4R,5S,6S)-5-amino-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexane-1,4-diol (12). Amino derivatives 9 and 12 were transformed to (1R,2R,3S,6S)-6-(6-amino-9H-purin-9-yl)-4,4-bis(hydroxymethyl)cyclohexane-1,2,3-triol (7), (1R,2R,3S,6S)-6-[6-(cyclopropylamino)-9H-purin-9-yl]-4,4- bis(hydroxymethyl)cyclohexane-1,2,3-triol (16), (1S,2S,3S,4R)-3-[6-(cyclopropylamino)-9H-purin-9-yl]-6,6-bis(hydroxymethyl)cyclohexane-1,2,4-triol (20), (1S,2S,3S,4R)-3-(6-amino-9H-purin-9-yl)-6,6-bis(hydroxymethyl)cyclohexane-1,2,4-triol (22), and 2-amino-9-[(1S,2R,3R,4S)- 2,3,4-trihydroxy-5,5-bis(hydroxymethyl)cyclohexyl]-9H-purin-6(1H)-one (27).

APA, Harvard, Vancouver, ISO, and other styles

50

Kim, Dae-Kee, Namkyu Lee, Guang-Jin Im, Hun-Taek Kim, and Key H. Kim. "Synthesis and evaluation of 2-amino-6-fluoro-9-(2-hydroxyethoxymethyl)purine esters as potential prodrugs of acyclovir." Bioorganic & Medicinal Chemistry 6, no. 12 (December 1998): 2525–30. http://dx.doi.org/10.1016/s0968-0896(98)80026-6.

Full text

APA, Harvard, Vancouver, ISO, and other styles

We offer discounts on all premium plans for authors whose works are included in thematic literature selections. Contact us to get a unique promo code!