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Thematische Bibliographien / Purine (2,6-diamino) / Zeitschriftenartikel

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Zeitschriftenartikel zum Thema „Purine (2,6-diamino)“

Autor: Grafiati

Veröffentlicht am 4. Juni 2021

Zuletzt aktualisiert am 17. Februar 2022

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1

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.

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(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*

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2

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.

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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 diisopropoxyphospho

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3

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.

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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 h

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4

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.

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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 corr

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5

Bosco, Bartolomeo, Andrea Defant, Andrea Messina, et al. "Synthesis of 2,6-Diamino-Substituted Purine Derivatives and Evaluation of Cell Cycle Arrest in Breast and Colorectal Cancer Cells." Molecules 23, no. 8 (2018): 1996. http://dx.doi.org/10.3390/molecules23081996.

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Reversine is a potent antitumor 2,6-diamino-substituted purine acting as an Aurora kinases inhibitor and interfering with cancer cell cycle progression. In this study we describe three reversine-related molecules, designed by docking calculation, that present structural modifications in the diamino units at positions 2 and 6. We investigated the conformations of the most stable prototropic tautomers of one of these molecules, the N6-cyclohexyl-N6-methyl-N2-phenyl-7H-purine-2,6-diamine (3), by Density Functional Theory (DFT) calculation in the gas phase, water and chloroform, the last solvent c

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6

Elbert, Tomáš, Petra Břehová, and Antonín Holý. "The preparation of 3H-labeled acyclic nucleoside phosphonates and study of their stability." Collection of Czechoslovak Chemical Communications 75, no. 7 (2010): 757–66. http://dx.doi.org/10.1135/cccc2010020.

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9-(2-Phosphonomethoxyethyl)-2,6-diamino-[8-3H]purine (4), 9-(2-phosphonomethoxyethyl)-[8-3H]guanine (6) and (R)-9-(2-phosphonomethoxypropyl)-[8-3H]adenine (11) with specific activities of 10.9, 7.9 and 16 Ci/mmol, respectively, were prepared by a catalytic dehalogenation of the corresponding 8-bromo derivatives 1, 2 and 9. The rate of the exchange of the tritium label on C-8 of the purine ring in title compounds with the hydrogen of water under physiological pH at 20 °C was studied using 3H NMR. The loss of 3H-label attained 7% in [8-3H]tenofovir (11), 10% in [8-3H]PMEDAP (4) and 12% in [8-3H]

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7

Alaoui, A. M. El, A. Faraj, C. Pierra та ін. "Inhibition of Hepatitis B Virus Replication by Nucleoside Enantiomers of β-2′,3′-Dideoxypurine Analogues". Antiviral Chemistry and Chemotherapy 7, № 5 (1996): 276–80. http://dx.doi.org/10.1177/095632029600700508.

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Various purine β-L-2′,3′-dideoxynucleoside analogues with both sugar and base modifications including β-L-ddG, β-L-ddl, β-L-ddA, 2′-azido-β-L-araddA, 2′-amino-β-L-araddA, 2′,5′-anhydro-β-L-araddA, 2′-azido-β-L-ddA, 2′-amino-β-L-ddA, 2′-fluoro-β-L-ddA, 3′-azido-β-L-ddA, 3′-amino-β-L-ddA, 3′-fluoro-β-L-ddA, 2,6-diamino-β-L-2′,3′-dideoxyfuranosylpurine, 6-cyclopropylamino-β-L-ddA, 2′-azido-6-N-triphenylphosphine-β-L-araddA, 2-amino-6-methylamino-β-L-2′,3′-dideoxyfuranosylpurine, 2-amino-6-cyclopropylamino-β-L-2′,3′-dideoxyfuranosylpurine, 2-amino-6-cyclopentylamino-β-L-2′,3′-dideoxyfuranosylpurin

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8

Schinkmanová, Markéta, Ivan Votruba, Riri Shibata, et al. "Human N6-Methyl-AMP/DAMP Aminohydrolase (Abacavir 5'-Monophosphate Deaminase) is Capable of Metabolizing N6-Substituted Purine Acyclic Nucleoside Phosphonates." Collection of Czechoslovak Chemical Communications 73, no. 2 (2008): 275–91. http://dx.doi.org/10.1135/cccc20080275.

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Recombinant human abacavir monophosphate deaminase (hABC-MP deaminase) was compared with the recently described ratN6-methyl-AMP (meAMP) aminohydrolase. hABC-MP deaminase, a 42 kDa polypeptide, exists predominantly as a monomer under non-denaturing conditions. Similar to the rat enzyme, hABC-MP deaminase efficiently catalyzes the hydrolytic deamination of natural substrates meAMP (5),N6,N6-dimethyl-AMP (13) and medAMP (6). Acyclic nucleoside phosphonate (ANP)N6-cyclopropyl-2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (cPrPMEDAP) (1), an intermediate intracellular metabolite of antileukemic

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9

Naesens, L., L. Lenaerts, G. Andrei, et al. "Antiadenovirus Activities of Several Classes of Nucleoside and Nucleotide Analogues." Antimicrobial Agents and Chemotherapy 49, no. 3 (2005): 1010–16. http://dx.doi.org/10.1128/aac.49.3.1010-1016.2005.

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ABSTRACT The absence of any formally licensed antiadenovirus drugs and the increasing incidence of life-threatening adenovirus infections in immunosuppressed patients warrant the development of effective antiadenovirus compounds. A detailed study was performed on the antiadenovirus activities of several classes of nucleoside and nucleotide analogues in human embryonic lung fibroblast cells. The antiadenovirus activities were evaluated by three methods, viz., evaluating the adenoviral cytopathic effect, monitoring cell viability by a colorimetric assay, and real-time PCR quantitation of viral D

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10

Cheng, Heng, Inkyu Hwang, Youhoon Chong, et al. "Synthesis and biological evaluation of N-{4-[5-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-2-(2,2,2-trifluoroacetyl)pentyl]benzoyl}-l-glutamic acid as a potential inhibitor of GAR Tfase and the de novo purine biosynthetic pathway." Bioorganic & Medicinal Chemistry 13, no. 10 (2005): 3593–99. http://dx.doi.org/10.1016/j.bmc.2004.11.049.

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11

Meszárosová, Kateřina, Antonín Holý, and Milena Masojídková. "Synthesis of Acyclic Adenine 8,N-Anhydronucleosides." Collection of Czechoslovak Chemical Communications 65, no. 7 (2000): 1109–25. http://dx.doi.org/10.1135/cccc20001109.

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9-(4-Hydroxybutyl)adenine (10) was obtained by reaction of adenine with 4-[(2-tetrahydropyran-2-yl)oxy]butyl chloride (7) in the presence of DBU. 8-Bromo-9-(4-hydroxybutyl)adenine (13) was prepared by bromination of 10 or by alkylation of 8-bromoadenine (11) with 4-bromoethyl acetate followed by methanolysis. Tosylation of compound 13 afforded the 4-tosyloxy derivative 15 which gave on heating with methylamine or cyclopropylamine 6-methyl- (17a) or 6-cyclopropyl-7,8,9,10-tetrahydro-6H-[1,3]diazepino[1,2-e]purin-4-amine (17b), while the reaction with hydrazine afforded 7,8,9,10-tetrahydro-6H-[1

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12

Kubík, Richard, and Josef Kuthan. "Sterically Crowded Heterocycles. V. Incorporation of Melamine and Adenine Moieties into Imidazo[1,2]heteroaromatic Molecules." Collection of Czechoslovak Chemical Communications 61, no. 5 (1996): 770–73. http://dx.doi.org/10.1135/cccc19960770.

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Melamine and adenine react with 2,4,6-triphenylpyrylium perchlorate to corresponding quaternary pyridinium salts 1 and 2, respectively. Ferricyanide oxidation of salt 1 in alkaline medium gave (Z)-3-(2,4-diamino-7-phenylimidazo[1,2-a][1,3,5]triazin-6-yl]-1,3-diphenylprop-2-en-1-one (3). Analogous oxidation of perchlorate 2 afforded (Z)-3-(8-phenylimidazo[1,2-f]-4H-purin-7-yl)-1,3-diphenylprop-2-en-1-one (5).

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13

Srinivas, K., P. Shanthan Rao, B. Narsaiah, and J. Madhusudana Rao. "ChemInform Abstract: Reactions of 2-Chloro-4,5-diamino-6-methylpyrimidine with 1,3-Diketones - Formation of New Substituted Purines." ChemInform 32, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.200128158.

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14

Chen, Huaping, Sadia Afrin, Yingqiu Guo, et al. "Radiolabeled 6-(2, 3-Dichlorophenyl)-N4-methylpyrimidine-2, 4-diamine (TH287): A Potential Radiotracer for Measuring and Imaging MTH1." International Journal of Molecular Sciences 21, no. 22 (2020): 8860. http://dx.doi.org/10.3390/ijms21228860.

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MTH1 (MutT homolog 1) or NUDT1 (Nudix Hydrolase 1), also known as oxidized purine nucleoside triphosphatase, has potential as a biomarker for monitoring cancer progression and quantifying target engagement for relevant therapies. In this study, we validate one MTH1 inhibitor TH287 as a PET MTH1 radiotracer. TH287 was radiolabeled with tritium and the binding of [3H]TH287 to MTH1 was evaluated in live glioblastoma cells (U251MG) through saturation and competitive binding assays, together with in vitro enzymatic assays. Furthermore, TH287 was radiolabeled with carbon-11 for in vivo microPET stud

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15

Mohammad, Taj, Sagar Batra, Rashmi Dahiya, et al. "Identification of High-Affinity Inhibitors of Cyclin-Dependent Kinase 2 Towards Anticancer Therapy." Molecules 24, no. 24 (2019): 4589. http://dx.doi.org/10.3390/molecules24244589.

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Cyclin-dependent kinase 2 (CDK2) is an essential protein kinase involved in the cell cycle regulation. The abnormal activity of CDK2 is associated with cancer progression and metastasis. Here, we have performed structure-based virtual screening of the PubChem database to identify potent CDK2 inhibitors. First, we retrieved all compounds from the PubChem database having at least 90% structural similarity with the known CDK2 inhibitors. The selected compounds were subjected to structure-based molecular docking studies to investigate their pattern of interaction and estimate their binding affinit

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16

Tutughamiarso, Maya, Guido Wagner, and Ernst Egert. "Cocrystals of 5-fluorocytosine. I. Coformers with fixed hydrogen-bonding sites." Acta Crystallographica Section B Structural Science 68, no. 4 (2012): 431–43. http://dx.doi.org/10.1107/s010876811202561x.

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The antifungal drug 5-fluorocytosine (4-amino-5-fluoro-1,2-dihydropyrimidin-2-one) was cocrystallized with five complementary compounds in order to better understand its drug–receptor interaction. The first two compounds, 2-aminopyrimidine (2-amino-1,3-diazine) and N-acetylcreatinine (N-acetyl-2-amino-1-methyl-5H-imidazol-4-one), exhibit donor–acceptor sites for R 2 2(8) heterodimer formation with 5-fluorocytosine. Such a heterodimer is observed in the cocrystal with 2-aminopyrimidine (I); in contrast, 5-fluorocytosine and N-acetylcreatinine [which forms homodimers in its crystal structure (II

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17

Kewn, Stephen, Laurene H. Wang, Patrick G. Hoggard, et al. "Enzymatic Assay for Measurement of Intracellular DXG Triphosphate Concentrations in Peripheral Blood Mononuclear Cells from Human Immunodeficiency Virus Type 1-Infected Patients." Antimicrobial Agents and Chemotherapy 47, no. 1 (2003): 255–61. http://dx.doi.org/10.1128/aac.47.1.255-261.2003.

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ABSTRACT DXG {[2R-cis]-2-amino-1,9-dihydro-9-[2-[hydroxymethyl]-1,3-dioxolan-4-yl]-6H-purin-6-one} and its prodrug DAPD ([2R-cis]-4-[2,6-diamino-9H-purin-9-yl]-1,3-dioxolane-2-methanol; amdoxovir) are novel 2′,3′-dideoxynucleosides (ddNs) displaying activity against human immunodeficiency virus type 1 (HIV-1). In this paper, we describe the development of an enzymatic assay for determining the intracellular active metabolite of DXG and DAPD, DXG triphosphate (DXGTP), in peripheral blood mononuclear cells (PBMCs) from HIV-infected patients. The assay involves inhibition of HIV reverse transcrip

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