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Journal articles on the topic 'Purine compounds'

Author: Grafiati

Published: 7 September 2021

Last updated: 29 July 2025

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1

Hasník, Zbyněk, Radek Pohl, Blanka Klepetářová, and Michal Hocek. "Synthesis of (purin-6-yl)acetates and their transformations to 6-(2-hydroxyethyl)- and 6-(carbamoylmethyl)purines." Collection of Czechoslovak Chemical Communications 74, no. 7-8 (2009): 1035–59. http://dx.doi.org/10.1135/cccc2009042.

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A novel approach to the synthesis of (purin-6-yl)acetates was developed based on Pd-catalyzed cross-coupling reactions of 6-chloropurines with a Reformatsky reagent. Their reduction with NaBH4 and treatment with MnO2 gave 6-(2-hydroxyethyl)purines, while reactions with amines in presence of NaCN afforded 6-(carbamoylmethyl)purines. Mesylation of the 6-(2-hydroxyethyl)purines followed by nucleophilic substitutions gave rise to several 6-(2-substituted ethyl)purines. This methodology was successfully applied to the synthesis of substituted purine bases and nucleosides for cytostatic and antivira

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2

Almeida, Catarina, Márcia C. Neves, and Mara G. Freire. "Towards the Use of Adsorption Methods for the Removal of Purines from Beer." Molecules 26, no. 21 (2021): 6460. http://dx.doi.org/10.3390/molecules26216460.

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Beer corresponds to a fermented alcoholic beverage composed of several components, including purine compounds. These molecules, when ingested by humans, can be catabolized into uric acid, contributing to uric acid’s level increase in serum, which may lead to hyperuricemia and gout. To assure a proper management of this disease, physicians recommend restrictive dietary measures, particularly by avoiding the consumption of beer. Therefore, it is of relevance to develop efficient methods to remove purine compounds from alcoholic beverages such as beer. In this review, we provide an introduction o

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3

Ziganshin, A. U., and L. E. Ziganshina. "Prospects for clinical use of agents acting on ATP receptors - P2-purinoreceptors." Kazan medical journal 77, no. 2 (1996): 134–36. http://dx.doi.org/10.17816/kazmj104293.

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In addition to the well-known role of purine compounds in cell metabolism, growth, and reproduction, extensive factual material has been accumulated over the past two decades, demonstrating the important role of purines in intercellular interactions. It has been established that a number of physiological and pathophysiological reactions lead to the release of purine compounds (mainly adenosine and adenosine-5'-triphosphoric acid-ATP) by cells, which can interact with special receptors for them, purine receptors. The latter are subdivided into two main classes: PPpurinoreceptors and P2-purinore

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4

Jin, Wei Jun, Hai Rong Zhang, Xin Yang, and Chang Song Liu. "Comparison of Room-Temperature Phosphorescence Properties of Three Purine Compounds with Cadmium Acetate as a Source of Heavy Atom Perturbation." Applied Spectroscopy 49, no. 3 (1995): 320–23. http://dx.doi.org/10.1366/0003702953963481.

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Cadmium acetate salts can greatly enhance room-temperature phosphorescence (RTP) of purine and 6-mercaptopurine. 6-Mercapto-substituent and 6-hydroxy-substituent appear quite different in their effect on the RTP of purine. The effects of cadium salt matrix and pH on the RTP of purine compounds were also investigated in detail. With cadmium acetate as a source of heavy atom perturbation, nanogram or subnanogram amounts of purines can be detected.

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5

Frame, I. J., Emilio F. Merino, Vern L. Schramm, María B. Cassera, and Myles H. Akabas. "Malaria parasite type 4 equilibrative nucleoside transporters (ENT4) are purine transporters with distinct substrate specificity." Biochemical Journal 446, no. 2 (2012): 179–90. http://dx.doi.org/10.1042/bj20112220.

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Malaria, caused by Plasmodia parasites, affects hundreds of millions of people. As purine auxotrophs, Plasmodia use transporters to import host purines for subsequent metabolism by the purine salvage pathway. Thus purine transporters are attractive drug targets. All sequenced Plasmodia genomes encode four ENTs (equilibrative nucleoside transporters). During the pathogenic intraerythrocytic stages, ENT1 is a major route of purine nucleoside/nucleobase transport. Another plasma membrane purine transporter exists because Plasmodium falciparum ENT1-knockout parasites survive at supraphysiological

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6

Kapilinskis, Zigfrīds, Irina Novosjolova, and Māris Turks. "Purine-Furan and Purine-Thiophene Conjugates." Molbank 2018, no. 4 (2018): M1024. http://dx.doi.org/10.3390/m1024.

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Furyl and thienyl moieties were introduced into a purine structure to elevate its fluorescence properties, while a trityl group was used to increase the amorphous properties of the purine compounds. The title compounds were prepared by a sequence involving a Mitsunobu, a SNAr and a Suzuki–Miyaura reaction and their photophysical properties were studied. Quantum yields in the solution reached up to 88% but only up to 5% in the thin layer.

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7

Martinez-Peinado, Nieves, Álvaro Lorente-Macías, Alejandro García-Salguero, et al. "Novel Purine Chemotypes with Activity against Plasmodium falciparum and Trypanosoma cruzi." Pharmaceuticals 14, no. 7 (2021): 638. http://dx.doi.org/10.3390/ph14070638.

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Malaria and Chagas disease, caused by Plasmodium spp. and Trypanosoma cruzi parasites, remain important global health problems. Available treatments for those diseases present several limitations, such as lack of efficacy, toxic side effects, and drug resistance. Thus, new drugs are urgently needed. The discovery of new drugs may be benefited by considering the significant biological differences between hosts and parasites. One of the most striking differences is found in the purine metabolism, because most of the parasites are incapable of de novo purine biosynthesis. Herein, we have analyzed

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8

Enos-Berlage, Jodi L., and Diana M. Downs. "Biosynthesis of the Pyrimidine Moiety of Thiamine Independent of the PurF Enzyme (Phosphoribosylpyrophosphate Amidotransferase) in Salmonella typhimurium: Incorporation of Stable Isotope-Labeled Glycine and Formate." Journal of Bacteriology 181, no. 3 (1999): 841–48. http://dx.doi.org/10.1128/jb.181.3.841-848.1999.

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ABSTRACT Genetic analyses have suggested that the pyrimidine moiety of thiamine can be synthesized independently of the first enzyme of de novo purine synthesis, phosphoribosylpyrophosphate amidotransferase (PurF), in Salmonella typhimurium. To obtain biochemical evidence for and to further define this proposed synthesis, stable isotope labeling experiments were performed with two compounds, [2-13C]glycine and [13C]formate. These compounds are normally incorporated into thiamine pyrophosphate (TPP) via steps in the purine pathway subsequent to PurF. Gas chromatography-mass spectrometry analyse

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9

Gajewska, Danuta, and Natalia Brzezińska. "Assessment of nutrition of adults with hyperuricemia." Biuletyn Głównej Biblioteki Lekarskiej 57, no. 382 (2024): 121–32. https://doi.org/10.2478/bgbl-2024-0011.

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Abstract Introduction. Hyperuricemia is a common problem in clinical practice. According to estimations, it may affect approximately 8.9% to 24.4% of the general population. The results of studies analyzing the effect of the intake of purine compounds from different products on the risk of hyperuricemia are inconsistent. Objective. The assessment of nutrition of adults with hyperuricemia. Material and methods. The study comprised 58 adults, including 43 women and 15 men. The mean age was 54 ± 10.6 years. The study was conducted using a questionnaire method. Dietary intake was assessed through

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10

Logan, Samantha R., Mark Seegobin, R. J. Neil Emery, and Craig R. Brunetti. "Components of the Nucleotide Salvage Pathway Increase Frog Virus 3 (FV3) Replication." Viruses 15, no. 8 (2023): 1716. http://dx.doi.org/10.3390/v15081716.

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Viruses are obligate intracellular parasites that alter host metabolic machinery to obtain energy and macromolecules that are pivotal for replication. Ranavirus, including the type species of the genus frog virus 3 (FV3), represent an ecologically important group of viruses that infect fish, amphibians, and reptiles. It was established that fatty acid synthesis, glucose, and glutamine metabolism exert roles during iridovirus infections; however, no information exists regarding the role of purine metabolism. In this study, we assessed the impact of exogenously applied purines adenine, adenosine

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11

Lin, Shu-Yu, Wen-Chieh Huang, Shwu-Chen Tsay, et al. "6-Chlorocoumarin Conjugates with Nucleobases and Nucleosides as Potent Anti-Hepatitis C Virus Agents." Molecules 30, no. 8 (2025): 1776. https://doi.org/10.3390/molecules30081776.

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On the basis of a “chemo-combination strategy”, (6-chloro)coumarin was incorporated to purines and pyrimidines, as well as their corresponding nucleosides, with a –SCH2– linker at different positions under alkaline conditions. These conjugates were found to exert an antiviral effect on the 1b subgenomic replicon replication of the hepatitis C virus (HCV) in Huh 5-2 and Huh 9-13 cells. In this compound library containing 14 new compounds, 6-[(6′-chlorocoumarin-3′-yl)methylthio]purine, 6-(6′-chlorocoumarin-3′-yl)methylthio-9-(β-D-ribofuranos-1″-yl)purine, and 2-[(6′-chlorocoumarin-3′-yl)methylth

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12

Sebris, Armands, Kaspars Traskovskis, Irina Novosjolova, and Māris Turks. "Synthesis and Photophysical Properties of Purine-Phenoxazine and Purine-Phenothiazine Conjugates." Key Engineering Materials 903 (November 10, 2021): 155–61. http://dx.doi.org/10.4028/www.scientific.net/kem.903.155.

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Electron donating phenoxazine and phenothiazine groups were introduced in an electron deficient purine structure through a benzene ring bridge to facilitate thermally activated delayed fluorescence. Mitsunobu and Suzuki-Miyaura reactions were used to synthesize the target compounds. Photophysical properties of target compounds were explored and quantum yields in the thin layer film reached up to 8 % and in the PMMA doped thin layer film up to 15 %.

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13

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.

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(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*)

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14

Boukhallout, Fath Eddine, Mohamed Dehamchia, Samir Bayou, Chaima Adaika, Abdelhafeez M. A. Mohammed, and Zine Regainia. "Synthesis and biological activity of new imidazo[1,2-c]pyrimidin-5(6H)-one, imidazo[2,1-b]purin-4(5H)-one and imidazo[2,1-i]purine as antioxidant and antibacterial agents." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 34, no. 03 (2024): 421. http://dx.doi.org/10.59467/ijhc.2024.34.421.

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This paper investigates the antioxidant and antibacterial applications of new fusedimidazo[1,2-c]pyrimidin- 5(6H)-one, imidazo[2,1-i]purine,andimidazo[2,1-b]purin-4(5H)-one synthesized by the reaction of a-bromoacetophenone with nucleobases (adenine, guanine, and cytosine). The newly synthesized compounds were structurally confirmed using spectral studies and elemental analysis. All the products were screened for their antioxidant capacity by applying the methods of scavenging free radicals (ABTS and DPPH). The antibacterial activity was examined against three bacterial strains: Pseudomonas ae

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15

Hocek, Michal, Milena Masojídková, Antonín Holý, et al. "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.

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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 fro

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16

Krasnov, Victor P., Olga A. Vozdvizhenskaya, Maria A. Baryshnikova, et al. "Synthesis and Cytotoxic Activity of the Derivatives of N-(Purin-6-yl)aminopolymethylene Carboxylic Acids and Related Compounds." Molecules 28, no. 4 (2023): 1853. http://dx.doi.org/10.3390/molecules28041853.

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Testing a number of N-[omega-(purin-6-yl)aminoalkanoyl] derivatives of 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine in a panel of nine tumor cell lines has shown that the studied compounds exhibit high cytotoxic activity, especially against 4T1 murine mammary carcinoma, COLO201 human colorectal adenocarcinoma, SNU-1 human gastric carcinoma, and HepG2 human hepatocellular carcinoma cells. Synthesis and study of structural analogs of these compounds made it possible to find that the presence of both a difluorobenzoxazine fragment and a purine residue bound via a linker of a certain leng

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17

Verma, P., B. Chauhan, R. Singh, A. K. Gupta, and D. Rani. "In silico study, Synthesis and evaluation purine analogues as potential antimalarial agents." Research Journal of Chemistry and Environment 26, no. 7 (2022): 77–84. http://dx.doi.org/10.25303/2607rjce077084.

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The challenges concerning the control of malaria remain due to the continuous emergence of drug resistant strains. Available treatments for this disease present several limitations such as lack of efficacy, toxic side effects and drug resistance. One of the most striking differences was found in the purine metabolism, because parasites are incapable of de novo purine biosynthesis in which enzyme HGPRT is central to the purine salvage pathway and whose activity is critical for the production of the nucleotides required for DNA/RNA synthesis within this protozoan parasite. Thus, new drugs are ur

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18

Stuer-Lauridsen, Birgitte, and Per Nygaard. "Purine Salvage in Two Halophilic Archaea: Characterization of Salvage Pathways and Isolation of Mutants Resistant to Purine Analogs." Journal of Bacteriology 180, no. 3 (1998): 457–63. http://dx.doi.org/10.1128/jb.180.3.457-463.1998.

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ABSTRACT In exponentially growing cultures of the extreme halophileHalobacterium halobium and the moderate halophileHaloferax volcanii, growth characteristics including intracellular protein levels, RNA content, and nucleotide pool sizes were analyzed. This is the first report on pool sizes of nucleoside triphosphates, NAD, and PRPP (5-phosphoribosyl-α-1-pyrophosphate) in archaea. The presence of a number of salvage and interconversion enzymes was determined by enzymatic assays. The levels varied significantly between the two organisms. The most significant difference was the absence of GMP re

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19

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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20

Areias, Filipe, Carla Correia, Ashly Rocha, et al. "2-Aryladenine Derivatives as a Potent Scaffold for Adenosine Receptor Antagonists: The 6-Morpholino Derivatives." Molecules 29, no. 11 (2024): 2543. http://dx.doi.org/10.3390/molecules29112543.

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A set of 2-aryl-9-H or methyl-6-morpholinopurine derivatives were synthesized and assayed through radioligand binding tests at human A1, A2A, A2B, and A3 adenosine receptor subtypes. Eleven purines showed potent antagonism at A1, A3, dual A1/A2A, A1/A2B, or A1/A3 adenosine receptors. Additionally, three compounds showed high affinity without selectivity for any specific adenosine receptor. The structure-activity relationships were made for this group of new compounds. The 9-methylpurine derivatives were generally less potent but more selective, and the 9H-purine derivatives were more potent bu

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21

Schnitzler, E., M. Kobelnik, G. F. C. Sotelo, G. Bannach, and M. Ionashiro. "Thermoanalytical study of purine derivatives compounds." Eclética Química 29, no. 1 (2004): 71–78. http://dx.doi.org/10.1590/s0100-46702004000100009.

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Thermal methods of analysis are now used in a very large range of scientific investigations. In this work simultaneous thermogravimetry-differential thermal analysis (TG-DTA), X-Ray powder diffractometry and infrared spectroscopy were used to study the derivative compounds of purine, i. e. aminophylline, theophylline, caffeine and uric acid. The results led to informations about the thermal stability and thermal decomposition of these compounds.

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22

Schnitzler, Egon, Marcelo Kobelnik, Gabriel Federico Calle Sotelo, Gilbert Bannach, and Massao Ionashiro. "Thermoanalytical study of purine derivatives compounds." Ecletica Quimica 29, no. 1 (2004): 71–78. http://dx.doi.org/10.26850/1678-4618eqj.v29.1.2004.p71-78.

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Thermal methods of analysis are now used in a very large range of scientific investigations. Inthis work simultaneous thermogravimetry-differential thermal analysis (TG-DTA), X-Ray powderdiffractometry and infrared spectroscopy were used to study the derivative compounds of purine, i. e.aminophylline, theophylline, caffeine and uric acid. The results led to informations about the thermalstability and thermal decomposition of these compounds.

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23

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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24

Zuccarini, Mariachiara, Patricia Giuliani, Francesco Caciagli, Renata Ciccarelli, and Patrizia Di Iorio. "In Search of a Role for Extracellular Purine Enzymes in Bone Function." Biomolecules 11, no. 5 (2021): 679. http://dx.doi.org/10.3390/biom11050679.

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Bone is one of the major tissues that undergoes continuous remodeling throughout life, thus ensuring both organic body growth during development and protection of internal organs as well as repair of trauma during adulthood. Many endogenous substances contribute to bone homeostasis, including purines. Their role has increasingly emerged in recent decades as compounds which, by interacting with specific receptors, can help determine adequate responses of bone cells to physiological or pathological stimuli. Equally, it is recognized that the activity of purines is closely dependent on their inte

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25

Hayallah, Alaa M. "Design, Molecular Modeling and Synthesis of Some New Purine-diones and Pyridopyrimidine-diones with Anticancer Activity." JOURNAL OF ADVANCES IN CHEMISTRY 13, no. 2 (2017): 5959–76. http://dx.doi.org/10.24297/jac.v13i12.6043.

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An olomoucine analogues of 2-[(1-substituted)-2,6-dioxo-2,3,6,7â€“tetrahydro-1H-purin-8-ylsulfanyl]-N-substituted acetamide 6a-g and 7a-g, 1-substituted-8-[2-(4-substituted phenyl)-2-oxoethylsulphanyl]-3,7-dihydro-1H-purine-2,6-diones 9a-g and 10a-g, 3-(2-substituted benzyl)-6-(4-substituted phenyl)-1H-thiazolo[2,3-f]purine-2,4-dione 11a-g and 12a-g and their isosteres 3-substituted benzyl-5-methyl-7-substituted-1H-pyrido[2,3-d]pyrimidine-2,4-dione 13a-c and 14a-c were designed and synthesized. The target compounds 11a-g and 12a-g were prepared by cyclodehydration of 9a-g and 10a-g in PPA, whi

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26

Szupryczyński, Kamil, and Beata Szefler. "Interactions of Nedaplatin with Nucleobases and Purine Alkaloids: Their Role in Cancer Therapy." Biomedicines 13, no. 7 (2025): 1551. https://doi.org/10.3390/biomedicines13071551.

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Background: Nedaplatin is a platinum-based anticancer drug that combines the benefits of Cisplatin and Carboplatin, retaining Cisplatin’s anticancer activity while reducing toxicity similar to Carboplatin. After hydrolysis, Nedaplatin targets purines in DNA and forms cross-links that induce cell death via apoptosis. However, it is important to consider how the presence of other chemical compounds with structural similarities to Adenine or Guanine, such as aromatic, purine, or pyrimidine compounds containing a nitrogen atom with a free electron pair, might influence its activity at the cellular

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27

Bertrand, Jeanluc, Hana Dostálová, Vladimír Kryštof, et al. "Design, Synthesis, In Silico Studies and Inhibitory Activity towards Bcr-Abl, BTK and FLT3-ITD of New 2,6,9-Trisubstituted Purine Derivatives as Potential Agents for the Treatment of Leukaemia." Pharmaceutics 14, no. 6 (2022): 1294. http://dx.doi.org/10.3390/pharmaceutics14061294.

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We report 31 new compounds designed, synthesized and evaluated on Bcr-Abl, BTK and FLT3-ITD as part of our program to develop 2,6,9-trisubstituted purine derivatives as inhibitors of oncogenic kinases. The design was inspired by the chemical structures of well-known kinase inhibitors and our previously developed purine derivatives. The synthesis of these purines was simple and used a microwave reactor for the final step. Kinase assays showed three inhibitors with high selectivity for each protein that were identified: 4f (IC50 = 70 nM for Bcr-Abl), 5j (IC50 = 0.41 μM for BTK) and 5b (IC50 = 0.

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28

Szyk, Piotr, Beata Czarczynska-Goslinska, Dariusz T. Mlynarczyk, et al. "Polymer-Based Nanoparticles as Drug Delivery Systems for Purines of Established Importance in Medicine." Nanomaterials 13, no. 19 (2023): 2647. http://dx.doi.org/10.3390/nano13192647.

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Many purine derivatives are active pharmaceutical ingredients of significant importance in the therapy of autoimmune diseases, cancers, and viral infections. In many cases, their medical use is limited due to unfavorable physicochemical and pharmacokinetic properties. These problems can be overcome by the preparation of the prodrugs of purines or by combining these compounds with nanoparticles. Herein, we aim to review the scientific progress and perspectives for polymer-based nanoparticles as drug delivery systems for purines. Polymeric nanoparticles turned out to have the potential to augmen

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29

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 (2016): 307–13. http://dx.doi.org/10.1107/s2056989016001833.

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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 s

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30

ZINN, R. A., and F. N. OWENS. "A RAPID PROCEDURE FOR PURINE MEASUREMENT AND ITS USE FOR ESTIMATING NET RUMINAL PROTEIN SYNTHESIS." Canadian Journal of Animal Science 66, no. 1 (1986): 157–66. http://dx.doi.org/10.4141/cjas86-017.

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A rapid method for separation and quantitation of purines was applied to ruminal and intestinal digesta for estimating net microbial protein synthesis in the rumen. The procedure combines standard literature methods for hydrolysis of nucleotides by perchloric acid followed by precipitation of free purines with silver nitrate to separate the purines from interfering compounds. Acid resolubilized purines were quantitated spectrophotometrically at 260 nm. Microbial protein was estimated by the ratio of purines to N of isolated bacteria. The procedure is rapid, simple, precise and not costly. Duod

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31

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.

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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 compoun

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32

N., Fernández-Sáez, Campos J.M., E. Camacho M., and Dora Carrión M. "NMR studies of new heterocycles tethered to purine moieties with anticancer activity." Magnetic Resonance in Chemsitry 57 (March 18, 2019): 331–34. https://doi.org/10.1002/mrc.4871.

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This article details the unambiguous structural elucidation of several families of compounds with heterocyclic rings linked to purine residues by one- or two-methylene unit spacers, which have been evaluated as antitumour agents and shown to possess interesting antiproliferative properties, as well as the elucidation of the structures of their predecessor intermediates. The synthesised derivatives combine a six-membered heterocycle condensed with benzene (benzo-1,4-oxazines and tetrahydroquinolines) or a pyridine heterocycle condensed with a 1,4-oxazine (pyridoxazines) attached, in turn, to va

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33

O. Salas, Cristian, Ana Maria Zarate, Vladimir Kryštof, 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 (2019): 161. http://dx.doi.org/10.3390/ijms21010161.

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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%

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34

Kapadiya, Khushal, Kishor Kavadia, Jyoti Gohel, and Ranjan Khunt. "Regioselective synthesis of triazolo[3,4-e]purine derivatives and their anti-cancer activity against NCI-60 cell-lines." Folia Medica 63, no. 2 (2021): 213–20. http://dx.doi.org/10.3897/folmed.63.e52891.

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Introduction: Due to the vast medicinal importance of purine nucleoside, a hybrid molecule of triazole with purine ring might&nbsp;explode a lead molecule in the pharma sector and based on the last decade&rsquo;s studies suggested that the nitrogen-rich molecules possess a wide range of medicinal importance. Aim: Due to the vast application of purine nucleoside itself in the field of cancer research, we synthesized triazolo[3,4-e]purines and screened them for their anti-cancer study against NCI-60 cell lines by the protocol used by NIH. Materials and methods: The targeted molecules, 4-

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35

Krasnov, Victor P., Galina L. Levit, Vera V. Musiyak, Dmitry A. Gruzdev, and Valery N. Charushin. "Fragment-based approach to novel bioactive purine derivatives." Pure and Applied Chemistry 92, no. 8 (2020): 1277–95. http://dx.doi.org/10.1515/pac-2019-1214.

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AbstractUsing purine as a scaffold, the methods for preparation of novel 2-aminopurine and purine derivatives substituted at position C6 by the fragments of natural amino acids, short peptides, and N-heterocycles, including enantiopure ones, have been proposed. The methods for determination of the enantiomeric purity of the obtained chiral compounds have been developed. Conjugates exhibiting high antimycobacterial or anti-herpesvirus activity against both laboratory and multidrug-resistant strains were revealed among the obtained compounds.

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36

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.

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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-hydro

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37

Geant, Pierre-Yves, Jean-Pierre Uttaro, Christian Périgaud, and Christophe Mathé. "Synthesis and Antiviral Evaluation of 3′-Fluoro-5′-norcarbocyclic Nucleoside Phosphonates Bearing Uracil and Cytosine as Potential Antiviral Agents." Molecules 25, no. 16 (2020): 3708. http://dx.doi.org/10.3390/molecules25163708.

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Carbocyclic nucleoside analogues are an essential class of antiviral agents and are commonly used in the treatment of viral diseases (hepatitis B, AIDS). Recently, we reported the racemic synthesis and the anti-human immunodeficiency virus activities (HIV) of 3′-fluoro-5′-norcarbocyclic nucleoside phosphonates bearing purines as heterocyclic base. Based on these results, the corresponding racemic norcarbocyclic nucleoside phosphonates bearing pyrimidine bases were synthesized. The prepared compounds were evaluated against HIV, but none of them showed marked antiviral activity compared to their

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38

Karskela, Tuomas, Karel D. Klika та Harri Lönnberg. "Synthesis of 7-substituted 3-β-D-ribofuranosyl-3H-imidazo[2,1-i]purines". Collection of Czechoslovak Chemical Communications 76, № 8 (2011): 1043–54. http://dx.doi.org/10.1135/cccc2011069.

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A method for the synthesis of 7-substituted 3-β-D-ribofuranosyl-3H-imidazo[2,1-i]purines has been devised whereby compounds were prepared in a few steps from a common intermediate, 3-(2′,3′-O-isopropylidene-β-D-ribofuranosyl)-3H-imidazo[2,1-i]purine-7-carbaldehyde, obtained from the reaction of 2′,3′-O-isopropylideneadenosine with bromomalonaldehyde. The formyl group of the carbaldehyde was subsequently reductively aminated and the resulting secondary amines were then further derivatized either by acylation, lactamization or reductive alkylation.

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39

Takenaga, Naoko, Toshitaka Shoji, Takayuki Menjo, et al. "Nucleophilic Arylation of Halopurines Facilitated by Brønsted Acid in Fluoroalcohol." Molecules 24, no. 21 (2019): 3812. http://dx.doi.org/10.3390/molecules24213812.

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Various aryl-substituted purine derivatives were synthesized through the direct arylation of halopurines with aromatic compounds, facilitated by the combination of triflic acid and fluoroalcohol. This metal-free method is complementary to conventional coupling reactions using metal catalysts and reagents for the syntheses of aryl-substituted purine analogues.

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40

Rouchal, Michal, Jana Rudolfová, Vladimír Kryštof, Veronika Vojáčková, Richard Čmelík та Robert Vícha. "Adamantane-Substituted Purines and Their β-Cyclodextrin Complexes: Synthesis and Biological Activity". International Journal of Molecular Sciences 22, № 23 (2021): 12675. http://dx.doi.org/10.3390/ijms222312675.

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Cyclin-dependent kinases (CDKs) play an important role in the cell-division cycle. Synthetic inhibitors of CDKs are based on 2,6,9-trisubstituted purines and are developed as potential anticancer drugs; however, they have low solubility in water. In this study, we proved that the pharmaco-chemical properties of purine-based inhibitors can be improved by appropriate substitution with the adamantane moiety. We prepared ten new purine derivatives with adamantane skeletons that were linked at position 6 using phenylene spacers of variable geometry and polarity. We demonstrated that the adamantane

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41

Piškor, Martina, Astrid Milić, Sanja Koštrun, et al. "Synthesis, Antiproliferative Activity, and ADME Profiling of Novel Racemic and Optically Pure Aryl-Substituted Purines and Purine Bioisosteres." Biomolecules 15, no. 3 (2025): 351. https://doi.org/10.3390/biom15030351.

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The aim of this study was to synthesize new racemic and optically pure aryl-substituted purine bioisosteres using ultrasound-assisted Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition. Regioselective synthesis of α-azido alcohols was applied to afford heterocycles with a 2-hydroxyeth-1-yl linker. Catalytic asymmetric synthesis using halohydrin dehalogenase in the ring-opening of epoxides gave enantioenriched azido alcohols, which subsequently afforded R- and S-enantiomers of purine and pyrrolo[2,3-d]pyrimidines with a 1-hydroxyeth-2-yl linker. The newly synthesized compounds were evaluated in

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42

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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43

Spinaci, Andrea, Catia Lambertucci, Michela Buccioni, et al. "A2A Adenosine Receptor Antagonists: Are Triazolotriazine and Purine Scaffolds Interchangeable?" Molecules 27, no. 8 (2022): 2386. http://dx.doi.org/10.3390/molecules27082386.

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The A2A adenosine receptor (A2AAR) is one of the four subtypes activated by nucleoside adenosine, and the molecules able to selectively counteract its action are attractive tools for neurodegenerative disorders. In order to find novel A2AAR ligands, two series of compounds based on purine and triazolotriazine scaffolds were synthesized and tested at ARs. Compound 13 was also tested in an in vitro model of neuroinflammation. Some compounds were found to possess high affinity for A2AAR, and it was observed that compound 13 exerted anti-inflammatory properties in microglial cells. Molecular model

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Krasnov, Victor P., Vera V. Musiyak, Galina L. Levit, et al. "Synthesis of Pyrimidine Conjugates with 4-(6-Amino-hexanoyl)-7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and Evaluation of Their Antiviral Activity." Molecules 27, no. 13 (2022): 4236. http://dx.doi.org/10.3390/molecules27134236.

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A series of pyrimidine conjugates containing a fragment of racemic 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and its (S)-enantiomer attached via a 6-aminohexanoyl fragment were synthesized by the reaction of nucleophilic substitution of chlorine in various chloropyrimidines. The structures of the synthesized compounds were confirmed by 1H, 19F, and 13C NMR spectral data. Enantiomeric purity of optically active derivatives was confirmed by chiral HPLC. Antiviral evaluation of the synthesized compounds has shown that the replacement of purine with a pyrimidine fragment leads to a dec

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45

Eakin, A. E., A. Guerra, P. J. Focia, J. Torres-Martinez, and S. P. Craig. "Hypoxanthine phosphoribosyltransferase from Trypanosoma cruzi as a target for structure-based inhibitor design: crystallization and inhibition studies with purine analogs." Antimicrobial Agents and Chemotherapy 41, no. 8 (1997): 1686–92. http://dx.doi.org/10.1128/aac.41.8.1686.

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The hypoxanthine phosphoribosyltransferase (HPRT) from Trypanosoma cruzi is a potential target for enzyme structure-based inhibitor design, based on previous studies which indicate that these parasites lack the metabolic enzymes required for de novo synthesis of purine nucleotides. By using a bacterial complement selection system, 59 purine analogs were assayed for their interaction with the HPRTs from T. cruzi and Homo sapiens. Eight compounds were identified from the bacterial assay to have an affinity for the trypanosomal enzyme. Inhibition constants for four of these compounds against puri

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46

Kapadiya, Khushal M., and Ranjan C. Khunt. "Discovery of Hybrid Purine-quinoline Molecules and Their Cytotoxic Evaluation." Letters in Drug Design & Discovery 16, no. 1 (2018): 21–28. http://dx.doi.org/10.2174/1570180815666180419151742.

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Background: Apart from the “hit drugs”, there are many others being studied for their potent activity against several hostilities. To date, anticancer research has been exploited on the inherent versatility and active core skeleton of the compounds. Literature suggests that nitrogen rich molecules are most active and found in their potent cancer activity. Purine-based compounds such as olomoucine and roscovitine, which contain other heterobicyclic ring systems, are useful for the cell proliferation inhibitors in the treatment of many types of cancer. Methods: We put forward the novel purine ba

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47

Chen, X. B., E. R. Ørskov, and F. D. DeB Hovell. "Excretion of purine derivatives by ruminants: endogenous excretion, differences between cattle and sheep." British Journal of Nutrition 63, no. 1 (1990): 121–29. http://dx.doi.org/10.1079/bjn19900097.

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The endogenous urinary excretion of the purine derivatives allantoin, uric acid and xanthine plus hypoxanthine were measured in twenty-nine lambs, ten cattle (six steers, one cow and three preruminant calves) and four pigs. The sheep and mature cattle were nourished by intragastric infusion and the calves were given a milk-substitute. The pigs were fed on a purine-free diet. The excretion of total purine derivatives was substantially greater by the cattle, being 514 (se 20.6) μmol/kg live weight (W)0·75 per d compared with 168 (se 5·0) μmol/kg W0·75 per d by the sheep and 166 (se 2·6) μmol/kg

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48

Sufrin, J. R., D. Rattendi, A. J. Spiess, S. Lane, C. J. Marasco, and C. J. Bacchi. "Antitrypanosomal activity of purine nucleosides can be enhanced by their conversion to O-acetylated derivatives." Antimicrobial Agents and Chemotherapy 40, no. 11 (1996): 2567–72. http://dx.doi.org/10.1128/aac.40.11.2567.

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Fifteen purine nucleosides and their O-acetylated ester derivatives were examined for in vitro antitrypanosomal activity against the LAB 110 EATRO isolate of Trypanosoma brucei brucei and two clinical isolates of Trypanosoma brucei rhodesiense. Initial comparisons of activity were made for the LAB 110 EATRO isolate. Three nucleoside analogs exhibited no significant activity (50% inhibitory concentrations [IC50s] of > 100 microM), whether they were O acetylated or unacetylated; three nucleosides showed almost equal activity (IC50s of < 5 microM) for the parent compound and the O-acetylate

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Raynaud, Florence I., Peter M. Fischer, Bernard P. Nutley, Phyllis M. Goddard, David P. Lane, and Paul Workman. "Cassette dosing pharmacokinetics of a library of 2,6,9-trisubstituted purine cyclin-dependent kinase 2 inhibitors prepared by parallel synthesis." Molecular Cancer Therapeutics 3, no. 3 (2004): 353–62. http://dx.doi.org/10.1158/1535-7163.353.3.3.

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Abstract Determination of pharmacokinetic properties in the intact animal remains a major bottleneck in drug discovery. Cassette dosing involves administration of a cocktail of drugs to individual animals. Here we describe the cassette dosing properties of a 107-membered library of 2,6,9-trisubstituted purine cyclin-dependent kinase 2 (CDK2) inhibitors. A three-step parallel synthesis approach produced compounds with purity ranging from 63% to 100%. Cassette dosing was validated by comparing the pharmacokinetic parameters obtained following i.v. administration of a mixture of olomoucine, R-ros

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Burcevs, Aleksejs, Māris Turks, and Irina Novosjolova. "Synthesis of Pyridinium Moiety Containing Triazolyl Purines." Molbank 2024, no. 3 (2024): M1855. http://dx.doi.org/10.3390/m1855.

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Pyridinium salts of 2-piperidinyl-6-triazolylpurine derivatives were obtained by the introduction of pyridinium moieties into the propane-1,3-diol fragment at the N(9) position of purine to enhance the solubility of 2-amino-6-triazolylpurine derivatives in water. Target structures were obtained using the tosylation of hydroxyl groups of 2-(6-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-2-(piperidin-1-yl)-9H-purin-9-yl)propane-1,3-diol, the subsequent introduction of pyridine, and ion exchange. The compounds were characterized using 1H- and 13C-NMR spectra, FTIR, UV–Vis, and HRMS data.

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