Detail of compound @ czechem

Molecular Formula: C₅H₅N₅

Molecular weight: 135.1267

InChi: InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)

InChi Key: GFFGJBXGBJISGV-UHFFFAOYSA-N

SMILES: c12c(ncnc1N)[nH]cn2

Chemical Name
6-aminopurine
9H-purin-6-ylamine-9-ate
A
Ade
adenine
SJ000286496
vitamin B4

External Links
PubChem

Authors of compound

Cerny, Miloslav
Budesinsky, Milos
Krecmerova, Marcela
Holy, Antonin
Jindrich, Jindrich
et al.
Dracinsky, Martin
Dvorakova, Hana
Stibor, Ivan
Sedlak, Milos
Simunek, Petr
Jansa, Petr
Saman, David
Hocek, Michal
Votruba, Ivan
Masojidkova, Milena
Andrei, Graciela
Snoeck, Robert
Balzarini, Jan
De Clercq, Erik
Hockova, Dana
Marek, Radek
Pohl, Radek
Klepetarova, Blanka
Cerna, Igor
Marek, Jaromir
Belohradsky, Martin
Holy, Petr
Rosenberg, Ivan
Hrebabecky, Hubert
Merta, Ales
Kohoutova, Jitka
Liboska, Radek
Sigel, Helmut
Alexander, Petr
Spassova, Maria
Cvorakova, Hana
Guenter, Jaroslav
Jurikova, Kristina
Smrckova, Svatava
Votavova, Hana
Janeba, Zlatko
Gomez-Coca, Raquel B.
Kapinos, Larisa E.
Vilaplana, Rosario A.
Gonzalez-Vilchez, Francisco
Meszarosova, Katerina
Naesens, Lieve
Vrbkova, Silvie
Keough, Dianne T.
De Jersey, John
Guddat, Luke W.
Jersey, John de
Mertlikova-Kaiserova, Helena
Rejman, Dominik
Kolman, Viktor
Kostinova, Alexandra
Kralikova, Sarka
Kocalka, Petr
Vanek, Vaclav
Rinnova, Marketa
Antonietti, Markus
Koudelka, Juraj

Articles

Cerny, Miloslav; Budesinsky, Milos; Krecmerova, Marcela; Holy, Antonin, UTILIZATION OF 1,6-ANHYDROHEXOSES FOR THE PREPARATION OF SOME ALIPHATIC ADENOSINE ANALOGS. Collect. Czech. Chem. Commun. 1989, 54(10), 2753 - 2766.

Hocek, Michal; Pohl, Radek; Klepetarova, Blanka; Cerna, Igor, Synthesis of 6,8,9-tri- and 2,6,8,9-tetrasubstituted purines by a combination of the Suzuki cross-coupling, N-arylation, and direct C-H arylation reactions. Journal of Organic Chemistry 2008, 73(22), 9048 - 9054, 10.1021/jo8018126

Hocek, Michal; Pohl, Radek; Klepetarova, Blanka; Cerna, Igor, Intramolecular direct C-H arylation approach to fused purines. Synthesis of purino[8, 9-f]phenanthridines and 5, 6-dihydropurino[8, 9-a]isoquinolines. Journal of Organic Chemistry 2010, 75(7), 2302 - 2308, 10.1021/jo100111t

Holy, Antonin; Dvorakova, Hana; Rosenberg, Ivan, SYNTHESIS OF N-(2-(2-PHOSPHONYLETHOXY)ETHYL) DERIVATIVES OF HETEROCYCLIC BASES. Collect. Czech. Chem. Commun. 1990, 55(3), 809 - 818.

Holy, Antonin, PREPARATION AND SYNTHETIC UTILIZATION OF 3-(ADENIN-9-YL)-2-HYDROXYALKANOIC ACIDS AND THEIR DERIVATIVES. Collect. Czech. Chem. Commun. 1984, 49(9), 2148 - 2166.

Holy, Antonin; Rosenberg, Ivan, SYNTHESIS OF 9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE AND RELATED COMPOUNDS. Collect. Czech. Chem. Commun. 1987, 52(11), 2801 - 2809.

Holy, Antonin; Votruba, Ivan; Merta, Ales; Kohoutova, Jitka, 9-(AMINOALKYL)-8-HYDROXYADENINES: PREPARATION, MECHANISM OF FORMATION AND USE IN AFFINITY CHROMATOGRAPHY OF S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE. Collect. Czech. Chem. Commun. 1986, 51(2), 459 - 477.

Holy, Antonin, SYNTHESIS OF EIGHT STEREOISOMERIC 5-(ADENIN-9-YL)-2,3,4-TRIHYDROXYPENTANOIC ACIDS. Collect. Czech. Chem. Commun. 1982, 47(11), 2969 - 2988.

Holy, Antonin; Masojidkova, Milena; Rosenberg, Ivan, PHOSPHONYLMETHOXYALKYL AND PHOSPHONYLALKYL DERIVATIVES OF ADENINE. Collect. Czech. Chem. Commun. 1988, 53(11B), 2753 - 2777.

Holy, Antonin, BRANCHED-CHAIN DERIVATIVES OF ACYCLIC ADENOSINE ANALOGS: ALKYL AND HYDROXYMETHYL DERIVATIVES OF S-ADENOSYL-L-HOMOCYSTEINASE INHIBITORS SUBSTITUTED AT THE 2- AND 3-POSITION OF THE SIDE CHAIN. Collect. Czech. Chem. Commun. 1989, 54(1), 248 - 265.

Holy, Antonin, SYNTHESIS OF 3-AMINO- AND 3-AZIDOANALOGS OF 9-(3-HYDROXY-2-PHOSPHONYLMETHOXYPROPYL)ADENINE (HPMPA). Collect. Czech. Chem. Commun. 1989, 54(2), 446 - 454.

Holy, Antonin, STEREOSPECIFIC SYNTHESIS OF ISOMERIC 4-SUBSTITUTED 9-(2,3-DIHYDROXYBUTYL)ADENINES. Collect. Czech. Chem. Commun. 1982, 47(1), 173 - 189.

Holy, Antonin; Jindrich, Jindrich; Dvorakova, Hana, SYNTHESIS OF ISOMERIC N-(3-FLUORO-2-HYDROXYPROPYL) AND N-(2-FLUORO-3-HYDROXYPROPYL) DERIVATIVES OF PURINE AND PYRIMIDINE BASES. Collect. Czech. Chem. Commun. 1992, 57(7), 1466 - 1482, 10.1135/cccc19921466

Holy, Antonin, SYNTHESES OF ENANTIOMERIC N-(3-HYDROXY-2-PHOSPHONOMETHOXYPROPYL)DERIVATIVES OF PURINE AND PYRIMIDINE BASES. Collect. Czech. Chem. Commun. 1993, 58(3), 649 - 674, 10.1135/cccc19930649

Holy, Antonin; Alexander, Petr, GENERAL METHOD OF PREPARATION OF N-<(S)-(3-HYDROXY-2-PHOSPHONOMETHOXYPROPYL)> DERIVATIVES OF HETEROCYCLIC BASES. Collect. Czech. Chem. Commun. 1993, 58, 1151 - 1163, 10.1135/cccc19931151

Budesinsky, Milos; Holy, Antonin; Dvorakova, Hana; Masojidkova, Milena; Spassova, Maria, SYNTHEIS OF N-(3-AZIDO-2-HYDROXYPROPYL), N-(3-PHTHALIMIDO-2-HYDROXYPROPYL) AND N-(3-AMINO-2-HYDROXYPROPYL)DERIVATIVES OF HETEROCYCLIC BASES. Collect. Czech. Chem. Commun. 1994, 59(5), 1153 - 1174, 10.1135/cccc19941153

Holy, Antonin; Masojidkova, Milena; Alexander, Petr, SYNTHESIS OF 9-(2-PHOSPHONOMETHOXYETHYL)ADENINE AND RELATED COMPOUNDS. Collect. Czech. Chem. Commun. 1994, 59(8), 1870 - 1878, 10.1135/cccc19941870

Holy, Antonin; Rosenberg, Ivan; Cvorakova, Hana, SYNTHESIS OF SOME 2'-C-ALKYL DERIVATIVES OF 9-(2-PHOSPHONOMETHOXYETHYL)ADENINE AND RELATED COMPOUNDS. Collect. Czech. Chem. Commun. 1994, 59(9), 2069 - 2094, 10.1135/cccc19942069

Holy, Antonin; et al.; Dvorakova, Hana; Votruba, Ivan; Hockova, Dana; Guenter, Jaroslav, SYNTHESIS OF 2-DEOXY-β-D-RIBONUCLEOSIDES AND2,3-DIDEOXY.β-D-PENTOFURANOSIDES ON IMMOBILIZED BACTERIAL CELLS. Collect. Czech. Chem. Commun. 1994, 59(10), 2303 - 2330, 10.1135/cccc19942303

Holy, Antonin; Jurikova, Kristina; Smrckova, Svatava, SYNTHESIS OF BASE-MODIFIED "ABBREVIATED" NAD ANALOGUES. Collect. Czech. Chem. Commun. 1995, 60(2), 237 - 250, 10.1135/cccc19950237

Holy, Antonin; Masojidkova, Milena, SYNTHESIS OF ENANTIOMERIC N-(2-PHOSPHONOMETHOXYPROPYL) DERIVATIVES OF PURINE AND PYRIMIDINE BASES. I. THE STEPWISE APPROACH. Collect. Czech. Chem. Commun. 1995, 60(7), 1196 - 1212, 10.1135/cccc19951196

Holy, Antonin; Dvorakova, Hana; Masojidkova, Milena, SYNTHESIS OF ENANTIOMERIC N-(2-PHOSPHONOMETHOXYPROPYL)DERIVATIVES OF PURINE AND PYRIMIDINE BASES. II. THE SYNTHON APPROACH. Collect. Czech. Chem. Commun. 1995, 60(8), 1390 - 1409, 10.1135/cccc19951390

Holy, Antonin; Masojidkova, Milena; Votavova, Hana; Janeba, Zlatko, Intramolecular cyclization of some acyclic nucleoside analogs. Collect. Czech. Chem. Commun. 1996, 61(3), 442 - 457, 10.1135/cccc19960442

Holy, Antonin; Dvorakova, Hana; Masojidkova, Milena; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; De Clercq, Erik, Synthesis of 2'-aminomethyl derivatives of N-(2- (phosphonomethoxy)ethyl) nucleotide analogues as potential antiviral agents. Journal of Medicinal Chemistry 1996, 39(17), 3263 - 3268, 10.1021/jm9601314

Holy, Antonin; Masojidkova, Milena; Hockova, Dana, "Abbreviated" NADanalogues containing a phosphonate function. Collect. Czech. Chem. Commun. 1996, 61(10), 1538 - 1548, 10.1135/cccc19961538

Holy, Antonin; Hockova, Dana, "Abbreviated" NAD Analogues Containing a Phosphonate Function. Collect. Czech. Chem. Commun. 1996, 61, S52 - S54.

Holy, Antonin; Hockova, Dana, Synthesis of some "abbreviated" NAD analogues. Collect. Czech. Chem. Commun. 1997, 62(6), 948 - 956.

Holy, Antonin; Dvorakova, Hana; Masojidkova, Milena; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; De Clercq, Erik; Guenter, Jaroslav, Structure-antiviral activity relationship in the series of pyrimidine and purine N-[2-(2-phosphonomethoxy)ethyl] nucleotide analogues. 1. Derivatives substituted at the carbon atoms of the base. Journal of Medicinal Chemistry 1999, 42(12), 2064 - 2086, 10.1021/jm9811256

Budesinsky, Milos; Holy, Antonin; Hockova, Dana; Marek, Radek; Marek, Jaromir, Regioselective preparation of N- and N-alkyl derivatives of N- [(dimethylamino)methylene]adenine bearing an active methylene group and their further derivatization leading to α-branched acyclic nucleoside analogues. European Journal of Organic Chemistry 1999(10), 2675 - 2682.

Holy, Antonin; Hrebabecky, Hubert, Synthesis of carba analogues of 2′-deoxy-4′-C-(hydroxymethyl)nucleosides. Collect. Czech. Chem. Commun. 1999, 64(9), 1485 - 1496.

Holy, Antonin; Sigel, Helmut; Gomez-Coca, Raquel B.; Kapinos, Larisa E.; Vilaplana, Rosario A.; Gonzalez-Vilchez, Francisco, Metal ion-binding properties of 9-(4-phosphonobutyl)adenine (dPMEA), a sister compound of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA), and quantification of the equilibria involving four Cu(PMEA) isomers. Journal of the Chemical Society, Dalton Transactions 2000(13), 2077 - 2084, 10.1039/b001588l

Holy, Antonin; Masojidkova, Milena; Meszarosova, Katerina, Synthesis of acyclic adenine 8,N-anhydronucleosides. Collect. Czech. Chem. Commun. 2000, 65(7), 1109 - 1125.

Holy, Antonin; Masojidkova, Milena; Janeba, Zlatko, Synthesis of acyclic nucleoside and nucleotide analogs derived from 6-amino-7H-purin-8(9H)-one. Collect. Czech. Chem. Commun. 2000, 65(7), 1126 - 1144.

Holy, Antonin; Masojidkova, Milena; Hrebabecky, Hubert, Synthesis of racemic 2-hydroxy-4- and 2-hydroxy-5-(hydroxymethyl)cyclohexane nucleoside analogues. Collect. Czech. Chem. Commun. 2002, 67(11), 1681 - 1699, 10.1135/cccc20021681

Budesinsky, Milos; Krecmerova, Marcela; Holy, Antonin; Masojidkova, Milena, Synthesis of optically active N-alkyl derivatives of (R)-3-(adenin-9-yl)-2-hydroxypropanoic acid and related compounds. Collect. Czech. Chem. Commun. 2003, 68(5), 931 - 950, 10.1135/cccc20030931

Holy, Antonin; Sigel, Helmut; Gomez-Coca, Raquel B.; Vilaplana, Rosario A.; Gonzalez-Vilchez, Francisco, Solution structures of binary and ternary metal ion complexes of 9-(5-phosphonopentyl)adenine (3′-deoxa-PEEA). A nucleotide analogue related to the antivirally active 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). European Journal of Inorganic Chemistry 2003(16), 2937 - 2947.

Holy, Antonin; Masojidkova, Milena; Hrebabecky, Hubert, Synthesis of purine nucleoside analogues derived from carbocyclic 5-C-(hydroxymethyl)hexopyranoses. Collect. Czech. Chem. Commun. 2004, 69(2), 435 - 452.

Krecmerova, Marcela; Holy, Antonin; Masojidkova, Milena, Synthesis of N- and N-[2-hydroxy-3- (phosphonomethoxy)-propyl] derivatives of N-substituted adenines, 2,6-diaminopurines and related compounds. Collect. Czech. Chem. Commun. 2004, 69(10), 1889 - 1913, 10.1135/cccc20041889

Holy, Antonin; Dracinsky, Martin; Vrbkova, Silvie, Bifunctional acyclic nucleoside phosphonates: synthesis of chiral 9-{3-hydroxy[1,4-bis(phosphonomethoxy)]butan-2-yl} derivatives of purines. Tetrahedron Asymmetry 2007, 18(18), 2233 - 2247, 10.1016/j.tetasy.2007.09.021

Holy, Antonin; Dracinsky, Martin; Vrbkova, Silvie, Synthesis of phosphonomethoxyethyl or 1,3-bis(phosphonomethoxy)propan-2-yl lipophilic esters of acyclic nucleoside phosphonates. Tetrahedron 2007, 63(46), 11391 - 11398, 10.1016/j.tet.2007.08.081

Holy, Antonin; Dracinsky, Martin; Vrbkova, Silvie, Bifunctional acyclic nucleoside phosphonates: 2. Symmetrical 2-{[bis(phosphono)methoxy]methyl}ethyl derivatives of purines and pyrimidines. Collect. Czech. Chem. Commun. 2007, 72(7), 965 - 983, 10.1135/cccc20070965

Holy, Antonin; Masojidkova, Milena; Janeba, Zlatko, Alternative synthesis of 9-{3-[(diisopropoxyphosphoryl)-methoxy]-2- hydroxypropyl}adenine and its free phosphonates substituted at the c-8 position of purine base. Collect. Czech. Chem. Commun. 2010, 75(3), 371 - 381, 10.1135/cccc2009569

Holy, Antonin; Masojidkova, Milena; Hockova, Dana; Keough, Dianne T.; Guddat, Luke W.; Jersey, John de, Synthesis of branched 9-[2-(2-phosphonoethoxy)ethyl]purines as a new class of acyclic nucleoside phosphonates which inhibit Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase. Bioorganic and Medicinal Chemistry 2009, 17(17), 6218 - 6232, 10.1016/j.bmc.2009.07.044

Holy, Antonin; Hockova, Dana; Naesens, Lieve; Keough, Dianne T.; De Jersey, John; Guddat, Luke W., 6-oxopurine phosphoribosyltransferase: A target for the development of antimalarial drugs. Current Topics in Medicinal Chemistry 2011, 11(16), 2085 - 2102, 10.2174/156802611796575911

Dracinsky, Martin; Jansa, Petr; Janeba, Zlatko; Mertlikova-Kaiserova, Helena; Kolman, Viktor; Kostinova, Alexandra, Efficient synthesis and biological properties of the 2'-trifluoromethyl analogues of acyclic nucleosides and acyclic nucleoside phosphonates. Collect. Czech. Chem. Commun. 2011, 76(10), 1187 - 1198, 10.1135/cccc2011105

Masojidkova, Milena; Rosenberg, Ivan; Liboska, Radek, Carbocyclic phosphonate-based nucleotide analogs related to PMEA II. Racemic cis-configured derivatives. Collect. Czech. Chem. Commun. 1996, 61(5), 778 - 790, 10.1135/cccc19960778

Masojidkova, Milena; Rosenberg, Ivan; Liboska, Radek, Carbocyclic phosphonate-based nucleotide analogs related to pmea. I. Racemic trans-configured derivatives. Collect. Czech. Chem. Commun. 1996, 61(2), 313 - 332, 10.1135/cccc19960313

Rosenberg, Ivan; Kralikova, Sarka, A Simple Synthetic Route to the Preparation of 2-(1-Phosphonoalkoxy)ethyl Derivatives of heterocyclic Bases as Novel Nucleotide Analogs Related to PMEA. Collect. Czech. Chem. Commun. 1996, 61, S81 - S84.

Pohl, Radek; Rosenberg, Ivan; Rejman, Dominik; Kocalka, Petr, Synthesis of racemic and enantiomeric 3-pyrrolidinyl derivatives of nucleobases. Tetrahedron 2006, 62(24), 5763 - 5774, 10.1016/j.tet.2006.03.078

Budesinsky, Milos; Rosenberg, Ivan; Vanek, Vaclav; Rinnova, Marketa, Prolinol-based nucleoside phosphonic acids: new isosteric conformationally flexible nucleotide analogues. Tetrahedron 2009, 65(4), 862 - 876, 10.1016/j.tet.2008.11.035

Masojidkova, Milena; Pohl, Radek; Rosenberg, Ivan; Rejman, Dominik; Kocalka, Petr, Pyrrolidine N-alkylphosphonates and related nucleotide analogues: synthesis and stereochemistry. Tetrahedron 2009, 65(18), 3673 - 3681, 10.1016/j.tet.2009.02.071

Sedlak, Milos; Simunek, Petr; Antonietti, Markus, Synthesis and N NMR characterization of 4-vinylbenzyl substituted bases of nucleic acids. Journal of Heterocyclic Chemistry 2003, 40(4), 671 - 675.

et al.; Stibor, Ivan; Saman, David; Belohradsky, Martin; Holy, Petr; Koudelka, Juraj, CROWN AND AZACROWN ETHERS WITH PENDANT ADENINE GROUP. Collect. Czech. Chem. Commun. 1987, 52(12), 2971 - 2982.