Molecular Formula: C8H12N5O4P
Molecular weight: 273.185741
InChi: InChI=1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)
InChi Key: SUPKOOSCJHTBAH-UHFFFAOYSA-N
SMILES: c12c(c(ncn2)N)ncn1CCOCP(=O)(O)O
Chemical Name
9-(2-phosphonylmethoxy-ethyl)adenine
9-[2-(phosphonomethoxy)ethyl]adenine
Adefovir
ADV
bis(POM)-PMEA
PMEA
[14C]-Adefovir
9-(2-phosphonylmethoxy-ethyl)adenine
9-[2-(phosphonomethoxy)ethyl]adenine
Adefovir
ADV
bis(POM)-PMEA
PMEA
[14C]-Adefovir
Authors of compound
Krecmerova, Marcela
Holy, Antonin
Dracinsky, Martin
Dvorakova, Hana
Jansa, Petr
Cesnek, Michal
Smidkova, Marketa
Votruba, Ivan
Masojidkova, Milena
Andrei, Graciela
Snoeck, Robert
Balzarini, Jan
De Clercq, Erik
Hockova, Dana
Klepetarova, Blanka
Cihlar, Tomas
Tloust'Ova, Eva
Rosenberg, Ivan
Clercq, Erik de
Horska, Kvetoslava
Sigel, Helmut
Alexander, Petr
Guenter, Jaroslav
Otova, Berta
Janeba, Zlatko
Zidek, Zdenek
Blindauer, Claudia A.
Olsanska, Lenka
Frankova, Daniela
Krejcova, Romana
Kampf, Gunnar
Lueth, Marc Sven
Mueller, Jens
Lippert, Bernhard
Naesens, Lieve
Hajek, Miroslav
Keith, Kathy A.
Hitchcock, Michael J. M.
Lee, William A.
Kern, Earl R.
Kmonickova, Eva
Matulova, Nadezda
Potmesil, Petr
Boubelik, Michael
Draber, Petr
Kmoniekova, Eva
Piskala, Alois
Neyts, Johan
Lebeau, Ilya
Vrbkova, Silvie
Duraffour, Sophie
Van Den Oord, Joost
De Vos, Rita
Crance, Jean-Marc
Garin, Daniel
Pechar, Michal
Braunova, Alena
Subr, Vladimir
Ulbrich, Karel
Tichy, Tomas
Baszczynski, Ondrej
Mertlikova-Kaiserova, Helena
Prochazkova, Eliska
BALZARINI, Jan, Marie, Rene
DE CLERCQ, Erik, Desire, Alice
Dvorakova, Alexandra
Holy, Antonin
Dracinsky, Martin
Dvorakova, Hana
Jansa, Petr
Cesnek, Michal
Smidkova, Marketa
Votruba, Ivan
Masojidkova, Milena
Andrei, Graciela
Snoeck, Robert
Balzarini, Jan
De Clercq, Erik
Hockova, Dana
Klepetarova, Blanka
Cihlar, Tomas
Tloust'Ova, Eva
Rosenberg, Ivan
Clercq, Erik de
Horska, Kvetoslava
Sigel, Helmut
Alexander, Petr
Guenter, Jaroslav
Otova, Berta
Janeba, Zlatko
Zidek, Zdenek
Blindauer, Claudia A.
Olsanska, Lenka
Frankova, Daniela
Krejcova, Romana
Kampf, Gunnar
Lueth, Marc Sven
Mueller, Jens
Lippert, Bernhard
Naesens, Lieve
Hajek, Miroslav
Keith, Kathy A.
Hitchcock, Michael J. M.
Lee, William A.
Kern, Earl R.
Kmonickova, Eva
Matulova, Nadezda
Potmesil, Petr
Boubelik, Michael
Draber, Petr
Kmoniekova, Eva
Piskala, Alois
Neyts, Johan
Lebeau, Ilya
Vrbkova, Silvie
Duraffour, Sophie
Van Den Oord, Joost
De Vos, Rita
Crance, Jean-Marc
Garin, Daniel
Pechar, Michal
Braunova, Alena
Subr, Vladimir
Ulbrich, Karel
Tichy, Tomas
Baszczynski, Ondrej
Mertlikova-Kaiserova, Helena
Prochazkova, Eliska
BALZARINI, Jan, Marie, Rene
DE CLERCQ, Erik, Desire, Alice
Dvorakova, Alexandra
Articles
Holy, Antonin;
Rosenberg, Ivan, SYNTHESIS OF 9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE AND RELATED COMPOUNDS. Collect. Czech. Chem. Commun. 1987, 52(11), 2801 - 2809.
Holy, Antonin;
Dvorakova, Hana;
Rosenberg, Ivan, SYNTHESIS OF N-(2-PHOSPHONYLMETHOXYETHYL) DERIVATIVES OF HETEROCYCLIC BASES. Collect. Czech. Chem. Commun. 1989, 54(8), 2190 - 2210.
Holy, Antonin;
Dvorakova, Hana;
Masojidkova, Milena, FLUORESCENT ANALOGUES OF ACYCLIC INHIBITORS OF S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE. Collect. Czech. Chem. Commun. 1988, 53(8), 1779 - 1794.
Holy, Antonin;
Masojidkova, Milena;
Alexander, Petr, PREPARATION OF 9-(2-PHOSPHONOMETHOXYETHYL)ADENINE ESTERS AS POTENTIAL PRODRUGS. Collect. Czech. Chem. Commun. 1994, 59(8), 1853 - 1869, 10.1135/cccc19941853 
.
.
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;
Votruba, Ivan;
Zidek, Zdenek, Inhibition of Murine Lymphocyte Proliferation by N-Substituted Acyclic Purine Nucleoside Phosphonates. Collect. Czech. Chem. Commun. 1996, 61, S182 - S187.
Holy, Antonin;
Votruba, Ivan;
Cihlar, Tomas;
Olsanska, Lenka, Transport of adefovir (PMEA) in human T-lymphoblastoid cells. Collect. Czech. Chem. Commun. 1997, 62(5), 821 - 828.
Holy, Antonin;
Dvorakova, Hana;
Sigel, Helmut;
Blindauer, Claudia A., Solution properties of antiviral adenine-nucleotide analogues. The acid - Base properties of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) and of its N1, N3 and N7 deaza derivatives in aqueous solution. Journal of the Chemical Society. Perkin Transactions 2 1997(11), 2353 - 2363.
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 .
.
Holy, Antonin;
Otova, Berta;
Zidek, Zdenek;
Frankova, Daniela, Suppression of rat adjuvant arthritis by some acyclic nucleotide analogs. Eur. J. Pharmacol. 1995, 286(3), 307 - 310, 10.1016/0014-2999(95)00586-3 .
.
Holy, Antonin;
Votruba, Ivan;
Horska, Kvetoslava;
Krejcova, Romana, Phosphorylation of purine (phosphonomethoxy)alkyl derivatives by mitochondrial AMP kinase (AK2 type) from L1210 cells. Collect. Czech. Chem. Commun. 2000, 65(10), 1653 - 1668.
Holy, Antonin;
Sigel, Helmut;
Kampf, Gunnar;
Lueth, Marc Sven;
Mueller, Jens;
Lippert, Bernhard, Properties of the ternary (Dien)Pt(PMEA-N7) complex containing diethylenetriamine (Dien) and the antiviral 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). Synthesis, biological screening, acid-base behaviour, and metal ion-binding in aqueous solution. Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences 2000, 55(12), 1141 - 1152.
Holy, Antonin;
Votruba, Ivan;
Masojidkova, Milena;
Andrei, Graciela;
Snoeck, Robert;
Balzarini, Jan;
De Clercq, Erik;
Naesens, Lieve, 6-[2-(Phosphonomethoxy)alkoxy]pyrimidines with antiviral activity. Journal of Medicinal Chemistry 2002, 45(9), 1918 - 1929, 10.1021/jm011095y .
.
Holy, Antonin;
Masojidkova, Milena;
Andrei, Graciela;
Snoeck, Robert;
Balzarini, Jan;
De Clercq, Erik;
Hockova, Dana, 5-Substituted-2,4-diamino-6-[2-(phosphonomethoxy) ethoxy]pyrimidines-Acyclic Nucleoside Phosphonate Analogues with Antiviral Activity. Journal of Medicinal Chemistry 2003, 46(23), 5064 - 5073.
Holy, Antonin;
Keith, Kathy A.;
Hitchcock, Michael J. M.;
Lee, William A.;
Kern, Earl R., Evaluation of nucleoside phosphonates and their analogs and prodrugs for inhibition of orthopoxvirus replication. Antimicrobial Agents and Chemotherapy 2003, 47(7), 2193 - 2198, 10.1128/AAC.47.7.2193-2198.2003 .
.
Holy, Antonin;
Votruba, Ivan;
Tloust'Ova, Eva;
Hajek, Miroslav;
Matulova, Nadezda, Inhibition of human telomerase by diphosphates of acyclic nucleoside phosphonates. Biochemical Pharmacology 2005, 70(6), 894 - 900, 10.1016/j.bcp.2005.06.007 .
.
Holy, Antonin;
Zidek, Zdenek;
Frankova, Daniela;
Boubelik, Michael;
Draber, Petr, Inhibition of murine macrophage nitric oxide synthase expression by a pivoxil prodrug of antiviral acyclic nucleotide analogue 9-(2-phosphonomethoxyethyl)adenine. Biochemical Pharmacology 1997, 54(8), 855 - 861, 10.1016/S0006-2952(97)00228-1 .
.
Holy, Antonin;
Zidek, Zdenek;
Potmesil, Petr;
Kmoniekova, Eva, Immunobiological activity of N-[2-(phosphonomethoxy)alkyl] derivatives of N-substituted adenines, and 2,6-diaminopurines. Eur. J. Pharmacol. 2003, 475(1-3), 149 - 159, 10.1016/S0014-2999(03)02110-1 .
.
Holy, Antonin;
Masojidkova, Milena;
Andrei, Graciela;
Snoeck, Robert;
Balzarini, Jan;
De Clercq, Erik;
Hockova, Dana, Synthesis and antiviral activity of 2,4-diamino-5-cyano-6-[2- (phosphonomethoxy)ethoxy]pyrimidine and related compounds. Bioorganic and Medicinal Chemistry 2004, 12(12), 3197 - 3202, 10.1016/j.bmc.2004.04.002 .
.
Krecmerova, Marcela;
Holy, Antonin;
Andrei, Graciela;
Snoeck, Robert;
De Clercq, Erik;
Lebeau, Ilya, Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains. Antimicrobial Agents and Chemotherapy 2007, 51(6), 2268 - 2273, 10.1128/AAC.01422-06 .
.
Krecmerova, Marcela;
Holy, Antonin;
Andrei, Graciela;
Snoeck, Robert;
De Clercq, Erik;
Duraffour, Sophie;
Van Den Oord, Joost;
De Vos, Rita;
Crance, Jean-Marc;
Garin, Daniel, Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models. Antimicrobial Agents and Chemotherapy 2007, 51(12), 4410 - 4419, 10.1128/AAC.00838-07 .
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Holy, Antonin;
Zidek, Zdenek;
Kmonickova, Eva, Secretion of antiretroviral chemokines by human cells cultured with acyclic nucleoside phosphonates. Eur. J. Pharmacol. 2007, 574(1), 77 - 84, 10.1016/j.ejphar.2007.07.024 .
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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 .
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Holy, Antonin;
Pechar, Michal;
Braunova, Alena;
Subr, Vladimir;
Ulbrich, Karel, Polymemc conjugates of 9-[2-(phosphonomethoxy)ethyl]purine with potential antiviral and cytostatic activity. Collect. Czech. Chem. Commun. 2006, 71(8), 1211 - 1220, 10.1135/cccc20061211 .
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Holy, Antonin;
Dracinsky, Martin;
Jansa, Petr;
Votruba, Ivan;
Balzarini, Jan;
Klepetarova, Blanka;
Clercq, Erik de;
Janeba, Zlatko;
Baszczynski, Ondrej, Synthesis and antiviral activity of N-[3-fluoro-2- (phosphonomethoxy)propyl] analogues derived from N-substituted adenines and 2,6-diaminopurines. Bioorganic and Medicinal Chemistry 2011, 19(7), 2114 - 2124, 10.1016/j.bmc.2011.02.050 .
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Krecmerova, Marcela;
Holy, Antonin;
Dracinsky, Martin;
Andrei, Graciela;
Snoeck, Robert;
Balzarini, Jan;
Tichy, Tomas, New prodrugs of Adefovir and Cidofovir. Bioorganic and Medicinal Chemistry 2011, 19(11), 3527 - 3539, 10.1016/j.bmc.2011.04.016 .
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Holy, Antonin;
Andrei, Graciela;
Snoeck, Robert;
Balzarini, Jan;
Hockova, Dana, Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity. Bioorganic and Medicinal Chemistry 2011, 19(15), 4445 - 4453, 10.1016/j.bmc.2011.06.045 .
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Holy, Antonin;
Zidek, Zdenek;
Potmesil, Petr, Cytostatic activity of antiviral acyclic nucleoside phosphonates in rodent lymphocytes. Toxicology and Applied Pharmacology 2003, 192(3), 246 - 253, 10.1016/S0041-008X(03)00215-1 .
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Dracinsky, Martin;
Jansa, Petr;
Janeba, Zlatko;
Baszczynski, Ondrej;
Prochazkova, Eliska, Microwave-assisted hydrolysis of phosphonate diesters: An efficient protocol for the preparation of phosphonic acids. Green Chemistry 2012, 14(8), 2282 - 2288, 10.1039/c2gc35547g .
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Cesnek, Michal;
Smidkova, Marketa;
Tloust'Ova, Eva;
Janeba, Zlatko;
Mertlikova-Kaiserova, Helena;
Dvorakova, Alexandra, Amidate prodrugs of 9-[2-(phosphonomethoxy)ethyl]adenine as inhibitors of adenylate cyclase toxin from Bordetella pertussis. Antimicrobial Agents and Chemotherapy 2014, 58(2), 664 - 671, 10.1128/AAC.01685-13 .
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