Detail of compound @ czechem

Molecular Formula: C₈H₁₄N₃O₆P

Molecular weight: 279.187021

InChi: InChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)/t6-/m0/s1

InChi Key: VWFCHDSQECPREK-LURJTMIESA-N

SMILES: P(=O)(CO[C@@H](Cn1c(=O)nc(cc1)N)CO)(O)O

Chemical Name
(S)-1-(3-hydroxy-2-(phosphonylmethoxy)propyl)cytosine
(S)-1-(3-hydroxy-2-phosphonyl-methoxypropyl)-cytosine
(S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cytosine
Cidofovir
Vistide(R)
Vistide.(R).
[3H]-Cidofovir

External Links
PubChem

Authors of compound

Krecmerova, Marcela
Holy, Antonin
Dracinsky, Martin
Votruba, Ivan
Masojidkova, Milena
Andrei, Graciela
Snoeck, Robert
Balzarini, Jan
De Clercq, Erik
Hockova, Dana
Pohl, Radek
Otmar, Miroslav
Cihlar, Tomas
Rosenberg, Ivan
Clercq, Erik de
Horska, Kvetoslava
Liboska, Radek
Alexander, Petr
Otova, Berta
Janeba, Zlatko
Zidek, Zdenek
Frankova, Daniela
Naesens, Lieve
Keith, Kathy A.
Hitchcock, Michael J. M.
Lee, William A.
Kern, Earl R.
Pomeisl, Karel
Naesens
Lenaerts
Andrei
Snoeck
Van Beers
Horejsi, Katerina
Chalupova, Sarka
Piskala, Alois
Neyts, Johan
Lebeau, Ilya
Duraffour, Sophie
Van Den Oord, Joost
De Vos, Rita
Crance, Jean-Marc
Garin, Daniel
Tichy, Tomas
Brehova, Petra
Laflamme, Genevieve
Hui, Hon
Robins, Morris J.

Articles

Holy, Antonin; Votruba, Ivan; Cihlar, Tomas; Rosenberg, Ivan; Horska, Kvetoslava; Liboska, Radek, METABOLISM OF 1-(S)-(3-HYDROXY-2-PHOSPHONOMETHOXYPROPYL)CYTOSINE (HPMPC) IN HUMAN EMBRYONIC LUNG CELLS. Collect. Czech. Chem. Commun. 1992, 57(3), 661 - 672, 10.1135/cccc19920661

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

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; Masojidkova, Milena; Otmar, Miroslav, An alternative synthesis of HPMPC and HPMPA diphosphoryl derivatives. Collect. Czech. Chem. Commun. 2001, 66(3), 500 - 506, 10.1135/cccc20010500

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; Balzarini, Jan; De Clercq, Erik; Naesens; Lenaerts; Andrei; Snoeck; Van Beers, Antiadenovirus activities of several classes of nucleoside and nucleotide analogues. Antimicrobial Agents and Chemotherapy 2005, 49(3), 1010 - 1016, 10.1128/AAC.49.3.1010-1016.2005

Holy, Antonin; Masojidkova, Milena; Chalupova, Sarka, Synthesis of N-substituted derivatives of 1-[2- (phosphonomethoxy)ethyl]cytosine and its diisopropyl ester as a model reaction for the synthesis of N-substituted derivatives of cidofovir. Collect. Czech. Chem. Commun. 2005, 70(12), 2066 - 2074, 10.1135/cccc20052066

Holy, Antonin; Andrei, Graciela; Snoeck, Robert; Pohl, Radek; Clercq, Erik de; Horejsi, Katerina, Tricyclic etheno analogs of PMEG and PMEDAP: Synthesis and biological activity. Bioorganic and Medicinal Chemistry 2006, 14(23), 8057 - 8065, 10.1016/j.bmc.2006.07.036

Krecmerova, Marcela; Holy, Antonin; Masojidkova, Milena; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; De Clercq, Erik; Naesens, Lieve; Piskala, Alois; Neyts, Johan, Antiviral activity of triazine analogues of 1-(S)-[3-hydroxy-2- (phosphonomethoxy)propyl]cytosine (cidofovir) and related compounds. Journal of Medicinal Chemistry 2007, 50(5), 1069 - 1077, 10.1021/jm061281+

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

Krecmerova, Marcela; Holy, Antonin; Masojidkova, Milena; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; De Clercq, Erik; Pohl, Radek; Naesens, Lieve; Neyts, Johan, Ester prodrugs of cyclic 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-5- azacytosine: Synthesis and antiviral activity. Journal of Medicinal Chemistry 2007, 50(23), 5765 - 5772, 10.1021/jm0707166

Krecmerova, Marcela; Holy, Antonin; Votruba, Ivan; Andrei, Graciela; Snoeck, Robert; De Clercq, Erik; Naesens, Lieve; Neyts, Johan, Intracellular metabolism of the new antiviral compound 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine. Biochemical Pharmacology 2008, 76(8), 997 - 1005, 10.1016/j.bcp.2008.08.009

Krecmerova, Marcela; Holy, Antonin; Dracinsky, Martin; Masojidkova, Milena; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; De Clercq, Erik; Pohl, Radek; Cihlar, Tomas; Naesens, Lieve; Pomeisl, Karel; Neyts, Johan; Tichy, Tomas; Brehova, Petra; Laflamme, Genevieve; Hui, Hon, Synthesis of ester prodrugs of 9-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl] -2,6-diaminopurine (HPMPDAP) as anti-poxvirus agents. Journal of Medicinal Chemistry 2010, 53(19), 6825 - 6837, 10.1021/jm901828c

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

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

Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; De Clercq, Erik; Janeba, Zlatko; Robins, Morris J., Synthesis and biological evaluation of acyclic 3-[(2-hydroxyethoxy)methyl] analogues of antiviral furo- and pyrrolo[2,3-d]pyrimidine nucleosides. Journal of Medicinal Chemistry 2005, 48(14), 4690 - 4696, 10.1021/jm050291s

Krecmerova, Marcela; Dracinsky, Martin; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; Tichy, Tomas, Synthesis and antiviral activities of hexadecyloxypropyl prodrugs of acyclic nucleoside phosphonates containing guanine or hypoxanthine and a (S)-HPMP or PEE acyclic moiety. Eur. J. Med. Chem. 2012, 55, 307 - 314,8, 10.1016/j.ejmech.2012.07.027

Krecmerova, Marcela; Masojidkova, Milena; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; Pohl, Radek, N-Acyl derivatives as lipophilic prodrugs of cidofovir and its 5-azacytosine analogue, (S)-HPMP-5-azaC: Chemistry and antiviral activity. Bioorganic and Medicinal Chemistry 2014, 22(10), 2896 - 2906, 10.1016/j.bmc.2014.03.031

Patents

Krecmerova, Marcela; Holy, Antonin; Andrei, Graciela; Snoeck, Robert; De Clercq, Erik; Naesens, Lieve; Piskala, Alois; Neyts, Johan, AZACYTOSINE DERIVATIVES USEFUL AS ANTIVIRAL AGENTS, WO2007/65231, 2007.