Detail of compound @ czechem

Molecular Formula: C₁₄H₂₃O₆PS

Molecular weight: 350.367581

InChi: InChI=1S/C14H23O6PS/c1-11(2)19-21(15,20-12(3)4)10-18-22(16,17)14-8-6-13(5)7-9-14/h6-9,11-12H,10H2,1-5H3

InChi Key: ZAAQMNVHSKISRP-UHFFFAOYSA-N

SMILES: P(=O)(COS(=O)(=O)c1ccc(cc1)C)(OC(C)C)OC(C)C

Chemical Name
bis(2-propyl) ((p-tolylsulfonyl)oxy)methanephosphonate
bis(2-propyl)<<(p-tolylsulfonyl)oxy>methyl>phosphonate
diisopropyl [(p-toluenesulphonyloxy)methyl]phosphonate
Diisopropyl<(p-toluenesulfonyl)oxy>methanephosphonate
diisopropyl<(p-tolylsulfonyl)oxy>methanephosphonate
TsOCH2PO(O-iPr)2
TsOCH2PO(OiPr)2

External Links
PubChem

Authors of compound

Cisarova, Ivana
Budesinsky, Milos
Krecmerova, Marcela
Holy, Antonin
Jindrich, Jindrich
Dracinsky, Martin
Dvorakova, Hana
Jansa, Petr
Petricek, Vaclav
Hocek, Michal
Votruba, Ivan
Masojidkova, Milena
Andrei, Graciela
Snoeck, Robert
Balzarini, Jan
De Clercq, Erik
Hockova, Dana
Pohl, Radek
Klepetarova, Blanka
Cihlar, Tomas
Snasel, Jan
Tloustova, Eva
Rosenberg, Ivan
Clercq, Erik de
Liboska, Radek
Alexander, Petr
Cvorakova, Hana
Janeba, Zlatko
Andrei, Graciella
Naesens, Lieve
Slouf, Miroslav
Pomeisl, Karel
Chalupova, Sarka
Vrbovska, Silvie
Piskala, Alois
Neyts, Johan
Vrbkova, Silvie
Kasicka, Vaclav
Tichy, Tomas
Brehova, Petra
Laflamme, Genevieve
Hui, Hon
Baszczynski, Ondrej
Stepan, George
Sazelova, Petra
Rejman, Dominik
BALZARINI, Jan, Marie, Rene
DE CLERCQ, Erik, Desire, Alice
Auwerx, Joeri
Kiss, Eleonora
Goris, Nesya
Pressova, Martina
Pav, Ondrej
Protivinska, Eva
Collinsova, Michaela
Jiracek, Jiri
Barvik, Ivan
Panova, Natalya
Koiova, Ivana
Budinsky, Milo
Zbornikova, Eva
Pav, Ondej

Articles

Holy, Antonin; Hocek, Michal; Masojidkova, Milena; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; De Clercq, Erik, Synthesis and antiviral activity of acyclic nucleotide analogues derived from 6-(aminomethyl)purines and purine-6-carboxamidines. Collect. Czech. Chem. Commun. 1996, 61(10), 1525 - 1537, 10.1135/cccc19961525

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; Dvorakova, Hana; Alexander, Petr, SYNTHESIS AND BIOLOGICAL EFFECTS OF 9-(3-HYDROXY-2-PHOSPHONOMETHOXYPROPYL) DERIVATIVES OF DEAZAPURINE BASES. Collect. Czech. Chem. Commun. 1993, 58, 1403 - 1418, 10.1135/cccc19931403

Holy, Antonin; Jindrich, Jindrich; Dvorakova, Hana, SYNTHESIS OF N-(3-FLUORO-2-PHOSPHONOMETHOXYPROPYL) (FPMP) DERIVATIVES OF HETEROCYCLIC BASES. Collect. Czech. Chem. Commun. 1993, 58(7), 1645 - 1667, 10.1135/cccc19931645

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

Budesinsky, Milos; Holy, Antonin; Masojidkova, Milena; Hockova, Dana, ACYCLIC NUCLEOSIDE AND NUCLEOTIDE ANALOGS DERIVED FROM 2-AZAADENINE. Collect. Czech. Chem. Commun. 1995, 60(2), 224 - 236, 10.1135/cccc19950224

Krecmerova, Marcela; Holy, Antonin, PREPARATION OF PHOSPHONOMETHYL ETHERS DERIVED FROM 2-PHENYLETHANOL AND ITS AMINO DERIVATIVES. Collect. Czech. Chem. Commun. 1995, 60(4), 659 - 669, 10.1135/cccc19950659

Krecmerova, Marcela; Holy, Antonin; Masojidkova, Milena, SYNTHESIS OF 3-(4-PYRIDINYL)-, 3-(2-CHLORO-4-PYRIDINYL)- AND 3-(2-AMINO-4-PYRIDINYL)PROPOXYMETHANEPHOSPHONIC ACID. Collect. Czech. Chem. Commun. 1995, 60(4), 670 - 680, 10.1135/cccc19950670

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; 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

Budesinsky, Milos; Holy, Antonin; Jindrich, Jindrich; Dvorakova, Hana; Masojidkova, Milena; Balzarini, Jan; De Clercq, Erik; Andrei, Graciella, Acyclic nucleotide analogs derived from 8-azapurines: Synthesis and antiviral activity. Journal of Medicinal Chemistry 1996, 39(20), 4073 - 4088, 10.1021/jm960314q

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.

Budesinsky, Milos; Holy, Antonin; Masojidkova, Milena; Alexander, Petr, Synthesis of acyclic nucleotide analogues derived from N-substituted isoguanine. Collect. Czech. Chem. Commun. 2000, 65(11), 1713 - 1725.

Holy, Antonin; Votruba, Ivan; Masojidkova, Milena; Tloustova, Eva, Synthesis and cytostatic activity of N-[2-(phosphonomethoxy)alkyl] derivatives of N-substituted adenines, 2,6-diaminopurines and related compounds. Collect. Czech. Chem. Commun. 2001, 66(10), 1545 - 1592.

Cisarova, Ivana; Holy, Antonin; Petricek, Vaclav; Slouf, Miroslav, Charge density study of hydrogen [(2,4-diaminopyrimidin-1-io)methyl]phosphonate monohydrate. Acta Crystallographica Section B: Structural Science 2002, 58(3 PART 2), 519 - 529, 10.1107/S0108768102004020

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

Holy, Antonin; Votruba, Ivan; Pohl, Radek; Pomeisl, Karel, Simple transformation of thymine 1-[3-hydroxy-2-(phosphonomethoxy)propyl] derivatives to their 1-[3-fluoro-2-(phosphonomethoxy)propyl] counterparts. Collect. Czech. Chem. Commun. 2005, 70(9), 1465 - 1481, 10.1135/cccc2

Holy, Antonin; Masojidkova, Milena; Chalupova, Sarka, Synthesis of some N-substituted derivatives of 1-[(S)-3-hydroxy-2-(phosphonomethoxy)propyl]cytosine (HPMPC, cidofovir). Collect. Czech. Chem. Commun. 2005, 70(12), 2053 - 2065, 10.1135/cccc20052053

Holy, Antonin; Masojidkova, Milena; Pohl, Radek; Vrbovska, Silvie, Bifunctional acyclic nucleoside phosphonates. 1. Symmetrical 1,3-bis[(phosphonomethoxy)propan-2-yl] derivatives of purines and pyrimidines. Collect. Czech. Chem. Commun. 2006, 71(4), 543 - 566, 10.1135/cccc20060543

Krecmerova, Marcela; Holy, Antonin; Masojidkova, Milena, Preparation of C-5 substituted cidofovir derivatives. Collect. Czech. Chem. Commun. 2006, 71(4), 579 - 594, 10.1135/cccc20060579

Holy, Antonin; Votruba, Ivan; Pohl, Radek; Pomeisl, Karel, Syntheses of base and side-chain modified pyrimidine 1-[2- (phosphonomethoxy)propyl] derivatives as potent inhibitors of thymidine phosphorylase (PD-ECGF) from SD-lymphoma. Collect. Czech. Chem. Commun. 2006, 71(4), 595 - 624, 10.1135/cccc20060595

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; Votruba, Ivan; Pohl, Radek; Pomeisl, Karel, Syntheses of N-substituted thymine acyclic nucleoside phosphonates and a comparison of their inhibitory effect towards thymidine phosphorylase. Bioorganic and Medicinal Chemistry Letters 2008, 18(4), 1364 - 1367, 10.1016/j.bmcl.2008.01.006

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

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

Krecmerova, Marcela; Dracinsky, Martin; Jansa, Petr; Janeba, Zlatko; Neyts, Johan; Kasicka, Vaclav; Stepan, George; Sazelova, Petra; Auwerx, Joeri; Kiss, Eleonora; Goris, Nesya, 9-[2-(R)-(Phosphonomethoxy)propyl]-2,6-diaminopurine (R)-PMPDAP and its prodrugs: Optimized preparation, including identification of by-products formed, and antiviral evaluation in vitro. Bioorganic and Medicinal Chemistry 2013, 21(5), 1199 - 1208, 10.1016/j.bmc.2012.12.044

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

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

Masojidkova, Milena; Rosenberg, Ivan; Rejman, Dominik, Nucleosidyl-O-methylphosphonates: A pool of monomers for modified oligonucleotides. Nucleosides, Nucleotides and Nucleic Acids 2004, 23(11), 1683 - 1705, 10.1081/NCN-200033912

Budesinsky, Milos; Masojidkova, Milena; Snasel, Jan; Rosenberg, Ivan; Pressova, Martina; Pav, Ondrej; Protivinska, Eva; Collinsova, Michaela; Jiracek, Jiri, Activation of murine RNase L by isopolar 2′-phosphonate analogues of 2′,5′ oligoadenylates. Journal of Medicinal Chemistry 2006, 49(13), 3955 - 3962, 10.1021/jm050401v

Rosenberg, Ivan; Panova, Natalya; Koiova, Ivana; Budinsky, Milo, Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate. Organic and Biomolecular Chemistry 2011, 9(8), 2856 - 2860, 10.1039/c0ob00738b

Pohl, Radek; Rosenberg, Ivan; Barvik, Ivan; Koiova, Ivana; Budinsky, Milo; Pav, Ondej, Synthesis of oligoribonucleotides with phosphonate-modified linkages. Organic and Biomolecular Chemistry 2011, 9(17), 6120 - 6126, 10.1039/c1ob05488k

Snasel, Jan; Rosenberg, Ivan; Pav, Ondrej; Panova, Natalya; Zbornikova, Eva, Activation of human RNase L by 2′- and 5′-O-methylphosphonate- modified oligoadenylates. Bioorganic and Medicinal Chemistry Letters 2012, 22(1), 181 - 185, 10.1016/j.bmcl.2011.11.040

Patents

Holy, Antonin; Jindrich, Jindrich; Balzarini, Jan; De Clercq, Erik, Antiretroviral bases, EP454427, 1991.

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.

Holy, Antonin; Hockova, Dana; BALZARINI, Jan, Marie, Rene; DE CLERCQ, Erik, Desire, Alice, PYRIMIDINE COMPOUNDS HAVING PHOSPHONATE GROUPS AS ANTIVIRAL NUCLEOTIDE ANALOGS, WO2004/111064, 2004.