A Convenient Synthesis of 9-(2-Hydroxyethoxymethyl)guanine (Acyclovir) and Related Compounds
A convenient and economical synthesis of 9-(2-hydroxyethoxymethyl)guanine (1, acyclovir, Zovirax, or acyclic guanosine : an antiherpetic agent)from guanine was developed via N2, O-diacetylacyclovir. Two closely related compounds, N2-acetylacyclovir (7) and O-acetylacyclovir (8), were also prepared b...
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| Published in | Chemical & pharmaceutical bulletin Vol. 36; no. 3; pp. 1153 - 1157 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
TOKYO
The Pharmaceutical Society of Japan
1988
公益社団法人日本薬学会 Pharmaceutical Soc Japan Maruzen Japan Science and Technology Agency |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0009-2363 1347-5223 |
| DOI | 10.1248/cpb.36.1153 |
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| Abstract | A convenient and economical synthesis of 9-(2-hydroxyethoxymethyl)guanine (1, acyclovir, Zovirax, or acyclic guanosine : an antiherpetic agent)from guanine was developed via N2, O-diacetylacyclovir. Two closely related compounds, N2-acetylacyclovir (7) and O-acetylacyclovir (8), were also prepared by selective deacetylation. |
|---|---|
| AbstractList | A convenient and economical synthesis of 9-(2-hydroxyethoxymethyl)guanine (acyclovir, Zovirax, or acyclic guanosine: an antiherpetic agent) from guanine was developed via N super(2),O-diacetylacyclovir. Two closely related compounds, N super(2)-acetylacyclovir and O-acetylacyclovir were also prepared by selective deacetylation. A convenient and economical synthesis of 9-(2-hydroxyethoxymethyl)guanine (1, acyclovir, Zovirax, or acyclic guanosine : an antiherpetic agent)from guanine was developed via N2, O-diacetylacyclovir. Two closely related compounds, N2-acetylacyclovir (7) and O-acetylacyclovir (8), were also prepared by selective deacetylation. A convenient and economical synthesis of 9-(2-hydroxyethoxymethyl)guanine (1,acyclovir, Zovirax, or acyclic guanosine : an antiherpetic agent)from guanine was developed via N^2,O-diacetylacyclovir. Two closely related compounds, N^2-acetylacyclovir (7) and O-acetylacyclovir (8), were also prepared by selective deacetylation. |
| Author | MATSUMOTO, HIROATSU KANEKO, CHISATO MIZUNO, YOSHIHISA MORI, TAKEO YAMADA, KEIKO TAKEUCHI, TADAO |
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| Keywords | Acyclic nucleoside Temperature Nitrogen heterocycle Deprotection Herpes Guanidines Selectivity Acid catalysis Infection Hydroxyether Viral disease Bicyclic compound Antiviral |
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| References_xml | – reference: 2) H.J. Schaeffer, L. Beauchamp, P. de Miranda, G.B. Elion, D.J. Bauer, and P. Collins, Nature (London), 272, 583 (1978). – reference: 12) M.J. Robins and P.W. Hatfield, Can. J. Chem., 60, 547 (1982). – reference: 8) M. MacCoss, A. Chen, and R.L. Tolman, Tetrahedron Lett., 25, 4287 (1985). – reference: 17) L.M. Beauchamp, B.L. Dolmatch, H.J. Schaeffer, P. Collins, D.J. Bauer, P.M. Keller, and J.A. Fyfe, J. Med. Chem., 28, 982 (1985). – reference: 3) K.K. Ogilvie, H.R. Hanna, N. Nguyen-ba, and K.O. Smith, Nucleosides & Nucleotides, 4, 507 (1978). – reference: 7) T.-S. Lin and M.-C. Liu, Tetrahedron Lett., 25, 611 (1984). – reference: 16) M. Senkus, J. Am. Chem. Soc., 68, 734 (1946). – reference: 14) DHPG is another new potent and selective antiherpetic agent. a) J.C. Martin, C.A. Dvorak, D.F. Smee, T.R. No. 3 1157 – reference: b) M. MacCoss, R.L. Tolman, W.T. Ashton, A.F. Wagner, J. Hannah, A.K. Field., J.D. Karkas, and J.I. Germershausen, Chem. Scripta., 26, 113 (1986). – reference: 6) M.-C. Liu, S. Kouzmch, and T.-S. Lin, Tetrahedron Lett., 25, 905 (1984). – reference: 13) H.J. Schaeffer, Ger. Patent 2539963 (1974). – reference: 15) T. Sato, T. Shimadate, and Y. Ishido, Nippon Kagaku Zasshi, 81, 1440 (1960). – reference: Mattews, and J.P.H. Verheyden, J. Med. Chem., 26, 759 (1983); – reference: 4) J.D. Bryant, G.E. Keyser, and J.R. Barrio, J. Org. Chem., 44, 3733 (1979). – reference: 9) W.T. Ashton, J.D. Karkas, A.K. Field, and R.L. Tolman, Biochem. Biophys. Res. Commun., 108, 1716 (1982). – reference: 1) A part of this work was presented at the 14th Symposium on Nucleic Acids Chemistry, Tokushima, October 1986. – reference: 10) M. Hua, P.M. Korkowski, and R. Vince, J. Med. Chem., 30, 198 (1987). – reference: 5) M.R. Harnden and R.L. Jarvest, Tetrahedron Lett., 26, 4265 (1985). – reference: 11) J.R. Barrio, J.D. Bryant, and G.E. Keyser, J. Med. Chem., 23, 572 (1980). – volume: 26 start-page: 759 year: 1983 ident: WOS:A1983QM29100024 article-title: 9-[(1,3-DIHYDROXY-2-PROPOXY)METHYL]GUANINE - A NEW POTENT AND SELECTIVE ANTIHERPES AGENT publication-title: JOURNAL OF MEDICINAL CHEMISTRY – volume: 4 start-page: 507 year: 1978 ident: WOS:A1988M917100039.13 publication-title: NUCLEOS NUCLEOT – volume: 60 start-page: 547 year: 1982 ident: WOS:A1982NG28800001 article-title: NUCLEIC-ACID RELATED-COMPOUNDS .37. CONVENIENT AND HIGH-YIELD SYNTHESES OF N-[(2-HYDROXYETHOXY)METHYL] HETEROCYCLES AS ACYCLIC NUCLEOSIDE ANALOGS publication-title: CANADIAN JOURNAL OF CHEMISTRY – volume: 23 start-page: 572 year: 1980 ident: WOS:A1980JP79000020 article-title: A DIRECT METHOD FOR THE PREPARATION OF 2-HYDROXYETHOXYMETHYL DERIVATIVES OF GUANINE, ADENINE, AND CYTOSINE publication-title: JOURNAL OF MEDICINAL CHEMISTRY – volume: 26 start-page: 113 year: 1986 ident: WOS:A1986C502600023 article-title: SYNTHETIC, BIOCHEMICAL AND ANTIVIRAL ASPECTS OF SELECTED ACYCLONUCLEOSIDES AND THEIR DERIVATIVES publication-title: CHEMICA SCRIPTA – volume: 272 start-page: 583 year: 1978 ident: WOS:A1978EU45600019 article-title: 9-(2-HYDROXYETHOXYMETHYL)GUANINE ACTIVITY AGAINST VIRUSES OF HERPES GROUP publication-title: NATURE – volume: 26 start-page: 4265 year: 1985 ident: WOS:A1985AQE6000035 article-title: AN IMPROVED SYNTHESIS OF THE ANTIVIRAL ACYCLONUCLEOSIDE 9-(4-HYDROXY-3-HYDROXYMETHYLBUT-1-YL)GUANINE publication-title: TETRAHEDRON LETTERS – volume: 81 start-page: 1440 year: 1960 ident: WOS:A1988M917100039.15 publication-title: NIPPON KAGAKU ZASSHI – year: 1974 ident: WOS:A1988M917100039.1 – volume: 44 start-page: 3733 year: 1979 ident: WOS:A1979HQ55000033 article-title: ACYCLIC NUCLEOSIDE ANALOGS - SYNTHESIS OF OPEN-RING RIBOSIDE OR DEOXYRIBOSIDE ANALOGS LACKING C(3') OR THE C(3')-C(4') BOND publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 30 start-page: 198 year: 1987 ident: WOS:A1987F467400033 article-title: SYNTHESIS AND BIOLOGICAL EVALUATION OF ACYCLIC NEPLANOCIN ANALOGS publication-title: JOURNAL OF MEDICINAL CHEMISTRY – volume: 25 start-page: 611 year: 1984 ident: WOS:A1984SB67300007 article-title: SYNTHESIS OF 1-[(2-HYDROXY-1-(HYDROXYMETHYL)ETHOXY)METHYL]-1,2,4-TRIAZOLE-3- AND 5-CARBOXAMIDES publication-title: TETRAHEDRON LETTERS – volume: 28 start-page: 982 year: 1985 ident: WOS:A1985AMV9200002 article-title: MODIFICATIONS ON THE HETEROCYCLIC BASE OF ACYCLOVIR - SYNTHESES AND ANTIVIRAL PROPERTIES publication-title: JOURNAL OF MEDICINAL CHEMISTRY – volume: 26 start-page: 4287 year: 1985 ident: WOS:A1985AQV6700004 article-title: SYNTHESES OF ALL 4 POSSIBLE DIASTEREOMERS OF THE ACYCLONUCLEOSIDE 9-(1,3,4-TRIHYDROXY-2-BUTOXYMETHYL)GUANINE FROM CARBOHYDRATE PRECURSORS publication-title: TETRAHEDRON LETTERS – volume: 25 start-page: 905 year: 1984 ident: WOS:A1984SF96900003 article-title: SYNTHESIS OF 9-(2,3-DIHYDROXY-1-PROPOXYMETHYL) GUANINE - A NEW POTENTIAL ANTIVIRAL AGENT publication-title: TETRAHEDRON LETTERS – volume: 68 start-page: 734 year: 1946 ident: WOS:A1946UB30800003 article-title: REACTION OF SOME CYCLIC ACETALS WITH ACID ANHYDRIDES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 108 start-page: 1716 year: 1982 ident: WOS:A1982PP87100053 article-title: ACTIVATION BY THYMIDINE KINASE AND POTENT ANTIHERPETIC ACTIVITY OF 2'-NOR-2'-DEOXYGUANOSINE (2'NDG) publication-title: BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS |
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| Snippet | A convenient and economical synthesis of 9-(2-hydroxyethoxymethyl)guanine (1, acyclovir, Zovirax, or acyclic guanosine : an antiherpetic agent)from guanine was... A convenient and economical synthesis of 9-(2-hydroxyethoxymethyl)guanine (1,acyclovir, Zovirax, or acyclic guanosine : an antiherpetic agent)from guanine was... A convenient and economical synthesis of 9-(2-hydroxyethoxymethyl)guanine (1, acyclovir, Zovirax, or acyclic guanosine: an antiherpetic agent) from guanine was... A convenient and economical synthesis of 9-(2-hydroxyethoxymethyl)guanine (acyclovir, Zovirax, or acyclic guanosine: an antiherpetic agent) from guanine was... |
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| SubjectTerms | acyclovir Acyclovir - analogs & derivatives Acyclovir - chemical synthesis alkylation antiherpetic agnet Catalysis Chemical Phenomena Chemistry Chemistry, Medicinal Chemistry, Multidisciplinary Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Life Sciences & Biomedicine N^2-acetylacyclovir O-acetylacyclovir Organic chemistry p-toluenesulfonic acid Pharmacology & Pharmacy Physical Sciences Preparations and properties Science & Technology Temperature |
| Title | A Convenient Synthesis of 9-(2-Hydroxyethoxymethyl)guanine (Acyclovir) and Related Compounds |
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| ispartofPNX | Chemical and Pharmaceutical Bulletin, 1988/03/25, Vol.36(3), pp.1153-1157 |
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