[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2003.24.9.1284

Synthesis and Antiviral Evaluation of Novel Acyclic Nucleosides

Hong, Joon-Hee (College of Pharmacy, Chosun University)
Ko, Ok-Hyun (College of Pharmacy, Chosun University)

Publication Information

Bulletin of the Korean Chemical Society / v.24, no.9, 2003 , pp. 1284-1288 More about this Journal

Abstract

A very short and concise synthetic route for a novel acyclic version of d4T is described. The required quaternary carbon was successfully installed using a [3,3]-sigmatropic rearrangement. The condensation of the mesylates 16-18 with an adenine base under standard nucleophilic substitution conditions ( $K_2CO_3$ , 18-Crown- 6, DMF) in addition to deblocking afforded the target acyclic nucleosides 22-24. In addition, the antiviral evaluations against various viruses were performed.

Keywords

Acyclic nucleosides; [3,3]-Sigmatropic rearrangement; Antiviral agents;

Citations & Related Records

Times Cited By Web Of Science : 17 (Related Records In Web of Science)
Times Cited By SCOPUS : 19

Reference
Cited By SCOPUS

1	Vere Hodge, R. A.; Sutton, D.; Boyd, M. R.; Harnden, M. R.;Jarvest, R. L. Antimicrob. Agents Chemother. 1989, 33, 1765. DOI ScienceOn
2	Rousseau, R. J.; Robins, R.K.; Townsend, L. B. J. Am. Chem. Soc. 1968, 90, 2661. DOI
3	Martin, J. C.; Dvorak, C. A.; Smee, D. F.; Matthew, T. R.; Verheyden, J. P. H. J. Med. Chem. 1983, 26, 759. DOI
4	Hamzeh, F. M.; Lietman, P. S. Antimicrob. Agents. Chemother.1991, 35, 1818. DOI ScienceOn
5	Lee, J. Y.; Oh, C. H.; Ko, O. H.; Hong, J. H. Nucleosides,Nucleotides & Nucleic Acids 2002, 21, 709. DOI ScienceOn
6	De Clercq, E.; Descamps, J.; De Somer, P.; Holy, A. Science 1978,200, 563. DOI ScienceOn
7	Ko, O. H.; Hong, J. H. Tetrahedron Lett. 2002, 43, 6399. DOI ScienceOn
8	El Ashry, E. S. H.; El Kilany, Y. Acyclonucleosides: Part 1, 2, 3. inAdvances in Heterocyclic Chemistry; Academic Press: 1997; Vol,67, 68, 69.
9	Earnshaw, D. L.; Bacon, T. H.; Darlison, S. J.; Edmonds, K.;Perkins, R. M.; Vere Hodge, R. A. Antimicrob. Agents Chemother.1992, 36, 2747. DOI ScienceOn
10	Jeong, L. S.; Lee, Y. A.; Moon, H. R.; Chun, M. W. Nucleosides &Nucleotides 1998, 17, 1473. DOI ScienceOn
11	Krenitsky, T. A.; Hall, W. W.; De Miranda, P.; Beauchamp, L. M.;Schaeffer, H. J.; Whiteman, P. D. Proc. Natl. Acad. Sci. USA 1984,81, 3209. DOI ScienceOn
12	Panzica, R. P.; Rousseau, R. J.; Robins, R. K.; Townsend, L. B.J. Am. Chem. Soc. 1972, 94, 4708. DOI
13	Smith,K. O.; Galloway, K. S.; Kennell, W. L.; Oglivie, K. K.; Radatus, B.K. Antomicrob. Agents Chemother. 1982, 22, 55. DOI ScienceOn
14	Schaeffer, H. J.; Beauchamp, L.; De Miranda, P.; Elion, G .B.;Bauer, D. J.; Collins, P. Nature 1978, 272, 583. DOI ScienceOn
15	Crumpacker, C. S. N. Engl. J. Med. 1996, 335, 721. DOI ScienceOn
16	Hossain, N.;Rozenski, J.; De Clercq, E.; Herdewjn, P. Tetrahedron 1996, 52,13655. DOI ScienceOn
17	Hong, J. H.; Gao, M. Y.; Chu, C. K. Tetrahedron Lett. 1999, 40,231. DOI ScienceOn
18	Arimilli, M. N.; Kim, C. U.; Dougherty, J.; Mulato, A.; Oliyai, R.;Shaw, J. P.; Cundy, K. C.; Bischofberger, N. Antiviral Chem.Chemother. 1997, 8, 557.
19	Vandendriessche,F.; Snoeck, R.; Janssen, G.; Hoogmartens, J.; Van Aerschot, A.;De Clercq, E.; Herdwijn, P. J. Med. Chem. 1992, 35, 1458. DOI

10-11	Chang Hyun Oh. (2008) Nucleosides, Nucleotides and Nucleic Acids First Synthesis and Anti-HIV Evaluation of 4′-Methyl-Cyclopentanyl 9-Deazaadenosine / 27 (10-11) , 1144
12	Hua Li. (2008) Nucleosides, Nucleotides and Nucleic Acids Novel Synthesis and Anti-HIV Activity of 4′-Branched Exomethylene Carbocyclic Nucleosides Using a Ring-Closing Metathesis of Triene / 27 (12) , 1238
3	Qingbo Shen. (2008) Nucleosides, Nucleotides and Nucleic Acids )-Fluorovinyl Nucleosides / 27 (3) , 213
11-12	Aymn E. Rashad. (2010) Nucleosides, Nucleotides and Nucleic Acids A Facile Synthesis and Anti-Avian Influenza Virus (H5N1) Screening of Some Novel Pyrazolopyrimidine Nucleoside Derivatives / 29 (11-12) , 809
11	Hua Li. (2011) Nucleosides, Nucleotides and Nucleic Acids Synthesis of Novel Difluoro-Cyclopropyl Guanine Nucleosides and Their Phosphonate Analogues as Potent Antiviral Agents / 30 (11) , 945
12	Lien Kang. (2012) Bulletin of the Korean Chemical Society Synthesis and Conformation of Novel 4'-Fluorinated 5'-Deoxythreosyl Phosphonic Acid Nucleosides as Antiviral Agents / 33 (12) , 4007
10	Kyung Mi Kim. (2013) Nucleosides, Nucleotides and Nucleic Acids Efficient Electrophilic Fluorination for the Synthesis of Novel 2′-Fluoro-3′-Methyl-5′-Deoxyphosphonic Acid Apiosyl Nucleoside Analogues / 32 (10) , 555
3	Joon Hee Hong. (2006) Nucleosides, Nucleotides and Nucleic Acids Synthesis and antiviral evaluation of novel open-chain analogues of neplanocin A / 25 (3) , 341
9	Chang Hyun Oh. (2006) Archiv der Pharmazie Synthesis and Antiviral Evaluation of Novel Cyclopropyl Nucleosides, Phosphonate Nucleosides and Phosphonic Acid Nucleosides / 339 (9) , 507
7	Jin Woo Kim. (2005) Archives of Pharmacal Research Synthesis and antiviral evaluation of novel methyl branched cyclopropyl phosphonic acid nucleosides / 28 (7) , 745
2	(2005) Nucleosides, nucleotides & nucleic acids Concise Synthesis and Antiviral Activity of Novel Unsaturated Acyclic Pyrimidine Nucleosides / 24 (2) , 153
12	(2003) Bulletin of the Korean Chemical Society Stereoselective Synthesis and Antiviral Activity of Novel 4′(α)-Hydroxymethyl and 6′(α)-Methyl Dually Branched Carbocyclic Nucleosides / 25 (12) , 1812
5	(2003) Bulletin of the Korean Chemical Society The First Synthesis of Dually Modified Southern-Mimicking Nucleoside: 4'-Methyl Branched and Bicyclo [3.1.0] Hexane Locked Nucleoside / 25 (5) , 668
8	Joon Hee Hong. (2003) Chem Inform Synthesis and Antiviral Evaluation of Novel Acyclic Nucleosides. / 35 (8) , None
11	(2003) Bulletin of the Korean Chemical Society Simple Synthesis of Novel 1',4'-Dimethyl Branched Carbovir Analogues / 26 (11) , 1767
8	Aihong Kim. (2006) Nucleosides, nucleotides & nucleic acids Synthesis and Antiviral Evaluation of Novel 5&vprime;-Norcarboacyclic Phosphonic Acid Nucleosides / 25 (8) , 941
7	(2003) Bulletin of the Korean Chemical Society Synthesis of Novel Carbovir Analogue / 27 (7) , 976
9	(2003) Bulletin of the Korean Chemical Society Efficient Construction of Quaternary Carbon: Stereocontrolled Synthesis of Novel Abacavir Analogue / 28 (9) , 1545
12	Seyeon Kim. (2014) Nucleosides, nucleotides & nucleic acids Synthesis and Antiviral Evaluation of Novel 4′-Trifluoromethylated 5′-Deoxyapiosyl Nucleoside Phosphonic Acids / 33 (12) , 747

1	Stereoselective Synthesis and Antiviral Activity of Novel 4′(α)-Hydroxymethyl and 6′(α)-Methyl Dually Branched Carbocyclic Nucleosides / [Kim, Jin-Woo;Choi, Bo-Gil;Hong, Joon-Hee;] / Bulletin of the Korean Chemical Society
2	The First Synthesis of Dually Modified Southern-Mimicking Nucleoside: 4'-Methyl Branched and Bicyclo [3.1.0] Hexane Locked Nucleoside / [Kim, Kwan-Woo;Hong, Joon-Hee;] / Bulletin of the Korean Chemical Society
3	Synthesis and Antiviral Evaluation of Novel Methyl Branched Cyclopropyl Phosphonic Acid Nucleosides / [Kim, Jin-Woo;Ko, Ok-Hyun;Hong, Joon-Hee;] / Archives of Pharmacal Research
4	Synthesis and Conformation of Novel 4'-Fluorinated 5'-Deoxythreosyl Phosphonic Acid Nucleosides as Antiviral Agents / [Kang, Lien;Kim, Eunae;Choi, Eun Joo;Yoo, Jin Cheol;Lee, Wonjae;Hong, Joon Hee;] / Bulletin of the Korean Chemical Society
5	Simple Synthesis of Novel 1',4'-Dimethyl Branched Carbovir Analogues / [Kim, Ai-Hong;Hong, Joon-Hee;] / Bulletin of the Korean Chemical Society
6	Efficient Construction of Quaternary Carbon: Stereocontrolled Synthesis of Novel Abacavir Analogue / [Kim, Ai-Hong;Hong, Joon-Hee;] / Bulletin of the Korean Chemical Society

1	/ Bulletin of the Korean Chemical Society
2	/ Archiv der Pharmazie
3	/ Bulletin of the Korean Chemical Society
4	/ Bulletin of the Korean Chemical Society
5	/ Nucleosides, Nucleotides and Nucleic Acids
6	/ Farmaco
7	/ Archiv der Pharmazie
8	/ Archives of Pharmacal Research
9	/ Bulletin of the Korean Chemical Society
10	/ Nucleosides, Nucleotides and Nucleic Acids
11	/ Nucleosides, Nucleotides and Nucleic Acids
12	/ Nucleosides, Nucleotides and Nucleic Acids
13	/ Nucleosides, Nucleotides and Nucleic Acids
14	/ Archiv der Pharmazie
15	/ Bulletin of the Korean Chemical Society
16	/ Nucleosides, Nucleotides and Nucleic Acids
17	/ Nucleosides, Nucleotides and Nucleic Acids