Synthesis and antiviral activity of some 2-substituted 3-formyl- and 3-cyano-5,6-dichloroindole nucleosides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 24, Issue 10-12, 2005, Pages 1613-1626

  Williams, John D ^a   Drach, John C ^b   Townsend, Leroy B ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF MICHIGAN SCHOOL OF DENTISTRY   (United States)

Author keywords

Antiviral; Human cytomegalovirus (HCMV); Indole nucleoside; Nucleoside analog; TCRB

Indexed keywords

2,5,6 TRICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)BENZIMIDAZOLE; 3 CYANO 2 DIMETHYLAMINO 5,6 DICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)INDOLE; 3 CYANO 2 METHOXY 5,6 DICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)INDOLE; 3 CYANO 2 PYRROLIDINO 5,6 DICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)INDOLE; 3 CYANO 2,5,6 TRICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)INDOLE; 3 FORMYL 2 DIMETHYLAMINO 5,6 DICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)INDOLE; 3 FORMYL 2 ISOPROPYLAMINO 5,6 DICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)INDOLE; 3 FORMYL 2 METHOXY 5,6 DICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)INDOLE; 3 FORMYL 2 METHYLAMINO 5,6 DICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)INDOLE; 3 FORMYL 2 PYRROLIDINO 5,6 DICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)INDOLE; 3 FORMYL 2,5,6 TRICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)INDOLE; AMINE; ANTIVIRUS AGENT; FUNCTIONAL GROUP; GANCICLOVIR; INDOLE DERIVATIVE; NUCLEOSIDE DERIVATIVE; OXIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; CHLORINATION; CONTROLLED STUDY; DEPROTECTION REACTION; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HUMAN; HUMAN CELL; HUMAN CYTOMEGALOVIRUS; NONHUMAN; REACTION ANALYSIS;

ANTIVIRAL AGENTS; CELL LINE; CYTOMEGALOVIRUS; HERPESVIRUS 1, HUMAN; HUMANS; INDOLES; NUCLEOSIDES; VIRUS REPLICATION;

ANIMALIA; HUMAN HERPESVIRUS 1; HUMAN HERPESVIRUS 5;

EID: 29244473579     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770500265836     Document Type: Article

References (18)

1. Pass, R.F. Chapter 77: Cytomegalovirus. In Fields Virology, 4th Ed.; Knipe, D.M., Howley, P.M., Eds.; Lippincott, Williams & Wilkins: Philadephia, 2001; 2675-2705.
2. Alford, C.A.; Britt, W.J. Cytomegalovirus. In The Human Herpesviruses; Roizman, B., Whitley, R.J., Lopez, C., Eds.; Raven Press: New York, 1993; 227-256.
3. Britt, W.J. Infections associated with human cytomegalovirus. In Herpesvirus Infections; Glaser, R., Jones, J.F., Eds.; Marcel Dekker, Inc.: New York, 1994; 59-116.
4. Faulds, D.; Heel, R.C. Ganciclovir: A review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy in cytomegalovirus infections. Drugs 1990, 39, 597-638.
5. Curran, M.; Noble, S. Valganciclovir. Drugs 2001, 61, 1145-1150.
6. Lea, A.P.; Bryson, H.M. Cidofovir. Drugs 1996, 52, 225-230.
7. Wagstaff, A.J.; Bryson, H.M. Foscarnet: A reappraisal of its antiviral activity, pharmacokinetic properties, and therapeutic use in immunocompromised patients with viral infections. Drugs 1994, 48, 199-226.
8. Perry, C.M.; Barman-Balfour, J.A. Fomivirsen. Drugs 1999, 57, 375-380.
9. Townsend, L.B.; Devivar, R.V.; Turk, S.R.; Nassiri, M.R.; Drach, J.C. Design, synthesis, and antiviral activity of certain 2,5,6-trihalo-1-(β-D- ribofuranosyl)benzimidazoles. J. Med. Chem. 1995, 38, 4098-4105.
10. Good, S.S.; Owens, B.S.; Townsend, L.B.; Drach, J.C. The disposition in rats and monkeys of 2-bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (BDCRB) and its 2,5,6-trichloro congener. Antiviral Res. 1994, 23(S), 103.
11. Williams, J.D.; Chen, J.J.; Drach, J.C.; Townsend, L.B. Synthesis and antiviral activity of some 3-substituted 2,5,6-trichloroindole nucleosides. J. Med. Chem. 2004, 47, 5753-5765.
12. Comber, M.F.; Moody, C.J. 2-Chloro-1-methoxymethylindole-3- carboxaldehyde: Introduction of nucleophiles into the indole 2-position and an approach to the unusual TrpHis fragment of moroidin. Synthesis 1992, 731-733.
13. Monge, A.; Palop, J.; Ramirez, C.; Font, M.; Fernandez-Alvarez, E. New 5H-1,2,4-triazino[5,6-b] indole and aminoindole derivatives. Synthesis and studies as inhibitors of blood platelet aggregation, anti-hypertensive agents and thromboxane synthetase inhibitors. Eur. J. Med. Chem. 1991, 26, 179-188.
14. Shipman, C., Jr.; Smith, S.H.; Carlson, R.H.; Drach, J.C. Antiviral activity of arabinofuranosyl-adenosine and arabinofuranosylhypoxanthine in herpes simplex virus-infected KB cells. Antimicrob. Agents Chemother. 1976, 9, 120-127.
15. Turk, S.R.; Shipman, C., Jr.; Nassiri, M.R.; Genzlinger, G.; Krawczyk, S.H.; Townsend, L.B.; Drach, J.C. Pyrrolo[2,3-d]pyrimidine nucleosides as inhibitors of human cytomegalovirus. Antimicrob. Agents Chemother. 1987, 31, 544-550.
16. Prichard, M.N.; Turk, S.R.; Coleman, L.A.; Engelhardt, S.L.; Shipman, C., Jr.; Drach, J.C. A microtiter virus yield reduction assay for the evaluation of antiviral compounds. J. Virol. Methods 1990, 28, 101-106.
17. Prichard, M.N.; Shipman, C., Jr. A three dimensional model to analyze drug-drug interactions. Antiviral Res. 1990, 14, 181-206.
18. Prichard, M.N.; Prichard, L.E.; Baguley, W.A.; Nassiri, M.R.; Shipman, C., Jr. Three-dimensional analysis of synergistic cytotoxicity of ganciclovir and zidovudine. Antiviral Res. 1991, 35, 1060-1065.