Novel potential agents for human cytomegalovirus infection: Synthesis and antiviral activity evaluation of benzothiadiazine dioxide acyclonucleosides

Journal of Medicinal Chemistry

Volumn 42, Issue 7, 1999, Pages 1145-1150

  Martinez, Ana ^a   Esteban, Ana I ^a   Castro, Ana ^a   Gil, Carmen ^a   Conde, Santiago ^a   Andrei, Graciela ^b   Snoeck, Robert ^b   Balzarini, Jan ^b   De Clercq, Erik ^b  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZYL 3 (BENZYLOXYMETHYL) 2,1,3 BENZOTHIADIAZIN 4 ONE 2,2 DIOXIDE; BENZOTHIADIAZINE DERIVATIVE; BENZOTHIADIAZINE DIOXIDE ACYCLONUCLEOSIDE; NUCLEOSIDE ANALOG; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CYTOMEGALOVIRUS INFECTION; DEACYLATION; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LUNG FIBROBLAST; MOLECULAR MODEL; VIRUS INHIBITION;

ANTI-HIV AGENTS; ANTIVIRAL AGENTS; BENZOTHIADIAZINES; CELL LINE; CYCLIC S-OXIDES; CYTOMEGALOVIRUS; HIV-1; HIV-2; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

EID: 0033535533     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980327z     Document Type: Article

References (22)

1. Goldman, R. C.; Klein, L. L. Problems and Progress in Opportunistic Infections. Annu. Rep. Med. Chem. 1994, 29, 155-164.
2. Winston, D. J.; Ho, W. G.; Champlin, R. E. Cytomegalovirus Infection after Allogenic Bone Marrow Transplantation. Rev. Infect. Dis. 1990, 12, 5776-5792.
3. Glenn, J. Cytomegalovirus Infections Following Renal Transplatation. Rev. Infect. 1981, 3, 1151-1178.
4. Schrier, R. D.; Freeman, W. R.; Wiley, C. A.; McCutchan, J. A. Immune Predispositions for Cytomegalovirus Retinitis in AIDS. J. Clin. Invest. 1995, 95, 1741-1746.
5. 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.
6. Chrisp, P.; Clissold, S. P. Foscarnet. A Review of its Antiviral Activity, Pharmacokinetic Properties and Therapeutic use in Immunocompromised Patients with Cytomegalovirus Retinitis. Drugs 1991, 41, 104-129.
7. De Clercq, E. Therapeutic potential of HPMPC as an antiviral drug. Rev. Med. Virol. 1993, 3, 85-96.
8. McCarthy, M. Oral Ganciclovir Fails to Prevent CMV in HIV Trial. Lancet 1995, 346, 895-899.
9. Boivin, G.; Chou, S.; Quirk, M. R.; Erice, A.; Jordan, M. C. Detection of Ganciclovir Resistance Mutations and Quantitation of Cytomegalovirus (CMV) DNA in Leucocytes of Patients with Fatal Disseminated CMV Disease. J. Infect. Dis. 1996, 173, 523-528.
10. Martinez, A.; Esteban, A. I.; Juanes, O.; Conde, S.; Goya, P.; De Clercq, E. New 1,2,6-Thiadiazine Dioxide Acyclonucleosides: Synthesis and Antiviral Evaluation. Bioorg. Med. Chem. 1995, 3, 1527-1535.
11. Esteban, A. I.; De Clercq, E.; Martinez, A. Synthesis and Antiviral Activity of Modified 1,2,6-Thiadiazine Dioxide Acyclonucleosides. Nucleosides Nucleotides 1997, 16, 265-276.
12. Martinez, A.; Esteban, A. I.; De Clercq, E. Benzothiadiazine Dioxide Acyclonucleosides as Lead Compounds for the Development of New Agents Against Human Cytomegalovirus and Varicella-Zoster Virus Infections. Bioorg. Med. Chem. Lett. 1997, 7, 1031-1032.
13. Cohen, E.; Klarberg, B. Sulfamoyl Chloride, Sulfamides and Sulfimide. J. Am. Chem. Soc. 1962, 84, 1994-2002.
14. Vorbrüggen, H.; Niedballa, U. A General Synthesis of N-Glycosides. J. Org. Chem. 1974, 39, 3654-3660.
15. Esteban, A. I.; Juanes, O.; Conde, S.; Martinez, A. Regioselective Lipase-mediated Acylation-deacylation in Thiadiazine Diacyclonucleosides. Tetrahedron 1994, 50, 13865-13873.
16. De Clercq, E. In vitro and ex vivo Test Systems to Rationalize Drug Design and Delivery. In Minutes of an European Symposium; Crommelin, D., Couvreur, P., Duchêne, D., Eds.; Editions de Santé: Paris, 1994; p 108.
17. Andrei, G.; Snoeck, R.; Reymen, D.; Liesnard, C.; Goubau, P.; Desmyter, J.; De Clercq, E. Comparative activity of selected antiviral compounds against clinical isolates of varicalla-zoster virus. Eur. J. Clin. Microbiol. Infect. Dis. 1988, 14, 318-328.
18. Snoeck, R.; Schols, D.; Andrei, G.; Neyts, J.; De Clercq, E. Antiviral activity of anticytomegalovirus agents (HPMPC, HP-MPA) assessed by a flow-cytometric method and DNA hybridization technique. Antiviral Res. 1991, 16, 1-9.
19. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; AlLaham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revision B.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
20. Rosowsky, A.; Kim, S.; Wick, M. Synthesis and Antitumor Activity of an Acyclonucleoside Derivative of 5-Fluorouracil. J. Med. Chem. 1981, 24, 1177-1181.
21. Renault, J.; Laduree, D.; Robba, M. Synthesis and Antiviral Study of Dihydrothieno and Thianopyrimidine Diones Acyclic Nucleosides as Potential Anti-HIV Agents. Nucleosides Nucleotides 1994, 13, 1135-1145.
22. Hasan, A.; Srivastava, P. C. Synthesis and Biological Studies of Unsaturated Acyclonucleosides Analogues of S-adenosyl-L-homocysteine Hydrolase Inhibitors. J. Med. Chem. 1992, 35, 1435-1439.