Relationship between structural properties and affinity for herpes simplex virus type 1 thymidine kinase of bromine substituted 5-heteroaromatic 2′-deoxyuridines

Antiviral Research

Volumn 30, Issue 2-3, 1996, Pages 63-74

  Creuven, Isabelle ^a   Evrard, Christine ^a   Olivier, Anne ^a   Evrard, Guy ^a   Van Aerschot, Arthur ^b   Wigerinck, Piet ^b   Herdewijn, Piet ^b   Durant, Francois ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

5 substituted 2 deoxyuridine; Antiviral activity; Herpes simplex virus type 1 (HSV 1); Nucleoside; Thymidine kinase; X ray diffraction

Indexed keywords

HERPES; HUMAN HERPESVIRUS 1;

5 (3 BROMOTHIEN 2 YL) 2' DEOXYURIDINE; 5 (5 BROMOFURAN 2 YL) 2' DEOXYURIDINE; 5 (5 BROMOTHIEN 2 YL) 2' DEOXYURIDINE; 5 (5 FURAN 2 YL) 2' DEOXYURIDINE; 5 (5 THIEN 2 YL) 2' DEOXYURIDINE; ANTIVIRUS AGENT; DEOXYURIDINE DERIVATIVE; THYMIDINE KINASE; UNCLASSIFIED DRUG; VIRUS ENZYME;

ANTIVIRAL ACTIVITY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; CRYSTAL STRUCTURE; ENZYME INHIBITION; HERPES SIMPLEX VIRUS 1; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

ANTIVIRAL AGENTS; BROMINE; DEOXYURIDINE; HERPESVIRUS 1, HUMAN; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES; THYMIDINE KINASE; X-RAY DIFFRACTION;

EID: 0029994056     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/0166-3542(95)00838-1     Document Type: Article

References (20)

1. Bohman, C., Balzarini, J., Wigerinck, P., Van Aerschot, A., Herdewijn, P. and De Clercq, E. (1994) Mechanistic of cytostatic action of novel 5-(thien-2-yl)-and 5-(furan-2-yl) substituted pyrimidine nucleoside analogues against tumor cells transfected by the thymidine kinase gene of herpes simplex virus. J. Biol. Chem. 269, 8036-8043.
2. Creuven, I., Evrard, C., Olivier, A., Evrard, G., Wigerinck, P., Herdewijn, P. and Durant, F. (1995) 5-(Thien-2-yl) uracil analogues: 5-(5-methyithien-2-yl)-2′-deoxyuridine, 5-(5-thien-2-yl)-2′-deoxyuridine and 5-(5-bromothien-2-yl)-2′-de-oxyuridine. J. Chem. Crystallogr. submitted.
3. De Clercq, E. (1981) Nucleoside analogs as antiviral agents. Acta Microbiol. Acad. Sci. Hung. 28, 289-306.
4. De Clercq, E. and Torrence, P.F. (1978) Nucleoside analogs with antiviral activity. J. Carbohydr. Nucleosides Nucleotides 5, 187-224.
5. De Clercq, E., Descamps, J., De Somer, P., Barr, P.J., Jones, A. and Walker, R.T. (1979) Pharmacokinetics of (E)-5-(2-bromovinyl)-2′-deoxyuridine in mice. Proc. Natl. Acad. Sci. USA 76, 2947-2950.
6. De Clercq, E., Desgranges, C., Herdewijn, P., Sim, I.S., Jones, A.S., McLean, M.J. and Walker, R.T. (1986) Synthesis and antiviral activity of (E)-5-(2-bromovinyl)uracil and (E)-5-(2-bromovinyl)uridine. J. Med. Chem. 29, 213-217.
7. Derse, D.D., Cheng, Y.-C., Furman, P.A., St. Clair, M.H. and Elion, G.B. (1981) Inhibition of purified human and herpessimplex virus-induced DNA-polymerase by 9-(2-hydroxyethoxymethyl)guanine triphosphate effects on primer-template function. J. Biol. Chem. 256, 1447-1451.
8. Desgranges, C., Razaka, G., Rabaud, M., Bricaud, H., Balzarini, J. and De Clercq, E. (1983) Phosphorolysis of (E)-5-(2-bromovinyl)-2′-deoxyuridine (BVDU) and other 5-substituted-2′-deoxyuridine by purified human thymidine phosphorylase and intact blood platelets. Biochem. Pharmacol. 32, 3583-3590.
9. Elion, B.G., Furman, P.A., Fyfe, F.A., De Mirande, P., Beauchamps, L. and Schaffer, H.J. (1977) Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl)guanine. Proc. Natl. Acad. Sci. USA 74, 5716-5720.
10. Johnson, C.K. (1976) ORTEP Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennesse, USA.
11. Luyten, I., Jie, L., Van Aerschot, A., Pannecouque, C., Wigerinck. P., Rozenski, J., Hendrix, C., Wang, C., Wiebe, L., Balzarini, J., De Clercq, E. and Herdewijn, P. (1995) 2′-Deoxyuridine with 5-heteroaromatic substituent: synthesis and biological evolution. Antiviral Chem. Chemother. 6, 262-270.
12. Lozac'h, N. (1971) Adv. Heterocycl. Chem. 13, 161-234.
13. Olivier, A., Creuven, I., Evrard, C., Evrard, G., Dory, M., Van Aerschot, A., Wigerinck, P., Herdewijn, P. and Durant, F. (1994) Stereoelectronic properties of five anti-HSV-1 2′-deoxynucleosides analogues with heterocyclic substituents in the 5-position: a comparison with BVDU. Antiviral Res. 24, 289-304.
14. Ruth, J.L. and Cheng, Y.-C. (1981) Nucleoside analogs with clinical potential in antivirus chemotherapy. The effect of several thymidine and 2′-deoxycytidine analog 5′-triphosphates on purified human (alpha, beta) and herpes-simplex virus (type-1, type-2) DNA-polymerase. Mol. Pharmacol. 20, 415-422.
15. Sheldrick, G.M. (1986) SHELXS86. Program for the solution of crystal structures. Institut für Anorganische Chemie der Universität, Göttingen, Germany.
16. Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure determination. Institut fuer Anorg. Chemie, Univ. of Göttingen, Germany.
17. Spek, A. L. (1990) PLATON92. Acta Cryst. A 46, C3.
18. Wigerinck, P., Pannecouque, C., Snoeck, T., Claes, P., De Clercq, E. and Herdewijn, P. (1991a) 5-(5-Bromothien-2-yl)-2′-deoxyuridine and 5-(5-chlorothien-2-yl)-2′-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2′-deoxyuridine in the inhibition of herpes simplex virus type-1 replication. J. Med. Chem. 34, 2383-2389.
19. Wigerinck, P., Snoeck, R., Claes, P., De Clercq, E. and Herdewijn, P. (1991b) Synthesis and antiviral activity of 5-heteroaryl substituted 2′-deoxyuridine. J. Med. Chem. 34, 1767-1772.
20. Wigerinck, P., Kerremans, L., Claes, P., Snoeck, R., Maudgal, P., De Clercq, E. and Herdewijn, P. (1993) Synthesis and antiviral activity of 5-thien-2-yl-2′-deoxyuridine analogues. J. Med. Chem. 31, 538-543.