Synthesis and antiherpesvirus activities of 5-alkyl-2-thiopyrimidine nucleoside analogues

Antiviral Chemistry and Chemotherapy

Volumn 13, Issue 2, 2002, Pages 67-82

  Shigeta, S ^a   Mori, S ^a   Watanabe, F ^a   Takahashi, K ^a   Nagata, T ^b   Koike, N ^b   Wakayama, T ^b   Saneyoshi, M ^c  

^a FUKUSHIMA MEDICAL UNIVERSITY   (Japan)

^b Base Technology Center   (Japan)

^c TEIKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Antiviral; HSV; Pyrimidine nucleoside; Synthesis; VZV

Indexed keywords

2 THIOCYTOSINE ARABINOSIDE; 2 THIOPYRIMIDINE NUCLEOSIDE; 2' DEOXY 5 ETHYL 2 THIOCYTIDINE; 2' DEOXY 5 ETHYL 2 THIOURIDINE; 2' DEOXY 5 PROPYL 2 THIOCYTIDINE; 2' DEOXY 5 PROPYL 2 THIOURIDINE; 5 BROMOVINYL 2 THIOURACIL ARABINOSIDE; 5 PROPYL 2 THIOCYTIDINE; 5 STYRYL 2 THIOURACIL ARABINOSIDE; ACICLOVIR; ANTIVIRUS AGENT; ARABINOSIDE; NUCLEOSIDE ANALOG; THYMIDINE KINASE; TN 51; TN 53; TN 54; TN 65; TN 67; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; EMBRYO; FIBROBLAST; HERPES SIMPLEX VIRUS 1; HUMAN; HUMAN CELL; HUMAN CYTOMEGALOVIRUS; IN VITRO STUDY; LYMPHOBLASTOID CELL; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY; VARICELLA ZOSTER VIRUS;

EID: 0038749419     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.1177/095632020201300201     Document Type: Article

References (17)

1. Barr PJ, Jones AS, Verhelst G & Walker RT (1981) Synthesis of some 5-halogenovinyl derivatives of uracil and their conversion into 2′-deoxyribonucleosides. Journal of Chemical Society, Perkin Transartions I 1665-1670.
2. De Clercq E & Shugar D (1975) Antiviral activity of 5-ethyl pyrimidine deoxynucleosides. Biochemical Pharmacology 24:1073-1078.
3. De Clercq E, Descamps J & Shugar D (1978) 5-Propyl-2′-deoxyuridine: a specific anti-herpes agent. Antimicrobial Agents and Chemotherapy 13:545-547.
4. De Clercq E, Descamps J, Verhelst G, Walker RT, Jones AS, Torrence PF & Shugar D (1980) Comparative efficacy of antiherpes drugs against different strains of herpes simplex virus. Journal of Infectious Diseases 141:563-574.
5. De Clercq E, Descamps J, Ogata M & Shigeta S (1982) In vitro susceptibility of varicella-zoster virus to E-5-(2-bromovinyl)-2′-deoxyuridine and related compounds. Antimicrobial Agents and Chemotherapy 21:33-38.
6. Hamamura EK, Prystasz M, Verheyden JPH, Moffatt JG, Yamaguchi K, Uchida N, Sato K, Nomura A, Shiratori O, Takase S & Katagiri K (1976) Reaction of 2-Acyloxyisobutyryl halide with nucleosides. 6. Synthesis and biological evaluation of some 3′-acyl derivatives of 2,2′-anhydro-1-(β′D-arabinofuranosyl) cytosine hydrochloride. Journal of Medicinal Chemistry 19:654-662.
7. Kira T, Awano H, Shuto S, Matsuda A, Baba M, Konno K & Shigeta S (1996) The FIAU derivative (2′S)-2′-deoxy-2′-C-methyl-5-iodouridine (SMIU) is a novel, less cytotoxic and potent anti-HSV and anti-VZV agent. Antiviral Chemistry & Chemotherapy 7:209-212.
8. Machida H (1986a) Comparison of susceptibility of varicella zoster virus and herpes simplex virus to nucleoside analogues. Antimicrobial Agents and Chemotherapy 29:524-526.
9. Machida H (1986b) Suceptibility of varicella-zoster virus to thymidine analogues. Biken Journal 29:1-6.
10. Machida H, Nishitani M, Suzutani T & Hayashi K (1991) Different antiviral potencies of BV-araU and related nucleoside analogues against herpes simplex type 1 in human cell lines and Vero cells. Microbiology & Immunology 35:963-973.
11. McGuigan C, Yarnold CJ, Jones G, Velazquez S, Barucki H, Brancale A, Andrei G, Snoeck R, De Clercq E & Balzarini J (1999) Potent and selective inhibition of varicella-zoster virus (VZV) by nucleoside analogues with an unusual bicyclic base. Journal of Medicinal Chemisty 42:4479-4484.
12. McGuigan C, Brancale A, Barucki H, Srinvasan S, Jones G, Pathirana R, Sally B, Alvarez R, Yarnold CJ, Caragio A, Velazquez S, Andrei G, Snoeck R, De Clercq E & Balzarini J (2000) Fluorescent bicyclic furo pyrimidine deoxynucleoside analogs as potent and selective inhibitors of VZV and potential future drugs for the treatment of chickenpox and shingles. Drugs of the Future 25:1151-1161.
13. Shigeta S, Yokota T, Iwabuchi M, Baba M, Konno K, Ogata M & De Clercq E (1983) Comparative efficacy of antiherpes drugs against verious strains of varicella-zoster virus. Journal of Infectious Diseases 147:576-584.
14. Shigeta S, Konno K, Baba M, Yokota T & De Clercq E (1991) Comparative inhibitory effects of nucleoside analogues on different clinical isolates of human cytomegalovirus in vitro. Journal of Infectious Diseases 163:270-275.
15. Shigeta S, Mori S, Kira T, Takahashi K, Kodama E, Konno K, Nagata T, Kato H, Wakayama T, Koike N & Saneyoshi M (1999) Anti-herpesvirus activities and cytotoxicities of 2-thiopyrimidine nucleoside analogues in vitro. Antiviral Chemistry & Chemotherapy 10:195-209.
16. Srinivasan S, McGuigan C, Andrei G, Snoeck R, De Clercq E & Balzarini J (2001) Bicyclic nucleoside inhibitors of varicella-zoster virus (VZV): The effect of terminal unsaturation in the side chain. Bioorganic & Medicinal Chemistry Letters 11:391-393.
17. Vorbrüggen H & Strehlke P (1973) Nucleosid synthesen, VII. Eine einfache synthese von 2-thiopyrimidin-nucleosiden. Chemische Berichte 106:3039-3061.