(Z)- and (E)-2-(hydroxymethylcyclopropylidene)-methylpurines and pyrimidines as antiviral agents

Antiviral Chemistry and Chemotherapy

Volumn 9, Issue 4, 1998, Pages 341-352

  Qiu, Y L ^a   Ptak, R G ^b   Breitenbach, J M ^b   Lin, J S ^c   Cheng, Y C ^c   Kern, E R ^d   Drach, J C ^b   Zemlicka, J ^a  

^a WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

^c YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d University of Alabama at Birmingham   (United States)

Author keywords

2 hydroxymethylcyclopropylidenemethylpurines and pyrimidines; 2 amino 6 cyclopropylaminopurines; EBV; HBV; HCMV; HHV 6; HIV 1; HSV 1; HSV 2; MCMV; Methylenecyclopropane analogues; VZV

Indexed keywords

1 (2 HYDROXYMETHYLCYCLOPROPYLIDENEMETHYL)CYTOSINE; 2 AMINO 6 CYCLOPROPYLAMINO 9 (2 HYDROXYMETHYLCYCLOPROPYLIDENEMETHYL)PURINE; 2,6 DIAMINO 9 (2 HYDROXYMETHYLCYCLOPROPYLIDENEMETHYL)PURINE; ADENALLENE; ANTIVIRUS AGENT; CYTALLENE; GANCICLOVIR; METHYLENECYCLOPROPANE DERIVATIVE; NUCLEOSIDE ANALOG; SYNADENOL; SYNCYTOL; SYNGUANOL; SYNTHYMOL; UNCLASSIFIED DRUG; ZALCITABINE; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOMEGALOVIRUS; DRUG POTENCY; DRUG SYNTHESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; EPSTEIN BARR VIRUS; HEPATITIS B VIRUS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN HERPESVIRUS 6; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; VARICELLA ZOSTER VIRUS;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; CYCLOPROPANES; CYTOMEGALOVIRUS; HEPATITIS B VIRUS; HERPESVIRUS 3, HUMAN; HERPESVIRUS 4, HUMAN; HIV; HUMANS; MOLECULAR STRUCTURE; PURINES; PYRIMIDINES; RATS; VIRUS REPLICATION;

EID: 0031849741     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (18)

1. Daluge SM, Good SS, Faletto MB, Miller WH, St Clair MH, Boone LR, Tisdale M, Parry NR, Reardon JE, Dornsife RE, Averett DR & Krenitsky TA (1997) 1592U89, a novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity. Antimicrobial Agents and Chemotherapy 41:1082-1093.
2. Danyluk SS (1979) Nuclear magnetic resonance studies of nucleoside conformational properties. In Nucleoside Analogues: Chemistry, Biology and Medical Applications, pp. 15-34. Edited by RT Walker, E De Clercq & F Eckstein. New York Plenum Press.
3. Faletto MB, Miller WH, Garvey EP, St Clair MH, Daluge SM & Good SS (1997) Unique intracellular activation of the potent antihuman immunodeficiency virus agent 1592U89. Antimicrobial Agents and Chemotherapy 41:1099-1107.
4. Holý A & Zemlicka J (1969) Oligonucleotidic compounds. XXXIII. A study of hydrolysis of N-dimethylaminomethylenecytidine, -adenosine, -guanosine and related 2′-deoxy compounds. Collection of Czechoslovak Chemical Communications 34:2449-2458.
5. Iwai I, Nishimura T & Shimizu B (1968) Anomeric pentofuranosyluracils and pentofuranosyl-thymines. In Synthetic Procedures in Nucleic Acid Chemistry, vol. 1, pp. 388-394. Edited by WW Zorbach & RS Tipson. New York: John Wiley and Sons.
6. Mitsuya H, Yarchoan R & Broder S (1990) Molecular targets for AIDS therapy. Science 249:1533-1544.
7. Otter BA & Fox JJ (1968) N-Acyl derivatives of 2′-deoxycytidine. In Synthetic Procedures in Nucleic Acid Chemistry, vol. 1, pp. 285-287. Edited by WW Zorbach & RS Tipson. New York; John Wiley and Sons.
8. Parker WB & Cheng Y-C (1994) Mitochondrial toxicity of antiviral nucleoside analogs. Journal of NIH Research 6:57-61.
9. Phadtare S, Kessel D, Corbett TH, Renis HE, Court BA & Zemlicka J (1991) Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity. Journal of Medicinal Chemistry 34:421-429.
10. Qiu Y-L, Zemlicka J, Ksebati MB & Drach JC (1997) Synthesis and isomeric assignment of 2-hydroxymethylcyclopropylidenepurines and -pyrimidines. Antiviral Research 34:A83.
11. Qiu Y-L, Ksebati MB, Ptak RG, Fan BY, Breitenbach JM, Drach JC, Cheng Y-C, Kern ER & Zemlicka J (1998) (Z)-and (E)-2-(Hydroxymethylcyclopropylidene)methyladenine and -guanine - new nucleoside analogues with a broad-spectrum antiviral activity. Journal of Medicinal Chemistry 41:10-23.
12. Van Draanen NA, Freeman GA, Short SA, Harvey R, Jansen G, Szczech G & Koszalka, GW (1996) Synthesis and antiviral activity of 2′-deoxy-4′-thio purine nucleosides. Journal of Medicinal Chemistry 39:538-542.
13. Zemlicka J (1993) Allenols derived from nucleic acid bases - a new class of anti-HIV agents: chemistry and biological activity. In Nucleosides and Nucleotides as Antitumor and Antiviral Agents, pp. 73-100. Edited by CK Chu & DC Baker. New Yorlc Plenum Press.
14. Zemlicka J (1996) Antiviral nucleoside analogues with axial chirality. Nucleosides & Nucleotides 16:1003-1012.
15. Zemlicka J & Holý A (1967) Preparation of N-dimethylaminomethylene derivatives - a new method of a selective substitution of nucleoside amino groups. Collection of Czechoslovak Chemical Communications 32:3159-3168.
16. 6 chemical shift in pyrimidine nucleosides. Journal of the American Chemical Society 97:4089-4095.
17. Zemlicka J, Qiu Y-L, Kern ER, Ptak RG, Breitenbach JM & Drach JC (1997) 2-Hydroxymethylcyclopropylidenemethylpurines and -pyrimidines - new nucleoside analogs with a broad spectrum antiviral activity. Antiviral Research 34:A46.
18. Zhu YL, Pai SB, Liu SH, Grove KL, Jones BCNM, Simons C, Zemlicka J & Cheng Y-C (1997) Inhibition of replication of hepatitis B virus in vitro by cytallene. Antimicrobial Agents and Chemotherapy 41:1755-1760.