메뉴 건너뛰기




Volumn 5, Issue , 2007, Pages 113-165

Methylenecyclopropane Analogues of Nucleosides as Anti-herpes Agents

(1)  Zemlicka, Jiri a  

a NONE

Author keywords

[No Author keywords available]

Indexed keywords

HERPES; HERPESVIRIDAE;

EID: 40749114495     PISSN: 10758593     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1075-8593(06)05003-9     Document Type: Review
Times cited : (20)

References (84)
  • 1
    • 29244482292 scopus 로고    scopus 로고
    • Phosphoralaninate pronucleotides of pyrimidine methylenecyclopropane analogues of nucleosides: Synthesis and antiviral activity
    • Ambrose A.R., Zemlicka J., Kern E.R., Drach J.C., Gullen E., and Cheng Y.-C. Phosphoralaninate pronucleotides of pyrimidine methylenecyclopropane analogues of nucleosides: Synthesis and antiviral activity. Nucleosides Nucleotides Nucleic Acids 24 (2005) 1763-1774
    • (2005) Nucleosides Nucleotides Nucleic Acids , vol.24 , pp. 1763-1774
    • Ambrose, A.R.1    Zemlicka, J.2    Kern, E.R.3    Drach, J.C.4    Gullen, E.5    Cheng, Y.-C.6
  • 2
    • 0036888658 scopus 로고    scopus 로고
    • Z-isomers of 2-hydroxymethylcyclopropylidenemethyladenine (synadenol) and guanine (synguanol) are active against ganciclovir- and foscarnet-resistant human cytomegalovirus UL97 mutants
    • Baldanti F., Sarasini A., Drach J.C., Zemlicka J., and Gerna G. Z-isomers of 2-hydroxymethylcyclopropylidenemethyladenine (synadenol) and guanine (synguanol) are active against ganciclovir- and foscarnet-resistant human cytomegalovirus UL97 mutants. Antiviral Res. 56 (2002) 273-278
    • (2002) Antiviral Res. , vol.56 , pp. 273-278
    • Baldanti, F.1    Sarasini, A.2    Drach, J.C.3    Zemlicka, J.4    Gerna, G.5
  • 3
    • 0032979644 scopus 로고    scopus 로고
    • Comparative study of the anti-human cytomegalovirus activities and toxicities of a tetrahydrofuran phosphonate analogue of guanosine and cidofovir
    • Bedard J., May S., Lis M., Tryphonas L., Drach J., Huffman J., Sidwell R., Chan L., Bowlin T., and Rando R. Comparative study of the anti-human cytomegalovirus activities and toxicities of a tetrahydrofuran phosphonate analogue of guanosine and cidofovir. Antimicrob. Agents Chemother. 43 (1999) 557-567
    • (1999) Antimicrob. Agents Chemother. , vol.43 , pp. 557-567
    • Bedard, J.1    May, S.2    Lis, M.3    Tryphonas, L.4    Drach, J.5    Huffman, J.6    Sidwell, R.7    Chan, L.8    Bowlin, T.9    Rando, R.10
  • 4
    • 0242676754 scopus 로고    scopus 로고
    • In vitro and in vivo activity of the methylenecyclopropane analog, QYL-1064, against murine and human cytomegalovirus infections
    • Bidanset D.J., Hartline C.B., Collins D.J., Quenelle D.C., Chen X., Zemlicka J., and Kern E.R. In vitro and in vivo activity of the methylenecyclopropane analog, QYL-1064, against murine and human cytomegalovirus infections. Antiviral Res. 53 87 (2002) A61
    • (2002) Antiviral Res. , vol.53 , Issue.87
    • Bidanset, D.J.1    Hartline, C.B.2    Collins, D.J.3    Quenelle, D.C.4    Chen, X.5    Zemlicka, J.6    Kern, E.R.7
  • 5
    • 0029692308 scopus 로고    scopus 로고
    • Crystal structures of some acyclonucleosides with antiviral activity and related compounds
    • Birnbaum K.B. Crystal structures of some acyclonucleosides with antiviral activity and related compounds. Acta Biochim. Pol. 43 (1996) 65-76
    • (1996) Acta Biochim. Pol. , vol.43 , pp. 65-76
    • Birnbaum, K.B.1
  • 6
    • 0028260480 scopus 로고
    • Structure and conformation of the cyclic phosphate of ganciclovir, a broad-spectrum antiviral agent
    • Birnbaum K.B., Stolarski R., and Shugar D. Structure and conformation of the cyclic phosphate of ganciclovir, a broad-spectrum antiviral agent. Biochim. Biophys. Acta 1200 (1994) 55-63
    • (1994) Biochim. Biophys. Acta , vol.1200 , pp. 55-63
    • Birnbaum, K.B.1    Stolarski, R.2    Shugar, D.3
  • 9
    • 0037059540 scopus 로고    scopus 로고
    • Revision of absolute configuration of enantiomeric (methylenecyclopropyl)carbinols obtained from (R)-(-)- and (S)-(+)-epichlorohydrin and methylenetriphenylphosphorane. Implications for reaction mechanism and improved synthesis of antiviral methylenecyclopropane analogues of nucleosides
    • Chen X., and Zemlicka J. Revision of absolute configuration of enantiomeric (methylenecyclopropyl)carbinols obtained from (R)-(-)- and (S)-(+)-epichlorohydrin and methylenetriphenylphosphorane. Implications for reaction mechanism and improved synthesis of antiviral methylenecyclopropane analogues of nucleosides. J. Org. Chem. 67 (2002) 286-289
    • (2002) J. Org. Chem. , vol.67 , pp. 286-289
    • Chen, X.1    Zemlicka, J.2
  • 10
    • 0242500884 scopus 로고    scopus 로고
    • Structure-activity relationships of (S, Z)-2-aminopurine methylenecyclopropane analogues of nucleosides. Variation of purine-6 substituents and activity against herpesviruses and hepatitis B virus
    • Chen X., Kern E.R., Drach J.C., Gullen E., Cheng Y.-C., and Zemlicka J. Structure-activity relationships of (S, Z)-2-aminopurine methylenecyclopropane analogues of nucleosides. Variation of purine-6 substituents and activity against herpesviruses and hepatitis B virus. J. Med. Chem. 46 (2003) 1531-1537
    • (2003) J. Med. Chem. , vol.46 , pp. 1531-1537
    • Chen, X.1    Kern, E.R.2    Drach, J.C.3    Gullen, E.4    Cheng, Y.-C.5    Zemlicka, J.6
  • 11
    • 0032485470 scopus 로고    scopus 로고
    • 9-Hydroxymethylcyclopropylidene-methylenyladenine: The design, facile synthesis, isomer separation and anti-HIV activities
    • Cheng C., Shimo T., Somekawa K., and Baba M. 9-Hydroxymethylcyclopropylidene-methylenyladenine: The design, facile synthesis, isomer separation and anti-HIV activities. Tetrahedron 54 (1998) 2031-2040
    • (1998) Tetrahedron , vol.54 , pp. 2031-2040
    • Cheng, C.1    Shimo, T.2    Somekawa, K.3    Baba, M.4
  • 15
    • 0022448521 scopus 로고
    • In vitro and in vivo activities of phosphate derivatives of 9-(1,3-dihydroxy-2-propoxymethyl)-guanine against cytomegalovirus
    • Duke A.E., Smee D.F., Chernow M., Boehme R., and Matthews T.R. In vitro and in vivo activities of phosphate derivatives of 9-(1,3-dihydroxy-2-propoxymethyl)-guanine against cytomegalovirus. Antiviral Res. 6 (1986) 299-308
    • (1986) Antiviral Res. , vol.6 , pp. 299-308
    • Duke, A.E.1    Smee, D.F.2    Chernow, M.3    Boehme, R.4    Matthews, T.R.5
  • 18
    • 0034629299 scopus 로고    scopus 로고
    • Spiropentane mimics of nucleosides: analogues of 2′-deoxyadenosine and 2′-deoxyguanosine. Synthesis of all stereoisomers, isomeric assignment, and biological activity
    • Guan H.-P., Ksebati M.B., Cheng Y.-C., Drach J.C., Kern E.R., and Zemlicka J. Spiropentane mimics of nucleosides: analogues of 2′-deoxyadenosine and 2′-deoxyguanosine. Synthesis of all stereoisomers, isomeric assignment, and biological activity. J. Org. Chem. 65 (2000) 1280-1290
    • (2000) J. Org. Chem. , vol.65 , pp. 1280-1290
    • Guan, H.-P.1    Ksebati, M.B.2    Cheng, Y.-C.3    Drach, J.C.4    Kern, E.R.5    Zemlicka, J.6
  • 19
    • 0034714564 scopus 로고    scopus 로고
    • Approaches to unsaturated analogues of nucleosides comprising four- and six-membered rings
    • Guan H.-P., Ksebati M.B., Kern E.R., and Zemlicka J. Approaches to unsaturated analogues of nucleosides comprising four- and six-membered rings. J. Org. Chem. 65 (2000) 5177-5184
    • (2000) J. Org. Chem. , vol.65 , pp. 5177-5184
    • Guan, H.-P.1    Ksebati, M.B.2    Kern, E.R.3    Zemlicka, J.4
  • 20
    • 0037157807 scopus 로고    scopus 로고
    • Synthesis of phosphonate derivatives of methylenecyclopropane nucleoside analogues by alkylation-elimination method and unusual opening of cyclopropane ring
    • Guan H.-P., Qiu Y.-L., Ksebati M.B., Kern E.R., and Zemlicka J. Synthesis of phosphonate derivatives of methylenecyclopropane nucleoside analogues by alkylation-elimination method and unusual opening of cyclopropane ring. Tetrahedron 58 (2002) 6047-6059
    • (2002) Tetrahedron , vol.58 , pp. 6047-6059
    • Guan, H.-P.1    Qiu, Y.-L.2    Ksebati, M.B.3    Kern, E.R.4    Zemlicka, J.5
  • 21
    • 0033584922 scopus 로고    scopus 로고
    • The stereoselective synthesis of cyclopropylphosphonate analogs of nucleotides
    • Hah J.H., Gil J.M., and Oh D.Y. The stereoselective synthesis of cyclopropylphosphonate analogs of nucleotides. Tetrahedron Lett. 40 (1999) 8235-8238
    • (1999) Tetrahedron Lett. , vol.40 , pp. 8235-8238
    • Hah, J.H.1    Gil, J.M.2    Oh, D.Y.3
  • 22
    • 0024354624 scopus 로고
    • Prodrugs of the selective antiherpesvirus agent 9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]guanine (BRL 39123) with improved gastrointestinal absorption properties
    • Harnden M.R., Jarvest R.L., Boyd M.R., Sutton D., and Vere Hodge R.A. Prodrugs of the selective antiherpesvirus agent 9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]guanine (BRL 39123) with improved gastrointestinal absorption properties. J. Med. Chem. 32 (1989) 1738-1743
    • (1989) J. Med. Chem. , vol.32 , pp. 1738-1743
    • Harnden, M.R.1    Jarvest, R.L.2    Boyd, M.R.3    Sutton, D.4    Vere Hodge, R.A.5
  • 23
    • 0007621056 scopus 로고
    • Adenallene and cytallene: Acyclic nucleoside analogues that inhibit replication and cytopathic effect of human immunodeficiency virus in vitro
    • Hayashi S., Phadtare S., Zemlicka J., Matsukura M., Mitsuya H., and Broder S. Adenallene and cytallene: Acyclic nucleoside analogues that inhibit replication and cytopathic effect of human immunodeficiency virus in vitro. Proc. Natl. Acad. Sci. USA 85 (1988) 6127-6131
    • (1988) Proc. Natl. Acad. Sci. USA , vol.85 , pp. 6127-6131
    • Hayashi, S.1    Phadtare, S.2    Zemlicka, J.3    Matsukura, M.4    Mitsuya, H.5    Broder, S.6
  • 24
    • 4544276732 scopus 로고    scopus 로고
    • Synthesis and properties of allenic natural products and pharmaceuticals
    • Hoffmann-Röder A., and Krause N. Synthesis and properties of allenic natural products and pharmaceuticals. Angew. Chem., Int. Ed. 43 (2004) 1196-1216
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1196-1216
    • Hoffmann-Röder, A.1    Krause, N.2
  • 25
    • 0142171945 scopus 로고    scopus 로고
    • Synthesis and biological activity of isopolar acyclic nucleotide analogs
    • Chu C.K. (Ed), Elsevier, Amsterdam
    • Holý A. Synthesis and biological activity of isopolar acyclic nucleotide analogs. In: Chu C.K. (Ed). Recent Advances in Nucleosides: Chemistry and Chemotherapy (2002), Elsevier, Amsterdam 167-238
    • (2002) Recent Advances in Nucleosides: Chemistry and Chemotherapy , pp. 167-238
    • Holý, A.1
  • 26
    • 48349145815 scopus 로고    scopus 로고
    • Unsaturated acyclic nucleosides and nucleotides: synthesis and antiviral properties
    • Schinazi R.F., and Liotta D.C. (Eds), IHL Press, Tucker, Georgia, USA
    • Ivanov A.V., and Jasko M.V. Unsaturated acyclic nucleosides and nucleotides: synthesis and antiviral properties. In: Schinazi R.F., and Liotta D.C. (Eds). Frontiers in Nucleosides and Nucleic Acids (2004), IHL Press, Tucker, Georgia, USA 365-399
    • (2004) Frontiers in Nucleosides and Nucleic Acids , pp. 365-399
    • Ivanov, A.V.1    Jasko, M.V.2
  • 27
    • 9644281600 scopus 로고    scopus 로고
    • Oral activity of a methylenecyclopropane analog, cyclopropavir, in animal models for cytomegalovirus infections
    • Kern E.R., Bidanset D.J., Hartline C.B., Yan Z., Zemlicka J., and Quenelle D.C. Oral activity of a methylenecyclopropane analog, cyclopropavir, in animal models for cytomegalovirus infections. Antimicrob. Agents Chemother. 48 (2004) 4745-4753
    • (2004) Antimicrob. Agents Chemother. , vol.48 , pp. 4745-4753
    • Kern, E.R.1    Bidanset, D.J.2    Hartline, C.B.3    Yan, Z.4    Zemlicka, J.5    Quenelle, D.C.6
  • 29
    • 0001713670 scopus 로고
    • Ionic iodocarbocyclization reactions of 4-alkenyl and 4-alkylmalonate derivatives
    • Kitagawa O., Inoue T., Hirano K., and Taguchi T. Ionic iodocarbocyclization reactions of 4-alkenyl and 4-alkylmalonate derivatives. J. Org. Chem. 58 (1993) 3106-3112
    • (1993) J. Org. Chem. , vol.58 , pp. 3106-3112
    • Kitagawa, O.1    Inoue, T.2    Hirano, K.3    Taguchi, T.4
  • 32
    • 0000776069 scopus 로고
    • Mechanistic study on the inactivation of general acyl-CoA dehydrogenase by a metabolite of hypoglycin A
    • Lai M.-t., Liu L.-d., and Liu H.-w. Mechanistic study on the inactivation of general acyl-CoA dehydrogenase by a metabolite of hypoglycin A. J. Am. Chem. Soc. 113 (1991) 7388-7397
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7388-7397
    • Lai, M.-t.1    Liu, L.-d.2    Liu, H.-w.3
  • 33
    • 2042490269 scopus 로고
    • New convenient access to optically active methylidenecyclopropylcarbinols
    • Le Corre M., Hercouet A., and Bessieres B. New convenient access to optically active methylidenecyclopropylcarbinols. J. Org. Chem. 59 (1994) 5483-5484
    • (1994) J. Org. Chem. , vol.59 , pp. 5483-5484
    • Le Corre, M.1    Hercouet, A.2    Bessieres, B.3
  • 34
    • 0036632590 scopus 로고    scopus 로고
    • BCH-1868 [(-)-2-R-dihydroxyphosphinoyl-5-(S)-(guanin-9′-yl-methyl) tetrahydrofuran]: A cyclic nucleoside phosphonate with antitumor activity
    • Leblond L., Attardo G., Hamelin B., Bouffard D.Y., Nguyen-Ba N., and Gourdeau H. BCH-1868 [(-)-2-R-dihydroxyphosphinoyl-5-(S)-(guanin-9′-yl-methyl) tetrahydrofuran]: A cyclic nucleoside phosphonate with antitumor activity. Mol. Cancer Ther. 1 (2002) 737-746
    • (2002) Mol. Cancer Ther. , vol.1 , pp. 737-746
    • Leblond, L.1    Attardo, G.2    Hamelin, B.3    Bouffard, D.Y.4    Nguyen-Ba, N.5    Gourdeau, H.6
  • 35
    • 0014271211 scopus 로고
    • Selective N-debenzoylation of N,O-polybenzoylnucleosides
    • Letsinger R.L., Miller P.S., and Grams G.W. Selective N-debenzoylation of N,O-polybenzoylnucleosides. Tetrahedron Lett. 9 (1968) 2621-2624
    • (1968) Tetrahedron Lett. , vol.9 , pp. 2621-2624
    • Letsinger, R.L.1    Miller, P.S.2    Grams, G.W.3
  • 36
    • 11844255399 scopus 로고    scopus 로고
    • Bioisosterism: A useful strategy for molecular modification and drug design
    • Lima L.M., and Barreiro E.J. Bioisosterism: A useful strategy for molecular modification and drug design. Curr. Med. Chem. 12 (2005) 23-49
    • (2005) Curr. Med. Chem. , vol.12 , pp. 23-49
    • Lima, L.M.1    Barreiro, E.J.2
  • 37
    • 0026561408 scopus 로고
    • Aryl phosphate derivatives of AZT retain activity against HIV-1 in cell lines which are resistant to the action of AZT
    • McGuigan C., Pathirana R.N., Mahmood N., Devine K.G., and Hay A.J. Aryl phosphate derivatives of AZT retain activity against HIV-1 in cell lines which are resistant to the action of AZT. Antiviral Res. 17 (1992) 311-321
    • (1992) Antiviral Res. , vol.17 , pp. 311-321
    • McGuigan, C.1    Pathirana, R.N.2    Mahmood, N.3    Devine, K.G.4    Hay, A.J.5
  • 38
    • 0026499634 scopus 로고
    • (R)-(-)- and (S)-(+)-Adenallene: synthesis, absolute configuration, enantioselectivity of antiretroviral effect, and enzymic deamination
    • Megati S., Goren Z., Silverton J.V., Orlina J., Nishimura H., Shirasaki T., Mitsuya H., and Zemlicka J. (R)-(-)- and (S)-(+)-Adenallene: synthesis, absolute configuration, enantioselectivity of antiretroviral effect, and enzymic deamination. J. Med. Chem. 35 (1992) 4098-4104
    • (1992) J. Med. Chem. , vol.35 , pp. 4098-4104
    • Megati, S.1    Goren, Z.2    Silverton, J.V.3    Orlina, J.4    Nishimura, H.5    Shirasaki, T.6    Mitsuya, H.7    Zemlicka, J.8
  • 39
    • 0023753835 scopus 로고
    • New methodologies for the synthesis of C-2 functionalized hypoxanthine nucleosides
    • Nair V., Turner G.A., Buenger G.S., and Chamberlain S.D. New methodologies for the synthesis of C-2 functionalized hypoxanthine nucleosides. J. Org. Chem. 53 (1988) 3051-3057
    • (1988) J. Org. Chem. , vol.53 , pp. 3051-3057
    • Nair, V.1    Turner, G.A.2    Buenger, G.S.3    Chamberlain, S.D.4
  • 42
    • 0000333591 scopus 로고
    • One-pot synthesis of enantiomerically pure (methylenecyclopropyl)carbinol: A key intermediate to the synthesis of the causative agent of Jamaican vomiting sickness
    • Okuma K., Tanaka Y., Yoshihara K., Ezaki A., Koda G., Ohta H., Hara K., and Kashimura S. One-pot synthesis of enantiomerically pure (methylenecyclopropyl)carbinol: A key intermediate to the synthesis of the causative agent of Jamaican vomiting sickness. J. Org. Chem. 58 (1993) 5915-5917
    • (1993) J. Org. Chem. , vol.58 , pp. 5915-5917
    • Okuma, K.1    Tanaka, Y.2    Yoshihara, K.3    Ezaki, A.4    Koda, G.5    Ohta, H.6    Hara, K.7    Kashimura, S.8
  • 43
    • 0021971882 scopus 로고
    • Inhibition of HSV-transformed murine cells by nucleoside analogs, 2′-NDG and 2′-nor-cGMP. Mechanism of inhibition and reversal by exogenous nucleosides
    • Oliver S., Bubley G., and Crumpacker C. Inhibition of HSV-transformed murine cells by nucleoside analogs, 2′-NDG and 2′-nor-cGMP. Mechanism of inhibition and reversal by exogenous nucleosides. Virology 145 (1985) 84-93
    • (1985) Virology , vol.145 , pp. 84-93
    • Oliver, S.1    Bubley, G.2    Crumpacker, C.3
  • 44
    • 0034631778 scopus 로고    scopus 로고
    • Fluorinated nucleosides
    • Pankiewicz K.W. Fluorinated nucleosides. Carbohydr. Res. 327 (2000) 87-105
    • (2000) Carbohydr. Res. , vol.327 , pp. 87-105
    • Pankiewicz, K.W.1
  • 45
    • 0000946769 scopus 로고
    • Nucleic acid derived allenols: Unusual analogues of nucleosides with antiretroviral activity
    • Phadtare S., and Zemlicka J. Nucleic acid derived allenols: Unusual analogues of nucleosides with antiretroviral activity. J. Am. Chem. Soc. 111 (1989) 5925-5931
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 5925-5931
    • Phadtare, S.1    Zemlicka, J.2
  • 46
    • 30344470782 scopus 로고    scopus 로고
    • Synthesis, antiviral and antitumor activity of 2-substituted purine methylenecyclopropane analogues of nucleosides
    • Qin X., Chen X., Wang K., Polin L., Kern E.R., Drach J.C., Gullen E., Cheng Y.-C., and Zemlicka J. Synthesis, antiviral and antitumor activity of 2-substituted purine methylenecyclopropane analogues of nucleosides. Bioorg. Med. Chem. 14 (2006) 1247-1254
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 1247-1254
    • Qin, X.1    Chen, X.2    Wang, K.3    Polin, L.4    Kern, E.R.5    Drach, J.C.6    Gullen, E.7    Cheng, Y.-C.8    Zemlicka, J.9
  • 47
    • 48349142623 scopus 로고    scopus 로고
    • X. Qin, J. Zemlicka, unpublished results
    • X. Qin, J. Zemlicka, unpublished results
  • 48
    • 0031756538 scopus 로고    scopus 로고
    • A new efficient synthesis of antiviral methylenecyclopropane analogs of purine nucleosides
    • Qiu Y.-L., and Zemlicka J. A new efficient synthesis of antiviral methylenecyclopropane analogs of purine nucleosides. Synthesis (1998) 1447-1452
    • (1998) Synthesis , pp. 1447-1452
    • Qiu, Y.-L.1    Zemlicka, J.2
  • 53
    • 17544400595 scopus 로고    scopus 로고
    • Synthesis and enantioselectivity of the antiviral effects of (R,Z)-, (S,Z)-methylenecyclopropane analogues of purine nucleosides and phosphoralaninate prodrugs: influence of heterocyclic base, type of virus and host cells
    • Qiu Y.-L., Geiser F., Kira T., Gullen E., Cheng Y.-C., Ptak R.G., Breitenbach J.M., Drach J.C., Hartline C.B., Kern E.R., and Zemlicka J. Synthesis and enantioselectivity of the antiviral effects of (R,Z)-, (S,Z)-methylenecyclopropane analogues of purine nucleosides and phosphoralaninate prodrugs: influence of heterocyclic base, type of virus and host cells. Antiviral Chem. Chemother. 11 (2000) 191-202
    • (2000) Antiviral Chem. Chemother. , vol.11 , pp. 191-202
    • Qiu, Y.-L.1    Geiser, F.2    Kira, T.3    Gullen, E.4    Cheng, Y.-C.5    Ptak, R.G.6    Breitenbach, J.M.7    Drach, J.C.8    Hartline, C.B.9    Kern, E.R.10    Zemlicka, J.11
  • 54
    • 0343674498 scopus 로고    scopus 로고
    • Synthesis of (Z)- and (E)-9-[(2-hydroxy-ethylidene)cyclopropyl]adenine-new methylenecyclopropane analogues of adenosine and their substrate activity for adenosine deaminase
    • Qiu Y.-L., Ksebati M.B., and Zemlicka J. Synthesis of (Z)- and (E)-9-[(2-hydroxy-ethylidene)cyclopropyl]adenine-new methylenecyclopropane analogues of adenosine and their substrate activity for adenosine deaminase. Nucleosides Nucleotides Nucleic Acids 19 (2000) 31-37
    • (2000) Nucleosides Nucleotides Nucleic Acids , vol.19 , pp. 31-37
    • Qiu, Y.-L.1    Ksebati, M.B.2    Zemlicka, J.3
  • 55
    • 0019781093 scopus 로고
    • Nucleic acid related compounds. 34. Non-aqueous diazotization with tert-butyl nitrite. Introduction of fluorine, chlorine, and bromine at C-2 of purine nucleosides
    • Robins M.J., and Uznanski B. Nucleic acid related compounds. 34. Non-aqueous diazotization with tert-butyl nitrite. Introduction of fluorine, chlorine, and bromine at C-2 of purine nucleosides. Can. J. Chem. 59 (1981) 2608-2611
    • (1981) Can. J. Chem. , vol.59 , pp. 2608-2611
    • Robins, M.J.1    Uznanski, B.2
  • 56
    • 0000397115 scopus 로고
    • Structural chemistry of cyclopropane derivatives
    • Rappoport Z. (Ed), Wiley, New York loc. cit. p. 187
    • Rozsondai B. Structural chemistry of cyclopropane derivatives. In: Rappoport Z. (Ed). The Chemistry of the Cyclopropyl Group, vol. 2 (1995), Wiley, New York 139-221 loc. cit. p. 187
    • (1995) The Chemistry of the Cyclopropyl Group, vol. 2 , pp. 139-221
    • Rozsondai, B.1
  • 57
    • 0032867614 scopus 로고    scopus 로고
    • Effective treatment of murine cytomegalovirus infections with methylenecyclopropane analogues of nucleosides
    • Rybak R.J., Zemlicka J., Qiu Y.-L., Hartline C.B., and Kern E.R. Effective treatment of murine cytomegalovirus infections with methylenecyclopropane analogues of nucleosides. Antiviral Res. 43 (1999) 175-188
    • (1999) Antiviral Res. , vol.43 , pp. 175-188
    • Rybak, R.J.1    Zemlicka, J.2    Qiu, Y.-L.3    Hartline, C.B.4    Kern, E.R.5
  • 60
    • 0001668820 scopus 로고
    • Cyclic phosphates. IV. Ribonucleoside-3′,5′ cyclic phosphates. A general method of synthesis and some properties
    • Smith M., Drummond G.I., and Khorana H.G. Cyclic phosphates. IV. Ribonucleoside-3′,5′ cyclic phosphates. A general method of synthesis and some properties. J. Am. Chem. Soc. 83 (1961) 698-706
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 698-706
    • Smith, M.1    Drummond, G.I.2    Khorana, H.G.3
  • 62
    • 0026720227 scopus 로고
    • A protein kinase homologue controls phosphorylation of ganciclovir in human cytomegalovirus-infected cells
    • Sullivan V., Talarico C.L., Stanat C.S., Davis M., Coen D.M., and Biron K.K. A protein kinase homologue controls phosphorylation of ganciclovir in human cytomegalovirus-infected cells. Nature 358 (1992) 162-164
    • (1992) Nature , vol.358 , pp. 162-164
    • Sullivan, V.1    Talarico, C.L.2    Stanat, C.S.3    Davis, M.4    Coen, D.M.5    Biron, K.K.6
  • 65
    • 11544318102 scopus 로고
    • Mechanism of hydrogenation of unsaturated cyclopropanes
    • Ullman E.F. Mechanism of hydrogenation of unsaturated cyclopropanes. J. Am. Chem. Soc. 81 (1959) 5386-5392
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 5386-5392
    • Ullman, E.F.1
  • 67
    • 0033736202 scopus 로고    scopus 로고
    • Pronucleotides: toward the in vivo delivery of antiviral and anticancer nucleotides
    • Wagner C.R., Iyer V.V., and McIntee E.J. Pronucleotides: toward the in vivo delivery of antiviral and anticancer nucleotides. Med. Res. Rev. 20 (2000) 417-451
    • (2000) Med. Res. Rev. , vol.20 , pp. 417-451
    • Wagner, C.R.1    Iyer, V.V.2    McIntee, E.J.3
  • 68
    • 0035829404 scopus 로고    scopus 로고
    • Methylene-gem-difluorocyclopropane analogues of nucleosides: synthesis, cyclopropene-methylenecyclopropane rearrangement, and biological activity
    • Wang R., Ksebati M.B., Corbett T.H., Kern E.R., Drach J.C., and Zemlicka J. Methylene-gem-difluorocyclopropane analogues of nucleosides: synthesis, cyclopropene-methylenecyclopropane rearrangement, and biological activity. J. Med. Chem. 44 (2001) 4019-4022
    • (2001) J. Med. Chem. , vol.44 , pp. 4019-4022
    • Wang, R.1    Ksebati, M.B.2    Corbett, T.H.3    Kern, E.R.4    Drach, J.C.5    Zemlicka, J.6
  • 70
    • 0037264387 scopus 로고    scopus 로고
    • Synthesis and biological activity of 2-aminopurine methylenecyclopropane analogues of nucleosides
    • Wang R., Chen X., Drach J.C., Kern E.R., and Zemlicka J. Synthesis and biological activity of 2-aminopurine methylenecyclopropane analogues of nucleosides. Nucleosides Nucleotides Nucleic Acids 22 (2003) 135-144
    • (2003) Nucleosides Nucleotides Nucleic Acids , vol.22 , pp. 135-144
    • Wang, R.1    Chen, X.2    Drach, J.C.3    Kern, E.R.4    Zemlicka, J.5
  • 71
    • 0142124180 scopus 로고    scopus 로고
    • Inhibition of human immunodeficiency virus reverse transcriptase by synadenol triphosphate and its E-isomer
    • Wang R., Harada S., Mitsuya H., and Zemlicka J. Inhibition of human immunodeficiency virus reverse transcriptase by synadenol triphosphate and its E-isomer. J. Med. Chem. 46 (2003) 4799-4802
    • (2003) J. Med. Chem. , vol.46 , pp. 4799-4802
    • Wang, R.1    Harada, S.2    Mitsuya, H.3    Zemlicka, J.4
  • 73
    • 12144255999 scopus 로고    scopus 로고
    • Nucleotides and pronucleotides of 2,2-bis(hydroxymethyl)methylenecyclopropane analogues of purine nucleosides: Synthesis and antiviral activity
    • Yan Z., Kern E.R., Gullen E., Cheng Y.-C., Drach J.C., and Zemlicka J. Nucleotides and pronucleotides of 2,2-bis(hydroxymethyl)methylenecyclopropane analogues of purine nucleosides: Synthesis and antiviral activity. J. Med. Chem. 48 (2005) 91-99
    • (2005) J. Med. Chem. , vol.48 , pp. 91-99
    • Yan, Z.1    Kern, E.R.2    Gullen, E.3    Cheng, Y.-C.4    Drach, J.C.5    Zemlicka, J.6
  • 74
    • 32644453359 scopus 로고    scopus 로고
    • Synthesis of methylenecyclopropane analogues of antiviral nucleoside phosphonates
    • Yan Z., Zhou S., Kern E.R., and Zemlicka J. Synthesis of methylenecyclopropane analogues of antiviral nucleoside phosphonates. Tetrahedron 62 (2006) 2608-2615
    • (2006) Tetrahedron , vol.62 , pp. 2608-2615
    • Yan, Z.1    Zhou, S.2    Kern, E.R.3    Zemlicka, J.4
  • 75
    • 0002208958 scopus 로고
    • Allenols derived from nucleic acid bases-a new class of anti-HIV agents: Chemistry and biological activity
    • Chu C.K., and Baker D.C. (Eds), Plenum Press, New York
    • Zemlicka J. Allenols derived from nucleic acid bases-a new class of anti-HIV agents: Chemistry and biological activity. In: Chu C.K., and Baker D.C. (Eds). Nucleosides and Nucleotides as Antitumor and Antiviral Agents (1993), Plenum Press, New York 73-100
    • (1993) Nucleosides and Nucleotides as Antitumor and Antiviral Agents , pp. 73-100
    • Zemlicka, J.1
  • 76
    • 0030732774 scopus 로고    scopus 로고
    • Antiviral nucleoside analogues with axial chirality
    • Zemlicka J. Antiviral nucleoside analogues with axial chirality. Nucleosides & Nucleotides 16 (1997) 1003-1012
    • (1997) Nucleosides & Nucleotides , vol.16 , pp. 1003-1012
    • Zemlicka, J.1
  • 77
    • 0037130291 scopus 로고    scopus 로고
    • Lipophilic phosphoramidates as antiviral pronucleotides
    • Zemlicka J. Lipophilic phosphoramidates as antiviral pronucleotides. Biochim. Biophys. Acta 1587 (2002) 276-286
    • (2002) Biochim. Biophys. Acta , vol.1587 , pp. 276-286
    • Zemlicka, J.1
  • 78
    • 0038094034 scopus 로고    scopus 로고
    • Unusual analogues of nucleosides: Chemistry and biological activity
    • Chu C.K. (Ed), Elsevier, Amsterdam
    • Zemlicka J. Unusual analogues of nucleosides: Chemistry and biological activity. In: Chu C.K. (Ed). Recent Advances in Nucleosides: Chemistry and Chemotherapy (2002), Elsevier, Amsterdam 327-357
    • (2002) Recent Advances in Nucleosides: Chemistry and Chemotherapy , pp. 327-357
    • Zemlicka, J.1
  • 79
    • 20544432454 scopus 로고    scopus 로고
    • Methylenecyclopropane analogues of nucleosides as antiviral agents
    • Schinazi R.F., and Liotta D.C. (Eds), IHL Press, Tucker, Georgia, USA
    • Zemlicka J., and Chen X. Methylenecyclopropane analogues of nucleosides as antiviral agents. In: Schinazi R.F., and Liotta D.C. (Eds). Frontiers in Nucleosides and Nucleic Acids (2004), IHL Press, Tucker, Georgia, USA 267-307
    • (2004) Frontiers in Nucleosides and Nucleic Acids , pp. 267-307
    • Zemlicka, J.1    Chen, X.2
  • 80
    • 48349120293 scopus 로고    scopus 로고
    • J. Zemlicka, J.C. Drach, Methylenecyclopropane analogues of purine nucleosides as agents against drug-resistant cytomegalovirus, in: 228th American Chemical Society National Meeting, Philadelphia, Pennsylvania, August 22-26, Abstract MEDI 166, 2004
    • J. Zemlicka, J.C. Drach, Methylenecyclopropane analogues of purine nucleosides as agents against drug-resistant cytomegalovirus, in: 228th American Chemical Society National Meeting, Philadelphia, Pennsylvania, August 22-26, Abstract MEDI 166, 2004
  • 82
    • 1642458720 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of (Z)- and (E)-2,2-[bis(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines: Second-generation methylenecyclopropane analogues of nucleosides
    • Zhou S., Breitenbach J.M., Borysko K.Z., Drach J.C., Kern E.R., Gullen E., Cheng Y.-C., and Zemlicka J. Synthesis and antiviral activity of (Z)- and (E)-2,2-[bis(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines: Second-generation methylenecyclopropane analogues of nucleosides. J. Med. Chem. 47 (2004) 566-575
    • (2004) J. Med. Chem. , vol.47 , pp. 566-575
    • Zhou, S.1    Breitenbach, J.M.2    Borysko, K.Z.3    Drach, J.C.4    Kern, E.R.5    Gullen, E.6    Cheng, Y.-C.7    Zemlicka, J.8
  • 83
    • 11144233616 scopus 로고    scopus 로고
    • (Z)- and (E)-[2-fluoro-2-(hydroxymethyl)cyclopropylidene]methyl-purines and -pyrimidines, a new class of methylenecyclopropane analogues of nucleosides: synthesis and antiviral activity
    • Zhou S., Kern E.R., Gullen E., Cheng Y.-C., Drach J.C., Matsumi S., Mitsuya H., and Zemlicka J. (Z)- and (E)-[2-fluoro-2-(hydroxymethyl)cyclopropylidene]methyl-purines and -pyrimidines, a new class of methylenecyclopropane analogues of nucleosides: synthesis and antiviral activity. J. Med. Chem. 47 (2004) 6964-6972
    • (2004) J. Med. Chem. , vol.47 , pp. 6964-6972
    • Zhou, S.1    Kern, E.R.2    Gullen, E.3    Cheng, Y.-C.4    Drach, J.C.5    Matsumi, S.6    Mitsuya, H.7    Zemlicka, J.8
  • 84
    • 20544439584 scopus 로고    scopus 로고
    • A new alkylation-elimination method for synthesis of antiviral fluoromethylenecyclopropane analogues of nucleosides
    • Zhou S., and Zemlicka J. A new alkylation-elimination method for synthesis of antiviral fluoromethylenecyclopropane analogues of nucleosides. Tetrahedron 61 (2005) 7112-7116
    • (2005) Tetrahedron , vol.61 , pp. 7112-7116
    • Zhou, S.1    Zemlicka, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.