메뉴 건너뛰기




Volumn 26, Issue 4, 2007, Pages 403-411

Short synthesis and antiviral evaluation of c-fluoro-branched cyclopropyl nucleosides

Author keywords

Antiviral agent; Cyclopropyl nucleoside; Simmons Smith cyclopropanation

Indexed keywords

1 [[2,2 BIS(HYDROXYMETHYL) 1' FLUORO 1' METHYL]CYCLOPROP 1' YL]CYTOSINE; 1 [[2,2 BIS(TERT BUTYLDIMETHYLSILANYLOXYMETHYL) 1' FLUORO 1' METHYL]CYCLOPROP 1' YL]5 FLUOROURACIL; 1 [[2,2 BIS(TERT BUTYLDIMETHYLSILANYLOXYMETHYL) 1' FLUORO 1' METHYL]CYCLOPROP 1' YL]5 IODOURACIL; 1 [[2,2 BIS(TERT BUTYLDIMETHYLSILANYLOXYMETHYL) 1' FLUORO 1' METHYL]CYCLOPROP 1' YL]THYMINE; 1 [[2,2 BIS(TERT BUTYLDIMETHYLSILANYLOXYMETHYL) 1' FLUORO 1' METHYL]CYCLOPROP 1' YL]URACIL; 9 [[2,2 BIS(HYDROXYMETHYL) 1' FLUORO 1' METHYL]CYCLOPROP 1' YL]ADENINE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34247853247     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770701297018     Document Type: Article
Times cited : (9)

References (16)
  • 1
    • 0023188122 scopus 로고
    • 3′-Substituted 2′,3′- dideoxynucleoside analogs as potential anti-HIV (HTLV-III/LAV) agents
    • (a) Herdewijn, P.; Balzarini, J.; De Clerq, E.; Pauwels, R.; Baba, M.; Broder, S.; Vanderhaeghe, H. 3′-Substituted 2′,3′- dideoxynucleoside analogs as potential anti-HIV (HTLV-III/LAV) agents. J. Med. Chem. 1987, 30, 1270-1278;
    • (1987) J. Med. Chem , vol.30 , pp. 1270-1278
    • Herdewijn, P.1    Balzarini, J.2    De Clerq, E.3    Pauwels, R.4    Baba, M.5    Broder, S.6    Vanderhaeghe, H.7
  • 2
    • 0023579197 scopus 로고
    • Perspectives for the chemotherapy of AIDS
    • (b) De Clerq, E. Perspectives for the chemotherapy of AIDS. Anticancer Res. 1987, 7, 1023-1038.
    • (1987) Anticancer Res , vol.7 , pp. 1023-1038
    • De Clerq, E.1
  • 4
    • 0032543455 scopus 로고    scopus 로고
    • Synthesis and anti-HIV activity of L-2′-fluoro-2′,3′-unsaturated purine nucleosides
    • Choi, Y.; Lee, K.; Hong, J.H.; Schinazi, R.F.; Chu, C.K. Synthesis and anti-HIV activity of L-2′-fluoro-2′,3′-unsaturated purine nucleosides. Tetrahedron Lett. 1998, 39, 4437-4440.
    • (1998) Tetrahedron Lett , vol.39 , pp. 4437-4440
    • Choi, Y.1    Lee, K.2    Hong, J.H.3    Schinazi, R.F.4    Chu, C.K.5
  • 5
    • 33746372978 scopus 로고    scopus 로고
    • Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules
    • For review on organofluorine compounds, see: a
    • For review on organofluorine compounds, see: (a) Kirk, K. Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules. J. Fluorine Chem. 2006, 127, 1013-1029;
    • (2006) J. Fluorine Chem , vol.127 , pp. 1013-1029
    • Kirk, K.1
  • 6
    • 33746356860 scopus 로고    scopus 로고
    • Recent advances in fluorinated pharmaceuticals based on natural products
    • (b) Bégué, J.-P.; Bonnet-Delpon, D. Recent advances in fluorinated pharmaceuticals based on natural products. J. Fluorine Chem. 2006, 127, 992-1012.
    • (2006) J. Fluorine Chem , vol.127 , pp. 992-1012
    • Bégué, J.-P.1    Bonnet-Delpon, D.2
  • 7
    • 0032542317 scopus 로고    scopus 로고
    • Qiu, Y.-L.; Hempel, A.; Camerman, N.; Camerman, A.; Geiser, F.; Ptak, R.G.; Brietenbach, J.M.; Kira, T., Li, L.; Gullen, E.; Cheng, Y.-C.; Drach, J.C.; Zemlicka, J. (R)-(?)-and (S)-(+)-Synadenol: Synthesis, absolute configuration, and enantioselectivity of antiviral effect. J. Med. Chem. 1998, 41, 5257-5264;
    • (a) Qiu, Y.-L.; Hempel, A.; Camerman, N.; Camerman, A.; Geiser, F.; Ptak, R.G.; Brietenbach, J.M.; Kira, T., Li, L.; Gullen, E.; Cheng, Y.-C.; Drach, J.C.; Zemlicka, J. (R)-(?)-and (S)-(+)-Synadenol: Synthesis, absolute configuration, and enantioselectivity of antiviral effect. J. Med. Chem. 1998, 41, 5257-5264;
  • 8
    • 15444353199 scopus 로고    scopus 로고
    • Qiu, Y.-L.; Ksebati, M.B.; Ptak, R.G.; Fan, B.Y.; Breitenbach, J.M.; Lin, J.-S.; Cheng, Y.-C.; Kern, E.R.; Drach, J.C.; Zemlicka, J. (Z)-and (E)-2[(Hydroxymethyl)clopropylidene]methyladenine and-guanine. New nucleoside analogues with a broad-spectrum antiviral activity. J. Med. Chem. 1998, 41, 10-23;
    • (b)Qiu, Y.-L.; Ksebati, M.B.; Ptak, R.G.; Fan, B.Y.; Breitenbach, J.M.; Lin, J.-S.; Cheng, Y.-C.; Kern, E.R.; Drach, J.C.; Zemlicka, J. (Z)-and (E)-2[(Hydroxymethyl)clopropylidene]methyladenine and-guanine. New nucleoside analogues with a broad-spectrum antiviral activity. J. Med. Chem. 1998, 41, 10-23;
  • 9
    • 0032482299 scopus 로고    scopus 로고
    • Synthesis of difluorocyclopropyl carbocyclic homo-nucleosides
    • (c) Csuk, R.; Eversmann, L. Synthesis of difluorocyclopropyl carbocyclic homo-nucleosides. Tetrahedron 1998, 54, 6445-6456;
    • (1998) Tetrahedron , vol.54 , pp. 6445-6456
    • Csuk, R.1    Eversmann, L.2
  • 10
    • 0033555766 scopus 로고    scopus 로고
    • Preparation of novel difluorocyclopropane nucleosides
    • (d) Csuk, R.; Thiede, G. Preparation of novel difluorocyclopropane nucleosides. Tetrahedron 1999, 55, 739-750;
    • (1999) Tetrahedron , vol.55 , pp. 739-750
    • Csuk, R.1    Thiede, G.2
  • 11
    • 0029100719 scopus 로고
    • 3 ring contraction in the key step of a novel cyclopropane carbocyclic nucleoside
    • 3 ring contraction in the key step of a novel cyclopropane carbocyclic nucleoside. Tetrahedron Lett. 1995, 36, 7441-7444;
    • (1995) Tetrahedron Lett , vol.36 , pp. 7441-7444
    • Mévellec, L.1    Huet, F.2
  • 12
    • 0030566792 scopus 로고    scopus 로고
    • Design and synthesis of 2′-hydroxyethylcyclopropyl carbocyclic nucleosides
    • (f) Yang, T.F.; Kim, H.; Kotra, L.P.; Chu, C.K. Design and synthesis of 2′-hydroxyethylcyclopropyl carbocyclic nucleosides. Tetrahedron Lett. 1996, 49, 8849-8852.
    • (1996) Tetrahedron Lett , vol.49 , pp. 8849-8852
    • Yang, T.F.1    Kim, H.2    Kotra, L.P.3    Chu, C.K.4
  • 13
    • 15444359037 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of novel acyclic nucleosides: Discovery of cyclopropyl nucleoside with potent inhibitory activity against herpesviruses
    • Sekiyama, T.; Hatsuya, S.; Tanaka, Y.; Uchiyama, M.; Ono, N.; Iwayama, S.; Oikawa, M.; Suzuki, K.; Okunishi, M.; Tsuji, T. Synthesis and antiviral activity of novel acyclic nucleosides: Discovery of cyclopropyl nucleoside with potent inhibitory activity against herpesviruses. J. Med. Chem. 1998, 41, 1284-1298.
    • (1998) J. Med. Chem , vol.41 , pp. 1284-1298
    • Sekiyama, T.1    Hatsuya, S.2    Tanaka, Y.3    Uchiyama, M.4    Ono, N.5    Iwayama, S.6    Oikawa, M.7    Suzuki, K.8    Okunishi, M.9    Tsuji, T.10
  • 14
    • 0035319597 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of fluoro-substituted apiodideoxynucleosides
    • Hong, J.H.; Kim, H.O.; Moon, H.R.; Jeong, L.S. Synthesis and antiviral activity of fluoro-substituted apiodideoxynucleosides. Arch. Pharm. Res. 2001, 24, 95-99.
    • (2001) Arch. Pharm. Res , vol.24 , pp. 95-99
    • Hong, J.H.1    Kim, H.O.2    Moon, H.R.3    Jeong, L.S.4
  • 16
    • 0023813086 scopus 로고
    • Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 11. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase
    • Borcherding, D.R.; Narayanan, S.; Hasobe, M.; McKee, J.G.; Keller, B.T.; Borchardt, R.T. Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 11. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase. J. Med. Chem. 1988, 31, 1729-1738.
    • (1988) J. Med. Chem , vol.31 , pp. 1729-1738
    • Borcherding, D.R.1    Narayanan, S.2    Hasobe, M.3    McKee, J.G.4    Keller, B.T.5    Borchardt, R.T.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.