Synthesis and biological evaluation of 2′,4′- and 3′,4′-bridged nucleoside analogues

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 18, 2011, Pages 5648-5669

  Nicolaou, K C ^a,b   Ellery, Shelby P ^a   Rivas, Fatima ^a   Saye, Karen ^a   Rogers, Eric ^a   Workinger, Tyler J ^c   Schallenberger, Mark ^a   Tawatao, Rommel ^c   Montero, Ana ^a   Hessell, Ann ^a   Romesberg, Floyd ^a   Carson, Dennis ^c   Burton, Dennis ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

Antiviral; Cytotoxic; Nucleosides; Synthesis

Indexed keywords

(3 (6 AMINO 2 (BUTYLAMINO) 9H PURIN 9 YL) 7 (BENZYLOXY) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 1 YL)METHANOL; (3 (6 AMINO 2 (ETHYLAMINO) 9H PURIN 9 YL) 7 (BENZYLOXY) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 1 YL)METHANOL; (3 (6 AMINO 2 (ISOBUTYLAMINO) 7H PURIN 7 YL) 7 (BENZYLOXY) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 1 YL)METHANOL; (3 (6 AMINO 2 (ISOBUTYLAMINO) 9H PURIN 9 YL) 1 (HYDROXYMETHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 1 YL)METHANOL; (3 (6 AMINO 2 (OCTYLAMINO) 9H PURIN 9 YL) 7 (BENZYLOXY) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 1 YL)METHANOL; (3 (6 BENZY(METHYL)LAMINO) 2 CHLORO 9H PURIN 9 YL) 1 (HYDROXYMETHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 7 OL; (3 (6 BENZYLAMINO) 2 CHLORO 9H PURIN 9 YL) 1 (HYDROXYMETHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 7 OL; (7 (BENZYLOXY) 3 (2,6 DIAMINO 7H PURIN 7 YL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 1 YL)METHANOL; (7 (BENZYLOXY) 3 (2,6 DIAMINO 9H PURIN 9 YL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 1 YL)METHANOL; (7 (BENZYLOXY) 3 (2,6 DIMETHOXY 9H PURIN 9 YL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 1 YL)METHANOL; 2 (6 AMINO 2 CHLORO 9H PURIN 9 YL) 4 (BENZYLOXY) 5 ((TERT BUTYLDIPHENYLSILYLOXY)METHYL) 5 (TOSYLOXYMETHYL)TETRAHYDROFURAN 3 YL ACETIC ACID; 2',4' NUCLEOSIDE DERIVATIVE; 3 (2,6 DIAMINO 7H PURIN 7 YL) 1 (HYDROXYMETHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 7 OL; 3 (2,6 DIAMINO 9H PURIN 9 YL) 1 (HYDROXYMETHYL) 2,5 DIOXABICYCLO [2.2.1]HEPTAN 7 OL; 3 (6 AMINO 2 (BUTYLAMINO) 9H PURIN 9 YL) 1 (HYDROXYMETHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 7 OL; 3 (6 AMINO 2 (ISOBUTYLAMINO) 9H PURIN 9 YL) 1 (HYDROXYMETHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 7 OL; 3',4' NUCLEOSIDE DERIVATIVE; 4 (BENZYLOXY) 5 ((TERT BUTYLDIPHENYLSILYLOXY)METHYL) 2 (2,6 DIAMINO 7H PURIN 7 YL) 5 (TOSYLOXYMETHYL)TETRAHYDROFURAN 3 YL ACETIC ACID; 4 (BENZYLOXY) 5 ((TERT BUTYLDIPHENYLSILYLOXY)METHYL) 2 (2,6 DIAMINO 9H PURIN 9 YL) 5 (TOSYLOXYMETHYL)TETRAHYDROFURAN 3 YL ACETIC ACID; 7 (7 (BENZYLOXY) 1 ((TERT BUTYLDIPHENYLSILYLOXY)METHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 3 YL) 7H PURINE 2,6 DIAMINE; 9 (7 (BENZYLOXY) 1 ((TERT BUTYLDIPHENYLSILYLOXY)METHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 3 YL) 2 CHLORO 9H PURIN 6 AMINE; 9 (7 (BENZYLOXY) 1 ((TERT BUTYLDIPHENYLSILYLOXY)METHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 3 YL) 9H PURINE 2,6 DIAMINE; 9 (7 (BENZYLOXY) 1 ((TERT BUTYLDIPHENYLSILYLOXY)METHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 3 YL) N2 BUTYL 9H PURINE 2,6 DIAMINE; 9 (7 (BENZYLOXY) 1 ((TERT BUTYLDIPHENYLSILYLOXY)METHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 3 YL) N2 ETHYL 9H PURINE 2,6 DIAMINE; 9 (7 (BENZYLOXY) 1 ((TERT BUTYLDIPHENYLSILYLOXY)METHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 3 YL) N2 ISOBUTYL 9H PURINE 2,6 DIAMINE; 9 (7 (BENZYLOXY) 1 ((TERT BUTYLDIPHENYLSILYLOXY)METHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 3 YL) N2 OCTYL 9H PURINE 2,6 DIAMINE; CLADRIBINE; N,N' (9 (7 (BENZYLOXY) 1 ((TERT BUTYLDIPHENYLSILYLOXY)METHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 3 YL) 9H PURINE 2,6 DIYL)BIS(N BENZOYLBENZAMIDE); N,N' (9 (7 (BENZYLOXY) 1 (HYDROXYMETHYL) 2,5 DIOXABICYCLO [2.2.1] HEPTAN 3 YL) 9H PURINE 2,6 DIYL)BIS(N BENZOYLBENZAMIDE); NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZIDOVUDINE;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; BINDING AFFINITY; CYCLIZATION; DESILYLATION; DRUG CONFORMATION; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; MINIMUM INHIBITORY CONCENTRATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; VIRUS NEUTRALIZATION;

ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; ESCHERICHIA COLI; HEK293 CELLS; HIV-1; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; NUCLEOSIDES; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80052576631     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.07.022     Document Type: Article

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