Synthesis and biological evaluation of endocyclic 2′,3′-didehydro-2′,3′-dideoxymethanocarba adenosine

Nucleosides, Nucleotides and Nucleic Acids

Volumn 21, Issue 10, 2002, Pages 665-680

  Quirk Dorr, Danaè R ^a   Vince, Robert ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[4 (6 AMINO 9H PURIN 9 YL)BICYCLO[3.1.0]HEX 2 YL]METHANOL; [4 (6 CHLORO 9H PURIN 9 YL)BICYCLO[3.1.0]HEX 2 YL]METHANOL; [4 (6 METHOXY 9H PURIN 9 YL)BICYCLO[3.1.0]HEX 2 YL]METHANOL; ADENOSINE DEAMINASE; NUCLEOSIDE DERIVATIVE; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG; 2',3' DIDEOXYADENOSINE; ANTIVIRUS AGENT; DRUG DERIVATIVE; NUCLEOSIDE; RECOMBINANT PROTEIN;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; HERPES SIMPLEX VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PREDICTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY; ANIMAL; CATTLE; CELL CULTURE; CERCOPITHECUS; CHEMICAL STRUCTURE; CONFORMATION; DRUG ANTAGONISM; DRUG EFFECT; HUMAN; MICROBIOLOGICAL EXAMINATION; SYNTHESIS; VERO CELL;

ADENOSINE DEAMINASE; ANIMALS; ANTIVIRAL AGENTS; CATTLE; CELLS, CULTURED; CERCOPITHECUS AETHIOPS; CRYSTALLOGRAPHY, X-RAY; DIDEOXYADENOSINE; HERPESVIRUS 1, HUMAN; HIV-1; HIV-1 REVERSE TRANSCRIPTASE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NUCLEOSIDES; RECOMBINANT PROTEINS; VERO CELLS;

EID: 0036445936     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120015724     Document Type: Article

References (26)

1. Siddiqui, M.A.; Ford, H.; George, C.; Marquez, V.E. Synthesis, conformational analysis, and biological activity of a rigid carbocyclic analog of 2′ deoxyaristomycin built on a bicyclo[3.1.0]hexane template. Nucleosides and Nucleotides 1996, 15 (1-3), 235-250.
2. Plavec, J.; Tong, W.; Chattopadhyay, J. How do the gauche and anomeric effects drive the pseudorotational equilibrium of the pentofuranose moiety of nucleosides. J. Am. Chem. Soc. 1993, 115, 9734-9746.
3. Altona, C.; Sundaralingam, M. Conformational analysis of the sugar ring in nucleosides and nucleotides. A new description using the concept of pseudorotation. J. Am. Chem. Soc. 1972, 94, 8205-8212.
4. Taylor, E.W.; Van Roey, P.; Schinazi, R.F.; Chu, C.K. A Stereochemical rationale for the activity of anti-HIV nucleosides. Antiviral Chemistry and Chemotherapy 1990, 1 (3), 163-173.
5. Moon, H.R.; Ford, H.; Marquez, V.E. A Remarkably simple chemicoenzymatic approach to structurally complex bicyclo[3.1.0]hexane carbocyclic nucleosides. Organic Lett. 2000, 2 (24), 3793-3796.
6. Vince, R.; Hua, M. Synthesis and anti-HIV activity of carbocyclic 2′,3′-didehydro-2′,3′-dideoxy 2,6-disubstituted purine nucleosides. J. Med. Chem. 1990, 33 (1), 17-21.
7. Katagiri, N.; Yamatoya, Y.; Ishikura, M. The first synthesis of a 2′,3′-methano carbocyclic nucleoside. Tetrahedron Lett. 1999, 40, 9069-9072.
8. Bhushan, R.G.; Vince, R. Synthesis of conformationally restricted 2′,3′-exo-methylene carbocyclic nucleosides built on a bicyclo[3.1.0]hexane template. Bioorg. Med. Chem. Lett. 2002, 10, 2325-2333.
9. Cermak, R.C.; Vince, R. (±)-4β-Amino-2α,3α-dihydroxy-1β -Cyclopentanemethanol hydrochloride. Carbocyclic ribofuranosylamine for the synthesis of carbocyclic nucleosides. Tetrahedron Lett. 1981, 22 (25), 2331-2322.
10. Daluge, S.; Vince, R. A synthetic route to carbocyclic aminonucleosides. Tetrahedron Lett. 1976, 35, 3005-3008.
11. Daluge, S.; Vince, R. Synthesis of carbocyclic aminonucleosides. J. Org. Chem. 1978, 43 (12), 2311-2320.
12. Dohmori, R.; Yoshimura, R.; Kitahara, S.; Tanaka, Y.; Naito, T. Syntheses of the urinary metabolites of 1-(4-methoxy-6-methyl-2-pyrimidinyl)-3-methyl-5-methoxypyrazole (mepirizole, DA-398). Chem. Pharm. Bull. 1970, 18, 1908-1914.
13. Brown, H.C.; Narasimhan, S.; Choi, Y.M. Selective reductions. 30. Effect of cation and solvent on the reactivity of saline borohydrides for reduction of carboxylic esters. Improved procedures for the conversion of esters to alcohols by metal borohydrides. J. Org. Chem. 1982, 47 (24), 4702-4708.
14. Kawabata, N.; Nakagawa, T.; Nakao, T.; Yamashita, S. Stereochemistry of the cycloaddition reaction of methyl carbenoid of zinc to cyclic allylic alcohols. J. Org. Chem. 1977, 42 (18), 3031-3035.
15. Simmons, H.E.; Blanchard, E.P. Cyclopropane synthesis from methylene iodide zinc-copper couple and Olefins. II. Nature of the intermediate. Organic and Biological Chemistry. 1964, 86, 1337-1347.
16. Russ, P.; Ezzirouni, A.; Marquez, V.E. Hydroxyl-versus amide-directed cyclopropanation from the allylic position in 1-hydroxy-4-N-acyl cyclopentenes under modified simmons-smith conditions. Tetrahedron Lett. 1997, 38 (5), 723-726.
17. Vince, R.; Donovan, J.; Nucleoside analogs. Synthesis of 6-(6-aminio-9-purinyl)-1,5-anhydro-6-deoxy-L-allitol. J. Med. Chem. 1969, 12, 175-176.
18. White, E.L.; Parker, W.B.; Macy, L.J.; Shaddix, S.C.; McCaleb, G.; Secrist, J.A., III; Vince, R.; Shannon, W.M. Comparison of the effect of carbovir, AZT, and dideoxynucleoside triphosphates on the activity of human immunodeficiency virus reverse transcriptase and selected human polymerases. Biochem. Biophys. Res. Comm. 1989, 161 (2), 393-398.
19. Tomaz, J. P1-(Thymidine-5′)-P1-aminotriphosphate: Synthesis, hydrolysis and reaction with cytidine in alkali. Nucleosides and Nucleotides 1983, 21, 445-448.
20. Saenger, W. In Principles of Nucleic Acid Structure; Cantor, C.R., Ed.; Springer-Verlag: New York, 1984.
21. Marquez, V.E.; Russ, P.; Alonso, R.; Siddiqui, M.A.; Shin, K.; George, C.; Nicklaus, M.C.; Dai, F.; Ford, H. Conformationally restricted nucleosides. The reaction of adenosine deaminase with substrates built on a bicyclo[3.1.0]hexane template. Nucleosides and Nucleotides 1999, 18 (4 & 5), 521-530.
22. Blessing, R. An empirical correction for absorption anisotropy. Acta Cryst. 1995, A51, 33-38.
23. Buckheit, R.W., Jr.; Watson, K.; Fliakas-Boltz, V.; Russell, J.; Loftus, T.L.; Osterling, M.C.; Turpin, J.A.; Pallansch, L.A.; White, L.E.; Lee, J.W.; Lee, S.H.; Oh, J.W.; Kwon, H.S.; Chung, S.G.; Cho, E.H. SJ-3366, a unique and highly potent nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1 (HIV-1) that also inhibits HIV-2. Antimicrobial Agents and Chemo. 2001, 45 (2), 393-400.
24. Vince, R.; Hua, M.; Brownell, J.; Daluge, S.; Lee, F.; Shannon, W.M.; Lavelle, G.C.; Qualls, J.; Weislow, O.S.; Kiser, R.; Canonico, P.G.; Schultz, R.H.; Harayanan, V.; Mayo, J.; Shoemaker, R.H.; Boyd, M.R. Potent and selective activity of a new carbocyclic nucleoside analog (carbovir: NSC 614846) against human immunodefiency virus in vitro. Biochem. Biophys. Res. Comm. 1988, 156, 1046-1053.
25. Parker, W.B.; White, E.L.; Shaddix, S.C.; Ross, L.J.; Buckheit, R.W., Jr.; Germany, J.M.; Secrist, J.A., III.; Vince, R.; Shannon, W.M. Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase and human DNA polymerases α, β, and γ by the 5′-triphosphates of carbovir, 3′-azido-3′deoxythymidine, 2′,3′-dideoxyguanosine and 3′-deoxythymidine. J. Biol. Chem. 1991, 266 (3), 1754-1762.
26. White, E.L.; Shaddix, S.C.; Brockman, R.W.; Bennett, L.L., Jr. Comparison of the Actions of 9-β-D-arabinofuranosyl-2-fluoroadenine and 9-β-D-rabinofuranosyladenine on target enzymes from mouse tumor cells. Cancer Res. 1982, 42 (6). 2260-2264.