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104 results on '"Wise, Dean S."'

1. Dimetalation of pyrazines. A one-pot synthesis of multisubstituted pyrazine C-nucleosides

Author

Liu, Weimin, Wise, Dean S., and Townsend, Leroy B.

Subjects
Chemistry, Organic -- Research, Pyridazine -- Research, Nucleosides -- Research, Bromine -- Physiological aspects, Iodine -- Physiological aspects, Biological sciences, Chemistry
Abstract

Research has been conducted on the pyrazine C-nucleosides. A sequential dilithiation-addition method developed for the synthesis of these nucleosides is discussed.

Published
2001

2. Synthesis of anti-restricted pyrimidine acyclic nucleosides

Author

Ling-Yih Hsu, Wise, Dean S., Kucera, Louis S., Drach, John C., and Townsend, Leroy B.

Subjects
Organic compounds -- Synthesis, Nucleosides -- Research, Pyrimidines -- Synthesis, AIDS (Disease) -- Research, Herpes simplex virus -- Research, Biological sciences, Chemistry
Abstract

The synthesis of acyclic pyrimidine nucleosides that are restricted in an anti conformation allows the study of their bioactivity against the Herpes and HIV viruses. The process involves treating dimethoxy pyrimidine with 1,3-bis(benzyloxy)-2-propanone then with acetic anhydride in dimethylsulfoxide, annulating with iodine in tetrahydrofuran and nucleophilic attack at the 8-position. Of the acyclic nucleosides bioassayed, only 8-amino-2,2,-bis(hydroxymethyl)-9-methyl-1H,4H-pyrimido(1,6-c)(1,3)oxazin-6- one exhibits mild activity against HIV at noncytotoxic levels. All the others are inactive.

Published
1992

4. A facile, multigram synthesis of ribofuranoid glycals

Author

Walker, John A., II, Chen, Jiong J., Wise, Dean S., and Townsend, Leroy B.

Subjects
Nucleoside analogs -- Research, Oxidation-reduction reaction -- Methods, Furans -- Research, Biological sciences, Chemistry
Abstract

A simple method for the synthesis of bis-silylated ribofuranoid glycals from 2-deoxy-D-ribose results to high yields on multigram levels. The starting material is protected at the 3- and 5-positions to give 3,5-bis-O-silylated products which are then reduced to 2-deoxy-D-erythro-pentofuranose derivatives. Over several reactions, ribofuranoid glycals are achieved following column chromatography.

Published
1996

7. Pyrido(2,3-b)pyrazines from pyrazine C-nucleosides: an unusual intramolecular rearrangement

Author

Chen, Jiong J., Wise, Dean S., and Townsend, Leroy B.

Subjects
Nucleosides -- Research, Rearrangements (Chemistry) -- Research, Pyridazine -- Research, Chemistry
Abstract

Pyrazine C-nucleosides are synthesized using a palladium-mediated coupling method that utilizes 3'-keto pyrazine nucleosides for its key intermediates. Some of the 3'-keto pyrazine nucleosides are shown to rearrange themselves to form pyrido 2,3-b pyrazine compounds. It is hypothesized that the rearrangement provides the nucleosides a way to form various other heterocycles.

Published
1996

8. Synthesis of 1-(2-aminopropyl)benzimidazoles, structurally related to the TIBO derivative R82150, with activity against human immunodeficiency virus.

Author

Department of Chemistry, College of Literature, Sciences, and Arts, College of Pharmacy, The University of Michigan, Ann Arbor, Michigan 48109, USA, Department of Medicinal Chemistry, College of Pharmacy, The University of Michigan, Ann Arbor, Michigan 48109, USA, Department of Biologic and Material Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109, USA, Department of Chemistry, College of Literature, Sciences, and Arts, College of Pharmacy, The University of Michigan, Ann Arbor, Michigan 48109, USA; Department of Medicinal Chemistry, College of Pharmacy, The University of Michigan, Ann Arbor, Michigan 48109, USA., Department of Microbiology and Immunology, Bowman Gray School of Medicine, Winston-Salem, NC 27157, USA, Microbiology Research Department, Southern Research Institute, Birmingham, AL 35205, USA, Swayze, Eric E., Peiris, Sithumini M., Kucera, Louis S., White, E. Lucile, Wise, Dean S., Drach, John C., Townsend, Leroy B., Department of Chemistry, College of Literature, Sciences, and Arts, College of Pharmacy, The University of Michigan, Ann Arbor, Michigan 48109, USA, Department of Medicinal Chemistry, College of Pharmacy, The University of Michigan, Ann Arbor, Michigan 48109, USA, Department of Biologic and Material Sciences, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109, USA, Department of Chemistry, College of Literature, Sciences, and Arts, College of Pharmacy, The University of Michigan, Ann Arbor, Michigan 48109, USA; Department of Medicinal Chemistry, College of Pharmacy, The University of Michigan, Ann Arbor, Michigan 48109, USA., Department of Microbiology and Immunology, Bowman Gray School of Medicine, Winston-Salem, NC 27157, USA, Microbiology Research Department, Southern Research Institute, Birmingham, AL 35205, USA, Swayze, Eric E., Peiris, Sithumini M., Kucera, Louis S., White, E. Lucile, Wise, Dean S., Drach, John C., and Townsend, Leroy B.

Abstract

A number of 1-(2-aminopropyl)-2-mercaptobenzimidazoles related to the TIBO derivatives R82150 have been prepared and tested for their activity against human immunodeficiency virus type 1 (HIV-1). These compounds were all modest inhibitors of the cytophatic effects of HIV-1 in vitro, but only very weak inhibitors of HIV-1 reverse transcriptase (RT).A number of 1-(2-aminopropyl)-2-mercaptobenzimidazole derivatives related to the TIBO derivative R82150 have been prepared and tested for their activity against human immunodeficiency virus type 1 (HIV-1). These compounds are all modest inhibitors of the cytopathic effects of HIV-1 in vitro, but were only weak inhibitors of HIV-1 reverse transcriptase (RT).

Published
2006

9. The synthesis and chemistry of certain anthelmintic benzimidazoles

Author

Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA, Townsend, Leroy B., Wise, Dean S., Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA, Townsend, Leroy B., and Wise, Dean S.

Abstract

A basis for interest in the benzimidazole ring system as a nucleus from which to develop potential chemotherapeutic agents was established in the 1950s when it was found that 5,6-dimethyl-l-([alpha]-D-ribofuranosyl)benzimidazole (I) was an integral part of the structure of vitamin B12. As a result of these interests and extensive studies, one health related arena that has benefited greatly has been the treatment of parasitic diseases. The discovery of thiabendazole in 1961 further spurred chemists around the world to design and synthesize several thousand benzimidazoles for screening for anthelmintic activity but less than twenty of them have reached commercial use. Much of this work has been done by pharmaceutical companies and is only reported in the patent literature. In this paper, Leroy Townsend and Dean Wise review the development of some of the synthetic methods that have been critical to the preparation of the benzimidazoles of anthelmintic importance. Only a few molecules that demonstrate the processes are discussed here, but numerous reviews of the synthesis and chemistry of other benzimidazoles are available1-3.

Published
2006

10. A further investigation of the stannic chloride-catalyzed condensation reaction of 1-hexene and 1,2,3,5-tetra-O-acyl-[beta]--ribofuranoses

Author

Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109 U.S.A., Cupps, Thomas L., Wise, Dean S., Townsend, Leroy B., Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109 U.S.A., Cupps, Thomas L., Wise, Dean S., and Townsend, Leroy B.

Abstract

The reaction of 1-hexene with either 1-O-acetyl-2,3,5-tri-O-benzoyl-[beta]--ribofuranose (5b) or 1,2,3,5-tetra-O-acetyl-[beta]--ribofuranose (5a) in the presence of stannic chloride leads to the formation of a complex mixture of products. By a combination of 1H-n.m.r. and mass spectroscopy, the products were shown to be anomeric and diastereomeric mixtures of the 8,9,11-tri-O-acyl-protected derivatives of 7,10-anhydro-1,2,3,4,5,6-hexadeoxy--allo(altro)-undec-4-enitol (1) and 7,10-anhydro-5-chloro-1,2,3,4,5,6-hexadeoxy--allo(altro)-undecitol (2). The [alpha] anomer of 1 was the predominant anomer, whereas the [alpha] and [beta] anomers of 2 were present in approximately equal amounts. It was found that 2 was not formed when trimethylsilyl trifluoromethanesulfonate was used as the catalyst instead of stannic chloride. The acyl-protected sugar 3,6-anhydro-2-deoxy--allo(altro)-heptose (3), prepared by ozonolysis of 1, reacted with tert-butoxycarbonylmethyltriphenylphosphorane to give tert-butyl trans-5,8-anhydro-6,7,9-tri-O-acetyl-2,3,4-trideoxy--allo(altro)-non-2-enanate (4). The basicity of the ylide was sufficient to cause anomerization and resulted in an [alpha], [beta] ratio of 5:1 in the product, 4.

Published
2006

13. The Oxidative DNA Lesion 8,5′-(S)-Cyclo-2′-deoxyadenosine Is Repaired by the Nucleotide Excision Repair Pathway and Blocks Gene Expression in Mammalian Cells

Author

Brooks, Philip J., primary, Wise, Dean S., additional, Berry, David A., additional, Kosmoski, Joseph V., additional, Smerdon, Michael J., additional, Somers, Robert L., additional, Mackie, Hugh, additional, Spoonde, Alexander Y., additional, Ackerman, Eric J., additional, Coleman, Katherine, additional, Tarone, Robert E., additional, and Robbins, Jay H., additional

Published
2000
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