Synthesis of 2',3'-dideoxy- and 3'-azido-2',3'-dideoxy-pyridazine nucleosides as potential antiviral agents

Article abstract of DOI:10.1080/15257779408013255

The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3- dideoxy-β-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6, 19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-β-D- erythro-pentofuranosyl)pyridazin-6-one (13) in 67% and its α-anomer 14 in 12% yield, respectively. A series of 3'-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1-(3-azido-2,3-dideoxy-β-D- erythro-pentofuranosyl)pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.

Full text of DOI:10.1080/15257779408013255

This article was downloaded by: [York University Libraries]
On: 12 August 2014, At: 01:20
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered
office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Nucleosides and Nucleotides
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/lncn19
Synthesis of 2′,3′-Dideoxy- and 3′-
Azido-2′,3′-dideoxy-pyridazine
Nucleosides as Potential Antiviral Agents
Biserka Kasnar a b c d , Dean S. Wise a b c d , Louis S. Kucera a b c d
John C. Drach a b c d & Leroy B. Townsend a b c d
,
a Department of Medicinal Chemistry , College of Pharmacy , Ann
Arbor, MI, 48109
b Department of Chemistry , College of Literature, Sciences, and
Arts , Ann Arbor, MI, 48109
c Department of Biologic and Materials Sciences , School of
Dentistry, University of Michigan , Ann Arbor, MI, 48109
d Department of Microbiology and Immunology , Wake Forest
University Medical Center , Winston-Salem, NC, 27157
Published online: 23 Sep 2006.
To cite this article: Biserka Kasnar , Dean S. Wise , Louis S. Kucera , John C. Drach & Leroy
B. Townsend (1994) Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine
Nucleosides as Potential Antiviral Agents, Nucleosides and Nucleotides, 13:1-3, 459-479, DOI:
10.1080/15257779408013255
To link to this article: http://dx.doi.org/10.1080/15257779408013255
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the
“Content”) contained in the publications on our platform. However, Taylor & Francis,
our agents, and our licensors make no representations or warranties whatsoever as to
the accuracy, completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content
should not be relied upon and should be independently verified with primary sources
of information. Taylor and Francis shall not be liable for any losses, actions, claims,
proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or
howsoever caused arising directly or indirectly in connection with, in relation to or arising
out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,

systematic supply, or distribution in any form to anyone is expressly forbidden. Terms &
Conditions of access and use can be found at http://www.tandfonline.com/page/terms-
and-conditions