Synthesis of C2 symmetric potential inhibitors of HIV-1 protease from D-mannitol

Article abstract of DOI:10.1080/07328309608005674

D-Mannitol was used as precursor for the synthesis of acyclic C₂ symmetric potential HIV-1 protease inhibitors. The 1-and 6-hydroxy groups of D-mannitol were substituted by -NHBoc, -NHValZ, -SAr, -SOAr and -SO₂Ar and the 2-and 5-hydroxy groups were benzylated. In some products one of the central hydroxyl groups was either inverted or deoxygenated. Despite a close structural similarity to previously published inhibitors none of the products showed significant inhibitory activity against HIV-1 protease.

Full text of DOI:10.1080/07328309608005674

This article was downloaded by: [University of Toronto Libraries]
On: 25 December 2014, At: 17:32
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
Journal of Carbohydrate Chemistry
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/lcar20
Synthesis of C 2 Symmetric Potential
Inhibitors of HIV-1 Protease From D-
Mannitol
Gunilla Niklasson a , Ingemar Kvarnström a , Björn Classon b , Bertil
Samuelsson b , Ulrika Nillroth c , Helena Danielson c , Anders Karlén d
& Anders Hallberg d
a Department of Chemistry , Linköping University , S-581 83,
Linköping, Sweden
b Department of Organic Chemistry , Arrhenius Laboratory
Stockholm University , S-106 91, Stockholm, Sweden
c Department of Biochemistry , Uppsala University BMC , S-751 23,
Uppsala, Sweden
d Department of Organic Pharmaceutical Chemistry , Uppsala
University BMC , S-751 23, Uppsala, Sweden
Published online: 22 Aug 2006.
To cite this article: Gunilla Niklasson , Ingemar Kvarnström , Björn Classon , Bertil Samuelsson ,
Ulrika Nillroth , Helena Danielson , Anders Karlén & Anders Hallberg (1996) Synthesis of C 2 Symmetric
Potential Inhibitors of HIV-1 Protease From D-Mannitol, Journal of Carbohydrate Chemistry, 15:5,
555-569, DOI: 10.1080/07328309608005674
To link to this article: http://dx.doi.org/10.1080/07328309608005674
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