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Solid phase assisted synthesis of HIV-1 protease inhibitors. Expedient entry to unsymmetrical substitution of a C-2 symmetric template
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden Linkoping Univ, Dept Chem, S-58183 Linkoping, Sweden Univ Uppsala, BMC, Dept Organ Pharmaceut Chem, S-75123 Uppsala, Sweden Medivir AB, SE-14144 Huddinge, Sweden.
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden Linkoping Univ, Dept Chem, S-58183 Linkoping, Sweden Univ Uppsala, BMC, Dept Organ Pharmaceut Chem, S-75123 Uppsala, Sweden Medivir AB, SE-14144 Huddinge, Sweden.
Linköping University, The Institute of Technology. Linköping University, Department of Physics, Chemistry and Biology, Organic Chemistry .
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2000 (English)In: Canadian journal of chemistry (Print), ISSN 0008-4042, E-ISSN 1480-3291, Vol. 78, no 6, 829-837 p.Article in journal (Refereed) Published
Abstract [en]

A solid phase synthesis has been developed leading up to unsymmetrical HIV-1 protease inhibitors that are not readily available by conventional solution phase chemistry (18a-g). To prepare these compounds the hydroxyl group of (1S,2R)-(-)-cis-1-phthalimido-2-indanol (3) was coupled to a Merrifield resin via a dihydropyrane linker. Cleavage of the phthalimido protecting group and reaction of the liberated amine with the bis-activated symmetrical diacid 15 resulted in the resin bound amide 16. Coupling of 16 with amino acids and amines followed by hydrolysis produced the desired unsymmetrical products 18a-g from which potent HIV-1 protease inhibitors were identified, e.g., 18e (k(i) = 0.1 nM), 18a (k(i) = 0.2 nM) and 18c (k(i) = 2 nM).

Place, publisher, year, edition, pages
2000. Vol. 78, no 6, 829-837 p.
Keyword [en]
HIV, inhibitor, protease, solid phase
National Category
Engineering and Technology
Identifiers
URN: urn:nbn:se:liu:diva-49707OAI: oai:DiVA.org:liu-49707DiVA: diva2:270603
Available from: 2009-10-11 Created: 2009-10-11 Last updated: 2017-12-12

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Kvarnström, Ingemar

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