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Solid phase assiste...
Solid phase assisted synthesis of HIV-1 protease inhibitors. Expedient entry to unsymmetrical substitution of a C-2 symmetric template
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- Oscarsson, K (author)
- 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
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- Classon, B (author)
- 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
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- Kvarnström, Ingemar (author)
- Linköpings universitet,Tekniska högskolan,Organisk Kemi
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Hallberg, A (author)
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Samuelsson, B (author)
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(creator_code:org_t)
- 2000
- 2000
- English.
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In: Canadian journal of chemistry (Print). - 0008-4042 .- 1480-3291. ; 78:6, s. 829-837
- Related links:
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https://urn.kb.se/re...
Abstract
Subject headings
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- 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).
Keyword
- HIV
- inhibitor
- protease
- solid phase
- TECHNOLOGY
- TEKNIKVETENSKAP
Publication and Content Type
- ref (subject category)
- art (subject category)
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