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  • Oscarsson, K, et al. (author)
  • Solid phase assisted synthesis of HIV-1 protease inhibitors. Expedient entry to unsymmetrical substitution of a C-2 symmetric template
  • 2000
  • In: Canadian journal of chemistry (Print). - 0008-4042 .- 1480-3291. ; 78:6, s. 829-837
  • Journal article (peer-reviewed)abstract
    • 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).
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  • Result 1-1 of 1
Type of publication
journal article (1)
Type of content
peer-reviewed (1)
Author/Editor
Hallberg, A (1)
Samuelsson, B (1)
Kvarnström, Ingemar (1)
Classon, B. (1)
Oscarsson, K (1)
University
Linköping University (1)
Language
English (1)
Year
2000 (1)

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