Tetrahydrofuran as a scaffold for peptidomimetics. Application to the design and synthesis of conformationally constrained metalloproteinase inhibitors

Authors
Hanessian, S Moitessier, N Wilmouth, S
Citation
S. Hanessian et al., Tetrahydrofuran as a scaffold for peptidomimetics. Application to the design and synthesis of conformationally constrained metalloproteinase inhibitors, TETRAHEDRON, 56(39), 2000, pp. 7643-7660
Citations number
83
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
39
Year of publication
2000
Pages
7643 - 7660
Database
ISI
SICI code
0040-4020(20000922)56:39<7643:TAASFP>2.0.ZU;2-1
Abstract
Enantiopure functionalized tetrahydrofurans were synthesized as prototypica l conformationally constrained analogs of acyclic succinic acid-based inhib itors of metalloproteinases. While preliminary docking study showed good co ngruence with a potent inhibitor, the biological results were disappointing . Molecular dynamics simulation revealed the weakness of the H-bond interac tions. (C) 2000 Elsevier Science Ltd. All rights reserved.