323178-17-2Relevant academic research and scientific papers
Amino acid-derived, 7-membered cyclic sulfamides and methods of synthesizing the same
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, (2010/01/30)
New sulfamide compounds and methods of forming those compounds are provided. The inventive methods comprise subjecting a template opened-ring sulfamide compound to a ring-closing metathesis reaction in the presence of a Grubbs catalyst to yield a heterocyclic sulfamide. Advantageously, the template structures can be provided with a wide array of functional groups (e.g., substituted and unsubstituted amino acid side chains, peptides) chosen to provide particular properties to the compound. The preferred heterocyclic sulfamides are represented by a formula selected from the group consisting of
Ring-closing metathesis strategies to cyclic sulfamide peptidomimetics
Dougherty, Joseph M,Probst, Donald A,Robinson, Randall E,Moore, Joel D,Klein, Thomas A,Snelgrove, Kelley A,Hanson, Paul R
, p. 9781 - 9790 (2007/10/03)
Ring-closing metathesis (RCM) strategies toward the synthesis of a number of constrained sulfamides are discussed. This approach exploits the inherent chemistry of sulfamides and sulfonyl carbamates to generate both symmetric and unsymmetric cyclic sulfamides. Two strategies are revealed, one centers on the RCM reaction of allylated sulfamides 9a-e to generate the C2-symmetric cyclic sulfamides 4a-e in high yields. A second RCM strategy utilizes the known sulfonyl carbamate 15 to prepare unsymmetric cyclic sulfamides 16 and 6 in two four-step sequences. Overall, the routes described are applicable to the synthesis of a variety of constrained dipeptidal sulfamides representing novel peptidomimetic scaffolds. (C) 2000 Published by Elsevier Science Ltd.
