Your browser doesn't support javascript.
loading
Show: 20 | 50 | 100
Results 1 - 3 de 3
Filter
Add more filters










Database
Language
Publication year range
1.
Tetrahedron ; 68(4): 1029-1051, 2012 Jan 28.
Article in English | MEDLINE | ID: mdl-22287031

ABSTRACT

Peptidomimetic-based macrocycles typically have improved pharmacokinetic properties over those observed with peptide analogs. Described are the syntheses of 13 peptidomimetic derivatives that are based on active Sansalvamide A structures, where these analogs incorporate heterocycles (triazoles, oxazoles, thiazoles, or pseudoprolines) along the macrocyclic backbone. The syntheses of these derivatives employ several approaches that can be applied to convert a macrocyclic peptide into its peptidomimetic counterpart. These approaches include peptide modifications to generate the alkyne and azide for click chemistry, a serine conversion into an oxazole, a Hantzsch reaction to generate the thiazole, and protected threonine to generate the pseudoproline derivatives. Furthermore, we show that two different peptidomimetic moieties, triazoles and thiazoles, can be incorporated into the macrocyclic backbone without reducing cytotoxicity: triazole and thiazole.

2.
Org Lett ; 12(14): 3136-9, 2010 Jul 16.
Article in English | MEDLINE | ID: mdl-20565133

ABSTRACT

Cyclic tetrapeptides have generated great interest because of their broad-ranging biological properties. In order to synthesize these highly strained 12-membered cyclic compounds, a cyclization strategy using pseudoprolines as removable turn inducers has been developed. The pseudoproline derivatives induce a cisoid amide bond in the linear peptide backbone which facilitates cyclization. After cyclization, the turn inducers can be readily removed to afford cyclic tetrapeptides containing serine or threonine residues.


Subject(s)
Oligopeptides/chemistry , Oligopeptides/chemical synthesis , Peptides, Cyclic/chemistry , Peptides, Cyclic/chemical synthesis , Proline/analogs & derivatives , Thiazoles/chemistry , Models, Molecular , Molecular Conformation , Proline/chemistry , Stereoisomerism
3.
Org Lett ; 8(15): 3395-8, 2006 Jul 20.
Article in English | MEDLINE | ID: mdl-16836414

ABSTRACT

[Structure: see text] A formal total synthesis of diisocyanoadociane, a marine diterpenoid with potent antimalarial properties, has been completed. The synthesis begins with a phenanthrenoid precursor that is transformed into a pyrene-derived intermediate by means of an intramolecular Michael reaction. Nitrogen functionality is introduced via a double Curtius reaction.


Subject(s)
Antimalarials/chemical synthesis , Diterpenes/chemical synthesis , Nitriles/chemical synthesis , Pyrenes/chemical synthesis , Animals , Antimalarials/pharmacology , Diterpenes/pharmacology , Marine Biology , Molecular Structure , Nitriles/pharmacology , Porifera/chemistry , Pyrenes/pharmacology
SELECTION OF CITATIONS
SEARCH DETAIL
...