Solid-supported syntheses of 3-thio-1,2,4-triazoles |
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Authors: | Wilson Michael W Hernández Andrés S Calvet Alain P Hodges John C |
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Institution: | (1) Exploratory Chemistry, Parke-Davis Pharmaceutical Research, Division of Warner-Lambert Company, 2800 Plymouth Road, Ann Arbor, MI, 48105, U.S.A;(2) Biomolecular Structure and Drug Design, Parke-Davis Pharmaceutical Research, Division of Warner-Lambert Company, 2800 Plymouth Road, Ann Arbor, MI, 48105, U.S.A |
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Abstract: | Two solid-supported synthesis strategies for the preparation of 3-thio-1,2,4-triazoles are described. In the first, Rink amide
resin is combined with Fmoc-protected ω-amino acids, acid hydrazides, and alkyl halides to provide diverse sets of starting
materials from which numerous triazoles may be prepared. The second employs t-alkylcarbamateresin (Boc resin) which permits
the use of additional pools of starting materials, including isothiocyanates and α- and ω-amino esters, resulting in triazoles
with patterns of functional groups that are not possible from the initial route. The combination of multiple resins and resin
attachment sites allows the preparation of a diverse library based upon the3-thio-1,2,4-triazole scaffold and avoids the pitfallof
having a single linker functionality present at the same position in all library members. General synthetic procedures and
representative products from each route are presented. A similarity analysis of representative sublibraries from each synthesis
strategy concludes that variation of the solid-phase linker chemistry and attachment site can enhance molecular diversity
of the combined triazole library.
This revised version was published online in August 2006 with corrections to the Cover Date. |
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Keywords: | combinatorial library molecular similarity parallel synthesis solid-supported synthesis Tanimoto coefficient 1 2 4-triazole |
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