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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Research Article

Synthesis of Open-Resorcinarene Dendrimers with L-serine (Ibuprofen) Derivatives

Author(s): Luis Daniel Pedro-Hernández and Marcos Martínez-García*

Volume 26, Issue 1, 2022

Published on: 17 December, 2021

Page: [71 - 80] Pages: 10

DOI: 10.2174/1385272825666211130164548

Price: $65

Abstract

A new class of dendrimers with open-resorcinarenes has been synthesized in good yields (77-85%). The open-resorcinarenes showed a high capacity for functionalization, having eight hydroxyl groups. The Williamson reaction with N,N-bis(2-azidoethyl)-2-bromo acetamide did not show any steric effect, obtaining sixteen azide terminal groups, which gave us the possibility to obtain a high molecular weight dendrimer via the azide-alkyne click reaction with prop-2-yn-1-yl-(ibuprofen)L-serinate derivatives to obtain the triazole ring spacers and the L-serinate(ibuprofen) derivatives as terminal groups. Also, we carried out the deprotection reaction of the L-serinate moiety terminal groups of the dendrimer 10 in good yields (95%). Three novel open-resorcinarene den-drimers with sixteen ibuprofen-L-serinate derivatives and hydroxyl, tert-butyl, and carboxylic acid; therefore, with three different terminal groups, with possible nanomedical activity are reported.

Keywords: Open-resorcinarenes, dendrimers, L-serine, ibuprofen, click reaction, triazole.

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