Design and synthesis by click triazole formation of paclitaxel mimics with simplified core and side-chain structures

• Published in: Tetrahedron letters Vol. 52; no. 13; pp. 1462 - 1465
• Main Authors: Manach, Claire Le, Baron, Aurélie, Guillot, Régis, Vauzeilles, Boris, Beau, Jean-Marie
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 30.03.2011; Elsevier
• Subjects: Alicyclic compounds, terpenoids, prostaglandins, steroids; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemical Sciences; Chemistry; Chemistry, Organic; Click chemistry; Combinatorial analysis; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; l-glucuronolactone; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Searching; Strategy; Sugar scaffold; Synthesis (chemistry); Taxane; Taxoid mimic; Taxol; Terpenoids; Tetrahedrons; Triazoles; Tubulin depolymerization; Taxoid mimic; Sugar scaffold; Click chemistry; Tubulin depolymerization; l-glucuronolactone; BIOACTIVITY; AZIDES; CONVERSION; ACIDS; L-glucuronolactone; ALPHA-BETA-TUBULIN; TAXOL ANALOGS; GLUCOSE; CHEMISTRY; Terpenoid; Aminoalcohol; Molecular structure; Nitrogen heterocycle; Combinatorial chemistry; Oside; Depolymerization; Terpene; Side chain; Tubulin; Hydroxyacid; Chemical compound library; Taxane derivatives; Paclitaxel; Diterpene; Triazole derivatives; Chemical synthesis

A library of paclitaxel (taxol) mimics was obtained by a straightforward strategy involving rational design and an efficient synthesis of a simplified taxane core substitute, together with a click-chemistry combinatorial search for phenylisoserine side-chain surrogates.