Solid-Phase Synthesis of Anagrelide Sulfonyl Analogues

McMaster, Claire; Fülöpová, Veronika; Popa, Igor; Grepl, Martin; Soural, Miroslav

doi:10.1021/co400119c

Cited by 20 publications

(25 citation statements)

References 14 publications

(19 reference statements)

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“…Ion pairing between N + (C 4 H 9 ) 4 and S 2 O 4 2− makes the reducing agent soluble in organic media allowing it to diffuse to the nitro compounds. While it has been successfully used for solid-phase synthetic protocols [170,171], our tests reveal that this PTC approach does not produce 15 from 14 in acceptable yields.…”

Section: Selective Reduction Of Nitro Groups In Aa Conjugatesmentioning

confidence: 87%

Biomimetic and bioinspired molecular electrets. How to make them and why does the established peptide chemistry not always work?

Skonieczny

Espinoza

Derr

et al. 2019

Pure and Applied Chemistry

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Abstract“Biomimetic” and “bioinspired” define different aspects of the impacts that biology exerts on science and engineering. Biomimicking improves the understanding of how living systems work, and builds tools for bioinspired endeavors. Biological inspiration takes ideas from biology and implements them in unorthodox manners, exceeding what nature offers. Molecular electrets, i.e. systems with ordered electric dipoles, are key for advancing charge-transfer (CT) science and engineering. Protein helices and their biomimetic analogues, based on synthetic polypeptides, are the best-known molecular electrets. The inability of native polypeptide backbones to efficiently mediate long-range CT, however, limits their utility. Bioinspired molecular electrets based on anthranilamides can overcome the limitations of their biological and biomimetic counterparts. Polypeptide helices are easy to synthesize using established automated protocols. These protocols, however, fail to produce even short anthranilamide oligomers. For making anthranilamides, the residues are introduced as their nitrobenzoic-acid derivatives, and the oligomers are built from their C- to their N-termini via amide-coupling and nitro-reduction steps. The stringent requirements for these reduction and coupling steps pose non-trivial challenges, such as high selectivity, quantitative yields, and fast completion under mild conditions. Addressing these challenges will provide access to bioinspired molecular electrets essential for organic electronics and energy conversion.

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Section: Selective Reduction Of Nitro Groups In Aa Conjugatesmentioning

confidence: 87%

Biomimetic and bioinspired molecular electrets. How to make them and why does the established peptide chemistry not always work?

Skonieczny

Espinoza

Derr

et al. 2019

Pure and Applied Chemistry

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“…A solid-phase synthesis of analogous BGs 187, based on the 3,10-dihydro-2H-benzo[e]imidazo [1,2-b] [1,2,4]thiazin-2one 5,5-dioxide scaffold, was described in 2014. [97] The target 6+5 compounds were synthesised from Fmoc-α-amino acids and 2-nitrobenzenesulfonyl chlorides. The synthesis was performed on Wang resin.…”

Section: Synthesis Of Bgs On a Polystyrene Supportmentioning

confidence: 99%

Synthetic Strategies for Preparing Bicyclic Guanidines

Lemrová

Soural

2015

Eur J Org Chem

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Different synthetic approaches leading to compounds containing bicyclic guanidine scaffolds are summarised. Because of the diversity within this group of target molecules and the wide range of individually reported synthetic routes, this review is divided into three subsections according to the key intermediate used to obtain the bicyclic structure. The first section is dedicated to strategies in which monocyclic guanidine derivatives are used as the key intermediates. The second section presents direct syntheses of bicyclic guanidines from acyclic or non‐guanidine starting materials. The last part of the text addresses the synthesis of target compounds through the use of polymer‐supported chemistry. The applicability of each synthetic approach for the preparation of target molecules with certain x+y combinations of individual cycles is specified.

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“…In our recent work, it was demonstrated that either full 19 or partial 20 racemization of the α-amino acid stereocenter can occur, even under mild reaction conditions. To evaluate the stereochemical outcome of this synthetic method, compound 7 DL (1,3,1,1) was prepared as the racemic standard.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Novel N⁹-Substituted Purine Derivatives from Polymer Supported α-Amino Acids

et al. 2015

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Solid-phase synthesis of purine derivatives bearing an α-amino acid motif in position 9 is described herein. Polymer supported amines were acylated with various Fmoc-α-amino acids and, after cleavage of the protecting group, arylation with 4,6-dichloro-5-nitropyrimidine or 2,4-dichloro-5-nitropyrimidine was performed. The second chlorine atom was replaced with various amines. Subsequent reduction of the nitro group, followed by reaction with aldehydes, afforded the purine scaffold. After cleavage from the polymer support, the target compounds were obtained in very good crude purity, good overall yields, and excellent enantiomeric purity. The anticancer activity of prepared compounds was tested in vitro against human cancer cell lines MCF7 and K562, and they were found to have mild, but clear dose-dependent effects.

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Solid-Phase Synthesis of Anagrelide Sulfonyl Analogues

Cited by 20 publications

References 14 publications

Biomimetic and bioinspired molecular electrets. How to make them and why does the established peptide chemistry not always work?

Biomimetic and bioinspired molecular electrets. How to make them and why does the established peptide chemistry not always work?

Synthetic Strategies for Preparing Bicyclic Guanidines

Synthesis of Novel N⁹-Substituted Purine Derivatives from Polymer Supported α-Amino Acids

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Solid-Phase Synthesis of Anagrelide Sulfonyl Analogues

Cited by 20 publications

References 14 publications

Biomimetic and bioinspired molecular electrets. How to make them and why does the established peptide chemistry not always work?

Biomimetic and bioinspired molecular electrets. How to make them and why does the established peptide chemistry not always work?

Synthetic Strategies for Preparing Bicyclic Guanidines

Synthesis of Novel N9-Substituted Purine Derivatives from Polymer Supported α-Amino Acids

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Product

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Synthesis of Novel N⁹-Substituted Purine Derivatives from Polymer Supported α-Amino Acids