Efficient synthesis of β-amino bromides

Nagle, A. S.; Salvatore, Ralph Nicholas; Chong, Byong-Don; Jung, Kyung Woon

doi:10.1016/s0040-4039(00)00330-0

Cited by 39 publications

(19 citation statements)

References 6 publications

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“…Mono‐amine functionalized mPEG was synthesized via a three‐step sequence of mesylation, azidation, and subsequent reduction of mPEG ( M = 1 100 g · mol −1 ) analogously to the literature 43, 44. Hyperbranched polyglycerol 37, 38 (HPG) was synthesized by a one‐step anionic, ring‐opening polymerization and subsequently modified by standard etherification with N,N ‐dibenzyl‐3‐bromopropan‐1‐amine 45 yielding HPG with statistically one dibenzylaminopropyl linker as determined by 1 H NMR (ESI, 4a ). Deprotection of the amine group by catalytic hydrogenation with Pd/C yielded the corresponding aminopropyl functionalized HPG (ESI, 4b ).…”

Section: Methodsmentioning

confidence: 99%

Linear and Hyperbranched Polyglycerol Derivatives as Excellent Bioinert Glass Coating Materials

et al. 2011

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The non‐specific adsorption of proteins to surfaces in contact with biofluids constitutes a major problem in the biomedical and biotechnological field, due to the initiation of biofilm formation and the resulting improper function of devices. Therefore, non‐fouling surfaces modified with poly(ethylene glycol) (PEG) are usually applied. In this study, we report the synthesis of triethoxysilane modified glycerol based polymers of linear and branched architecture for the preparation of covalently attached monolayers on glass. Evaluation of the biocompatibility of these surfaces was performed in comparison to bare non‐coated glass, hydrophobic hexadecane modified glass, and mPEG modified glass as the controls. Protein adsorption of BSA and fibrinogen (1 mg · mL−1 in PBS) after 4 and 24 h immersion was reduced by more than 96 and 90%, respectively, compared to the adsorption on bare glass substrates. In addition, mouse NIH‐3T3 fibroblast cells showed only marginal adhesion on the polyglycerol and mPEG coated slides after 3 and 7 d incubation in cell suspension, which demonstrates the long‐term stability of the applied glass coatings. The non‐adhesive properties of these coatings were further reflected in bacterial adhesion tests of Escherichia coli K12 and three clinically relevant Gram‐positive and negative strains (Staphylococcus aureus, Pseudomonas aeruginosa, and Aeromonas hydrophila), since linear polyglycerol (LPG(OH)), linear poly(methyl glycerol) (LPG(OMe)), and hyperbranched polyglycerol (HPG) reduced the adhesion for all tested strains by more than 99% compared to bare glass. Therefore, polyglycerol derivatives present an excellent non‐fouling surface coating as an alternative to PEG with feasibility for surface modification of various substrates.

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Section: Methodsmentioning

confidence: 99%

Linear and Hyperbranched Polyglycerol Derivatives as Excellent Bioinert Glass Coating Materials

et al. 2011

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“…Notably, N ‐alkyl prolinol derivatives could be transformed into 3‐chloropiperidines with good enantiomeric excess when prolinols were treated with SOCl 2 in CHCl 3 followed by a thermal process. In the case of bromopiperidines, they were formed when prolinols were treated with SOBr 2 in DMF/cyclohexane (Scheme ) 26. Intermediates G and H are probably responsible for the transformation of prolinols into 3‐halopiperidines (Scheme ).…”

Section: Synthesis Of 3‐halopiperidinesmentioning

confidence: 99%

Access to Optically Active 3‐Substituted Piperidines by Ring Expansion of Prolinols and Derivatives

Pardo

Cossy

2014

Chemistry A European J

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The ring expansion of prolinols via an aziridinium intermediate gives C3-substituted piperidines in good yields and enantiomeric excess, the substituent at the C3 position being derived from the most reactive nucleophile in the reaction mixture. Depending on the nucleophile, the reaction proceeds under thermodynamic or kinetic control. The regioselectivity of attack of nucleophiles on the aziridinium intermediate depends on the nature of the substituents on the nitrogen atom and the C4 position of the starting prolinols.

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“…The resulting methyl ester was reduced to primary alcohol 17, which was subsequently converted to corresponding bromide 18. 20 Nucleophilic substitution of 18 with phenols led to compounds 11−14. Alternatively, a Suzuki coupling of 16 with the corresponding boronic ester furnished 15.…”

Section: * S Supporting Informationmentioning

confidence: 99%

Structure-Based Design of Potent and Selective CK1γ Inhibitors

Huang

Acquaviva

Berry

et al. 2012

ACS Med. Chem. Lett.

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Aberrant activation of the Wnt pathway is believed to drive the development and growth of some cancers. The central role of CK1γ in Wnt signal transduction makes it an attractive target for the treatment of Wnt-pathway dependent cancers. We describe a structure-based approach that led to the discovery of a series of pyridyl pyrrolopyridinones as potent and selective CK1γ inhibitors. These compounds exhibited good enzyme and cell potency, as well as selectivity against other CK1 isoforms. A single oral dose of compound 13 resulted in significant inhibition of LRP6 phosphorylation in a mouse tumor PD model.

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Efficient synthesis of β-amino bromides

Cited by 39 publications

References 6 publications

Linear and Hyperbranched Polyglycerol Derivatives as Excellent Bioinert Glass Coating Materials

Linear and Hyperbranched Polyglycerol Derivatives as Excellent Bioinert Glass Coating Materials

Access to Optically Active 3‐Substituted Piperidines by Ring Expansion of Prolinols and Derivatives

Structure-Based Design of Potent and Selective CK1γ Inhibitors

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