- Enantiopure synthesis of 7-(1-pyrindanyl)propargyl ethers as rasagiline analogues via chemical or enzymatic resolution of 1-pyrindan-7-ol
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In this work, the enantiopure synthesis of 7-(1-pyrindanyl)propargyl ethers - rasagiline analogues - via chemical and/or enzymatic resolution of the racemic precursor 1-pyrindan-7-ol is described. (R)-Methoxyphenylacetic acid - (R)-MPAA - and (S)-methoxyphenylacetic acid - (S)-MPAA were used as chemical resolution agents, whereas Candida antarctica lipase B (CALB) was employed as kinetic resolution catalyst. The enzymatic resolution was successfully achieved by two different approaches: (1) transesterification of racemic 1-pyrindan-7-ol, which was found to selectively acylate the (R)-enantiomer with high efficiency; (2) hydrolysis of the racemic 7-(1-pyrindanyl)acetate, which was also highly selective to the (R)-enantiomer. The enzymatic hydrolysis was performed in a non-aqueous solvent using a lipase with significant absorbed water content. The configuration of the two enantiomers of 1-pyrindan-7-ol (and consequently of the 7-(1-pyrindanyl)propargyl ethers) were unequivocally determined by X-ray crystallography and/or specific optical rotation.
- Sousa, Carlos A. D.,Sampaio-Dias, Ivo E.,Rizzo-Aguiar, Fabio,Garcia-Mera, Xerardo,Rodríguez-Borges, José E.
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p. 104509 - 104515
(2015)
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- SMALL MOLECULE INHIBITORS OF NF-kB INDUCING KINASE
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The present invention relates to compounds that inhibit NIK and pharmaceutical compositions comprising such compounds and methods of using the same. These compounds and pharmaceutical compositions are envisaged to be useful for preventing or treating diseases such as cancer (such as B-cell malignancies including leukemias, lymphomas and myeloma), inflammatory disorders, autoimmune disorders, immunodermatologic disorders such as palmoplantar pustulosis and hidradenitis suppurativa, and metabolic disorders such as obesity and diabetes.
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Page/Page column 169
(2020/12/11)
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- Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis
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A series of methyl aluminum complexes bearing chiral biphenol-type ligands were found to be highly active catalysts in the asymmetric reduction of heterocyclic ketones (S/C = 100-500, ee up to 99%). The protocol is suitable for a wide range of substrates and has a high tolerance to functional groups. The formed 2-heterocyclic-alcohols are valuable building blocks in drug discovery or can be used as ligands in asymmetric catalysis. Isolation and comprehensive characterization of the reaction intermediates support a catalysis cycle proposed by DFT calculations.
- Lebedev, Yury,Polishchuk, Iuliia,Maity, Bholanath,Dinis Veloso Guerreiro, Miguel,Cavallo, Luigi,Rueping, Magnus
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supporting information
p. 19415 - 19423
(2019/12/24)
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- Synthesis of New Propargylated 1-Pyrindane Derivatives as Rasagiline Analogues
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Rasagiline is a compound with important neuroprotective activity applicable to the treatment of neurodegenerative diseases. This work describes an easy and straightforward methodology to the synthesis of new propargylated rasagiline analogues derived from commercially available 6,7-dihydro-5H-cyclopenta[b] pyridine. Georg Thieme Verlag Stuttgart - New York.
- Pereira, Cidáliasilva,Salgado, Sofia,Rizzo-Aguiar, Fabio,Garcia-Mera, Xerardo,Rodríguez-Borges, Josée.
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supporting information
p. 837 - 838
(2013/05/21)
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- Kinetic resolution of diols and pyridyl alcohols by cu(II)(borabox)- catalyzed acylation
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Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoylation of suitable pyridyl alcohols, where they outperformed bisoxazolines. In addition, highly enantioselective Cu(II)(borabox)-catalyzed benzoylation has been used for the synthesis of both enantiomers of a pyridyl alcohol.
- Mazet, Clement,Roseblade, Stephen,Koehler, Valentin,Pfaltz, Andreas
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p. 1879 - 1882
(2007/10/03)
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- Chemokine receptor binding heterocyclic compounds
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This invention relates to a novel class of heterocyclic compounds that bind chemokine receptors, inhibiting the binding of their natural ligands thereby. These compounds result in protective effects against infection by HIV through binding to chemokine receptors, including CXCR4 and CCR5, thus inhibiting the subsequent binding by these chemokines. The present invention provides a compound of Formula I wherein, W is a nitrogen atom and Y is absent or, W is a carbon atom and Y═H; R1to R7may be the same or different and are independently selected from hydrogen or straight, branched or cyclic C1-6alkyl; R8is a substituted heterocyclic group or a substituted aromatic group Ar is an aromatic or heteroaromatic ring each optionally substituted at single or multiple, non-linking positions with electron-donating or withdrawing groups; n and n′ are independently, 0-2; X is a group of the formula: Wherein, Ring A is an optionally substituted, saturated or unsaturated 5 or 6-membered ring, and P is an optionally substituted carbon atom, an optionally substituted nitrogen atom, sulfur or oxygen atom. Ring B is an optionally substituted 5 to 7-membered ring. Ring A and Ring B in the above formula can be connected to the group W from any position via the group V, wherein V is a chemical bond, a (CH2)n″group (where n″=0-2) or a C═O group. Z is, (1) a hydrogen atom, (2) an optionally substituted C1-6alkyl group, (3) a C0-6alkyl group substituted with an optionally substituted aromatic or heterocyclic group, (4) an optionally substituted C0-6alkylamino or C3-7cycloalkylamino group, (5) an optionally substituted carbonyl group or sulfonyl. These compounds further include any pharmaceutically acceptable acid addition salts and metal complexes thereof and any stereoisomeric forms and mixtures of stereoisomeric forms thereof.
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Page column 15
(2008/06/13)
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