2-Benzyl and 2-phenyl-3-hydroxypropyl pivalates as protein kinase C ligands

Lee, Jeeyeon; Lee, Ju‐Hyun; Kim, Su Yeon; Perry, Nicholas A.; Lewin, Nancy E.; Ayres, Jolene A.; Blumberg, Peter M.

doi:10.1016/j.bmc.2005.10.051

Cited by 15 publications

(16 citation statements)

References 17 publications

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“…The 1 H NMR data are in accordance with literature. (41) 13 C NMR (CDCl 3 , 75 MHz): δ 41.1, 70.0, 113.7, 116.0, 122.0, 127.6, 128.0, 128.6, 129.7, 134.7, 136.9, 159.0, 177.6. MS (EI, 70 eV): m / z = 242 (M + , 9), 91 (100), 65 (10).…”

Section: Methodsmentioning

confidence: 99%

Biocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids

et al. 2011

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A chemoenzymatic approach for the asymmetric total synthesis of the title compounds is described that employs an enantioselective oxidative C–C bond formation catalyzed by berberine bridge enzyme (BBE) in the asymmetric key step. This unique reaction yielded enantiomerically pure (R)-benzylisoquinoline derivatives and (S)-berbines such as the natural product (S)-scoulerine, a sedative and muscle relaxing agent. The racemic substrates rac-1 required for the biotransformation were prepared in 4–8 linear steps using either a Bischler–Napieralski cyclization or a C1–Cα alkylation approach. The chemoenzymatic synthesis was applied to the preparation of fourteen enantiomerically pure alkaloids, including the natural products (S)-scoulerine and (R)-reticuline, and gave overall yields of up to 20% over 5–9 linear steps.

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Section: Methodsmentioning

confidence: 99%

Biocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids

et al. 2011

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“…The benzylic bromide 49 was prepared from the corresponding benzylic alcohol according to literature. [33] Solutions of HAliBu 2 in THF were prepared from neat HAliBu 2 and absolute THF. The concentration of nBuLi in THF was determined by titration with diphenylacetic acid.…”

Section: Methodsmentioning

confidence: 99%

“…The acid 51, which was required as the starting material for the synthesis of succinic acid 48, was obtained in 72 % overall yield through alkylation of the lithium enolate of tert-butylacetate with bromide 49 [33] and hydrolysis of the thus formed ester 50 (Scheme 21). The asymmetric synthesis of succinic acid 48 was carried out by the oxazolidinone method, [34] which has already been successfully applied to the synthesis of structurally related acids.…”

Section: Synthesis Of a Protected Aggrecanase Inhibitor Mimicmentioning

confidence: 99%

Asymmetric Synthesis of Functionalized Bicyclic β‐Amino Alcohols by Cascade Hydrometallation–Cyclization–Reduction of Glycinyl‐Substituted Alkenylsulfoximines – Application to the Synthesis of an Aggrecanase Inhibitor Mimic

et al. 2011

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The treatment of exocyclic alkenylsulfoximines, which carry an α-glycinyl group at the allylic position, with HAliBu 2 caused cascade hydroalumination-cyclization-reduction and delivered the corresponding enantio-and diastereopure sulfoximine-substituted bicyclic β-amino alcohols with a bicyclo[3.3.0]octane and bicyclo[4.3.0]nonane skeleton in high yields. Three consecutive stereogenic C atoms of the bicyclic β-amino alcohols were generated in the cascade reactions with high diastereoselectivities. Application of the hydroalumination-cyclization-reduction to a ketal-substituted sixmembered exocyclic alkenylsulfoximine afforded the corresponding sulfoximine-substituted β-amino alcohol with a ketal-functionalized bicyclo[4.3.0]nonane skeleton. Reduction of a sulfoximine-substituted β-amino alcohol gave the parent β-amino alcohol, whereas its oxidative deamination afforded the corresponding sulfonyl-substituted β-amino alcohol. The

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“…Related in vitro and in silico assays showed that through the whole series, compound 13 is the most active with a K i value in the submicromolar range [89]. On the basis of these interesting data, our research group synthesized a small library of 13 analogues (general structure VII , Figure 9) - ester and amide derivatives—in order to understand which structural modifications on the pivalate template could cause retention or enhancement of affinity towards the C1 domain of PKC.…”

Section: Pkc Ligandsmentioning

confidence: 99%

PKC in Regenerative Therapy: New Insights for Old Targets

et al. 2017

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Effective therapies for chronic or non-healing wounds are still lacking. These tissue insults often result in severe clinical complications (i.e., infections and/or amputation) and sometimes lead to patient death. Accordingly, several research groups have focused their efforts in finding innovative and powerful therapeutic strategies to overcome these issues. On the basis of these considerations, the comprehension of the molecular cascades behind these pathological conditions could allow the identification of molecules against chronic wounds. In this context, the regulation of the Protein Kinase C (PKC) cascade has gained relevance in the prevention and/or reparation of tissue damages. This class of phosphorylating enzymes has already been considered for different physiological and pathological pathways and modulation of such enzymes may be useful in reparative processes. Herein, the recent developments in this field will be disclosed, highlighting the pivotal role of PKC α and δ in regenerative medicine. Moreover, an overview of well-established PKC ligands, acting via the modulation of these isoenzymes, will be deeply investigated. This study is aimed at re-evaluating widely known PKC modulators, currently utilized for treating other diseases, as fruitful molecules in wound-healing.

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2-Benzyl and 2-phenyl-3-hydroxypropyl pivalates as protein kinase C ligands

Cited by 15 publications

References 17 publications

Biocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids

Biocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids

Asymmetric Synthesis of Functionalized Bicyclic β‐Amino Alcohols by Cascade Hydrometallation–Cyclization–Reduction of Glycinyl‐Substituted Alkenylsulfoximines – Application to the Synthesis of an Aggrecanase Inhibitor Mimic

PKC in Regenerative Therapy: New Insights for Old Targets

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2-Benzyl and 2-phenyl-3-hydroxypropyl pivalates as protein kinase C ligands

Cited by 15 publications

References 17 publications

Biocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids

Biocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids

Asymmetric Synthesis of Functionalized Bicyclic β‐Amino Alcohols by Cascade Hydrometallation–Cyclization–Reduction of Glycinyl‐Substituted Alkenylsulfox­imines – Application to the Synthesis of an Aggrecanase Inhibitor Mimic

PKC in Regenerative Therapy: New Insights for Old Targets

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Product

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Asymmetric Synthesis of Functionalized Bicyclic β‐Amino Alcohols by Cascade Hydrometallation–Cyclization–Reduction of Glycinyl‐Substituted Alkenylsulfoximines – Application to the Synthesis of an Aggrecanase Inhibitor Mimic