Design, synthesis and biological evaluation of novel tetrahydroisoquinoline derivatives as potential PDE4 inhibitors

Song, Gaopeng; Zhao, Dongsheng; Hu, De-Kun; Li, Yasheng; Jin, Hongwei; Cui, Zi‐Ning

doi:10.1016/j.bmcl.2015.08.043

Cited by 15 publications

(1 citation statement)

References 21 publications

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“…Amides of shikimic acid can be prepared by the conventional activation methods, such as with carbodiimide or iminium HATU salt, as reported for the triacylated 68 and nonacylated shikimic acid respectively (Scheme ). , Platinum(II) complexes with shikimic acid based ligands have been prepared by reaction of amide derivatives containing a diamine moiety with K 2 PtCl 4 (Scheme ), and have been shown to bound covalently to DNA, blocking the DNA synthesis and replication. The exact structure of the five water-soluble complexes of different alkyl chain lengths was not elucidated but purposed to have the ligands coordinated in a bidentate manner through the amine groups …”

Section: Synthetic Applications Of Shikimic Acidmentioning

confidence: 99%

Production and Synthetic Modifications of Shikimic Acid

2018

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Shikimic acid is a natural product of industrial importance utilized as a precursor of the antiviral Tamiflu. It is nowadays produced in multihundred ton amounts from the extraction of star anise (Illicium verum) or by fermentation processes. Apart from the production of Tamiflu, shikimic acid has gathered particular notoriety as its useful carbon backbone and inherent chirality provide extensive use as a versatile chiral precursor in organic synthesis. This review provides an overview of the main synthetic and microbial methods for production of shikimic acid and highlights selected methods for isolation from available plant sources. Furthermore, we have attempted to demonstrate the synthetic utility of shikimic acid by covering the most important synthetic modifications and related applications, namely, synthesis of Tamiflu and derivatives, synthetic manipulations of the main functional groups, and its use as biorenewable material and in total synthesis. Given its rich chemistry and availability, shikimic acid is undoubtedly a promising platform molecule for further exploration. Therefore, in the end, we outline some challenges and promising future directions.

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Section: Synthetic Applications Of Shikimic Acidmentioning

confidence: 99%

Production and Synthetic Modifications of Shikimic Acid

2018

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Metal‐Free Multicomponent Construction of Tetrahydroisoquinoline‐Indole Derivatives via In Situ Generated ortho‐Quinonoid Intermediate

Kaur

Gurjar²,

Kumar

et al. 2020

ChemistrySelect

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A metal‐ and ligand‐free multicomponent coupling of tetrahydroisoquinoline (THIQ), ortho‐hydroxybenzaldehydes and indoles under solvent‐free conditions is described. The developed protocol provided a waste‐free and concise access to C(1)‐functionalized THIQ‐indole derivatives under green conditions. The reactant molar ratio and neutral conditions were found crucial for controlling the selectivity of desired THIQ‐indole product over competitive by‐products i. e. oxazine and bis(indolyl)methane. The experimental and DFT study revealed the involvement of ortho‐quinonoid species which reacts with indoles in situ to form THIQ‐indole derivatives.

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Design, synthesis and biological evaluation of 2,4-disubstituted oxazole derivatives as potential PDE4 inhibitors

Zhao

et al. 2017

Bioorganic & Medicinal Chemistry

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Design, synthesis and biological evaluation of novel tetrahydroisoquinoline derivatives as potential PDE4 inhibitors

Cited by 15 publications

References 21 publications

Production and Synthetic Modifications of Shikimic Acid

Production and Synthetic Modifications of Shikimic Acid

Metal‐Free Multicomponent Construction of Tetrahydroisoquinoline‐Indole Derivatives via In Situ Generated ortho‐Quinonoid Intermediate

Design, synthesis and biological evaluation of 2,4-disubstituted oxazole derivatives as potential PDE4 inhibitors

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