β-Phenylethylamines and the isoquinoline alkaloids

Bentley, K. W.

doi:10.1039/np9971400387

Cited by 23 publications

(7 citation statements)

References 285 publications

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“…Protoberberine (5,6-dihydrodibenzo[a,g]quinolizinium) alkaloids found in the bark, rhizomes, roots, and stems of Berberis vulgaris L. (Berberidaceae) 2 have been shown to exhibit many different types of biological activities. Among the most well studied of these compounds is berberine (1), which has antifungal, 3 anti-inflammatory, 4 antimalarial, 5 anti-HIV, 6 antihyperglycemic, 7 immunoregulatory, 8 antitumor, 9 and cholesterol-lowering 10 effects.…”

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confidence: 99%

Berberine and Its Metabolites: Relationship between Physicochemical Properties and Plasma Levels after Administration to Human Subjects

et al. 2014

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Berberine (1) is an alkaloid used widely in the treatment of several diseases. However, its physicochemical properties, pharmacokinetics, and metabolism remain unclear, and conflicting data have been reported. In this study, the main physicochemical properties of 1 and its metabolites were evaluated, including lipophilicity, solubility, pKa, and albumin binding. A sensitive HPLC-ESIMS/MS method was developed and validated to identify 1 and its main metabolites in human plasma. This method was used to quantify their levels in the plasma of healthy volunteers and hypercholesterolemic patients following a single dose and chronic administration, respectively. In both cases, berberrubine (2) was found to be the main metabolite. Surprisingly, 2 is more lipophilic than 1, which suggests that this compound tautomerizes to a highly conjugated, electroneutral quinoid structure. This was confirmed by NMR studies. These results indicate that the higher plasma concentration of 2 was a consequence of a more efficient intestinal absorption, suggesting that berberrubine is potentially more pharmacologically active than berberine.

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confidence: 99%

Berberine and Its Metabolites: Relationship between Physicochemical Properties and Plasma Levels after Administration to Human Subjects

et al. 2014

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“…Most of this work is summarized in an excellent review by Leonard [81]. We confine this section to the syntheses of magallanesine ( 97 ) by Danishefsky and Kurihara, which were also mentioned by Evans and Bentley [82–83]. …”

Section: Reviewmentioning

confidence: 99%

The chemistry of isoindole natural products

Speck¹,

Magauer²

2013

Beilstein J. Org. Chem.

316

163

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SummaryThis review highlights the chemical and biological aspects of natural products containing an oxidized or reduced isoindole skeleton. This motif is found in its intact or modified form in indolocarbazoles, macrocyclic polyketides (cytochalasan alkaloids), the aporhoeadane alkaloids, meroterpenoids from Stachybotrys species and anthraquinone-type alkaloids. Concerning their biological activity, molecular structure and synthesis, we have limited this review to the most inspiring examples. Within different congeners, we have selected a few members and discussed the synthetic routes in more detail. The putative biosynthetic pathways of the presented isoindole alkaloids are described as well.

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“…Isoindoline alkaloids constitute a large collection of functionally diverse natural products possessing interesting biological activities. [1,2] Exemplary naturally occurring molecules such as fumaridine (I), [3,4] magallanesine (II), [5,6] chilenine (III), [7] aristolactam (IV) [8] and many more contain 3-substituted-isoindolinone skeletons (Figure 1), which are crucial for displaying bioactivities. [1] Furthermore isoindolinone scaffold is a useful surrogates for the variety of poly-heterocyclic compounds, several pharmaceutical agents and synthetic dyes.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Synthesis of Functionalized Isoindolinones and Their Bis(isoindolinone)ethane Derivatives

et al. 2022

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Highly efficient one‐pot synthesis of a series of substituted 3‐methylene‐isoindolinones (3 a–x), bis(isoindolinone)ethanes (4 a–d) and 3‐hydroxy‐isoindolinones (6 a–h) derivatives is portrayed from easily accessible starting materials such as 2‐cyanobenzaldehydes (1 a–h) and different aryl/heteroaryl methyl ketones (2 a–k). The structure of Z‐isomer of 3‐methylene‐isoindolinone 3 x was confirmed by single crystal X‐ray analysis. The reaction mechanism studies by control experiments and using O18‐labelled water revealed that the reaction was initiated by attack of a conjugate base of aryl/heteroaryl methyl ketones (2 a–k) to aldehyde group of 1 a–h followed by intramolecular oxidative cyclization involving nitrile functionality to furnish isoindolinone derivatives in good to excellent yields.

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β-Phenylethylamines and the isoquinoline alkaloids

Cited by 23 publications

References 285 publications

Berberine and Its Metabolites: Relationship between Physicochemical Properties and Plasma Levels after Administration to Human Subjects

Berberine and Its Metabolites: Relationship between Physicochemical Properties and Plasma Levels after Administration to Human Subjects

The chemistry of isoindole natural products

One‐Pot Synthesis of Functionalized Isoindolinones and Their Bis(isoindolinone)ethane Derivatives

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