Harmicine, a Tetracyclic Tetrahydro-β-Carboline: From the First Synthetic Precedent to Isolation from Natural Sources to Target-Oriented Synthesis (Review)*

Lood, Christopher S.; Koskinen, Ari M. P.

doi:10.1007/s10593-014-1602-4

Cited by 22 publications

(4 citation statements)

References 86 publications

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“…Harmicine Apocynaceae: Kopsia griffithii King & Gamble [40,41] Harmine Malpighiaceae: Banisteriopsis caapi (Spruce ex Griseb.) Morton; Malvaceae: Grewia bicolor Juss.…”

Section: -39]unclassified

LC‐HRMS for the Identification of β‐Carboline and Canthinone Alkaloids Isolated from Natural Sources

Amaral¹,

Ramos²,

Ferreira³

et al. 2017

Mass Spectrometry

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β-carboline and canthinone alkaloids are widely distributed in the Angiosperms. Due to their diverse biological activities, the structures of these alkaloids have been used as important models for the synthesis of novel therapeutic drugs. Combining highperformance liquid chromatography (HPLC) with high-resolution mass spectrometry (HRMS) has provided a valuable tool in the analysis of these alkaloids in, for example, plants, insects, marine creatures, human tissues and body fluids. In this review, we summarized the main β-carboline and canthinone alkaloids studied by liquid chromatography high-resolution mass spectrometry (LC-HRMS) associated with mass analyzers, molecular weight information, mass fragmentation and biological activities, presenting an overview of increasing interest for carboline alkaloids study by LC-HRMS.

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“…Harmicine Apocynaceae: Kopsia griffithii King & Gamble [40,41] Harmine Malpighiaceae: Banisteriopsis caapi (Spruce ex Griseb.) Morton; Malvaceae: Grewia bicolor Juss.…”

Section: -39]unclassified

LC‐HRMS for the Identification of β‐Carboline and Canthinone Alkaloids Isolated from Natural Sources

Amaral¹,

Ramos²,

Ferreira³

et al. 2017

Mass Spectrometry

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“…Recently, tryptoline derivatives have attracted attention because of their anti-HIV, anti-inflammatory, anti-leishmanial, anti-trypanosomal, and anti-tumor activities [1][2][3][4]. Among these derivatives, 1,3-disubstituted tryptoline derivatives have attracted attention because of the relation between their stereochemistry and biological activities based on their asymmetric carbons.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of All Stereoisomers of 1-(4-Methoxyphenyl)-2,3,4,9-tetrahydro-N-methyl-1H-pyrido[3,4-b]indole-3-carboxamide

Onda

Higashida

Hirano

et al. 2018

Molbank

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Abstract:In this study, all four stereoisomers of tryptoline or tetrahydro-β-carboline were synthesized in high yields by the catalyst-free amidation of methyl ester using methylamine under mild conditions. All isomers of the obtained amide and the precursor methyl ester were subjected to cell viability measurements on HeLa cells. The results indicated that the stereochemistry of the derivatives is clearly related to cell viability.

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“…1) are widespread in both the plant and animal kingdom, mostly marine microorganisms, with high affinity for benzodiazepine, serotonin and dopamine receptor sites. [5][6][7] They also exhibit a vast diversity of biological activities, very often significant antitumor action, 8 by DNA intercalation, [9][10][11] DNA binding, 12,13 or DNA synthesis inhibition 14 among others. Very recently, tetrahydro-b-carboline derivatives demonstrated antileishmanial activity against the transgenic infrared fluorescent Leishmania infantum strain.…”

Section: Introductionmentioning

confidence: 99%

One-pot reaction of pyranoindolones with phenylisocyanates: a simple and regioselective approach to β-carbolines

Livadiotou

Hatzimimikou

Tsitsi

et al. 2016

Tetrahedron Letters

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Harmicine, a Tetracyclic Tetrahydro-β-Carboline: From the First Synthetic Precedent to Isolation from Natural Sources to Target-Oriented Synthesis (Review)*

Cited by 22 publications

References 86 publications

LC‐HRMS for the Identification of β‐Carboline and Canthinone Alkaloids Isolated from Natural Sources

LC‐HRMS for the Identification of β‐Carboline and Canthinone Alkaloids Isolated from Natural Sources

Synthesis of All Stereoisomers of 1-(4-Methoxyphenyl)-2,3,4,9-tetrahydro-N-methyl-1H-pyrido[3,4-b]indole-3-carboxamide

One-pot reaction of pyranoindolones with phenylisocyanates: a simple and regioselective approach to β-carbolines

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