Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• tumor cytotoxicity effects for a number of the berberine derivatives. Keywords: benzylisoquinoline; berberine; chelerythrine; drug discovery; plant-derived antimicrobials; Introduction The isolation, or creation of novel antimicrobial agents is currently at the forefront of modern healthcare due to

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet–Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

• Marco Keller,
• Karl Sauvageot-Witzku,
• Franz Geisslinger,
• Nicole Urban,
• Michael Schaefer,
• Karin Bartel and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183

• relationships in this chemotype. Keywords: acyl Pictet–Spengler reaction; alkaloids; antiproliferative activity; benzyltetrahydroisoquinolines; ion channels; protective group; total synthesis; Introduction The benzylisoquinoline alkaloids are a large and diverse class of plant secondary metabolites including

• has been reported for benzylisoquinoline alkaloids, including spasmolytic, narcotic, dopaminergic, ion-channel modulating, and cytotoxic properties. Occurrence, biosynthesis and pharmacology of benzylisoquinoline alkaloids has been reviewed comprehensively by Hagel and Facchini [1]. Synthetic

• second benzylisoquinoline moiety of the bisbenzylisoquinolines [15]. Antiproliferative activity Several anticancer effects have been reported for benzylisoquinoline alkaloids, for instance antiproliferative and antimigratory as well as chemoresistance-reversing activities [6][15][46][47]. Yet, detailed

Aminomethylation/hydrogenolysis as an alternative to direct methylation of metalated isoquinolines – a novel total synthesis of the alkaloid 7-hydroxy-6-methoxy-1-methylisoquinoline

• Benedikt C. Melzer,
• Jan G. Felber and
• Franz Bracher

Beilstein J. Org. Chem. 2018, 14, 130–134, doi:10.3762/bjoc.14.8

• published. This prompted us to work out a novel synthetic access to alkaloid 1. Our new strategy was fueled by our previous findings in the course of new approaches to benzylisoquinoline, oxoaporphine [7], and oxoisoaporphine alkaloids [8], where we could demonstrate the power of regioselective direct ring

A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines

• Benedikt C. Melzer and
• Franz Bracher

Beilstein J. Org. Chem. 2017, 13, 1564–1571, doi:10.3762/bjoc.13.156

• cytotoxicity against the HL-60 tumor cell line. Keywords: directed ortho/remote metalation; Eaton’s reagent; isoquinolines; Suzuki cross-coupling; Introduction Benzylisoquinoline alkaloids represent a very large group of plant secondary metabolites, which includes about 2,500 known structures. Besides simple

• , biosynthesis and pharmacology of benzylisoquinoline alkaloids have been reviewed recently by Hagel and Facchini [1]. The subgroup of aporphinoid alkaloids [2] consists of the aporphines and oxoaporphines (e.g., liriodenine (1)), as well as several truncated chemotypes like aristolactams and azafluoranthenes

• from 1-benzyltetrahydroisoquinoline intermediates, albeit a hypothesis of Kunitomo postulates a biosynthesis from a benzylisoquinoline precursor involving a rearrangement (Figure 1) [4]. Menisporphine (2), first isolated from Menispermum dauricum DC [4], shows antiangiogenic activity. Some, partly

Zanthoxoaporphines A–C: Three new larvicidal dibenzo[de,g]quinolin-7-one alkaloids from Zanthoxylum paracanthum (Rutaceae)

• Fidelis N. Samita,
• Louis P. Sandjo,
• Isaiah O. Ndiege,
• Ahmed Hassanali and
• Wilber Lwande

Beilstein J. Org. Chem. 2013, 9, 447–452, doi:10.3762/bjoc.9.47

• , namely isoquinolines represented by benzophenanthridines [8], oxoaporphines [9], aporphines [10] and benzylisoquinoline [11]; and quinolines represented by quinolones [12] and furoquinolines [10]. Others include carbazoles [13], pyrido-indoles [12] and quinazolines [14]. Arylethanamides and amines have

Screening of ligands for the Ullmann synthesis of electron-rich diaryl ethers

• Nicola Otto and
• Till Opatz

Beilstein J. Org. Chem. 2012, 8, 1105–1111, doi:10.3762/bjoc.8.122

• with copper iodide as the Cu-source was chosen, as this ligand has been successfully applied by us in a synthesis of two dimeric benzylisoquinoline alkaloids [26]. This model system was optimized with respect to the influence of different bases, molecular sieves, solvents, and temperatures (Table 1