Synthesis of functionalized, 13-alkyl-substituted coralyne derivatives and investigation of their interactions with duplex and abasic site-containing DNA

• Laurin Beckmann,
• Jason Lennard Kunze,
• Hannah Karola Strunk,
• Maurice Michel and
• Heiko Ihmels

Beilstein J. Org. Chem. 2026, 22, 1057–1066, doi:10.3762/bjoc.22.84

• released from a Boc-protected precursor and that the corresponding coralyne–alkoxyamine conjugate can operate as a ligand for AP-DNA and as inhibitor of enzymatic repair of abasic sites. Keywords: APE1 inhibition; DNA binders; N-hetarenes; papaverine; protoberberines; Introduction DNA is a main target in

• novel DNA-binding N-hetarenes still constitutes a cornerstone in current drug development and in the search for promising drug candidates. Along these lines, the protoberberines, such as, e.g., berberine (1a), palmatine (1b), or jatrorrhizine (1c) (Figure 1), may be considered as privileged structures

• because they provide a favorable combination of versatile and strong association with nucleic acids with pronounced DNA-targeted biological activity [10][16][17]. Particularly noteworthy within the series of known protoberberines is coralyne (2a). This synthetic dibenzo[a,g]quinolizinium derivative is

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

• derivatives, compound B8 represents the natural compound pseudopalmatine [39]. The synthesis of this compound has been reported, albeit through alternative methods [33][38][40]. Reports indicated that unlike most other plant-derived protoberberines, pseudopalmatine has had far less pharmacological

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

• about 2,500 known structures. Among these are “simple” benzylisoquinolines and, even more important, their 1,2,3,4-tetrahydro analogues and bisbenzylisoquinolines derived thereof, as well as more complex tetra- and pentacylic ring systems (aporphines, protoberberines, cularines, morphinane-type

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

• benzylisoquinolines, more complex tetracyclic ring systems like aporphines, protoberberines, cularines, pavines, as well as pentacyclic morphinane-type alkaloids belong to this class. Biosynthetically, all of these chemotypes are derived from the 1-benzyltetrahydroisoquinoline (S)-norcoclaurine. The structures