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

• abasic site-containing DNA (AP-DNA), different synthetic routes towards the functionalization of coralyne were tested. In particular, the alkylation of the benzylic position in papaverine and subsequent cyclization by treatment with acetic anhydride in sulfuric acid led to the synthesis of a coralyne

• 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

• The synthesis of the coralyne derivatives started with papaverine (3a), as it is a readily available starting material and its transformation to coralyne (2a) is an established and reliable synthetic route [41][42][43]. Moreover, the alkylation of the benzylic position of papaverine (3a) is well

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

• . For example, Liu and colleagues demonstrated the electrochemical oxidation of benzylic C–H bonds to ketones using tert-butyl hydroperoxide as the radical initiator [14]. This method was applied to functionalize bioactive molecules, with celestolide, ibuprofen methyl ester, and papaverine being

Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

• Hans Sterckx,
• Johan De Houwer,
• Carl Mensch,
• Wouter Herrebout,
• Kourosch Abbaspour Tehrani and
• Bert U. W. Maes

Beilstein J. Org. Chem. 2016, 12, 144–153, doi:10.3762/bjoc.12.16

• drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP–MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit. Keywords: base metal; benzylic

• benzylic position of the antispasmodic drug papaverine (14) applying our oxidation protocol (Scheme 3). The resulting compound is known as papaveraldine (15), a byproduct from the extraction of papaverine from Papaver somniferum. Papaverine is a challenging substrate as besides the methylene part it also

• was used to quantify the monodeuterated species. Benzylic oxygenation of benzoannulated azines and diazines (5). Classical (top) and new formal (bottom) synthesis of Mefloquine. Iron-catalyzed aerobic oxidation of papaverine (15). Iron-catalyzed aerobic oxidation of phenyl-substituted 4

Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents

• Paul Knochel,
• Matthias A. Schade,
• Sebastian Bernhardt,
• Georg Manolikakes,
• Albrecht Metzger,
• Fabian M. Piller,
• Christoph J. Rohbogner and
• Marc Mosrin

Beilstein J. Org. Chem. 2011, 7, 1261–1277, doi:10.3762/bjoc.7.147

• readily converted to the desired zinc reagents 31. The Pd-catalyzed cross-coupling of 31 with the iodoquinoline 32 and with S-Phos as ligand [15][16][17] provides the alkaloid papaverine (33) in 68% yield (Scheme 5) [13]. Ni-catalyzed cross-couplings can also be realized [14]. Thus, the reaction of the