Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

• Josipa Matić,
• Tana Tandarić,
• Marijana Radić Stojković,
• Filip Šupljika,
• Zrinka Karačić,
• Ana Tomašić Paić,
• Lucija Horvat,
• Robert Vianello and
• Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

• 48% for Phen-Py-1 and Phen-Py-2, respectively). The phenanthridine nitrogen was protonated under weakly acidic conditions, which made the phenanthridinium moiety relatively electron deficient compared to the electron-rich pyrene moiety that favored intramolecular stacking. Molecular dynamics

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

• Alessandra Del Tito,
• Havall Othman Abdulla,
• Davide Ravelli,
• Stefano Protti and
• Maurizio Fagnoni

Beilstein J. Org. Chem. 2020, 16, 1476–1488, doi:10.3762/bjoc.16.123

• opportunity on the route towards metal-free protocols for the synthesis of the phenanthrene and phenanthridine cores, a topic of current interest also in related thermal methods [94][95]. Bioactive phenanthridine and phenanthridinium derivatives. Carbon-centered and nitrogen-centered radicals used for the

Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts

• Anthony Choi,
• Rebecca M. Morley and
• Iain Coldham

Beilstein J. Org. Chem. 2019, 15, 1480–1484, doi:10.3762/bjoc.15.149

• tricyclic products 3 (Scheme 1) [41][49]. Similar examples with phenanthridinium and related ylides make use of ketones to stabilise the ylide [50][51][52][53][54]. The only exception (as far as we are aware) to the use of quinolinium ylides with ketones as stabilising groups are isolated reports with a

A journey in bioinspired supramolecular chemistry: from molecular tweezers to small molecules that target myotonic dystrophy

• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 125–138, doi:10.3762/bjoc.12.14

• would prevent such stacking, it would not prevent mono-intercalation; therefore, we sought a spacer that would enforce a C-shape on the intercalator units. Compound 3 was one of two highly rigid tweezers proposed (Figure 3). The R-substituent, –CH2CH2NMe3+, along with the phenanthridinium units (“wide

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• improved synthetic approaches. Keywords: ds-DNA and ds-RNA binding; intercalation; minor groove binding; nucleic acids; organic synthesis; phenanthridine; phenanthridinium; Introduction The search for therapeutic agents of the phenanthridine type has increased when the outstanding trypanocidal activity

• of some phenanthridinium compounds became apparent [1]. One of the most studied and used phenanthridine derivatives is 3,8-diamino-5-ethyl-6-phenylphenanthridinium known as ethidium bromide (EB), for many decades applied as gold-standard DNA- and RNA-fluorescent marker, and its close analogue

• -bromoethylphenanthridinium bromide to give DPP-dicarbonitrile and DPP-indandione, respectively. Particularly an interesting property of these DPP products is the reversible, pH controlled ring-opening-cyclisation process, whereby at acidic conditions DPP undergoes rearomatisation of the phenanthridinium ring system (Scheme

Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization

• Ryan Pearson,
• Shuyu Zhang,
• Gang He,
• Nicola Edwards and
• Gong Chen

Beilstein J. Org. Chem. 2013, 9, 891–899, doi:10.3762/bjoc.9.102

• phenanthridine 17 was obtained as a side product. Compound 17 is presumably generated through the PhI(OAc)2-mediated oxidation of the benzylic C–H bond to form a phenanthridinium intermediate 18, which then undergoes a removal of the PA group. Encouraged by these observations, we proceeded to explore whether the