Synthesis of pyrrolo[3,2-d]pyrimidine-2,4(3H)-diones by domino C–N coupling/hydroamination reactions

• Ruben Manuel Figueira de Abreu,
• Robin Tiedemann,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2025, 21, 1010–1017, doi:10.3762/bjoc.21.82

• batzelladine A (D), isolated from a Bahamian sponge, possesses anti-HIV and cancerostatic activities. Antiviral properties have been identified for sangivamycin (E), which was isolated from Streptomyces rimosus (Figure 1) [16][17][18][19][20][21]. Consequently, several pyrrolopyrimidines have been synthesized

• activities. Development of drugs based on pyrrolopyrimidines: A: Cadeguomycin. B: Tubercidin. C: Toyocamycin. D: Batzelladine A. E: Sangivamycin. F: Pemetrexed. G: Immucillin H. H: TAK-285 (tyrosine kinase inhibitor). UV–vis absorption (left) and emission (right, λex = 300 nm) spectra of compounds 4a, 4j, 4k

Synthesis of electrophile-tethered preQ₁ analogs for covalent attachment to preQ₁ RNA

• Laurin Flemmich and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35

• novel compound DPQ1. Keywords: deazapurines; heterocycles; pyrrolopyrimidines; queuosine; riboswitches; ribozymes; RNA alkylation; RNA labelling; Introduction Pre-queuosine 1 (preQ1) is a biosynthetic precursor of the hypermodified nucleoside queuosine (Q) that is found in the wobble position of

A new route for the synthesis of 1-deazaguanine and 1-deazahypoxanthine

• Raphael Bereiter,
• Marco Oberlechner and
• Ronald Micura

Beilstein J. Org. Chem. 2022, 18, 1617–1624, doi:10.3762/bjoc.18.172

• Raphael Bereiter Marco Oberlechner Ronald Micura Institute of Organic Chemistry, Center for Molecular Biosciences, Innsbruck (CMBI), Innrain 80-82, 6020 Innsbruck, Austria 10.3762/bjoc.18.172 Abstract Imidazopyridines and pyrrolopyrimidines are an important class of compounds in medicinal

• nitration. A further strength of our route is divergency, additionally enabling the synthesis of 1-deazahypoxanthine (c1I base). Keywords: deazapurine; heterocycles; imidazopyridines; nucleoside; nucleotides; pyrrolopyrimidines; RNA atomic mutagenesis; Introduction Deazapurines (imidazopyridines and

• pyrrolopyrimidines) are N-heterocycles that have become an indispensable part of research in medicinal chemistry [1][2][3]. Especially, derivatives of 3-deazaguanine (imidazo[4,5-c]pyridines) [4], 7-deazaguanine/-hypoxanthine (pyrrolo[2,3-d]pyrimidines) [5][6], and 9-deazaguanine/-hypoxanthine (pyrrolo[3,2-d

Synthesis of O⁶-alkylated preQ₁ derivatives

• Laurin Flemmich,
• Sarah Moreno and
• Ronald Micura

Beilstein J. Org. Chem. 2021, 17, 2295–2301, doi:10.3762/bjoc.17.147

• scaffold. Keywords: deazapurines; heterocycles; pyrrolopyrimidines; queuosine; RNA cofactors; RNA methylation; Introduction Methylated preQ1 has attracted much attention recently because this compound has been found to function as cofactor for the conserved fold of a non-coding RNA, namely the preQ1