title: Pyrimidine-fused heterocyclic frameworks based on an N4-arylcytosine scaffold: synthesis, characterization, and PNA oligomerization of the fluorescent cytosine analogue 5,6-benzopC.
abstract: A synthesis of an intrinsically fluorescent cytosine analogue 5,6-benzopC has been developed utilizing the reductive Ni-mediated cyclization of an N4-aryl,N4-(Boc)cytosine intermediate as a key step. 5,6-BenzopC was found to possess interesting fluorescence properties (Φ = 0.79, EtOH; Stoke's shift 113 nm). Peptide nucleic acid (PNA) oligomerization of the 5,6-benzopC monomer was carried out, followed by hybridization studies with complementary deoxyribonucleic acid (DNA) and ribonucleic acid (RNA) which showed the modification to be well tolerated in the sequence contexts examined. Initial attempts to synthesize the heterocyclic skeleton present in 5,6-benzopC resulted in the discovery of routes to the pyrimido[1,6-a]benzimidazole, pyrimido[1,6-a]quinazoline, and pyrimido[1,6-a]benzo[b]6-bora-1,3-diazine heterocyclic frameworks.
authors.affiliation: Department of Chemistry, The University of Western Ontario , London, ON N6A 5B7, Canada.
authors.forename: Mojmír
authors.initials: M
authors.lastname: Suchý
authors.forename: Robert H E
authors.initials: RH
authors.lastname: Hudson
mesh_terms: D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D003596:Cytosine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009693:Nucleic Acid Hybridization; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001562:Benzimidazoles; D005456:Fluorescent Dyes; D006571:Heterocyclic Compounds; D009841:Oligonucleotides; D020135:Peptide Nucleic Acids; D011743:Pyrimidines; C000592671:pyrimido(1,6-a)benzimidazole; D003596:Cytosine; C030986:pyrimidine