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Isomeric Naphtho‐Fused 7‐Deazapurine Nucleosides and Nucleotides: Synthesis, Biological Activity, Photophysical Properties and Enzymatic Incorporation to Nucleic Acids
Author(s) -
Ghosh Ketaki,
Perlíková Pavla,
Havlíček Vojtěch,
Yang Chao,
Pohl Radek,
Tloušťová Eva,
Hodek Jan,
Gurská Soňa,
Džubák Petr,
Hajdúch Marián,
Hocek Michal
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800165
Subject(s) - chemistry , deoxyribonucleoside , oligonucleotide , nucleotide , nucleobase , nucleoside , nucleic acid , oligonucleotide synthesis , dna , stereochemistry , combinatorial chemistry , indole test , biochemistry , gene
Two series of substituted benzo[ g ]‐ or benzo[ e ]pyrimido[4,5‐ b ]indole (naphtho‐fused 7‐deazapurine) ribonucleosides were synthesized. The heterocyclic nucleobases were obtained by Negishi cross‐coupling reaction of zincated pyrimidines with naphthyl iodides, nucleophilic substitution to tetrazoles/azides and thermal cyclization or photocyclization. Nucleosides were obtained by glycosylation followed by substitution reactions and deprotection. Resulting ribonucleosides were tested for their cytotoxic activity against cancer cell lines and antiviral activities. Some derivatives showed micromolar cytotoxic activities and moderate anti ‐hepatitis C virus activities. Naphtho‐fused 7‐deazapurine 2′‐deoxyribonucleoside triphosphate was successfully incorporated into DNA oligonucleotides by KOD XL DNA polymerase. Fluorescence properties of naphtho‐fused 7‐deazapurine nucleosides and oligonucleotides were also studied.