1. Synthesis and reactivity of acyclic and macrocyclic uracils bridged with five-membered heterocycles
- Author
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Alla V. Chernova, Vyacheslav E. Semenov, Evgeniya S. Krylova, Shamil K. Latypov, V. S. Reznik, I. V. Galyametdinova, and Sergey V. Kharlamov
- Subjects
chemistry.chemical_classification ,Stereochemistry ,Organic Chemistry ,Uracil ,Alkylation ,Biochemistry ,Chemical synthesis ,chemistry.chemical_compound ,chemistry ,Drug Discovery ,Structural isomer ,Thiol ,Molecule ,Reactivity (chemistry) ,Cyclophane - Abstract
Replacement of terminal atoms of Br in 1,3-bis(bromopentyl)-5(6)-substituted uracils with 2-mercapto-5-methyl-1,3,4-thiadiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercaptoimidazole, and 2-mercaptobenzimidazoles resulted in a series of acyclic compounds and isomeric heterocyclophanes. Structures of macrocyclic regioisomers were unambiguously determined by NMR data. One of the regioisomers exhibits a hypochromic effect with respect to model compounds. The acyclic uracils obtained bridged with five-membered heterocycles are alkylated with methyliodide and methyl tosylate, and oxidated with m-CPBA, H2O2, and I2.
- Published
- 2011