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New Imidazo[1,2‐ c ]pyrimidin‐5(6 H )‐Ones Derived from Cytosine: Synthesis, Structure, and Cytotoxic Activity
Author(s) -
Jansa Josef,
Lyčka Antonín,
Padělková Zdeňka,
Grepl Martin,
Konečný Petr,
Hajdúch Marián,
Džubák Petr
Publication year - 2015
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2243
Subject(s) - chemistry , cytotoxic t cell , stereochemistry , cytosine , aryl , combinatorial chemistry , biological activity , cytotoxicity , cell culture , in vitro , organic chemistry , dna , biochemistry , alkyl , biology , genetics
This work describes the synthesis of 8‐iodoimidazo[1,2‐ c ]pyrimidin‐5(6 H )‐one 2 from 5‐iodocytosine 1 . This compound was subjected to Suzuki cross‐coupling reaction with aryl and heteroarylboronic acids. After optimization, 10 products 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h , 3i , 3j were obtained in good yields 61‐90%. Cytotoxic activity of all new products was evaluated on seven tumor cell lines including resistant variants and on normal human fibroblasts. Two derivatives showed promising biological activity and good therapeutic index in the case of 3h .