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1‐Amino‐3‐(1 H ‐1,2,3‐triazol‐1‐yl)propylphosphonates as Acyclic Analogs of Nucleotides
Author(s) -
Głowacka Iwona E.,
Balzarini Jan,
Piotrowska Dorota G.
Publication year - 2014
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201300471
Subject(s) - hela , stereochemistry , chemistry , vesicular stomatitis virus , nucleotide , nucleobase , cell culture , cytotoxic t cell , amino acid , dna , in vitro , biochemistry , biology , gene , genetics
A new series of 1‐amino‐3‐(1 H ‐1,2,3‐triazol‐1‐yl)propylphosphonates ( R )‐ and ( S )‐ 16 were obtained from enantiomerically pure ( R )‐ and ( S )‐1‐ tert ‐butoxycarbonyl (Boc)‐amino‐3‐azidopropylphosphonates and N ‐propargylated nucleobases in good yields. All 1,2,3‐triazolylphosphonates ( R )‐ and ( S )‐ 16 were evaluated for their activities against a broad range of DNA and RNA viruses. Compound ( R )‐ 16g ( B = 3‐acetylindole) was moderately active against vesicular stomatitis virus in HeLa cell cultures (EC 50 = 45 µM). In addition, ( S )‐ 16c ( B = adenine), ( R )‐ 16f ( B = N 3 ‐Bz‐benzuracil), ( R )‐ 16g ( B = 3‐acetylindole), and ( R )‐ 16h ( B = 5,6‐dimethylbenzimidazole) were cytotoxic toward Crandell‐Rees feline kidney (CRFK) cells (CC 50 = 2.9, 45, 72, and 96 µM, respectively). Compounds ( R )‐ 16g , ( S )‐ 16g , and ( S )‐ 16h were slightly cytostatic to different tumor cell lines.