1‐Amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)propylphosphonates as Acyclic Analogs of Nucleotides
Identifieur interne : 001209 ( Main/Exploration ); précédent : 001208; suivant : 0012101‐Amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)propylphosphonates as Acyclic Analogs of Nucleotides
Auteurs : Iwona E. Głowacka [Pologne] ; Jan Balzarini [Belgique] ; Dorota G. Piotrowska [Pologne]Source :
- Archiv der Pharmazie [ 0365-6233 ] ; 2014-07.
Abstract
A new series of 1‐amino‐3‐(1H‐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 (EC50 = 45 µM). In addition, (S)‐16c (B = adenine), (R)‐16f (B = N3‐Bz‐benzuracil), (R)‐16g (B = 3‐acetylindole), and (R)‐16h (B = 5,6‐dimethylbenzimidazole) were cytotoxic toward Crandell‐Rees feline kidney (CRFK) cells (CC50 = 2.9, 45, 72, and 96 µM, respectively). Compounds (R)‐16g, (S)‐16g, and (S)‐16h were slightly cytostatic to different tumor cell lines.
Among a new series of 1‐amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)‐propylphosphonates, compound (R)‐16g (B = 3‐acetylindole) was found to be active against vesicular stomatitis virus in HeLa cell cultures. In addition, (S)‐16c (B = adenine), (R)‐16f (B = N3‐Bz‐benzuracil), (R)‐16g (B = 3‐acetylindole), and (R)‐16h (B = 5,6‐dimethylbenzimidazole) displayed cytotoxicity toward Crandell‐Rees feline kidney cells and compounds (R)‐16g, (S)‐16g, and (S)‐16h were slightly cytostatic to different tumor cell lines.
Url:
DOI: 10.1002/ardp.201300471
Affiliations:
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<front><div type="abstract">A new series of 1‐amino‐3‐(1H‐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 (EC50 = 45 µM). In addition, (S)‐16c (B = adenine), (R)‐16f (B = N3‐Bz‐benzuracil), (R)‐16g (B = 3‐acetylindole), and (R)‐16h (B = 5,6‐dimethylbenzimidazole) were cytotoxic toward Crandell‐Rees feline kidney (CRFK) cells (CC50 = 2.9, 45, 72, and 96 µM, respectively). Compounds (R)‐16g, (S)‐16g, and (S)‐16h were slightly cytostatic to different tumor cell lines.</div>
<div type="abstract">Among a new series of 1‐amino‐3‐(1H‐1,2,3‐triazol‐1‐yl)‐propylphosphonates, compound (R)‐16g (B = 3‐acetylindole) was found to be active against vesicular stomatitis virus in HeLa cell cultures. In addition, (S)‐16c (B = adenine), (R)‐16f (B = N3‐Bz‐benzuracil), (R)‐16g (B = 3‐acetylindole), and (R)‐16h (B = 5,6‐dimethylbenzimidazole) displayed cytotoxicity toward Crandell‐Rees feline kidney cells and compounds (R)‐16g, (S)‐16g, and (S)‐16h were slightly cytostatic to different tumor cell lines.</div>
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