1‐Amino‐3‐(1H‐1, 2, 3‐triazol‐1‐yl)propylphosphonates as Acyclic Analogs of Nucleotides. Issue 7 (6th April 2014)

• Record Type: Journal Article
• Authors: Głowacka, Iwona E.; Balzarini, Jan; Piotrowska, Dorota G.
• Is Part Of: Archiv der Pharmazie. Volume 347:Issue 7(2014:Jul.)
• Page Start: 496
• Page End: 505
• Publication Date: 2014-04-06
• Subjects: Pharmaceutical chemistry -- Periodicals; Pharmacology -- Periodicals; 615.19
• DOI: 10.1002/ardp.201300471
• Languages: English
• ISSNs: 0365-6233

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <sec id="ardp201300471-sec-0001" sec-type="section"> <p>A new series of 1‐amino‐3‐(1<italic>H</italic>‐1, 2, 3‐triazol‐1‐yl)propylphosphonates (<italic>R</italic>)‐ and (<italic>S</italic>)‐<bold>16</bold> were obtained from enantiomerically pure (<italic>R</italic>)‐ and (<italic>S</italic>)‐1‐<italic>tert</italic>‐butoxycarbonyl (Boc)‐amino‐3‐azidopropylphosphonates and <italic>N</italic>‐propargylated nucleobases in good yields. All 1, 2, 3‐triazolylphosphonates (<italic>R</italic>)‐ and (<italic>S</italic>)‐<bold>16</bold> were evaluated for their activities against a broad range of DNA and RNA viruses. Compound (<italic>R</italic>)‐<bold>16g</bold> (<bold>B</bold> = 3‐acetylindole) was moderately active against vesicular stomatitis virus in HeLa cell cultures (EC<sub>50</sub> = 45 µM). In addition, (<italic>S</italic>)‐<bold>16c</bold> (<bold>B</bold> = adenine), (<italic>R</italic>)‐<bold>16f</bold> (<bold>B</bold> = <italic>N</italic><sup>3</sup>‐Bz‐benzuracil), (<italic>R</italic>)‐<bold>16g</bold> (<bold>B</bold> = 3‐acetylindole), and (<italic>R</italic>)‐<bold>16h</bold> (<bold>B</bold> = 5, 6‐dimethylbenzimidazole) were cytotoxic toward Crandell‐Rees feline kidney (CRFK) cells (CC<sub>50</sub> = 2.9, 45, 72, and 96 µM, respectively). Compounds (<italic>R</italic>)‐<bold>16g</bold>, (<italic>S</italic>)‐<bold>16g</bold>, and (<italic>S</italic>)‐<bold>16h</bold> were slightly cytostatic to different tumor cell lines.</p> </sec> </abstract>