The novel phosphoramidate derivatives of NSAID 3-hydroxypropylamides: synthesis, cytostatic and antiviral activity evaluations.

Abstract

The target phosphoramidates 5a-e were prepared in one step from 3-hydroxypropyl derivatives 3a-e of nonsteroidal anti-inflammatory drugs (fenoprofen, ketoprofen, ibuprofen, indomethacin, diclofenac). The products 3a-e and 5a-e were evaluated for their cytostatic and antiviral activity against malignant tumour cell lines and normal human fibroblasts (WI 38). All phosphoramidate derivatives 5a-e possess significantly greater inhibitory activities than the corresponding 3-hydroxypropyl derivatives 3a-e, whereby compound 5a showed the most potent inhibitory activities against cervical, pancreatic and colon carcinoma cell lines (IC(50)=5-7 microM).

• Authors: K Wittine, K Benci, Z Rajić, B Zorc, M Kralj, M Marjanović, K Pavelić, E De Clercq, G Andrei, R Snoeck, J Balzarini, M Mintas
• Journal: European journal of medicinal chemistry (Eur J Med Chem) Vol. 44 Issue 1 Pg. 143-51 (Jan 2009) ISSN: 1768-3254 [Electronic] France
• PMID: 18485540 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Amides
• Anti-Inflammatory Agents, Non-Steroidal
• Antineoplastic Agents
• Antiviral Agents
• Cytostatic Agents
• Phosphoric Acids
• phosphoramidic acid

Topics

• Amides (chemical synthesis, pharmacology)
• Anti-Inflammatory Agents, Non-Steroidal (chemical synthesis, pharmacology)
• Antineoplastic Agents (chemical synthesis, pharmacology)
• Antiviral Agents
• Cell Line
• Cell Line, Tumor
• Cytostatic Agents (chemical synthesis)
• Fibroblasts
• Humans
• Inhibitory Concentration 50
• Phosphoric Acids (chemical synthesis, pharmacology)
• Structure-Activity Relationship