The Pudovik reaction: the synthesis of bioactive α-aminophosphonates with long alkyl chains

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 194; no. 4-6; pp. 463 - 466
• Main Authors: Galkina, Irina V., Khayarov, Khasan R., Davletshin, Rustam R., Gaynullin, Aynaz Z., Gerasimov, Alexander V., Shulaeva, Marina P., Pozdeev, Oskar K., Egorova, Svetlana N., Usupova, Luiza M., Galkin, Vladimir I.
• Format: Journal Article
• Language: English
• Published: Abingdon Taylor & Francis 27.05.2019; Taylor & Francis Ltd
• Subjects: Amines; antimicrobial activity; Chemical synthesis; long alkyl chains; NMR; Nuclear magnetic resonance; Phosphorus compounds; Stability analysis; Thermal stability; Thermogravimetry; Yeast; α-aminophosphonates
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426507.2018.1539848

In this research we investigated the reactions of substituted naphthaldehyde with amines. The condensation of do-, tetra-, hexa-, octadecan-1-amines with 2-hydroxy-1-naphthaldehyde yielded a series of azomethines in good yields. Subsequent reaction of these compounds with didodecylphosphine oxide yielded α-aminophosphonates. The in vitro microbiological activity of the synthesized phosphorus compounds against gram-positive, gram-negative bacteria and the yeast Candida albicans was determined in comparison to standard agents. The synthesized compounds showed a high antibacterial and antimycotic activity against human and animal pathogenic microflora. Every newly synthesized compound was characterized by elemental analyses, IR, 1 H NMR, 31 P NMR spectral studies. The thermal stability was studied by synchronous thermogravimetry and differential scanning calorimetry (TG/DSC).