Solvent-Free Synthesis of Pyrimidine Nucleoside-Aminophosphonate Hybrids and Their Biological Activity Evaluation

Abstract

A novel and highly efficient one-pot three-component synthesis of α-aminophosphonates under neat condition was developed. By employing this method, hybrid compounds of aminophosphonate with pyrimidine nucleosides were synthesized in good to excellent yields starting from 5-formyl-2′-deoxyuridine, aniline and dimethyl phosphite. The antiviral and antileishmanial activities of these novel hybrid compounds were also studied but none were found to be active.

Keywords:

• Pyrimidine nucleoside
• α-aminophosphonate
• hybrid
• solvent-free reaction
• biological activities

This work was financially supported by the National Natural Science Foundation of China (Nos. 20772025 and 20972042), Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 2008HASTIT006), Innovation Scientists and Technicians Troop Construction Projects of Henan Province (No. 104100510019), and the Natural Science Foundation of Henan Province (Nos. 092300410192 and 094300510054). The authors sincerely thank Prof. Dr. Paul F Torrence, Department of Chemistry, Northern Arizona University, USA, for his kind help and excellent instructions.

Notes

^a 1a: 1 mmol, 2a: 1 mmol, 3: 1.2 mmol.

^b 10 mL of solvent was used.

^c 1 mL of solvent was used.

^d Isolated yields.

^a 1d: 1 mmol, 2: 1 mmol, 3: 1.2 mmol.

^b Isolated yield.

^a 1b or 1c: 1 mmol, 2: 1 mmol, 3: 1.2 mmol.

^b Isolated yield.