Green synthesis, antibacterial, antiviral and molecular docking studies of α-aminophosphonates

Recent Advances in the Synthesis of α‐Aminophosphonates: A Review

“…A new simple route for the preparation of α ‐Aminophosphonates was developed using 2‐(1‐amino‐2‐(2,5‐dibromophenyl)ethyl)‐5‐bromophenol with different substituted aldehydes and dimethyl phosphite under catalyst‐ and solvent‐free conditions at room temperature using a ultrasonication method within 10–20 min [73] . (Scheme 22).…”

A One-Pot Approach to 2-Substituted-2-(Dimethoxyphosphoryl)-Pyrrolidines from Substituted tert-Butyl 4-Oxobutylcarbamates and Trimethyl Phosphite

“…6 Hz),79.2,77.0 (d,J = 8.9 Hz),61.2 (d,J = 168.8 Hz),53.1 (d,J = 7.2 Hz),52.8 (d,J = 7.4 Hz),44.5,29.8,27.7,25.3,17.4,31 2920,1594,1381,1252,1124,1032,837, 756 cm −1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.45 2H),3H),4.62 (ddd,J = 16.8,7.2,6.4 Hz,1H),6H),2H),1H), 2.14−2.03 (m, 1H), 1.49 (s, 9H), 0.93 (m, 9H), 0.17 (s, 3H), 0.14 (s, 3H) ppm; 13 C{ 1 H} NMR (100 MHz, DMSO-d 6 , Temp = 75 °C) δ 152. 3,130.7 (d,J = 2.2 Hz),128.3,122.1 (d,J = 2.6 Hz),86.4 (d,J = 2.1 Hz),85.7 (d,J = 9.0 Hz),81.9 (d,J = 4.3 Hz),79.1,61.6 (d,J = 167.4 Hz),53.2 (d,J = 7.3 Hz), 53.0 (d, J = 7.5 Hz), 44.4, 29.7, 27.7, 25.3, 17.4, −5.1, −5.3 7,138.5,131.5,129.1,119.7,…”

“…α-Aminophosphonic acids and their derivatives, classic isosteres of α-amino acids, have attracted great interest in organic and medicinal chemistry during the past few decades . Such functional analogues of natural and unnatural α-amino acids have been widely used in agrochemicals and medicines, such as antibacterial agents, antifungal agents, , antiviral agents, antibiotics, enzyme inhibitors, , and antitumor agents . In addition to the usual application as important synthetic intermediates in organic synthesis, they could also serve as probes in biology.…”

“…Colorless oil (95 mg, 65%). IR (film) ν max2969, 1698, 1387, 1244, 1156, 1111, 1031, 815 cm −1 ; 1 H NMR (400 MHz, CDCl 3 , rotamers) δ 3.86−3.70 (m, 6H), 3.61−3.41 (m, 2H), 2.59−2.45 (m, 1H), 2.02− 1.91 (m, 1H), 1.87−1.71 (m, 2H), 1.63−1.57 (d, J = 3.7 Hz, 3H), 1.47 (s, 9H) ppm; 13 C{ 1 H} NMR (100 MHz, DMSO-d 6 , Temp = 75 °C) δ 152 7,. 78.5, 60.6 (d, J = 156.4 Hz), 52.3 (d, J = 7.0 Hz), 52.1 (d, J = 7.5 Hz), 48.3, 38.1, 27.8, 21.7 (d, J = 7.1 Hz) (20.9) ppm; 31 P NMR (162 MHz, CDCl 3 , rotamers) δ 31.0 (30.1) ppm; HRMS (ESI-Orbitrap) m/z [M + Na] + calcd for C 12 H 24 NO 5 PNa + 316.1284, found 316.1279.tert-Butyl 2-butyl-2-(dimethoxyphosphoryl)pyrrolidine-1-carboxylate (7g).…”

In(OTf)3-catalyzed N-α phosphonylation of N,O-acetals with triethyl phosphite

“…4 As a prime instance, α-aminophosphonic acids and their derivatives have been widely used in medicines 5 and agrochemicals, 6 for example, as antifungal agents, 7 antiviral agents, 6 b ,8 antibacterial agents, 9 antitumor agents, 10 enzyme inhibitors 11 and antibiotics. 12…”