Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates

Abstract

α-Aminophosphonates are bioisosteres of amino acids and have several pharmacological activities. These compounds have been synthesized by various routes from reaction between amine, aldehyde, and phosphite compounds. In order to synthesize α-aminophosphonates, catalytic effect of CuCl2 was compared with FeCl3. Also all designed structures as well as griseofulvin were docked into the active site of microtubule (1JFF), using Autodock program. The results showed that the reactions were carried out in the presence of CuCl2 in lower yields, and also the time of reaction was longer in comparison with FeCl3. The chemical structures of the new compounds were confirmed by spectral analyses. The compounds were investigated for antifungal activity against several fungi in comparison with griseofulvin. An indole-derived bis(α-aminophosphonates) with the best negative ΔG in docking study showed maximum antifungal activity against Microsporum canis, and other investigated compounds did not have a good antifungal activity.

Review on the Synthesis of α-Aminophosphonate Derivatives

“…Zahara Rezai and cowokers 24 reported one pot three component synthesis of aldehydes, amines and diethyl phosphite using FeCl 3 as catalyst (Scheme 1). Methodology was compared with the synthesis carried by using CuCl 2 , results showed that FeCl 3 is more efficient than CuCl 2 .…”

Synthesis and ecotoxicological impact of ferrocene-derived amino-phosphonates using a battery of bioassays

“…[19][20][21][22][23] Therefore, considering the biological values and possibilities in the chemical modication of a-amino-phosphonates, the growing concern and the development of new organophosphorus compounds are still of great interest. [24][25][26][27][28][29][30] Plant growth testgermination, growth inhibition, dry and fresh matter…”

Synthesis and antimicrobial activity of novel 1,2,3‐triazole‐conjugates of quinazolin‐4‐ones

“…Following these observations several compounds containing C–P bond attracted a considerable interest in medicinal chemistry . Among them substituted alkylphosphonates as well as derivatives with various heterocyclic systems should be mentioned …”

“…[16] Following these observations several compounds containing C-P bond attracted a considerable interest in medicinal chemistry. [17][18][19] Among them substituted alkylphosphonates [20][21][22] as well as derivatives with various heterocyclic systems should be mentioned. [23][24][25][26][27][28][29][30] In continuation of our search for biologically active 1,2,3triazoles, [31][32][33][34][35][36] a new class of (1,2,3-triazol-1-yl)quinazolin-4-ones 9 was proposed.…”