Facile Synthesis, Antioxidant and Antimicrobial Activity of Amino Methylene Bisphosphonates

Abstract

A green and efficient preparation method for the amino bisphosphonates is accomplished by simple mixing and stirring of diethylphosphite, triethylorthoformate and various amines in the presence of amberlyst-15 as catalyst at room temperature under solvent free conditions. The title compounds are characterized by IR, 1 H-, 13 C-, 31 P-NMR and mass spectra, also studied their antimicrobial and antioxidant activity.

Applications of alkyl orthoesters as valuable substrates in organic transformations, focusing on reaction media

“…All compounds were screened for in vitro antioxidant (by nitric oxide, DPPH radical scavenging, H 2 O 2 methods), [136][137][138][139] and antimicrobial activities. 140…”

Synthesis and Antimicrobial Evaluation of Newly Synthesized N,S‐Bisphosphonate Derivatives

“…The latter may be responsible for several human diseases where calcium phosphate deposition is a hallmark, for example, cardiovascular disease, kidney stones, urological diseases, and various forms of autoimmune diseases . However, even though the emergence of bacteria resistant to antibiotics poses a major health problem, the antimicrobial activity of MBPs has not been attracting enough attention . On the basis of these considerations and in view of our interest in chemistry and biological activity of MBPs and as part of our current studies on the development of new skeletons of antimicrobial activity , we herein report on the synthesis and the microbial activity of a new series of N , S ‐MBP derivatives.…”

Synthesis of carboxyphosphonates and bisphosphonates as potential GGTase II and GGDPS inhibitors

“…Preparation of homonerolA similar sequence was conducted to obtain homogeraniol(112), where the β-keto acetate 108 was prepared using geranyl bromide and the branch point compound 102(Figure 28). With both the desired homonerol(107) and homogeraniol(112) in hand, conversion to the azide click precursor was the next step.…”

“…Formation of hetero linked triazole phosphonateTo form a hetero-linked bisphosphonate the sequence would need to have the heteroatom installed as the bisphosphonate to avoid the Wittig rearrangement. Shown inFigure 52is a variety of attempted reactions to form an ether linkage using diethylphosphite, triethyl orthoformate, propargyl alcohol, Amberlyst resign as an acid catalyst, and varying degrees of heat 107,108. Even after running some of the reactions several times, no ether-linked bisphosphonate was observed.…”

“…The papers used to develop this reaction gave no precedent for incorporation of an ether, but did show that an amine linkage might be possible. Unfortunately, the only amine linkage formed was observed in a test run to determine if the conditions work on a known reaction 107. Use of an aniline reagent may be needed for the reaction to occur along with removal of ethanol.…”