Synopsis of recent synthetic methods and biological applications of phosphinic acid derivatives

Asymmetric synthesis of organophosphorus compounds using H–P reagents derived from chiral alcohols

“…insecticides, herbicides and fungicides), [10][11][12] and finally pharmaceutically active compounds. [13][14][15][16][17][18] Selected pharmaceutically important applications of chiral organophosphorus molecules include [19][20][21][22][23][24][25][26][27] treatment of HIV and hepatitis B (Tenofovir), 19 treatment of heart failure, 20 antibiotics (Fosfamycin, 21 Valinophos, 22 Fosfazinomycin A 23 ), renin 24 and leucine aminopeptidase 25 inhibitors, antiviral agents, 26 and antibacterial and antifungal agents 27 (Fig. 1).…”

Deamination of 1-Aminoalkylphosphonic Acids: Reaction Intermediates and Selectivity

“…Organophosphorus compounds are a very interesting class of molecules well known to exist in nature, exhibit very intriguing activity, and have already found broad applications in various sectors of industry, such as in agrochemistry [1], pharmacy [2], catalysis [3], materials [4], as flame retardants [5], or chemical reagents [6]. Particular interest is devoted to substituted 1-aminoalkylphosphonic acids that can be considered structural analogs of natural 2-aminoalkanoic acids [7][8][9]. In that regard, the use of 1-aminoalkylphosphonic acids in drug discovery has proven successful in many cases, with prominent examples being potential drugs for the treatment of diabetes [10,11], asthma [12], inflammation [13], heart failure [14], cancer [15], malaria [16], and HIV [17].…”

Unprecedented Convergent Synthesis of Sugar-Functionalization of Phosphinic Acids under Metal-Free Conditions

“…The in vivo administration of phosphinic acid as a drug is subject to some restrictions compared with peptides owing to the P–OH moiety. − They are negatively charged at physiological pH and, due to their polarity, are unable to permeate cell membranes. To solve this problem, esters can be utilized as prodrugs.…”

“…Improved methods for phosphinate synthesis are still attracting a lot of interest since phosphinates show a multitude of distinct characteristics serving as prodrugs and drugs (Figure ). − Given their widespread application as pharmacological agents and important synthetic intermediates, the construction of the P–OR bond remains to be investigated. One of the central problems in phosphinate chemistry is the protecting group manipulation.…”