Synthesis of conformationally constrained analogues of (R)-2-amino-7-phosphonoheptanoic acid

Lithiated alkylidenebis(phosphonates): Reactive phosphorus intermediates in the synthesis of 3‐amino‐1‐alkenylphosphonates

“…However, this strategy has not been investigated extensively and only a few reports are available in the literature describing the design of novel enzymatic inhibitors [2a-2d, [8][9][10][11]13,14].…”

“…All compounds 1 were fully characterized on the basis of their 1 H, 13 C, and 31 P NMR, IR, and MS spectra. Characteristic signals in the 1 H NMR spectrum of 1a-1d are the signals corresponding to the CH alkene with a typical downfield shift for an E configuration (δ = 6.76-6.34 ppm).…”

“…It has been shown that 3-aminophosphonic derivatives were interesting as peptidomimetics of D-Ala-D-Ala [9], D-alanyl phosphate [10], 3-amino-2-mercapto-carboxylic acids [11], (S)-glutamic [12], and pyroglutamic acids [13]. Several 3-aminoalkenylphosphic acids and their analogues have been described as inhibitors of D-Ala-D-Ala-ligase [9,10], metallopeptidase [11], NMDA (N-methyl-D-aspartic acid)-receptor ligands [13], and human rhinovirus 3C protease [14].…”

Synthesis of Hexahydropyridazine-3-phosphonic Acid

“…Finally, N-Boc derivative 9a was hydrolyzed in boiling 6 N HCl and then treated with propylene oxide 12) in methanol to obtain the salt-free product to give piperidazine-3-phosphonic acid 3 in 62% yield (Chart 2), the structure of which was supported by the analytical and spectral data.…”

Reactions of diethyl 3-methylbuta-1,2-dienylphosphonate with 2-aminobenzothiazole

“…2,5, 6 However, only a few studies have been devoted to the synthesis of phosphonates functionalized in the β position with nitro gen containing heterocyclic fragments. 2,7, 8 We investigated a reaction of diethyl 3 methylbuta 1,2 dienylphosphonate 1 with 2 aminobenzothiazole 2. For this reaction, two pathways are possible: the central C atom of the allene system could be attacked by the ring N atom (adduct 3) or the N atom of the exocyclic amino group (adduct 4, Scheme 1).…”