“…Organophosphorus compounds are important substrates in the study of biochemical processes and tetracoordinated pentavalent phosphorus compounds are widely used as biologically active compounds and their utility as synthetic intermediates and they have found in a wide range of applications in the areas of industry, agriculture and medicinal chemistry [1][2][3][4][5]. Literature survey reveals that the analogues with C-P bond show broad spectrum of biological activity such as antifungal and insecticidal activity [6][7].…”
Section: Introductionmentioning
confidence: 99%
“…Recently, new vinyl phosphates have been reported to have potent mechanism based inhibitors of phosphatase [9][10][11] or phosphodiesterase [12][13]. For a long time the so-called 'phosphorus analogues' of the amino acids, in which the carboxylic acid group is replaced by a phosphonic, or phosphinic acid group, P(O)(OH)R (in which R may be H, alkyl, or aryl), as well as a phosphonate group, P(O)(OR) 2 (in which R may be alkyl, or aryl), have attracted particular interest in the preparation of isosteric or bioisosteric analogues of numerous natural products [14,15]. Therefore α-aminophosphonates have attracted considerable attention since they are considered as structural analogues of α-amino acids and they act as enzyme inhibitory neuroactive agents, HIV protease antagonists, collagenase inhibitors, peptide mimics [16], antibiotics, herbicides [17], pharmacological agents [18] and exhibited pesticidal [19] and antiviral [20] activity.…”
“…Organophosphorus compounds are important substrates in the study of biochemical processes and tetracoordinated pentavalent phosphorus compounds are widely used as biologically active compounds and their utility as synthetic intermediates and they have found in a wide range of applications in the areas of industry, agriculture and medicinal chemistry [1][2][3][4][5]. Literature survey reveals that the analogues with C-P bond show broad spectrum of biological activity such as antifungal and insecticidal activity [6][7].…”
Section: Introductionmentioning
confidence: 99%
“…Recently, new vinyl phosphates have been reported to have potent mechanism based inhibitors of phosphatase [9][10][11] or phosphodiesterase [12][13]. For a long time the so-called 'phosphorus analogues' of the amino acids, in which the carboxylic acid group is replaced by a phosphonic, or phosphinic acid group, P(O)(OH)R (in which R may be H, alkyl, or aryl), as well as a phosphonate group, P(O)(OR) 2 (in which R may be alkyl, or aryl), have attracted particular interest in the preparation of isosteric or bioisosteric analogues of numerous natural products [14,15]. Therefore α-aminophosphonates have attracted considerable attention since they are considered as structural analogues of α-amino acids and they act as enzyme inhibitory neuroactive agents, HIV protease antagonists, collagenase inhibitors, peptide mimics [16], antibiotics, herbicides [17], pharmacological agents [18] and exhibited pesticidal [19] and antiviral [20] activity.…”
“…Among these the posphonate moiety is an important pharmacophore in the pharmaceutical chemistry [1][2][3][4][5][6] and can be used as a building block for antibiotics [7][8][9][10], herbicides [11,12], insecticides [13], fungicides [14] and anti-viral agents [15]. Additionally, the phosphonic acids and their derivatives may be considered as long life analogues of transition states for tetrahedral intermediates in amide/ester hydrolysis [16]. Among others, these compounds also possess enzyme inhibition properties and consequently they can serve as antibacterial and anticancer drugs [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31].…”
The cis-and trans-2-methyl-2-oxo-2-trityl-1,3,2-dioxaphosphorinanes were obtained in the Arbuzov reaction of 2-methoxy-4-methyl-1,3,2-dioxaphosphorinane with trityl chloride. The NMR spectra ( 1 H, 13 C and 31 P) in solution indicated that trans isomer exists in the form of two noncongruent molecules and it adopts two different conformations: a halfchair and a sofa, while the cis isomer exists as the mixed half/chair-sofa conformer. The compounds crystallise as a pure chiral forms and as a racemates. The solid state structural studies show that NMR data are consistent with the single crystal X-ray analysis, but the conformation existing in the crystal structure is more complex than it can be supposed on sole NMR determination. Crystal data: cis-isomer chiral form: space group P3 2 , a = 8.
“…[1][2][3][4][5] In recent years, a significant attention has been focused on the synthesis and biological evaluation of α-aminophosphonic acids and their phosphonate derivatives. Since α-aminophosphonate derivatives are structural mimics of α-amino acids, some of these compounds exhibit very high potency in inhibiting the enzymes that are involved in the metabolism of the corresponding amino acids.…”
A novel series of carbazole-based α-aminophosphonates were synthesized by three component coupling of 6-bromo-9-ethyl-9H-carbazole-3-carbaldehyde, amine and diethyl phosphite using polyethylene glycol (PEG-400) as a green reaction media. The antiproliferative activity of these molecules was evaluated against three cancer cell lines. Of these, compounds 4c, 4e and 4m were found to exhibit good antiproliferative activity against three cancer cells, A549, MCF-7, and NCI-N87.
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