1995
DOI: 10.1021/jm00022a022
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.alpha.-Hydroxy Phosphinyl-Based Inhibitors of Human Renin

Abstract: The design and application of alpha-hydroxy phosphonates, a new class of transition state analogs, toward the discovery of novel and potent inhibitors of the aspartyl protease renin is described. Tripeptidic alpha-hydroxy diethyl phosphonate 3, the first example in this series, was found to be a good inhibitor of human renin (IC50 = 29 nM), and preliminary studies led to the choice of alpha-hydroxy dimethyl phosphonate 15 (IC50 = 16 nM) as a base-line compound for further structure-activity relationship study.… Show more

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Cited by 182 publications
(66 citation statements)
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“…They can be used as antihypertensive [34] and antiviral agents [35], antibiotics [36] and pesticides [37]. Series of the compounds featuring aryl or heteroaryl 1-hydroxyphosphonate derivatives were investigated as inhibitors of CD45 [38].…”
Section: калікс[4]арен α-гідроксифосфонові кислоти як потенційні інгіmentioning
confidence: 99%
“…They can be used as antihypertensive [34] and antiviral agents [35], antibiotics [36] and pesticides [37]. Series of the compounds featuring aryl or heteroaryl 1-hydroxyphosphonate derivatives were investigated as inhibitors of CD45 [38].…”
Section: калікс[4]арен α-гідроксифосфонові кислоти як потенційні інгіmentioning
confidence: 99%
“…In view of significant biological importance associated with -hydroxy phophonates, this synthon has attracted enhanced research interest. These are extensively used in pharmaceutical applications such as enzyme inhibitors of renin, HIV protease and EPSP synthase (Patel et al, 1995). They also exhibited potential biological activities, such as antibacterial, antiviral, anti-inflammatory, laxative, growth hormonal, and anticancer activities (Stowasser et al, 1992).…”
Section: Oxindolesmentioning
confidence: 99%
“…For absolute stereochemical assignment, diastereoisomers 16 and 17 were converted to the corresponding oxazolidinones. Based on proton nuclear magnetic resonance ( 1 H NMR) and 13 C NMR data and NOE experiments in oxazolidinones, diastereoisomer 16 was designated as having the (S)-anti stereochemistry.…”
Section: Hydrophosphinylation Of A-amino Aldehydesmentioning
confidence: 99%
“…In the same way, hydrophosphinylation of N-protected a-aminoaldehyde 15 was achieved using phosphine oxides and alkyl alkylphosphinates. 13 When the bromomagnesium phosphine oxide generated in situ by treatment of diethyl phosphite with 3 eq. of ethylmagnesium bromide was trapped directly with aldehyde 15, b-amino-a-hydroxy phosphine oxide 21 was obtained in high yield (87%) as a 1 : 1 3).…”
Section: Hydrophosphinylation Of A-amino Aldehydesmentioning
confidence: 99%
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