Synthesis and biological evaluation of isosteric analogues of FK866, an inhibitor of NAD salvage

Ubaldina GALLI; EMANUELA ERCOLANO; Lorenzo Roberto CARRARO; Blasi Roman CR; Giovanni SORBA; Pier Luigi CANONICO; Armando GENAZZANI; Gian Cesare TRON; Richard Andrew BILLINGTON

doi:10.1002/cmdc.200700311

Synthesis and biological evaluation of isosteric analogues of FK866, an inhibitor of NAD salvage

Ubaldina GALLI, EMANUELA ERCOLANO, Lorenzo Roberto CARRARO, Blasi Roman CR, Giovanni SORBA, Pier Luigi CANONICO, Armando GENAZZANI, Gian Cesare TRON, Richard Andrew BILLINGTON

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista

Abstract

One of the great challenges of medicinal chemistry is to create novel, effective, chemotherapeutic agents that show specificity for cancer cells combined with low systemic toxicity. A novel idea is to target the enzymes of the NAD biosynthesis and recycling pathways given that cancer cells display a higher NAD turnover rate than healthy cells. To this end, the compound FK866 (APO866; (E)-N-[4-(1-benzoylpiperidin-4-yl) butyl]-3-(pyridin-3-yl) acrylamide), which blocks nicotinamide phosphoribosyltransferase (NMPRTase) has entered clinical trials as a potential chemotherapeutic agent. Here we report the synthesis of analogues of FK866 synthesized by click chemistry.

Lingua originale	Inglese
pagine (da-a)	771-779
Numero di pagine	9
Rivista	ChemMedChem
Volume	3
Numero di pubblicazione	5
DOI	https://doi.org/10.1002/cmdc.200700311
Stato di pubblicazione	Pubblicato - 2008

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title = "Synthesis and biological evaluation of isosteric analogues of FK866, an inhibitor of NAD salvage",

abstract = "One of the great challenges of medicinal chemistry is to create novel, effective, chemotherapeutic agents that show specificity for cancer cells combined with low systemic toxicity. A novel idea is to target the enzymes of the NAD biosynthesis and recycling pathways given that cancer cells display a higher NAD turnover rate than healthy cells. To this end, the compound FK866 (APO866; (E)-N-[4-(1-benzoylpiperidin-4-yl) butyl]-3-(pyridin-3-yl) acrylamide), which blocks nicotinamide phosphoribosyltransferase (NMPRTase) has entered clinical trials as a potential chemotherapeutic agent. Here we report the synthesis of analogues of FK866 synthesized by click chemistry.",

author = "Ubaldina GALLI and EMANUELA ERCOLANO and CARRARO, \{Lorenzo Roberto\} and CR, \{Blasi Roman\} and Giovanni SORBA and CANONICO, \{Pier Luigi\} and Armando GENAZZANI and TRON, \{Gian Cesare\} and BILLINGTON, \{Richard Andrew\}",

year = "2008",

doi = "10.1002/cmdc.200700311",

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AU - GALLI, Ubaldina

AU - ERCOLANO, EMANUELA

AU - CARRARO, Lorenzo Roberto

AU - CR, Blasi Roman

AU - SORBA, Giovanni

AU - CANONICO, Pier Luigi

AU - GENAZZANI, Armando

AU - TRON, Gian Cesare

AU - BILLINGTON, Richard Andrew

PY - 2008

Y1 - 2008

N2 - One of the great challenges of medicinal chemistry is to create novel, effective, chemotherapeutic agents that show specificity for cancer cells combined with low systemic toxicity. A novel idea is to target the enzymes of the NAD biosynthesis and recycling pathways given that cancer cells display a higher NAD turnover rate than healthy cells. To this end, the compound FK866 (APO866; (E)-N-[4-(1-benzoylpiperidin-4-yl) butyl]-3-(pyridin-3-yl) acrylamide), which blocks nicotinamide phosphoribosyltransferase (NMPRTase) has entered clinical trials as a potential chemotherapeutic agent. Here we report the synthesis of analogues of FK866 synthesized by click chemistry.

AB - One of the great challenges of medicinal chemistry is to create novel, effective, chemotherapeutic agents that show specificity for cancer cells combined with low systemic toxicity. A novel idea is to target the enzymes of the NAD biosynthesis and recycling pathways given that cancer cells display a higher NAD turnover rate than healthy cells. To this end, the compound FK866 (APO866; (E)-N-[4-(1-benzoylpiperidin-4-yl) butyl]-3-(pyridin-3-yl) acrylamide), which blocks nicotinamide phosphoribosyltransferase (NMPRTase) has entered clinical trials as a potential chemotherapeutic agent. Here we report the synthesis of analogues of FK866 synthesized by click chemistry.

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DO - 10.1002/cmdc.200700311

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JO - ChemMedChem

JF - ChemMedChem

IS - 5

ER -

Synthesis and biological evaluation of isosteric analogues of FK866, an inhibitor of NAD salvage

Abstract

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