Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation

Ornella Mesenzani; Alberto Massarotti; Mariateresa Giustiniano; Tracey Pirali; Valentina Bevilacqua; Antonio Caldarelli; Pierluigi Canonico; Giovanni Sorba; Ettore Novellino; Armando A. Genazzani; Gian Cesare Tron

doi:10.1016/j.bmcl.2010.11.113

Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation

Ornella Mesenzani, Alberto Massarotti, Mariateresa Giustiniano, Tracey Pirali, Valentina Bevilacqua, Antonio Caldarelli, Pierluigi Canonico, Giovanni Sorba, Ettore Novellino, Armando A. Genazzani, Gian Cesare Tron

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

In the chalcone scaffold, it is thought that the double bond is an important structural linker but it is likely not essential for the interaction with tubulin. Yet, it may be a potential site of metabolic degradation and interaction with biological nucleophiles. In this letter, we have replaced this olefinic portion of chalcones with two metabolically stable and chemically inert heterocyclic rings, namely triazole or tetrazole. Yet, our biologic data suggest that, unlike in other antitubulinic structures, the olephinic ring might not be merely a structural linker.

Lingua originale	Inglese
pagine (da-a)	764-768
Numero di pagine	5
Rivista	Bioorganic and Medicinal Chemistry Letters
Volume	21
Numero di pubblicazione	2
DOI	https://doi.org/10.1016/j.bmcl.2010.11.113
Stato di pubblicazione	Pubblicato - 15 gen 2011

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10.1016/j.bmcl.2010.11.113

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Mesenzani, O., Massarotti, A., Giustiniano, M., Pirali, T., Bevilacqua, V., Caldarelli, A., Canonico, P., Sorba, G., Novellino, E., Genazzani, A. A., & Tron, G. C. (2011). Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation. Bioorganic and Medicinal Chemistry Letters, 21(2), 764-768. https://doi.org/10.1016/j.bmcl.2010.11.113

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title = "Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation",

abstract = "In the chalcone scaffold, it is thought that the double bond is an important structural linker but it is likely not essential for the interaction with tubulin. Yet, it may be a potential site of metabolic degradation and interaction with biological nucleophiles. In this letter, we have replaced this olefinic portion of chalcones with two metabolically stable and chemically inert heterocyclic rings, namely triazole or tetrazole. Yet, our biologic data suggest that, unlike in other antitubulinic structures, the olephinic ring might not be merely a structural linker.",

keywords = "Antiproliferative activity, Chalcone, Tetrazole, Triazole, Tubulin",

author = "Ornella Mesenzani and Alberto Massarotti and Mariateresa Giustiniano and Tracey Pirali and Valentina Bevilacqua and Antonio Caldarelli and Pierluigi Canonico and Giovanni Sorba and Ettore Novellino and Genazzani, {Armando A.} and Tron, {Gian Cesare}",

note = "Funding Information: Financial support from Universit{\`a} degli Studi del Piemonte Orientale and M.I.U.R. PRIN 2008 Italy, is gratefully acknowledged.",

year = "2011",

month = jan,

day = "15",

doi = "10.1016/j.bmcl.2010.11.113",

language = "English",

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Mesenzani, O, Massarotti, A, Giustiniano, M, Pirali, T, Bevilacqua, V, Caldarelli, A, Canonico, P, Sorba, G, Novellino, E, Genazzani, AA & Tron, GC 2011, 'Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation', Bioorganic and Medicinal Chemistry Letters, vol. 21, n. 2, pagg. 764-768. https://doi.org/10.1016/j.bmcl.2010.11.113

Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation. / Mesenzani, Ornella; Massarotti, Alberto; Giustiniano, Mariateresa et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 21, N. 2, 15.01.2011, pag. 764-768.

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

TY - JOUR

T1 - Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles

T2 - Synthesis and biological evaluation

AU - Mesenzani, Ornella

AU - Massarotti, Alberto

AU - Giustiniano, Mariateresa

AU - Pirali, Tracey

AU - Bevilacqua, Valentina

AU - Caldarelli, Antonio

AU - Canonico, Pierluigi

AU - Sorba, Giovanni

AU - Novellino, Ettore

AU - Genazzani, Armando A.

AU - Tron, Gian Cesare

N1 - Funding Information: Financial support from Università degli Studi del Piemonte Orientale and M.I.U.R. PRIN 2008 Italy, is gratefully acknowledged.

PY - 2011/1/15

Y1 - 2011/1/15

N2 - In the chalcone scaffold, it is thought that the double bond is an important structural linker but it is likely not essential for the interaction with tubulin. Yet, it may be a potential site of metabolic degradation and interaction with biological nucleophiles. In this letter, we have replaced this olefinic portion of chalcones with two metabolically stable and chemically inert heterocyclic rings, namely triazole or tetrazole. Yet, our biologic data suggest that, unlike in other antitubulinic structures, the olephinic ring might not be merely a structural linker.

AB - In the chalcone scaffold, it is thought that the double bond is an important structural linker but it is likely not essential for the interaction with tubulin. Yet, it may be a potential site of metabolic degradation and interaction with biological nucleophiles. In this letter, we have replaced this olefinic portion of chalcones with two metabolically stable and chemically inert heterocyclic rings, namely triazole or tetrazole. Yet, our biologic data suggest that, unlike in other antitubulinic structures, the olephinic ring might not be merely a structural linker.

KW - Antiproliferative activity

KW - Chalcone

KW - Tetrazole

KW - Triazole

KW - Tubulin

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M3 - Article

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

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Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation

Abstract

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