Cell division cycle 7 kinase inhibitors: 1H-pyrrolo[2,3-b]pyridines, synthesis and structure-activity relationships

Antonella Ermoli; Alberto Bargiotti; Maria Gabriella Brasca; Antonella Ciavolella; Nicoletta Colombo; Gabriele Fachin; Antonella Isacchi; Maria Menichincheri; Antonio Molinari; Alessia Montagnoli; Antonio Pillan; Sonia Rainoldi; Federico Riccardi Sirtori; Francesco Sola; Sandrine Thieffine; Marcellino Tibolla; Barbara Valsasina; Daniele Volpi; Corrado Santocanale; Ermes Vanotti

doi:10.1021/jm900248g

Cell division cycle 7 kinase inhibitors: 1H-pyrrolo[2,3-b]pyridines, synthesis and structure-activity relationships

Antonella Ermoli, Alberto Bargiotti, Maria Gabriella Brasca, Antonella Ciavolella, Nicoletta Colombo, Gabriele Fachin, Antonella Isacchi, Maria Menichincheri, Antonio Molinari, Alessia Montagnoli, Antonio Pillan, Sonia Rainoldi, Federico Riccardi Sirtori, Francesco Sola, Sandrine Thieffine, Marcellino Tibolla, Barbara Valsasina, Daniele Volpi, Corrado Santocanale, Ermes Vanotti

Molecular Biosciences

Oncology

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

55 Citations (Scopus)

Abstract

Cdc7 kinase has recently emerged as an attractive target for cancer therapy and low-molecular-weight inhibitors of Cdc7 kinase have been found to be effective in the inhibition of tumor growth in animal models. In this paper, we describe synthesis and structure-activity relationships of new 1H-pyrrolo[2, 3-b]pyridine derivatives identified as inhibitors of Cdc7 kinase. Progress from (Z)-2-phenyl-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-3,5-dihydro-4H-imidazol- 4-one (1) to [(Z)-2-(benzylamino)-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-1, 3-thiazol-4(5H)-one] (42), a potent ATP mimetic inhibitor of Cdc7 kinase with IC₅₀ value of 7 nM, is also reported.

Original language	English
Pages (from-to)	4380-4390
Number of pages	11
Journal	Journal of Medicinal Chemistry
Volume	52
Issue number	14
DOIs	https://doi.org/10.1021/jm900248g
Publication status	Published - 23 Jul 2009

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Ermoli, A., Bargiotti, A., Brasca, M. G., Ciavolella, A., Colombo, N., Fachin, G., Isacchi, A., Menichincheri, M., Molinari, A., Montagnoli, A., Pillan, A., Rainoldi, S., Sirtori, F. R., Sola, F., Thieffine, S., Tibolla, M., Valsasina, B., Volpi, D., Santocanale, C., & Vanotti, E. (2009). Cell division cycle 7 kinase inhibitors: 1H-pyrrolo[2,3-b]pyridines, synthesis and structure-activity relationships. Journal of Medicinal Chemistry, 52(14), 4380-4390. https://doi.org/10.1021/jm900248g

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title = "Cell division cycle 7 kinase inhibitors: 1H-pyrrolo[2,3-b]pyridines, synthesis and structure-activity relationships",

abstract = "Cdc7 kinase has recently emerged as an attractive target for cancer therapy and low-molecular-weight inhibitors of Cdc7 kinase have been found to be effective in the inhibition of tumor growth in animal models. In this paper, we describe synthesis and structure-activity relationships of new 1H-pyrrolo[2, 3-b]pyridine derivatives identified as inhibitors of Cdc7 kinase. Progress from (Z)-2-phenyl-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-3,5-dihydro-4H-imidazol- 4-one (1) to [(Z)-2-(benzylamino)-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-1, 3-thiazol-4(5H)-one] (42), a potent ATP mimetic inhibitor of Cdc7 kinase with IC50 value of 7 nM, is also reported.",

author = "Antonella Ermoli and Alberto Bargiotti and Brasca, \{Maria Gabriella\} and Antonella Ciavolella and Nicoletta Colombo and Gabriele Fachin and Antonella Isacchi and Maria Menichincheri and Antonio Molinari and Alessia Montagnoli and Antonio Pillan and Sonia Rainoldi and Sirtori, \{Federico Riccardi\} and Francesco Sola and Sandrine Thieffine and Marcellino Tibolla and Barbara Valsasina and Daniele Volpi and Corrado Santocanale and Ermes Vanotti",

year = "2009",

month = jul,

day = "23",

doi = "10.1021/jm900248g",

language = "English",

volume = "52",

pages = "4380--4390",

journal = "Journal of Medicinal Chemistry",

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Ermoli, A, Bargiotti, A, Brasca, MG, Ciavolella, A, Colombo, N, Fachin, G, Isacchi, A, Menichincheri, M, Molinari, A, Montagnoli, A, Pillan, A, Rainoldi, S, Sirtori, FR, Sola, F, Thieffine, S, Tibolla, M, Valsasina, B, Volpi, D, Santocanale, C & Vanotti, E 2009, 'Cell division cycle 7 kinase inhibitors: 1H-pyrrolo[2,3-b]pyridines, synthesis and structure-activity relationships', Journal of Medicinal Chemistry, vol. 52, no. 14, pp. 4380-4390. https://doi.org/10.1021/jm900248g

TY - JOUR

T1 - Cell division cycle 7 kinase inhibitors

T2 - 1H-pyrrolo[2,3-b]pyridines, synthesis and structure-activity relationships

AU - Ermoli, Antonella

AU - Bargiotti, Alberto

AU - Brasca, Maria Gabriella

AU - Ciavolella, Antonella

AU - Colombo, Nicoletta

AU - Fachin, Gabriele

AU - Isacchi, Antonella

AU - Menichincheri, Maria

AU - Molinari, Antonio

AU - Montagnoli, Alessia

AU - Pillan, Antonio

AU - Rainoldi, Sonia

AU - Sirtori, Federico Riccardi

AU - Sola, Francesco

AU - Thieffine, Sandrine

AU - Tibolla, Marcellino

AU - Valsasina, Barbara

AU - Volpi, Daniele

AU - Santocanale, Corrado

AU - Vanotti, Ermes

PY - 2009/7/23

Y1 - 2009/7/23

N2 - Cdc7 kinase has recently emerged as an attractive target for cancer therapy and low-molecular-weight inhibitors of Cdc7 kinase have been found to be effective in the inhibition of tumor growth in animal models. In this paper, we describe synthesis and structure-activity relationships of new 1H-pyrrolo[2, 3-b]pyridine derivatives identified as inhibitors of Cdc7 kinase. Progress from (Z)-2-phenyl-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-3,5-dihydro-4H-imidazol- 4-one (1) to [(Z)-2-(benzylamino)-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-1, 3-thiazol-4(5H)-one] (42), a potent ATP mimetic inhibitor of Cdc7 kinase with IC50 value of 7 nM, is also reported.

AB - Cdc7 kinase has recently emerged as an attractive target for cancer therapy and low-molecular-weight inhibitors of Cdc7 kinase have been found to be effective in the inhibition of tumor growth in animal models. In this paper, we describe synthesis and structure-activity relationships of new 1H-pyrrolo[2, 3-b]pyridine derivatives identified as inhibitors of Cdc7 kinase. Progress from (Z)-2-phenyl-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-3,5-dihydro-4H-imidazol- 4-one (1) to [(Z)-2-(benzylamino)-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-1, 3-thiazol-4(5H)-one] (42), a potent ATP mimetic inhibitor of Cdc7 kinase with IC50 value of 7 nM, is also reported.

UR - https://www.scopus.com/pages/publications/67650754045

U2 - 10.1021/jm900248g

DO - 10.1021/jm900248g

M3 - Article

SN - 0022-2623

VL - 52

SP - 4380

EP - 4390

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 14

ER -

Cell division cycle 7 kinase inhibitors: 1H-pyrrolo[2,3-b]pyridines, synthesis and structure-activity relationships

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