Design, synthesis and biological activity of acyl substituted 3-amino-5-methyl-1,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones as potential hypnotic drugs

José L. Falcó; Maia Lloveras; Irma Buira; Jordi Teixidó; José I. Borrell; Eva Méndez; José Terencio; Albert Palomer; Antonio Guglietta

doi:10.1016/j.ejmech.2005.06.008

Design, synthesis and biological activity of acyl substituted 3-amino-5-methyl-1,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones as potential hypnotic drugs

José L. Falcó, Maia Lloveras, Irma Buira, Jordi Teixidó, José I. Borrell, Eva Méndez, José Terencio, Albert Palomer, Antonio Guglietta

IQS School of Engineering

Research output: Indexed journal article › Article › peer-review

38 Citations (Scopus)

Abstract

Among the known non-benzodiazepinic hypnotic drugs acting on the α1 subunit of the GABA-A receptor, Zolpidem (2a), Zaleplon (1b) and Indiplon (1a) have showed high affinity and selectivity. Following a design methodology including pharmacophoric requirements and ADME-predicted properties, we have synthesized a library of 3-amino-4,5-dihydro-1H-pyrazolo[3,4-b]pyridin-6(7H)- ones (3) and their N1-alkyl derivatives (4) as new scaffolds for designing non-benzodiazepine BZ receptor ligands.

Original language	English
Pages (from-to)	1179-1187
Number of pages	9
Journal	European Journal of Medicinal Chemistry
Volume	40
Issue number	11
DOIs	https://doi.org/10.1016/j.ejmech.2005.06.008
Publication status	Published - Nov 2005

Keywords

ADME
Catalyst
Combinatorial chemistry
GABA-A receptor
Indiplon
Non-benzodiazepinic
Pyrazolo[3,4-b]pyridin-6-ones
Volsurf
Zaleplon
Zolpidem

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Falcó, J. L., Lloveras, M., Buira, I., Teixidó, J., Borrell, J. I., Méndez, E., Terencio, J., Palomer, A., & Guglietta, A. (2005). Design, synthesis and biological activity of acyl substituted 3-amino-5-methyl-1,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones as potential hypnotic drugs. European Journal of Medicinal Chemistry, 40(11), 1179-1187. https://doi.org/10.1016/j.ejmech.2005.06.008

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title = "Design, synthesis and biological activity of acyl substituted 3-amino-5-methyl-1,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones as potential hypnotic drugs",

abstract = "Among the known non-benzodiazepinic hypnotic drugs acting on the α1 subunit of the GABA-A receptor, Zolpidem (2a), Zaleplon (1b) and Indiplon (1a) have showed high affinity and selectivity. Following a design methodology including pharmacophoric requirements and ADME-predicted properties, we have synthesized a library of 3-amino-4,5-dihydro-1H-pyrazolo[3,4-b]pyridin-6(7H)- ones (3) and their N1-alkyl derivatives (4) as new scaffolds for designing non-benzodiazepine BZ receptor ligands.",

keywords = "ADME, Catalyst, Combinatorial chemistry, GABA-A receptor, Indiplon, Non-benzodiazepinic, Pyrazolo[3,4-b]pyridin-6-ones, Volsurf, Zaleplon, Zolpidem",

author = "Falc{\'o}, {Jos{\'e} L.} and Maia Lloveras and Irma Buira and Jordi Teixid{\'o} and Borrell, {Jos{\'e} I.} and Eva M{\'e}ndez and Jos{\'e} Terencio and Albert Palomer and Antonio Guglietta",

year = "2005",

month = nov,

doi = "10.1016/j.ejmech.2005.06.008",

language = "English",

volume = "40",

pages = "1179--1187",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

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Falcó, JL, Lloveras, M, Buira, I, Teixidó, J , Borrell, JI, Méndez, E, Terencio, J, Palomer, A & Guglietta, A 2005, 'Design, synthesis and biological activity of acyl substituted 3-amino-5-methyl-1,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones as potential hypnotic drugs', European Journal of Medicinal Chemistry, vol. 40, no. 11, pp. 1179-1187. https://doi.org/10.1016/j.ejmech.2005.06.008

TY - JOUR

T1 - Design, synthesis and biological activity of acyl substituted 3-amino-5-methyl-1,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones as potential hypnotic drugs

AU - Falcó, José L.

AU - Lloveras, Maia

AU - Buira, Irma

AU - Teixidó, Jordi

AU - Borrell, José I.

AU - Méndez, Eva

AU - Terencio, José

AU - Palomer, Albert

AU - Guglietta, Antonio

PY - 2005/11

Y1 - 2005/11

N2 - Among the known non-benzodiazepinic hypnotic drugs acting on the α1 subunit of the GABA-A receptor, Zolpidem (2a), Zaleplon (1b) and Indiplon (1a) have showed high affinity and selectivity. Following a design methodology including pharmacophoric requirements and ADME-predicted properties, we have synthesized a library of 3-amino-4,5-dihydro-1H-pyrazolo[3,4-b]pyridin-6(7H)- ones (3) and their N1-alkyl derivatives (4) as new scaffolds for designing non-benzodiazepine BZ receptor ligands.

AB - Among the known non-benzodiazepinic hypnotic drugs acting on the α1 subunit of the GABA-A receptor, Zolpidem (2a), Zaleplon (1b) and Indiplon (1a) have showed high affinity and selectivity. Following a design methodology including pharmacophoric requirements and ADME-predicted properties, we have synthesized a library of 3-amino-4,5-dihydro-1H-pyrazolo[3,4-b]pyridin-6(7H)- ones (3) and their N1-alkyl derivatives (4) as new scaffolds for designing non-benzodiazepine BZ receptor ligands.

KW - ADME

KW - Catalyst

KW - Combinatorial chemistry

KW - GABA-A receptor

KW - Indiplon

KW - Non-benzodiazepinic

KW - Pyrazolo[3,4-b]pyridin-6-ones

KW - Volsurf

KW - Zaleplon

KW - Zolpidem

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U2 - 10.1016/j.ejmech.2005.06.008

DO - 10.1016/j.ejmech.2005.06.008

M3 - Article

C2 - 16095764

AN - SCOPUS:26844510933

SN - 0223-5234

VL - 40

SP - 1179

EP - 1187

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 11

ER -

Design, synthesis and biological activity of acyl substituted 3-amino-5-methyl-1,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones as potential hypnotic drugs

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Keywords

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