Molecular modelling, synthesis and acetylcholinesterase inhibition of ethyl 5-amino-2-methyl-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate

Elena Soriano; Abdelouahid Samadi; Mourad Chioua; Cristóbal de los Ríos; José Marco-Contelles

doi:10.1016/j.bmcl.2010.03.010

Molecular modelling, synthesis and acetylcholinesterase inhibition of ethyl 5-amino-2-methyl-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate

Elena Soriano
, Abdelouahid Samadi
, Mourad Chioua
, Cristóbal de los Ríos
, José Marco-Contelles

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

In silico analysis of ethyl 5-amino-2-methyl-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate (2) predicts that this molecule should be successfully docked in the PAS, and easily accommodated in the CAS of AChE. The synthesis and the AChE/BuChE inhibition studies are reported, confirming that compound 2 is a potent and selective AChE inhibitor, and consequently, a new lead compound for further development into new dual CAS/PAS cholinergic agents for the treatment of Alzheimer's disease.

Original language	English
Pages (from-to)	2950-2953
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	9
DOIs	https://doi.org/10.1016/j.bmcl.2010.03.010
Publication status	Published - May 1 2010
Externally published	Yes

Keywords

AChE/BuChE inhibition
Alzheimer's disease
Ethyl 5-amino-2-methyl-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate
Molecular modelling

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2010.03.010

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Molecular modelling, synthesis and acetylcholinesterase inhibition of ethyl 5-amino-2-methyl-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate. / Soriano, Elena; Samadi, Abdelouahid; Chioua, Mourad et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 20, No. 9, 01.05.2010, p. 2950-2953.

Research output: Contribution to journal › Article › peer-review

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title = "Molecular modelling, synthesis and acetylcholinesterase inhibition of ethyl 5-amino-2-methyl-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate",

abstract = "In silico analysis of ethyl 5-amino-2-methyl-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate (2) predicts that this molecule should be successfully docked in the PAS, and easily accommodated in the CAS of AChE. The synthesis and the AChE/BuChE inhibition studies are reported, confirming that compound 2 is a potent and selective AChE inhibitor, and consequently, a new lead compound for further development into new dual CAS/PAS cholinergic agents for the treatment of Alzheimer's disease.",

keywords = "AChE/BuChE inhibition, Alzheimer's disease, Ethyl 5-amino-2-methyl-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate, Molecular modelling",

author = "Elena Soriano and Abdelouahid Samadi and Mourad Chioua and R{\'i}os, \{Crist{\'o}bal de los\} and Jos{\'e} Marco-Contelles",

note = "Funding Information: Abdelouahid Samadi thanks CSIC for a I3P post-doctoral contract. Mourad Chioua thanks Instituto de Salud Carlos III (ISCIII, MICINN) for a {\textquoteleft}Sara Borrell{\textquoteright} contract. Elena Soriano and Jos{\'e} Marco-Contelles (J.M.C.) thanks CSIC ( 200880I221 ), CAM-CSIC ( CCG08-CSIC/SAL-3696 ) and Ministerio de Ciencia e Innovaci{\'o}n (MICINN) ( SAF2006-08764-C02-01 ), Comunidad Aut{\'o}noma de Madrid ( S/SAL-0275-2006 ) and ISCIII [Red RENEVAS ( RD06/0026/1002 )] for support. J.M.C. thanks Prof. Antonio Garc{\'i}a Garc{\'i}a and Dr. Mercedes Villarroya (Departamento de Farmacolog{\'i}a y Terap{\'e}utica, Facultad de Medicina, Universidad Aut{\'o}noma de Madrid, C/Arzobispo Morcillo 4; 28029 Madrid, Spain) for continuous support and encouragement. ",

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AU - Samadi, Abdelouahid

AU - Chioua, Mourad

AU - Ríos, Cristóbal de los

AU - Marco-Contelles, José

N1 - Funding Information: Abdelouahid Samadi thanks CSIC for a I3P post-doctoral contract. Mourad Chioua thanks Instituto de Salud Carlos III (ISCIII, MICINN) for a ‘Sara Borrell’ contract. Elena Soriano and José Marco-Contelles (J.M.C.) thanks CSIC ( 200880I221 ), CAM-CSIC ( CCG08-CSIC/SAL-3696 ) and Ministerio de Ciencia e Innovación (MICINN) ( SAF2006-08764-C02-01 ), Comunidad Autónoma de Madrid ( S/SAL-0275-2006 ) and ISCIII [Red RENEVAS ( RD06/0026/1002 )] for support. J.M.C. thanks Prof. Antonio García García and Dr. Mercedes Villarroya (Departamento de Farmacología y Terapéutica, Facultad de Medicina, Universidad Autónoma de Madrid, C/Arzobispo Morcillo 4; 28029 Madrid, Spain) for continuous support and encouragement.

PY - 2010/5/1

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N2 - In silico analysis of ethyl 5-amino-2-methyl-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate (2) predicts that this molecule should be successfully docked in the PAS, and easily accommodated in the CAS of AChE. The synthesis and the AChE/BuChE inhibition studies are reported, confirming that compound 2 is a potent and selective AChE inhibitor, and consequently, a new lead compound for further development into new dual CAS/PAS cholinergic agents for the treatment of Alzheimer's disease.

AB - In silico analysis of ethyl 5-amino-2-methyl-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate (2) predicts that this molecule should be successfully docked in the PAS, and easily accommodated in the CAS of AChE. The synthesis and the AChE/BuChE inhibition studies are reported, confirming that compound 2 is a potent and selective AChE inhibitor, and consequently, a new lead compound for further development into new dual CAS/PAS cholinergic agents for the treatment of Alzheimer's disease.

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Molecular modelling, synthesis and acetylcholinesterase inhibition of ethyl 5-amino-2-methyl-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate

Abstract

Keywords

ASJC Scopus subject areas

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