Synthesis and muscarinic activities of O-[(benzyl- or benzoyl-pyrazolyl)propynyl]-oximes of N-methylpiperidinone, 3-tropinone, and 3-quinuclidinone

María Isabel Rodríguez-Franco; Isabel Dorronsoro; Ana Castro; Ana Martínez; Albert Badía; Josep E. Baños

doi:https://doi.org/10.1016/S0968-0896(03)00111-1

Synthesis and muscarinic activities of O-[(benzyl- or benzoyl-pyrazolyl)propynyl]-oximes of N-methylpiperidinone, 3-tropinone, and 3-quinuclidinone

María Isabel Rodríguez-Franco, Isabel Dorronsoro, Ana Castro, Ana Martínez, Albert Badía, Josep E. Baños

Department of Pharmacology, Therapeutics and Toxicology

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

13 Citations (Scopus)

Abstract

The synthesis of O-propynyloximes of N-methylpiperidinone, 3-tropinone, and 3-quinuclidinone, containing several pyrazole frameworks is described, together with their muscarinic receptor affinities. Compounds derived from N-methylpiperidinone or 3-tropinone and N-(4-methoxybenzyl)- or N-(2,4,6-trimethylbenzoyl)pyrazole showed moderate activity for muscarinic receptors in the rat central nervous system. A semi-empirical AM1 calculation has shown that the O-[(benzoyl-pyrazolyl)propynyl]-oximes of tropinone fit a previously described muscarinic pharmacophoric model, revealing structural features useful for the development of new muscarinic agents. © 2003 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	2263-2268
Journal	Bioorganic and Medicinal Chemistry
Volume	11
DOIs	https://doi.org/10.1016/S0968-0896(03)00111-1
Publication status	Published - 15 May 2003

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@article{1c2b234b7e0549c4b3600d2764efb5cb,

title = "Synthesis and muscarinic activities of O-[(benzyl- or benzoyl-pyrazolyl)propynyl]-oximes of N-methylpiperidinone, 3-tropinone, and 3-quinuclidinone",

abstract = "The synthesis of O-propynyloximes of N-methylpiperidinone, 3-tropinone, and 3-quinuclidinone, containing several pyrazole frameworks is described, together with their muscarinic receptor affinities. Compounds derived from N-methylpiperidinone or 3-tropinone and N-(4-methoxybenzyl)- or N-(2,4,6-trimethylbenzoyl)pyrazole showed moderate activity for muscarinic receptors in the rat central nervous system. A semi-empirical AM1 calculation has shown that the O-[(benzoyl-pyrazolyl)propynyl]-oximes of tropinone fit a previously described muscarinic pharmacophoric model, revealing structural features useful for the development of new muscarinic agents. {\textcopyright} 2003 Elsevier Science Ltd. All rights reserved.",

author = "Rodr{\'i}guez-Franco, {Mar{\'i}a Isabel} and Isabel Dorronsoro and Ana Castro and Ana Mart{\'i}nez and Albert Bad{\'i}a and Ba{\~n}os, {Josep E.}",

year = "2003",

month = may,

day = "15",

doi = "https://doi.org/10.1016/S0968-0896(03)00111-1",

language = "English",

volume = "11",

pages = "2263--2268",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

}

Synthesis and muscarinic activities of O-[(benzyl- or benzoyl-pyrazolyl)propynyl]-oximes of N-methylpiperidinone, 3-tropinone, and 3-quinuclidinone. / Rodríguez-Franco, María Isabel; Dorronsoro, Isabel; Castro, Ana; Martínez, Ana; Badía, Albert; Baños, Josep E.

In: Bioorganic and Medicinal Chemistry, Vol. 11, 15.05.2003, p. 2263-2268.

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

TY - JOUR

T1 - Synthesis and muscarinic activities of O-[(benzyl- or benzoyl-pyrazolyl)propynyl]-oximes of N-methylpiperidinone, 3-tropinone, and 3-quinuclidinone

AU - Rodríguez-Franco, María Isabel

AU - Dorronsoro, Isabel

AU - Castro, Ana

AU - Martínez, Ana

AU - Badía, Albert

AU - Baños, Josep E.

PY - 2003/5/15

Y1 - 2003/5/15

N2 - The synthesis of O-propynyloximes of N-methylpiperidinone, 3-tropinone, and 3-quinuclidinone, containing several pyrazole frameworks is described, together with their muscarinic receptor affinities. Compounds derived from N-methylpiperidinone or 3-tropinone and N-(4-methoxybenzyl)- or N-(2,4,6-trimethylbenzoyl)pyrazole showed moderate activity for muscarinic receptors in the rat central nervous system. A semi-empirical AM1 calculation has shown that the O-[(benzoyl-pyrazolyl)propynyl]-oximes of tropinone fit a previously described muscarinic pharmacophoric model, revealing structural features useful for the development of new muscarinic agents. © 2003 Elsevier Science Ltd. All rights reserved.

AB - The synthesis of O-propynyloximes of N-methylpiperidinone, 3-tropinone, and 3-quinuclidinone, containing several pyrazole frameworks is described, together with their muscarinic receptor affinities. Compounds derived from N-methylpiperidinone or 3-tropinone and N-(4-methoxybenzyl)- or N-(2,4,6-trimethylbenzoyl)pyrazole showed moderate activity for muscarinic receptors in the rat central nervous system. A semi-empirical AM1 calculation has shown that the O-[(benzoyl-pyrazolyl)propynyl]-oximes of tropinone fit a previously described muscarinic pharmacophoric model, revealing structural features useful for the development of new muscarinic agents. © 2003 Elsevier Science Ltd. All rights reserved.

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DO - https://doi.org/10.1016/S0968-0896(03)00111-1

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