Studies in the pyridine series. XXV. Dissociation constants of some piperidine and piperideine bases

Lakomý, J.; Silhankova, A.; Ferles, M.; Exner, Otto

doi:10.1135/cccc19681700

Cited by 7 publications

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“…The following intermediates were synthesized according to described procedures: 1-(3-chloropropyl)-4-phenylpiperazine (73), 78 1-(3-chloropropyl)-4-(2-methoxyphenyl)piperazine ( 74), 78 4-isopropylpiperidine (81), 79 4-cyclohexylpiperidine (82), 80 and 4-phenylpiperidine (83). 81 Spectral data of all described compounds were consistent with the proposed structures for series 75-80 and 39-72; here we include the data of compounds 75, 78, 39, 42, 45, 48, 50, 56, 58, 63 and 72.…”

Section: Methodsmentioning

confidence: 99%

Optimization of the Pharmacophore Model for 5-HT₇R Antagonism. Design and Synthesis of New Naphtholactam and Naphthosultam Derivatives

et al. 2003

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We present in this study an optimization of a preliminary pharmacophore model for 5-HT(7)R antagonism, with the incorporation of recently reported ligands and using an efficient procedure with the CATALYST program. The model consists of five features: a positive ionizable atom (PI), a H-bonding acceptor group (HBA), and three hydrophobic regions (HYD). This model has been supported by the design, synthesis, and biological evaluation of new naphtholactam and naphthosultam derivatives of general structure I (39-72). A systematic structure-affinity relationship (SAFIR) study on these analogues has allowed us to confirm that the model incorporates the essential structural features for 5-HT(7)R antagonism. In addition, computational simulation of the complex between compound 56 and a rhodopsin-based 3D model of the 5-HT(7)R transmembrane domain has permitted us to define the molecular details of the ligand-receptor interaction and gives additional support to the proposed pharmacophore model for 5-HT(7)R antagonism: (i) the HBA feature of the pharmacophore model binds Ser(5.42) and Thr(5.43), (ii) the HYD1 feature interacts with Phe(6.52), (iii) the PI feature forms an ionic interaction with Asp(3.32), and (iv) the HYD3 (AR) feature interacts with a set of aromatic residues (Phe(3.28), Tyr(7.43)). These results provide the tools for the design and synthesis of new ligands with predetermined affinities and pharmacological properties.

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Section: Methodsmentioning

confidence: 99%

Optimization of the Pharmacophore Model for 5-HT₇R Antagonism. Design and Synthesis of New Naphtholactam and Naphthosultam Derivatives

et al. 2003

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Part B. Partially Reduced Pyridines

Lyle¹

1974

Chemistry of Heterocyclic Compounds: A Series of Monographs

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The Fault Line in Prototropic Tautomerism

Taylor

Antonov

2016

Tautomerism

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Studies in the pyridine series. XXV. Dissociation constants of some piperidine and piperideine bases

Cited by 7 publications

References 0 publications

Optimization of the Pharmacophore Model for 5-HT₇R Antagonism. Design and Synthesis of New Naphtholactam and Naphthosultam Derivatives

Optimization of the Pharmacophore Model for 5-HT₇R Antagonism. Design and Synthesis of New Naphtholactam and Naphthosultam Derivatives

Part B. Partially Reduced Pyridines

The Fault Line in Prototropic Tautomerism

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Studies in the pyridine series. XXV. Dissociation constants of some piperidine and piperideine bases

Cited by 7 publications

References 0 publications

Optimization of the Pharmacophore Model for 5-HT7R Antagonism. Design and Synthesis of New Naphtholactam and Naphthosultam Derivatives

Optimization of the Pharmacophore Model for 5-HT7R Antagonism. Design and Synthesis of New Naphtholactam and Naphthosultam Derivatives

Part B. Partially Reduced Pyridines

The Fault Line in Prototropic Tautomerism

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Product

Resources

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Optimization of the Pharmacophore Model for 5-HT₇R Antagonism. Design and Synthesis of New Naphtholactam and Naphthosultam Derivatives

Optimization of the Pharmacophore Model for 5-HT₇R Antagonism. Design and Synthesis of New Naphtholactam and Naphthosultam Derivatives