N-[4-(Methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide

Koch, Michael; Ranter, C. J. De; Rolies, M.; Dideberg, O.

doi:10.1107/s0567740876008145

Cited by 18 publications

(8 citation statements)

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“…It is well known that for the most active representatives of the fentanyl series the aniline phenyl is perpendicular to the plane of the amide function [156,157]. For the whole series of ‘ring-closed’ compounds the perpendicular conformation of the anilido- moiety is excluded [150].…”

Section: Conformationally Restricted Analogs Of Fentanylmentioning

confidence: 99%

Fentanyl-Related Compounds and Derivatives: Current Status and Future Prospects for Pharmaceutical Applications

2014

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Fentanyl and its analogs have been mainstays for the treatment of severe to moderate pain for many years. In this review, we outline the structural and corresponding synthetic strategies that have been used to understand the structure–biological activity relationship in fentanyl-related compounds and derivatives and their biological activity profiles. We discuss how changes in the scaffold structure can change biological and pharmacological activities. Finally, recent efforts to design and synthesize novel multivalent ligands that act as mu and delta opioid receptors and NK-1 receptors are discussed.

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Section: Conformationally Restricted Analogs Of Fentanylmentioning

confidence: 99%

Fentanyl-Related Compounds and Derivatives: Current Status and Future Prospects for Pharmaceutical Applications

2014

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“…The X-ray crystallographic studies of the solid-state conformation of 1 [4] and a number of its derivatives [5][6][7][8] reveal that, in all analogs, the piperidine ring is in the chair conformation and both the 4-phenylpropanamide and the N-phenethyl substituents are equatorial. Information about the probable solution conformation of fentanyl in chloroform has been obtained through 1H NMR and IR spectroscopy [9].…”

Section: Introductionmentioning

confidence: 99%

Development of a conformational search strategy for flexible ligands: A study of the potent ?-selective opioid analgesic fentanyl

Cometta-Morini

Loew

1991

J Computer-Aided Mol Des

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An extensive conformational search of the potent opioid analgesic, fentanyl, was performed using the semiempirical quantum mechanical method AM1 and the CHARMm potential energy function. A combination of two procedures was used to search the conformational space for fentanyl, which included nested dihedral scans, geometry optimization and molecular dynamics simulation at different temperatures. In addition, the effect of a continuum solvent environment was taken into account by use of appropriate values for the dielectric constant in the CHARMm computations. The results of the conformational search allowed the determination of the probable conformation of fentanyl in polar and nonpolar solvents and of three candidate conformers for its bioactive form.

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“…Analysis of the crystal structures of fentanyl and its structural analogues indicate this is the case. 22,23 In addition, the N-phenethyl and propananilido moieties are extended in the crystal structure. 23 The amide function is planar and at a 90°a ngle to the mean plane of the piperidine ring.…”

Section: Resultsmentioning

confidence: 99%

Conformationally restrained fentanyl analogs. 2. Synthesis and analgetic evaluation of perhydro-1,6-naphthyridin-2-ones

Borne¹,

Fifer²,

Waters³

1984

J. Med. Chem.

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Conformational flexibility of the N-acyl portion of fentanyl-type analgetics was restricted through the synthesis of novel perhydro-1,6-naphthyridin-2-one derivatives. Neither the cis-fused derivative (5a), the trans-fused derivative(5b), nor the enamide 8a possessed analgetic activity in the mouse tail-flick assay, reaffirming the sensitivity of this portion of 4-anilidopiperidine analgetics to conformational restraint.

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N-[4-(Methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide

Abstract: Abstract. C24Ha2N202, M.W. 380"5; triclininc, PT; a= 15.965 (6), b=9.395 (4), c= 15.137 (5) ]k, ~=90.40 (2), fl=91.32 (1), 7=93-18 (2)°; 25°C; Z=4.

Cited by 18 publications

References 0 publications

Fentanyl-Related Compounds and Derivatives: Current Status and Future Prospects for Pharmaceutical Applications

Fentanyl-Related Compounds and Derivatives: Current Status and Future Prospects for Pharmaceutical Applications

Development of a conformational search strategy for flexible ligands: A study of the potent ?-selective opioid analgesic fentanyl

Conformationally restrained fentanyl analogs. 2. Synthesis and analgetic evaluation of perhydro-1,6-naphthyridin-2-ones

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