Structural studies of synthetic analgetics. IV. The crystal and molecular structure of (+-)-α-promedol alcohol

Ahmed, F. R.; Camp, W. H. De

doi:10.1107/s0567740872008234

Cited by 8 publications

(1 citation statement)

References 5 publications

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“…The factors contributing to these variations have been under investigation by pharmacological, spectroscopic and crystallographic techniques as described in a review article by Casy (1978). The structure-potency relations of the isomeric prodines (I) and the isomeric promedol alcohols (II) were summarized by Ahmed & De Camp (1972), and the present contribution extends the relations for the isomeric 1,2,3-trimethyl-4-phenyl-4-piperidinols (III). A brief account of these results has been reported by Cygler, Ahmed, Casy & Ogungbamila (1981 …”

Section: Introductionmentioning

confidence: 99%

Structure–potency relationships for three isomers of (±)-1,2,3-trimethyl-4-phenyl-4-piperidinol

Cygler¹,

Ahmed²

1984

Acta Crystallogr Sect B

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436 POLYTYPISM, TWINNING, AND DISORDER IN 2,2-AZIRIDINEDICARBOXAMIDE uniquely determined, because the alternative position is not compatible with the position of /:'5. Q3 may have one of four positions indicated by Q~, Q~i, Q~ii, Q~". If Q3 and P5 are fixed, Q4 is uniquely determined.Thus, only four stacking variants are in agreement with the observed lattice constants of form B.The atomic coordinates of form B (Br/ickner, 1982, deposited data) show that the variants (ii) and (iii) do not exist in form B, whereas both the variants (i) and (iv) are present. This results because:-it was impossible to decide between N and O ato'ms in the Fourier map; -variants (i) and (iv) are almost identical and may be transformed into each other by interchanging O atoms and NH2 groups.More precise information on the occurrence of (i) and (iv) in form B could be obtained from a detailed investigation of the distribution of the intensities in reciprocal space. Possible results are, for instance: -statistical occurrence of (i) and (iv) with approximately equal probabilities; -alternating occurrence of (i) and (iv); -the crystal consists of regions containing either only (i) or only (iv). The volume of the regions of type (i) and the volume of the regions of type (iv) are about the same. In both variants (i) and (iv) the two possible kinds of triples of layers are present. In (i) as well as in (iv) their proportion is 3:1 in favour of the triple existing in form A (see Fig. 3b).Concluding remark. The example discussed is also of interest in OD theory. No structure with a similar stacking of layers has been found so far. The combination of pairs of layers related by a centre of symmetry and pairs of layers related by a fourfold inversion axis is rather unusual. AbstractThe three isomers of the title compound, Ci4H21NO, are known to have propionate esters with potency rankings 3' > a >/3. The present X-ray analyses have shown their configurations to be: a-base, t-2-CH3, t-3-

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Section: Introductionmentioning

confidence: 99%

Structure–potency relationships for three isomers of (±)-1,2,3-trimethyl-4-phenyl-4-piperidinol

Cygler¹,

Ahmed²

1984

Acta Crystallogr Sect B

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An analysis of the stereochemical structure‐activity relationships of C‐methyl derivatives of the reversed ester of meperidine

Casy

1982

Medicinal Research Reviews

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The solute conformation of opioid ligands of the 4‐arylpiperidine class: α‐Promedol and related compounds

Casy¹

1992

Magnetic Reson in Chemistry

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The NMR spectra (chiefly 'H) of isomeric 2,5-and 2,3-dimethyl-4-phenyI-4-piperidinols, related esters and trans-2,6-dimethyl-4-propionyloxy-4-phenylpiperidine HCI (all N-methylated) have been assigned and analysed in terms of solute conformation. Preferred forms include 4-ax-phenyl and 4-eq-phenyl chairs and, in the case of the 7-2,s dimethyl-4-piperidinol base, a boat conformation. In several cases the existence of pairs of N-protonated epimers has been demonstrated. The findings are important both to the conformational analysis of saturated six-membered heterocycles and to stereoactivity analyses of opioid ligands of the 4-arylpiperidine class.

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Structural studies of synthetic analgetics. IV. The crystal and molecular structure of (+-)-α-promedol alcohol

Cited by 8 publications

References 5 publications

Structure–potency relationships for three isomers of (±)-1,2,3-trimethyl-4-phenyl-4-piperidinol

Structure–potency relationships for three isomers of (±)-1,2,3-trimethyl-4-phenyl-4-piperidinol

An analysis of the stereochemical structure‐activity relationships of C‐methyl derivatives of the reversed ester of meperidine

The solute conformation of opioid ligands of the 4‐arylpiperidine class: α‐Promedol and related compounds

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