ChemInform Abstract: BASE‐CATALYZED REARRANGEMENTS OF 3,9‐DIOXATRICYCLO(3.3.1.02,4)NONAN‐7‐ONES TO FORM M‐HYDROXYPHENYLCARBONYL COMPOUNDS

Foehlisch, B.; Herrscher, Otto

doi:10.1002/chin.198539115

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“…Nearly all of the requisite benzoic acid (36), benzyl alcohol (38), benzyl halide (39), and phenylacetonitrile (40) precursors were commercially available; the substituted benzaldehydes and benzoic acids necessary for the preparation of 17-19, 30, and 31 were synthesized according to literature methods. [22][23][24][25] In general, the intermediate benzyl alcohols 38 were prepared by reduction of the corresponding aldehydes 37 or acids 36 with NaBH 4 or LiAlH 4 , respectively. The alcohols were converted to the benzyl halides 39 by standard methods, and the halides were treated with NaCN to afford nitriles 40.…”

Section: Chemistrymentioning

confidence: 99%

Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

et al. 1998

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Benzylimidazolines may represent a class of 5-HT1D ligands that has yet to be exploited. On the basis of a previous report that the 2-(substituted-benzyl)imidazoline alpha-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT1D receptors, we explored the structure-affinity relationships of a series of related derivatives. Each of the aromatic substituents was removed and then reinstated in a systematic manner to determine the influence of the individual substituents on binding. It was found that all of the aromatic substituents of 8 act in concert to impart high affinity. However, although the 3-hydroxy group could be removed without significantly reducing affinity for h5-HT1D (i.e., human 5-HT1Dalpha) receptors, this modification reduced h5-HT1B (i.e., human 5-HT1Dbeta) receptor affinity by nearly 50-fold. The 2, 6-dimethyl groups also contribute to binding but seem to play a greater role for h5-HT1B binding than h5-HT1D binding. With the appropriate structural modifications, several compounds were identified that display 20- to >100-fold selectivity for h5-HT1D versus h5-HT1B receptors. Preliminary functional data suggest that these compounds behave as agonists. Given that 5-HT1D agonists are currently being explored for their antimigraine action and that activation of h5-HT1B receptors might be associated with cardiovascular side effects, h5-HT1D-selective agents may offer a new lead for the development of therapeutically efficacious agents.

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Section: Chemistrymentioning

confidence: 99%

Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

et al. 1998

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ChemInform Abstract: BASE‐CATALYZED REARRANGEMENTS OF 3,9‐DIOXATRICYCLO(3.3.1.02,4)NONAN‐7‐ONES TO FORM M‐HYDROXYPHENYLCARBONYL COMPOUNDS

Abstract: Die Epoxide (I) lagern sich unter der Bedingung A) glatt zu Hydroxyketonen des Typs (II) um.

Cited by 1 publication

References 1 publication

Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

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ChemInform Abstract: BASE‐CATALYZED REARRANGEMENTS OF 3,9‐DIOXATRICYCLO(3.3.1.02,4)NONAN‐7‐ONES TO FORM M‐HYDROXYPHENYLCARBONYL COMPOUNDS

Abstract: Die Epoxide (I) lagern sich unter der Bedingung A) glatt zu Hydroxyketonen des Typs (II) um.

Cited by 1 publication

References 1 publication

Benzylimidazolines as h5-HT1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

Benzylimidazolines as h5-HT1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

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Product

Resources

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Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation