N-(quinuclidin-3-YL)-1,8,-naphthalimides with 5-HT3 receptor antagonist and 5-HT4 receptor agonist properties

Clark, Robin D.; Weinhardt, Klaus K.; Berger, Joel G.; Lee, C.-H.; Leung, Edward; Wong, Erik H. F.; Smith, William L.; Eglen, Richard M.

doi:10.1016/s0960-894x(00)80352-2

Cited by 17 publications

(1 citation statement)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(−)-Quinine 1 is a member of the cinchona family of alkaloids, and these compounds and their derivatives have been used in a wide range of synthetic applications . Various quinuclidines have also been shown to be inhibitors of the muscarinic (M 1 ), serotonin-3 (5-HT 3 ), and neurokinin (NK 1 ) 7 receptors and also as squalene synthase inhibitors . The inhibition of these targets is important in the treatment of Alzheimer's dementia, eating disorders, sexual behavior and stress, depression, and cholesterol blood levels …”

mentioning

confidence: 99%

A Diastereoselective Radical Cyclization Approach to Substituted Quinuclidines

2006

View full text Add to dashboard Cite

A new, concise, and flexible approach to novel quinuclidines has been developed, which employs a phosphorus hydride mediated radical addition/cyclization reaction in the key step. 1,7-Diene 5 reacts with diethyl thiophosphite in an efficient and diastereoselective radical addition/cyclization reaction to give trisubstituted piperidines 4ab. Piperidines 4ab are subsequently converted into 2,5-disubstituted quinuclidines using S(N)2-type cyclizations. Finally, the resulting quinuclidines are shown to undergo novel Horner-Wadsworth-Emmons-type (HWE-type) reactions to give unsaturated quinuclidines 21a and 21b, which have structures similar to that of (-)-quinine 1.

show abstract

mentioning

confidence: 99%

A Diastereoselective Radical Cyclization Approach to Substituted Quinuclidines

2006

View full text Add to dashboard Cite

show abstract

Synthesis of tritium labelled (R) and (S)-3-aminoquinuclidine: A ubiquitous component of serotonin receptor ligands, part I

Masjedizadeh¹,

Parnes²

1996

J Label Compd Radiopharm

View full text Add to dashboard Cite

SUMMARY(R) and (S)-3-aminoquinuclidines-3H with the specific activity of 35 Ci/mmol were prepared. Reduction of enamide 2 with carrier free tritium gas over RhCODCl dimer, (2S, 3s) Chiraphos in methanol gave yacemk amide &. Hydrolysis followed by resolution of the enantiomers with (R)-methyl benzyl isocyanate gave (R) and (S)-3-aminoquinuclidine-3H 1Oc-S and lOc-q. The enantiopurity purity of both isomers was >99.5%.

show abstract

Ruthenium(II)‐Catalyzed C−H Alkenylation of 1,8‐Naphthalimide with Cyclic Imide as a Weakly Coordinating Directing Group

2022

View full text Add to dashboard Cite

Ruthenium-catalyzed direct CÀ H alkenylation of 1,8-naphthalimide has been explored using cyclic imide as a weak directing group and successfully introduce alkenyl group(s) into 1,8-naphthalimide skeleton at the inactive C2 and/or C7 position(s). The aromatic ring of 1,8-naphthalimide is substituted with electron-withdrawing and -donating groups, and N-alkyl/aryl groups on cyclic imide are compatible in these coupling reactions.

show abstract

N-(quinuclidin-3-YL)-1,8,-naphthalimides with 5-HT3 receptor antagonist and 5-HT4 receptor agonist properties

Cited by 17 publications

References 14 publications

A Diastereoselective Radical Cyclization Approach to Substituted Quinuclidines

A Diastereoselective Radical Cyclization Approach to Substituted Quinuclidines

Synthesis of tritium labelled (R) and (S)-3-aminoquinuclidine: A ubiquitous component of serotonin receptor ligands, part I

Ruthenium(II)‐Catalyzed C−H Alkenylation of 1,8‐Naphthalimide with Cyclic Imide as a Weakly Coordinating Directing Group

Contact Info

Product

Resources

About