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Synthesis and dopaminergic properties of benzo-fused analogues of quinpirole and quinelorane.

Publication ,  Journal Article
Doll, MK; Nichols, DE; Kilts, JD; Prioleau, C; Lawler, CP; Lewis, MM; Mailman, RB
Published in: J Med Chem
March 11, 1999

In an analogy to the potent catechol dopamine D1 agonists dihydrexidine (1) and dinapsoline (2), benzo rings were fused onto the structures of the dopamine D2-selective agonists quinelorane (3) and quinpirole (4). Each of the phenyl ring-substituted derivatives had significant affinity for D2 receptors, albeit somewhat lower than the two parent compounds, 3 and 4. Compounds with N-propyl and N-allyl substituents (5b, 5c, 6c, and 6d) had higher affinity for the D2 dopamine receptor than did their corresponding secondary amines (5a and 6a). Slightly different effects on affinity of an n-propyl and an n-allyl group in the new analogues of 3 and 4 suggest that different binding orientations may be invoked at the receptor.

Duke Scholars

Published In

J Med Chem

DOI

ISSN

0022-2623

Publication Date

March 11, 1999

Volume

42

Issue

5

Start / End Page

935 / 940

Location

United States

Related Subject Headings

  • Structure-Activity Relationship
  • Receptors, Dopamine D2
  • Receptors, Dopamine D1
  • Rats, Sprague-Dawley
  • Rats
  • Radioligand Assay
  • Quinolines
  • Neostriatum
  • Naphthols
  • Medicinal & Biomolecular Chemistry
 

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Doll, M. K., Nichols, D. E., Kilts, J. D., Prioleau, C., Lawler, C. P., Lewis, M. M., & Mailman, R. B. (1999). Synthesis and dopaminergic properties of benzo-fused analogues of quinpirole and quinelorane. J Med Chem, 42(5), 935–940. https://doi.org/10.1021/jm9804533
Doll, M. K., D. E. Nichols, J. D. Kilts, C. Prioleau, C. P. Lawler, M. M. Lewis, and R. B. Mailman. “Synthesis and dopaminergic properties of benzo-fused analogues of quinpirole and quinelorane.J Med Chem 42, no. 5 (March 11, 1999): 935–40. https://doi.org/10.1021/jm9804533.
Doll MK, Nichols DE, Kilts JD, Prioleau C, Lawler CP, Lewis MM, et al. Synthesis and dopaminergic properties of benzo-fused analogues of quinpirole and quinelorane. J Med Chem. 1999 Mar 11;42(5):935–40.
Doll, M. K., et al. “Synthesis and dopaminergic properties of benzo-fused analogues of quinpirole and quinelorane.J Med Chem, vol. 42, no. 5, Mar. 1999, pp. 935–40. Pubmed, doi:10.1021/jm9804533.
Doll MK, Nichols DE, Kilts JD, Prioleau C, Lawler CP, Lewis MM, Mailman RB. Synthesis and dopaminergic properties of benzo-fused analogues of quinpirole and quinelorane. J Med Chem. 1999 Mar 11;42(5):935–940.
Journal cover image

Published In

J Med Chem

DOI

ISSN

0022-2623

Publication Date

March 11, 1999

Volume

42

Issue

5

Start / End Page

935 / 940

Location

United States

Related Subject Headings

  • Structure-Activity Relationship
  • Receptors, Dopamine D2
  • Receptors, Dopamine D1
  • Rats, Sprague-Dawley
  • Rats
  • Radioligand Assay
  • Quinolines
  • Neostriatum
  • Naphthols
  • Medicinal & Biomolecular Chemistry