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Identification of the first trans-(3R,4R)- dimethyl-4-(3-hydroxyphenyl)piperidine derivative to possess highly potent and selective opioid kappa receptor antagonist activity.
J Med Chem. 2001 Aug 16; 44(17):2687-90.JM

Abstract

A structurally novel opioid kappa receptor selective ligand has been identified. This compound, (3R)-7-hydroxy-N-((1S)-1-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic, 10) demonstrated high affinity for the kappa receptor in the binding assay (kappa K(i) = 0.3 nM) and highly potent and selective kappa antagonism in the [(35)S]GTP-gamma-S assay using cloned opioid receptors (kappa K(i) = 0.006 nM, mu/kappa ratio = 570, delta/kappa ratio > 16600).

Authors+Show Affiliations

Chemistry and Life Sciences, Research Triangle Institute, Research Triangle Park, North Carolina 27709, USA.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

11495579

Citation

Thomas, J B., et al. "Identification of the First trans-(3R,4R)- Dimethyl-4-(3-hydroxyphenyl)piperidine Derivative to Possess Highly Potent and Selective Opioid Kappa Receptor Antagonist Activity." Journal of Medicinal Chemistry, vol. 44, no. 17, 2001, pp. 2687-90.
Thomas JB, Atkinson RN, Rothman RB, et al. Identification of the first trans-(3R,4R)- dimethyl-4-(3-hydroxyphenyl)piperidine derivative to possess highly potent and selective opioid kappa receptor antagonist activity. J Med Chem. 2001;44(17):2687-90.
Thomas, J. B., Atkinson, R. N., Rothman, R. B., Fix, S. E., Mascarella, S. W., Vinson, N. A., Xu, H., Dersch, C. M., Lu, Y., Cantrell, B. E., Zimmerman, D. M., & Carroll, F. I. (2001). Identification of the first trans-(3R,4R)- dimethyl-4-(3-hydroxyphenyl)piperidine derivative to possess highly potent and selective opioid kappa receptor antagonist activity. Journal of Medicinal Chemistry, 44(17), 2687-90.
Thomas JB, et al. Identification of the First trans-(3R,4R)- Dimethyl-4-(3-hydroxyphenyl)piperidine Derivative to Possess Highly Potent and Selective Opioid Kappa Receptor Antagonist Activity. J Med Chem. 2001 Aug 16;44(17):2687-90. PubMed PMID: 11495579.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Identification of the first trans-(3R,4R)- dimethyl-4-(3-hydroxyphenyl)piperidine derivative to possess highly potent and selective opioid kappa receptor antagonist activity. AU - Thomas,J B, AU - Atkinson,R N, AU - Rothman,R B, AU - Fix,S E, AU - Mascarella,S W, AU - Vinson,N A, AU - Xu,H, AU - Dersch,C M, AU - Lu,Y, AU - Cantrell,B E, AU - Zimmerman,D M, AU - Carroll,F I, PY - 2001/8/10/pubmed PY - 2001/9/8/medline PY - 2001/8/10/entrez SP - 2687 EP - 90 JF - Journal of medicinal chemistry JO - J Med Chem VL - 44 IS - 17 N2 - A structurally novel opioid kappa receptor selective ligand has been identified. This compound, (3R)-7-hydroxy-N-((1S)-1-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic, 10) demonstrated high affinity for the kappa receptor in the binding assay (kappa K(i) = 0.3 nM) and highly potent and selective kappa antagonism in the [(35)S]GTP-gamma-S assay using cloned opioid receptors (kappa K(i) = 0.006 nM, mu/kappa ratio = 570, delta/kappa ratio > 16600). SN - 0022-2623 UR - https://www.unboundmedicine.com/medline/citation/11495579/Identification_of_the_first_trans__3R4R___dimethyl_4__3_hydroxyphenyl_piperidine_derivative_to_possess_highly_potent_and_selective_opioid_kappa_receptor_antagonist_activity_ L2 - https://doi.org/10.1021/jm015521r DB - PRIME DP - Unbound Medicine ER -