奥列诺醇系列中κ阿片受体药效的结构决定因素：丁丙诺啡的7,7-螺环类似物 - Suppr

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Structural determinants of efficacy for kappa opioid receptors in the orvinol series: 7,7-spiro analogues of buprenorphine.

作者信息

Husbands S M, Lewis J W

机构信息

School of Chemistry, Cantock's Close, University of Bristol, Bristol, England.

出版信息

J Med Chem. 2000 Jan 27;43(2):139-41. doi: 10.1021/jm991165p.

DOI:10.1021/jm991165p

PMID:10649968

Abstract

摘要

相似文献

Structural determinants of efficacy for kappa opioid receptors in the orvinol series: 7,7-spiro analogues of buprenorphine.

J Med Chem. 2000 Jan 27;43(2):139-41. doi: 10.1021/jm991165p.

Ring-constrained orvinols as analogs of buprenorphine: differences in opioid activity related to configuration of C(20) hydroxyl group.

J Pharmacol Exp Ther. 1999 Dec;291(3):1093-9.

Buprenorphine antinociception is abolished, but naloxone-sensitive reward is retained, in mu-opioid receptor knockout mice.

Neuropsychopharmacology. 2004 Sep;29(9):1656-63. doi: 10.1038/sj.npp.1300463.

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J Pharmacol Exp Ther. 2006 Jul;318(1):282-7. doi: 10.1124/jpet.105.099937. Epub 2006 Mar 28.

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C-Homomorphinan Derivatives as Lead Compounds to Obtain Safer and More Clinically Useful Analgesics.

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Br J Pharmacol. 2001 Sep;134(2):441-7. doi: 10.1038/sj.bjp.0704280.

BU48: a novel buprenorphine analog that exhibits delta-opioid-mediated convulsions but not delta-opioid-mediated antinociception in mice.

J Pharmacol Exp Ther. 2000 Sep;294(3):1195-200.

Structure-activity relationships of dynorphin a analogues modified in the address sequence.

J Med Chem. 2003 May 22;46(11):2104-9. doi: 10.1021/jm020125+.

Ring constrained analogues of the orvinols: the furanomorphides.

Bioorg Med Chem Lett. 1999 Mar 22;9(6):831-4. doi: 10.1016/s0960-894x(99)00085-2.

引用本文的文献

Opioid Antagonists from the Orvinol Series as Potential Reversal Agents for Opioid Overdose.

ACS Chem Neurosci. 2022 Nov 2;13(21):3108-3117. doi: 10.1021/acschemneuro.2c00464. Epub 2022 Oct 12.

C7β-methyl analogues of the orvinols: the discovery of kappa opioid antagonists with nociceptin/orphanin FQ peptide (NOP) receptor partial agonism and low, or zero, efficacy at mu opioid receptors.

J Med Chem. 2015 May 28;58(10):4242-9. doi: 10.1021/acs.jmedchem.5b00130. Epub 2015 May 6.

Selectively promiscuous opioid ligands: discovery of high affinity/low efficacy opioid ligands with substantial nociceptin opioid peptide receptor affinity.

J Med Chem. 2014 May 22;57(10):4049-57. doi: 10.1021/jm401964y. Epub 2014 May 9.

Orvinols with mixed kappa/mu opioid receptor agonist activity.

J Med Chem. 2013 Apr 25;56(8):3207-16. doi: 10.1021/jm301543e. Epub 2013 Apr 3.

Structural determinants of opioid and NOP receptor activity in derivatives of buprenorphine.

J Med Chem. 2011 Oct 13;54(19):6531-7. doi: 10.1021/jm2003238. Epub 2011 Sep 7.

Cinnamoyl derivatives of 7alpha-aminomethyl-6,14-endo-ethanotetrahydrothebaine and 7alpha-aminomethyl-6,14-endo-ethanotetrahydrooripavine and related opioid ligands.

J Med Chem. 2007 Oct 18;50(21):5176-82. doi: 10.1021/jm070255o. Epub 2007 Sep 22.

Structural determinants of opioid activity in derivatives of 14-aminomorphinones: effect of substitution in the aromatic ring of cinnamoylaminomorphinones and codeinones.

J Med Chem. 2006 Aug 24;49(17):5333-8. doi: 10.1021/jm0604777.

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Structural determinants of efficacy for kappa opioid receptors in the orvinol series: 7,7-spiro analogues of buprenorphine.

作者信息

Husbands S M, Lewis J W

机构信息

School of Chemistry, Cantock's Close, University of Bristol, Bristol, England.

出版信息

J Med Chem. 2000 Jan 27;43(2):139-41. doi: 10.1021/jm991165p.

DOI:10.1021/jm991165p

PMID:10649968

Abstract

摘要

相似文献

Structural determinants of efficacy for kappa opioid receptors in the orvinol series: 7,7-spiro analogues of buprenorphine.

J Med Chem. 2000 Jan 27;43(2):139-41. doi: 10.1021/jm991165p.

Ring-constrained orvinols as analogs of buprenorphine: differences in opioid activity related to configuration of C(20) hydroxyl group.

J Pharmacol Exp Ther. 1999 Dec;291(3):1093-9.

Buprenorphine antinociception is abolished, but naloxone-sensitive reward is retained, in mu-opioid receptor knockout mice.

Neuropsychopharmacology. 2004 Sep;29(9):1656-63. doi: 10.1038/sj.npp.1300463.

Thienorphine is a potent long-acting partial opioid agonist: a comparative study with buprenorphine.

J Pharmacol Exp Ther. 2006 Jul;318(1):282-7. doi: 10.1124/jpet.105.099937. Epub 2006 Mar 28.

The role of spinal opioid receptors in antinociceptive effects produced by intrathecal administration of hydromorphone and buprenorphine in the rat.

Anesth Analg. 2002 Jun;94(6):1542-6, table of contents. doi: 10.1097/00000539-200206000-00031.

C-Homomorphinan Derivatives as Lead Compounds to Obtain Safer and More Clinically Useful Analgesics.

Chem Pharm Bull (Tokyo). 2017;65(10):920-929. doi: 10.1248/cpb.c17-00385.

HS-599: a novel long acting opioid analgesic does not induce place-preference in rats.

Br J Pharmacol. 2001 Sep;134(2):441-7. doi: 10.1038/sj.bjp.0704280.

BU48: a novel buprenorphine analog that exhibits delta-opioid-mediated convulsions but not delta-opioid-mediated antinociception in mice.

J Pharmacol Exp Ther. 2000 Sep;294(3):1195-200.

Structure-activity relationships of dynorphin a analogues modified in the address sequence.

J Med Chem. 2003 May 22;46(11):2104-9. doi: 10.1021/jm020125+.

Ring constrained analogues of the orvinols: the furanomorphides.

Bioorg Med Chem Lett. 1999 Mar 22;9(6):831-4. doi: 10.1016/s0960-894x(99)00085-2.

引用本文的文献

Opioid Antagonists from the Orvinol Series as Potential Reversal Agents for Opioid Overdose.

ACS Chem Neurosci. 2022 Nov 2;13(21):3108-3117. doi: 10.1021/acschemneuro.2c00464. Epub 2022 Oct 12.

C7β-methyl analogues of the orvinols: the discovery of kappa opioid antagonists with nociceptin/orphanin FQ peptide (NOP) receptor partial agonism and low, or zero, efficacy at mu opioid receptors.

J Med Chem. 2015 May 28;58(10):4242-9. doi: 10.1021/acs.jmedchem.5b00130. Epub 2015 May 6.

Selectively promiscuous opioid ligands: discovery of high affinity/low efficacy opioid ligands with substantial nociceptin opioid peptide receptor affinity.

J Med Chem. 2014 May 22;57(10):4049-57. doi: 10.1021/jm401964y. Epub 2014 May 9.

Orvinols with mixed kappa/mu opioid receptor agonist activity.

J Med Chem. 2013 Apr 25;56(8):3207-16. doi: 10.1021/jm301543e. Epub 2013 Apr 3.

Structural determinants of opioid and NOP receptor activity in derivatives of buprenorphine.

J Med Chem. 2011 Oct 13;54(19):6531-7. doi: 10.1021/jm2003238. Epub 2011 Sep 7.

Cinnamoyl derivatives of 7alpha-aminomethyl-6,14-endo-ethanotetrahydrothebaine and 7alpha-aminomethyl-6,14-endo-ethanotetrahydrooripavine and related opioid ligands.

J Med Chem. 2007 Oct 18;50(21):5176-82. doi: 10.1021/jm070255o. Epub 2007 Sep 22.

Structural determinants of opioid activity in derivatives of 14-aminomorphinones: effect of substitution in the aromatic ring of cinnamoylaminomorphinones and codeinones.

J Med Chem. 2006 Aug 24;49(17):5333-8. doi: 10.1021/jm0604777.