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Characterization of a region of steric interference at the cannabinoid receptor using the active analog approach

Cite this: J. Med. Chem. 1993, 36, 12, 1761–1771
Publication Date (Print):June 1, 1993
https://doi.org/10.1021/jm00064a010
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    Cited By

    This article is cited by 37 publications.

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    2. Outi M. H. Salo,, Juha R. Savinainen,, Teija Parkkari,, Tapio Nevalainen,, Maija Lahtela-Kakkonen,, Jukka Gynther,, Jarmo T. Laitinen,, Tomi Järvinen, and, Antti Poso. 3D-QSAR Studies on Cannabinoid CB1 Receptor Agonists:  G-Protein Activation as Biological Data. Journal of Medicinal Chemistry 2006, 49 (2) , 554-566. https://doi.org/10.1021/jm0505157
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    8. István Ujváry. Hexahydrocannabinol and closely related semi‐synthetic cannabinoids: A comprehensive review. Drug Testing and Analysis 2024, 16 (2) , 127-161. https://doi.org/10.1002/dta.3519
    9. Matthew Preteroti, Emily T. Wilson, David H. Eidelman, Carolyn J. Baglole. Modulation of pulmonary immune function by inhaled cannabis products and consequences for lung disease. Respiratory Research 2023, 24 (1) https://doi.org/10.1186/s12931-023-02399-1
    10. Matthew W Preteroti, Hussein Traboulsi, Patrick Greiss, Orsolya Lapohos, Gregory J Fonseca, David H Eidelman, Carolyn J Baglole. Receptor‐mediated effects of Δ 9 ‐tetrahydrocannabinol and cannabidiol on the inflammatory response of alveolar macrophages. Immunology & Cell Biology 2023, 101 (2) , 156-170. https://doi.org/10.1111/imcb.12614
    11. Pradeep Paudel, Samir Ross, Xing-Cong Li. Molecular Targets of Cannabinoids Associated with Depression. Current Medicinal Chemistry 2022, 29 (11) , 1827-1850. https://doi.org/10.2174/0929867328666210623144658
    12. Brian F. Thomas. Cannabidiol as a Treatment for Seizures, Convulsions and Epilepsy. 2017, 249-261. https://doi.org/10.1007/978-3-319-54564-6_11
    13. Sumner Burstein. Cannabidiol (CBD) and its analogs: a review of their effects on inflammation. Bioorganic & Medicinal Chemistry 2015, 23 (7) , 1377-1385. https://doi.org/10.1016/j.bmc.2015.01.059
    14. Patricia H. Reggio. Toward the design of cannabinoid CB 1 receptor inverse agonists and neutral antagonists. Drug Development Research 2009, 70 (8) , 585-600. https://doi.org/10.1002/ddr.20337
    15. Dow P. Hurst, Patricia H. Reggio. Models of Cannabinoid Inverse Agonism, Neutral Antagonism, and Agonism: Tools for Rational Drug Design. 2009, 235-278. https://doi.org/10.1007/978-1-59745-503-9_9
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    17. Ankur Kapur, Dow P. Hurst, Daniel Fleischer, Rob Whitnell, Ganesh A. Thakur, Alexandros Makriyannis, Patricia H. Reggio, Mary E. Abood. Mutation Studies of Ser7.39 and Ser2.60 in the Human CB 1 Cannabinoid Receptor: Evidence for a Serine-Induced Bend in CB 1 Transmembrane Helix 7. Molecular Pharmacology 2007, 71 (6) , 1512-1524. https://doi.org/10.1124/mol.107.034645
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    20. Káthia M. Honório, Albérico B. F. da Silva. A study on the influence of molecular properties in the psychoactivity of cannabinoid compounds. Journal of Molecular Modeling 2005, 11 (3) , 200-209. https://doi.org/10.1007/s00894-005-0243-z
    21. Joong‐Youn Shim, William J. Welsh, Allyn C. Howlett. Homology model of the CB 1 cannabinoid receptor: Sites critical for nonclassical cannabinoid agonist interaction. Peptide Science 2003, 71 (2) , 169-189. https://doi.org/10.1002/bip.10424
    22. K.M. Honório, A.B.F. da Silva. A theoretical study on the influence of the frontier orbitals HOMO and LUMO and the size of C4 and C2 substituents in the psychoactivity of cannabinoid compounds. Journal of Molecular Structure: THEOCHEM 2002, 578 (1-3) , 111-117. https://doi.org/10.1016/S0166-1280(01)00690-X
    23. Joong-Youn Shim, Elizabeth R. Collantes, William J. Welsh, Allyn C. Howlett. Unified Pharmacophoric Model for Cannabinoids and Aminoalkylindoles. 2000, 201-206. https://doi.org/10.1007/978-1-4615-4141-7_23
    24. John W. Huffman, John Liddle, Shu Yu, Mie Mie Aung, Mary E. Abood, Jenny L. Wiley, Billy R. Martin. 3-(1′,1′-Dimethylbutyl)-1-deoxy-Δ8-THC and related compounds: synthesis of selective ligands for the CB2 receptor. Bioorganic & Medicinal Chemistry 1999, 7 (12) , 2905-2914. https://doi.org/10.1016/S0968-0896(99)00219-9
    25. Sumner H Burstein. The Cannabinoid Acids. Pharmacology & Therapeutics 1999, 82 (1) , 87-96. https://doi.org/10.1016/S0163-7258(98)00069-2
    26. Allyn C. Howlett. The CB1Cannabinoid Receptor in the Brain. Neurobiology of Disease 1998, 5 (6) , 405-416. https://doi.org/10.1006/nbdi.1998.0215
    27. R. Mechoulam, L. Hanuš, Ester Fride. Towards cannabinoid drugs – revisited. 1998, 199-243. https://doi.org/10.1016/S0079-6468(08)70037-7
    28. D. P. Dolata, A. L. Parrill, W. P. Walters. CLEW: The Generation of Pharmacophore Hypotheses Through Machine Learning. SAR and QSAR in Environmental Research 1998, 9 (1-2) , 53-81. https://doi.org/10.1080/10629369808039149
    29. Nicholas S. Bodor, Ming-ju Huang. Theoretical study of the stereoisomers of tetrahydrocannabinols. International Journal of Quantum Chemistry 1997, 61 (1) , 127-135. https://doi.org/10.1002/(SICI)1097-461X(1997)61:1<127::AID-QUA15>3.0.CO;2-B
    30. D. R. Compton, L. S. Harris, A. H. Lichtman, B. R. Martin. Marihuana. 1996, 83-158. https://doi.org/10.1007/978-3-642-60963-3_3
    31. Yves Gareau, Claude Dufresne, Michel Gallant, Chantal Rochette, Nicole Sawyer, Deborah M. Slipetz, Nathalie Tremblay, Philip K. Weech, Kathleen M. Metters, Marc Labelle. Structure activity relationships of tetrahydrocannabinol analogues on human cannabinoid receptors. Bioorganic & Medicinal Chemistry Letters 1996, 6 (2) , 189-194. https://doi.org/10.1016/0960-894X(95)00573-C
    32. Richard E. Musty, Patricia Reggio, Paul Consroe. A review of recent advances in cannabinoid research and the 1994 international symposium on cannabis and the cannabinoids. Life Sciences 1995, 56 (23-24) , 1933-1940. https://doi.org/10.1016/0024-3205(95)00173-4
    33. P.H. Reggio, R.D. Bramblett, H. Yuknavich, H.H. Seltzman, D.N. Fleming, S.R. Fernando, L.A. Stevenson, R.G. Pertwee. The design, synthesis and testing of desoxy-CBD: Further evidence for a region of steric interference at the cannabinoid receptor. Life Sciences 1995, 56 (23-24) , 2025-2032. https://doi.org/10.1016/0024-3205(95)00185-9
    34. John W. Huffman, W. Kenneth Banner, Grace K. Zoorob, H. Howard Joyner, Patricia H. Reggio, Billy R. Martin, David R. Compton. Stereoselective synthesis of the epimeric Δ7-tetrahydrocannabinols. Tetrahedron 1995, 51 (4) , 1017-1032. https://doi.org/10.1016/0040-4020(94)00995-7
    35. Raphael Mechoulam, Lumir Hanuš, Billy R. Martin. Search for endogenous ligands of the cannabinoid receptor. Biochemical Pharmacology 1994, 48 (8) , 1537-1544. https://doi.org/10.1016/0006-2952(94)90197-X
    36. John W. Huffman, Dong Dai, Billy R. Martin, David R. Compton. Design, Synthesis and Pharmacology of Cannabimimetic Indoles. Bioorganic & Medicinal Chemistry Letters 1994, 4 (4) , 563-566. https://doi.org/10.1016/S0960-894X(01)80155-4
    37. P. H. Reggio. Cannabinoid Receptors and Their Ligands: Ligand—Ligand and Ligand—Receptor Modeling Approaches. , 247-281. https://doi.org/10.1007/3-540-26573-2_8

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