J W Huffman

Summary

Affiliation: Clemson University
Country: USA

Publications

  1. ncbi Synthesis of a tetracyclic, conformationally constrained analogue of delta8-THC
    J W Huffman
    H L Hunter Chemistry Laboratory, Clemson University, SC 29634 1905, USA
    Bioorg Med Chem 6:2281-8. 1998
  2. ncbi Structure-activity relationships for 1',1'-dimethylalkyl-Delta8-tetrahydrocannabinols
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem 11:1397-410. 2003
  3. ncbi Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem 13:89-112. 2005
  4. ncbi Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes
    J W Huffman
    H L Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    Curr Med Chem 12:1395-411. 2005
  5. ncbi 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem Lett 15:4110-3. 2005
  6. ncbi CB2 receptor ligands
    J W Huffman
    Howard L Hunter Chemistry Laboratory, Clemson University, South Carolina 29634 0973, USA
    Mini Rev Med Chem 5:641-9. 2005
  7. ncbi Enantioselective synthesis of 1-methoxy- and 1-deoxy-2'-methyl-delta8-tetrahydrocannabinols: new selective ligands for the CB2 receptor
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem 14:247-62. 2006
  8. ncbi 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem Lett 16:5432-5. 2006
  9. pmc Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem 16:322-35. 2008
  10. pmc Synthesis and pharmacology of 1-methoxy analogs of CP-47,497
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, United States
    Bioorg Med Chem 18:5475-82. 2010

Research Grants

Collaborators

Detail Information

Publications26

  1. ncbi Synthesis of a tetracyclic, conformationally constrained analogue of delta8-THC
    J W Huffman
    H L Hunter Chemistry Laboratory, Clemson University, SC 29634 1905, USA
    Bioorg Med Chem 6:2281-8. 1998
    ..LiA1H4/A1C1(3) reduction of 20 provided 2. Cannabinoid 2 has relatively low affinity for the cannabinoid brain receptor (Ki = 703+/-98 nM)...
  2. ncbi Structure-activity relationships for 1',1'-dimethylalkyl-Delta8-tetrahydrocannabinols
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem 11:1397-410. 2003
    ....
  3. ncbi Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem 13:89-112. 2005
    ..Docking studies indicated that the CB(1) receptor affinities of these compounds were consistent with their aromatic stacking interactions in the aromatic microdomain of the CB(1) receptor...
  4. ncbi Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes
    J W Huffman
    H L Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634 0973, USA
    Curr Med Chem 12:1395-411. 2005
    ..There is some evidence that the indoles bind to a somewhat different site on the receptor than traditional cannabinoids, and interact with the receptor primarily by aromatic stacking...
  5. ncbi 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem Lett 15:4110-3. 2005
    ..GTPgammaS determinations indicate that both compounds are highly efficacious agonists at the CB1 receptor and partial agonists at the CB2 receptor...
  6. ncbi CB2 receptor ligands
    J W Huffman
    Howard L Hunter Chemistry Laboratory, Clemson University, South Carolina 29634 0973, USA
    Mini Rev Med Chem 5:641-9. 2005
    ..This review will describe the current status of the results of these studies and discuss the SAR for these classes of ligands...
  7. ncbi Enantioselective synthesis of 1-methoxy- and 1-deoxy-2'-methyl-delta8-tetrahydrocannabinols: new selective ligands for the CB2 receptor
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem 14:247-62. 2006
    ..In the 1-deoxy-3-(2'-methylalkyl)-delta8-THC series, the 2'S-methyl compounds in general have greater affinity for the CB2 receptor than the corresponding 2'R isomers...
  8. ncbi 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem Lett 16:5432-5. 2006
    ..The high affinities of these pyrrole derivatives relative to JWH-030 (1, R=C(5)H(11)) support the hypothesis that these pyrroles interact with the CB(1) receptor primarily by aromatic stacking...
  9. pmc Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem 16:322-35. 2008
    ..The interactions of these 1-deoxy nontraditional cannabinoids with the CB(2) receptor are discussed...
  10. pmc Synthesis and pharmacology of 1-methoxy analogs of CP-47,497
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, United States
    Bioorg Med Chem 18:5475-82. 2010
    ..Modeling and receptor docking studies were carried out, which provide a rationalization for the weak affinities of these compounds for either receptor...
  11. ncbi 3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB(1) cannabinoid receptor
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, 29634 0973, Clemson, SC, USA
    Bioorg Med Chem 11:539-49. 2003
    ....
  12. pmc 1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Δ(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, United States
    Bioorg Med Chem 18:7809-15. 2010
    ..All of these compounds showed selectivity for the CB(2) receptor and one of them, 1-bromo-1-deoxy-3-(1',1'-dimethylhexyl)-Δ(8)-tetrahydrocannabinol (10), exhibits 52-fold selectivity for this receptor with good (28nM) affinity...
  13. ncbi Synthesis and pharmacology of the isomeric methylheptyl-delta8-tetrahydrocannabinols
    J W Huffman
    Howard L Hunter Laboratory, Clemson University, SC 29634 1905, USA
    Bioorg Med Chem 6:2383-96. 1998
    ..The 1'-, 2'- and 3'-methylheptyl analogues (3-5) are considerably more potent than delta8-THC. The 4'-, 5'- and 6'-methylheptyl isomers (6-8) are approximately equal in potency to delta8-THC...
  14. ncbi 1-Methoxy-, 1-deoxy-11-hydroxy- and 11-hydroxy-1-methoxy-Delta(8)-tetrahydrocannabinols: new selective ligands for the CB2 receptor
    John W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 1905, USA
    Bioorg Med Chem 10:4119-29. 2002
    ....
  15. ncbi 3-(1',1'-Dimethylbutyl)-1-deoxy-delta8-THC and related compounds: synthesis of selective ligands for the CB2 receptor
    J W Huffman
    Howard L Hunter Laboratory, Clemson University, SC 29634 1905, USA
    Bioorg Med Chem 7:2905-14. 1999
    ..3-(1',1'-Dimethylbutyl)-1-deoxy-delta8-THC (2, n = 2) has very high affinity for the CB2 receptor (Ki = 3.4 +/- 1.0 nM) and little affinity for the CB1 receptor (Ki = 677 +/- 132 nM)...
  16. ncbi Synthesis and pharmacology of a hybrid cannabinoid
    J W Huffman
    Howard L Hunter Laboratory, Clemson University, SC 29634 1905, USA
    Bioorg Med Chem 8:439-47. 2000
    ..The hybrid cannabinoid had affinity for the CB1 receptor approximately equal to that of delta8-THC (Ki = 19.3+/-3 nM), and shows comparable potency in vivo...
  17. ncbi A pyridone analogue of traditional cannabinoids. A new class of selective ligands for the CB(2) receptor
    J W Huffman
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 1905, USA
    Bioorg Med Chem 9:2863-70. 2001
    ..Neither alcohol 5 nor 21 have significant affinity for the CB(1) receptor (K(i) > 970 nM), but both have moderately high affinity for the CB(2) receptor (K(i) < 60 nM)...
  18. ncbi The search for selective ligands for the CB2 receptor
    J W Huffman
    Howard L Hunter Chemistry Laboratory, Clemson University, Box 341905, Clemson, South Carolina 29634 1905, USA
    Curr Pharm Des 6:1323-37. 2000
    ..This review will describe the current status of the results of these studies and discuss the SAR for both these classes of ligands...
  19. ncbi Synthesis and pharmacology of 11-nor-1-methoxy-9-hydroxyhexahydrocannabinols and 11-nor-1-deoxy-9-hydroxyhexahydrocannabinols: new selective ligands for the cannabinoid CB2 receptor
    Karla Sue C Marriott
    Howard L Hunter Laboratory, Clemson University, Clemson, SC 29634 0973, USA
    Bioorg Med Chem 14:2386-97. 2006
    ..3 nM. In general, the stereochemistry of the 9-hydroxy group is important and the beta-orientation enhances both CB2 receptor affinity and selectivity...
  20. ncbi Paradoxical pharmacological effects of deoxy-tetrahydrocannabinol analogs lacking high CB1 receptor affinity
    Jenny L Wiley
    Department of Pharmacology and Toxicology, Virginia Commonwealth University, Richmond, Virg, USA
    Pharmacology 66:89-99. 2002
    ..In addition, some of these analogs may be very low efficacy agonists at CB(1) receptors that act as full agonists in vivo, but lack the ability to displace high affinity and high efficacy binding ligands in vitro...
  21. ncbi Decrease in efficacy and potency of nonsteroidal anti-inflammatory drugs by chronic delta(9)-tetrahydrocannabinol administration
    Rene Anikwue
    Department of Pharmacology and Toxicology, Medical College of Virginia, Virginia Commonwealth University, Richmond, USA
    J Pharmacol Exp Ther 303:340-6. 2002
    ..Based upon these data, we hypothesize that human subjects who are chronic users of Delta(9)-THC may not respond to analgesic treatment with the above NSAIDs...
  22. ncbi Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor
    Karla Sue C Marriott
    Department of Natural Sciences and Mathematics, Savannah State University, Savannah, GA 31404, USA
    Curr Top Med Chem 8:187-204. 2008
    ..This review will discuss the current advances and recent results in the structure-activity relationships (SAR) of selective ligands for the cannabinoid CB(2) receptor...
  23. pmc Sensitivity to delta9-tetrahydrocannabinol is selectively enhanced in beta-arrestin2 -/- mice
    Christopher S Breivogel
    Department of Pharmaceutical Sciences, Campbell University School of Pharmacy Buies Creek, North Carolina 27506, USA
    Behav Pharmacol 19:298-307. 2008
    ..These data demonstrate that beta-arrestin2 may regulate cannabinoid CB1 receptor sensitivity in an agonist-specific manner...
  24. pmc Inhibition of skin tumor growth and angiogenesis in vivo by activation of cannabinoid receptors
    M Llanos Casanova
    Project on Cellular and Molecular Biology and Gene Therapy, Centro de Investigaciones Energeticas, Medioambientales y Tecnologicas, Madrid, Spain
    J Clin Invest 111:43-50. 2003
    ..Abrogation of EGF-R function was also observed in cannabinoid-treated tumors. These results support a new therapeutic approach for the treatment of skin tumors...
  25. pmc CB2-receptor stimulation attenuates TNF-alpha-induced human endothelial cell activation, transendothelial migration of monocytes, and monocyte-endothelial adhesion
    Mohanraj Rajesh
    Section on Oxidative Stress Tissue Injury, Laboratory of Physiological Studies, National Institute on Alcohol Abuse and Alcoholism, National Institutes of Health, Bethesda, Maryland 20892 9413, USA
    Am J Physiol Heart Circ Physiol 293:H2210-8. 2007
    ....
  26. ncbi Inhibition of tumor angiogenesis by cannabinoids
    Cristina Blazquez
    Department of Biochemistry and Molecular Biology I, School of Biology, Complutense University, Madrid, Spain
    FASEB J 17:529-31. 2003
    ..Inhibition of tumor angiogenesis may allow new strategies for the design of cannabinoid-based antitumoral therapies...

Research Grants21

  1. Synthesis of Cannabinoid Receptor Ligands
    John Huffman; Fiscal Year: 2005
    ..A number of new classical cannabinoids will be synthesized, including additional 1',2'-dimethylheptyl-delta8-tetrahydrocannabinol analogues and the six geminally disubstituted dimethylheptyl-delta8-tetrahydrocannabinols. ..
  2. SYNTHESIS OF CANNABINOIDS, ANALOGUES AND METABOLITES
    John Huffman; Fiscal Year: 1993
    ..Some polar cannabinoid analogues will be synthesized, including phosphate esters from several hydroxylated THC metabolites and analogues...
  3. SYNTHESIS OF CANNABINOIDS, ANALOGUES AND METABOLITES
    John Huffman; Fiscal Year: 2009
    ..There a possibility that these metabolites may be contributing to the enhanced potency of cannabinoids with a dimethylheptyl side chain. ..