CGP7930 was developed inNovartis and has been used extensively for scientific research. It hasanxiolytic effects in animal studies,[6][7] and has a synergistic effect with GABAB agonists such asbaclofen andGHB,[8][9] as well as reducing self-administration ofalcoholic drinks andcocaine.[10][11]
The chemical synthesis has been described:[13] Starting material:[14] Product of first step:[15][16]
2,6-Di-tert-butylphenol is treated with formaldehyde, base and methanol to give [87-97-8] (2). Base catalyzed reaction with isobutaldehyde gives CGP-13501 (3). Hydride reduction of the aldehyde gives the primary alcohol.
According to Krysin (Russia),2,6-Di-tert-butylphenol is reacted withNeopentyl glycol with lye in an autoclave. Although 1 step reaction, yield was quoted as merely 15%.[17]
^Chen Y, Menendez-Roche N, Sher E (June 2006). "Differential modulation by the GABAB receptor allosteric potentiator 2,6-di-tert-butyl-4-(3-hydroxy-2,2-dimethylpropyl)-phenol (CGP7930) of synaptic transmission in the rat hippocampal CA1 area".The Journal of Pharmacology and Experimental Therapeutics.317 (3):1170–7.doi:10.1124/jpet.105.099176.PMID16507713.
^Frankowska M, Filip M, Przegaliński E. "Effects of GABAB receptor ligands in animal tests of depression and anxiety".Pharmacological Reports.59 (6):645–55.PMID18195453.
^Jacobson LH, Cryan JF (April 2008). "Evaluation of the anxiolytic-like profile of the GABAB receptor positive modulator CGP7930 in rodents".Neuropharmacology.54 (5):854–62.doi:10.1016/j.neuropharm.2008.01.004.PMID18328507.
^Carai MA, Colombo G, Froestl W, Gessa GL (November 2004). "In vivo effectiveness of CGP7930, a positive allosteric modulator of the GABAB receptor".European Journal of Pharmacology.504 (3):213–6.doi:10.1016/j.ejphar.2004.10.008.PMID15541424.
^Parker DA, Marino V, Ong J, Puspawati NM, Prager RH (September 2008). "The CGP7930 analogue 2,6-di-tert-butyl-4-(3-hydroxy-2-spiropentylpropyl)-phenol (BSPP) potentiates baclofen action at GABA(B) autoreceptors".Clinical and Experimental Pharmacology & Physiology.35 (9):1113–5.doi:10.1111/j.1440-1681.2008.04948.x.PMID18430050.
^Liang JH, Chen F, Krstew E, Cowen MS, Carroll FY, Crawford D, et al. (April 2006). "The GABA(B) receptor allosteric modulator CGP7930, like baclofen, reduces operant self-administration of ethanol in alcohol-preferring rats".Neuropharmacology.50 (5):632–9.doi:10.1016/j.neuropharm.2005.11.011.PMID16406445.
^Filip M, Frankowska M, Przegaliński E (November 2007). "Effects of GABA(B) receptor antagonist, agonists and allosteric positive modulator on the cocaine-induced self-administration and drug discrimination".European Journal of Pharmacology.574 (2–3):148–57.doi:10.1016/j.ejphar.2007.07.048.PMID17698060.
^Ong, J., Kerr, D. I. B. (September 2005). "Clinical Potential of GABA B Receptor Modulators". CNS Drug Reviews. 11 (3): 317–334. doi:10.1111/j.1527-3458.2005.tb00049.x.
^Kerr, David I. B.; Khalafy, Jabbar; Ong, Jennifer; Perkins, Michael V.; Prager, Rolf H.; Puspawati, Ni Made; Rimaz, Mehdi (2006). "Synthesis and Biological Activity of Allosteric Modulators of GABABReceptors, Part 2. 3-(2,6-Bis-tert-butyl-4-hydroxyphenyl)propanols". Australian Journal of Chemistry. 59 (7): 457. doi:10.1071/CH06164.
^Richard Henry Kline, EP0027426 (1983 to The Goodyear Tire & Rubber Company).
^Kharasch, M. S., Joshi, B. S. (November 1957). "Reactions of Hindered Phenols. I. Reactions of 4,4'-Dihydroxy-3,5,3',5'-tetra-tert-butyl Diphenylmethane *".The Journal of Organic Chemistry.22 (11):1435–1438.doi:10.1021/jo01362a033.
^Rimaz, M., Khalafy, J., Badali, M., Ślepokura, K., Lis, T., Souldozi, A., Ramazani, A., Joo, S. W. (February 2013). "Single crystal X-ray structure of 2,6-di-tert-butyl-4-(3-(4-chlorophenyl)-4-methyl-4,5-dihydroisoxazol-5-yl)phenol 1,4-dioxane hemisolvate".Journal of Structural Chemistry.54 (1):217–222.doi:10.1134/S0022476613010368.
^Krysin, A. P.; Pustovskikh, I. I.; Koptyug, V. A. (2010). "Synthesis of 4-(ω-hydroxyalkyl)-2,6-di-tert-butylphenols and the properties of related sulfides". Russian Journal of General Chemistry. 80 (10): 2001–2006. doi:10.1134/S1070363210100208.
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