ＣＧＰ‐７９３０とは？わかりやすく解説

CGP-7930
臨床データ
識別子
	IUPAC名 2,6-Di-tert-butyl-4-(3-hydroxy-2,2-dimethyl-propyl)-phenol ;
CAS登録番号	57717-80-3;
PubChem CID	5024764;
IUPHAR/BPS	1079;
ChemSpider	4203613 ;
UNII	ZAM4WWA5Y4;
CompTox; ダッシュボード (EPA)	DTXSID90407620 ;
化学的および物理的データ
化学式	C19H32O2
分子量	292.46 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C)c1cc(CC(C)(C)CO)cc(C(C)(C)C)c1O ;
	InChI InChI=1S/C19H32O2/c1-17(2,3)14-9-13(11-19(7,8)12-20)10-15(16(14)21)18(4,5)6/h9-10,20-21H,11-12H2,1-8H3 ; Key:XLWJPQQFJNGUPA-UHFFFAOYSA-N ;
	(what is this?) (verify)

CGP-7930は、文献で初めて報告されたGABA_B受容体の陽性アロステリック調節因子である^[1]^[2]^[3]^[4]。CGP7930は、GABA_A受容体の陽性アロステリック調節因子であり、カリウムチャネル遮断薬でもある^[5]。

CGP7930はノバルティスによって開発され、科学研究に広く使用されてきた。動物実験では抗不安作用を持ち^[6]^[7]、バクロフェンやGHBなどのGABA_Bアゴニストとの相乗効果を持ち^[8]^[9]、アルコール飲料やコカインの自己投与を減少させる^[10]^[11]。

CNSレビュー：^[12]

合成

化学合成は以下の通りである^[13]：出発物質^[14]：第一段階の生成物^[15]^[16]：

2,6-ジ-tert-ブチルフェノールをホルムアルデヒド、塩基及びメタノールと反応させると、[87-97-8] (2)が得られる。イソブタールデヒドを用いた塩基触媒反応によりCGP-13501（3）が得られる。アルデヒドのヒドリド還元により、第一級アルコールが生成する。

Krysin（ロシア）によれば、2,6-ジ-tert-ブチルフェノール（英語版）はオートクレーブ内で苛性ソーダを用いてネオペンチルグリコール（英語版）と反応させる。一段階反応であるにもかかわらず、収率はわずか15%と報告されている^[17]。

出典

^ “Positive allosteric modulation of native and recombinant gamma-aminobutyric acid(B) receptors by 2,6-Di-tert-butyl-4-(3-hydroxy-2,2-dimethyl-propyl)-phenol (CGP7930) and its aldehyde analog CGP13501”. Molecular Pharmacology 60 (5): 963–71. (November 2001). PMID 11641424.
^ “The heptahelical domain of GABA(B2) is activated directly by CGP7930, a positive allosteric modulator of the GABA(B) receptor”. The Journal of Biological Chemistry 279 (28): 29085–91. (July 2004). doi:10.1074/jbc.M400930200. PMC 2557059. PMID 15126507.
^ “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. (June 2006). doi:10.1124/jpet.105.099176. PMID 16507713.
^ “CGP7930: a positive allosteric modulator of the GABAB receptor”. CNS Drug Reviews 13 (3): 308–16. doi:10.1111/j.1527-3458.2007.00021.x. PMC 6494120. PMID 17894647.
^ “CGP7930 - An allosteric modulator of GABABRs, GABAARs and inwardly-rectifying potassium channels”. Neuropharmacology 109644. (July 2023). doi:10.1016/j.neuropharm.2023.109644. PMID 37422181.
^ “Effects of GABAB receptor ligands in animal tests of depression and anxiety”. Pharmacological Reports 59 (6): 645–55. PMID 18195453.
^ “Evaluation of the anxiolytic-like profile of the GABAB receptor positive modulator CGP7930 in rodents”. Neuropharmacology 54 (5): 854–62. (April 2008). doi:10.1016/j.neuropharm.2008.01.004. PMID 18328507.
^ “In vivo effectiveness of CGP7930, a positive allosteric modulator of the GABAB receptor”. European Journal of Pharmacology 504 (3): 213–6. (November 2004). doi:10.1016/j.ejphar.2004.10.008. PMID 15541424.
^ “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. (September 2008). doi:10.1111/j.1440-1681.2008.04948.x. PMID 18430050.
^ “The GABA(B) receptor allosteric modulator CGP7930, like baclofen, reduces operant self-administration of ethanol in alcohol-preferring rats”. Neuropharmacology 50 (5): 632–9. (April 2006). doi:10.1016/j.neuropharm.2005.11.011. PMID 16406445.
^ “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. (November 2007). doi:10.1016/j.ejphar.2007.07.048. PMID 17698060.
^ 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).
^ “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. (November 1957). doi:10.1021/jo01362a033.
^ “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. (February 2013). 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.

[1] “Positive allosteric modulation of native and recombinant gamma-aminobutyric acid(B) receptors by 2,6-Di-tert-butyl-4-(3-hydroxy-2,2-dimethyl-propyl)-phenol (CGP7930) and its aldehyde analog CGP13501”. Molecular Pharmacology 60 (5): 963–71. (November 2001). PMID 11641424.

[2] “The heptahelical domain of GABA(B2) is activated directly by CGP7930, a positive allosteric modulator of the GABA(B) receptor”. The Journal of Biological Chemistry 279 (28): 29085–91. (July 2004). doi:10.1074/jbc.M400930200. PMC 2557059. PMID 15126507.

[3] “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. (June 2006). doi:10.1124/jpet.105.099176. PMID 16507713.

[4] “CGP7930: a positive allosteric modulator of the GABAB receptor”. CNS Drug Reviews 13 (3): 308–16. doi:10.1111/j.1527-3458.2007.00021.x. PMC 6494120. PMID 17894647.

[5] “CGP7930 - An allosteric modulator of GABABRs, GABAARs and inwardly-rectifying potassium channels”. Neuropharmacology 109644. (July 2023). doi:10.1016/j.neuropharm.2023.109644. PMID 37422181.

[6] “Effects of GABAB receptor ligands in animal tests of depression and anxiety”. Pharmacological Reports 59 (6): 645–55. PMID 18195453.

[7] “Evaluation of the anxiolytic-like profile of the GABAB receptor positive modulator CGP7930 in rodents”. Neuropharmacology 54 (5): 854–62. (April 2008). doi:10.1016/j.neuropharm.2008.01.004. PMID 18328507.

[8] “In vivo effectiveness of CGP7930, a positive allosteric modulator of the GABAB receptor”. European Journal of Pharmacology 504 (3): 213–6. (November 2004). doi:10.1016/j.ejphar.2004.10.008. PMID 15541424.

[9] “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. (September 2008). doi:10.1111/j.1440-1681.2008.04948.x. PMID 18430050.

[10] “The GABA(B) receptor allosteric modulator CGP7930, like baclofen, reduces operant self-administration of ethanol in alcohol-preferring rats”. Neuropharmacology 50 (5): 632–9. (April 2006). doi:10.1016/j.neuropharm.2005.11.011. PMID 16406445.

[11] “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. (November 2007). doi:10.1016/j.ejphar.2007.07.048. PMID 17698060.

[12] 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.

[13] 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.

[14] Richard Henry Kline, EP0027426 (1983 to The Goodyear Tire & Rubber Company).

[15] “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. (November 1957). doi:10.1021/jo01362a033.

[16] “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. (February 2013). doi:10.1134/S0022476613010368.

[17] 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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分子式：	C₁₉H₃₂O₂
その他の名称：	2,6-Di-tert-butyl-4-(2,2-dimethyl-3-hydroxypropyl)phenol、CGP-7930
体系名：	2,6-ジ-tert-ブチル-4-(2,2-ジメチル-3-ヒドロキシプロピル)フェノール


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ＣＧＰ‐７９３０とは？ わかりやすく解説

ＣＧＰ‐７９３０

CGP-7930

合成

出典

「ＣＧＰ‐７９３０」の関連用語

ＣＧＰ‐７９３０とは？わかりやすく解説