1006-59-3Relevant articles and documents
Cyclohexanol analogues are positive modulators of GABAA receptor currents and act as general anaesthetics in vivo
Hall, Adam C.,Griffith, Theanne N.,Tsikolia, Maia,Kotey, Francesca O.,Gill, Nikhila,Humbert, Danielle J.,Watt, Erin E.,Yermolina, Yuliya A.,Goel, Shikha,El-Ghendy, Bahaa,Hall, C. Dennis
, p. 175 - 181 (2011)
GABAA receptors meet all the pharmacological criteria required to be considered important general anaesthetic targets. In the following study, the modulatory effects of various commercially available and novel cyclohexanols were investigated on recombinant human γ-aminobutyric acid (GABA A, α1β2γ2s) receptors expressed in Xenopus oocytes, and compared to the modulatory effects on GABA currents observed with exposures to the intravenous anaesthetic agent, propofol. Submaximal EC20 GABA currents were typically enhanced by co-applications of 3-300 μM cyclohexanols. For instance, at 30 μM 2,6-diisopropylcyclohexanol (a novel compound) GABA responses were increased ～ 3-fold (although similar enhancements were achieved at 3 μM propofol). As regards rank order for modulation by the cyclohexanol analogues at 30 μM, the % enhancements for 2,6-dimethylcyclohexanol ～ 2,6-diethylcyclohexanol ～ 2,6-diisopropylcyclohexanol ～ 2,6-di-sec-butylcyclohexanol ?2,6-di-tert-butylcyclohexanol ～ 4-tert-butylcyclohexanol > cyclohexanol ～ cyclopentanol ～ 2-methylcyclohexanol. We further tested the potencies of the cyclohexanol analogues as general anaesthetics using a tadpole in vivo assay. Both 2,6-diisopropylcyclohexanol and 2,6- dimethylcyclohexanol were effective as anaesthetics with EC50s of 14.0 μM and 13.1 μM respectively, while other cyclohexanols with bulkier side chains were less potent. In conclusion, our data indicate that cyclohexanols are both positive modulators of GABAA receptors currents and anaesthetics. The positioning and size of the alkyl groups at the 2 and 6 positions on the cyclohexanol ring were critical determinants of activity.
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Adkins,Richards,Davis
, p. 1320,1322 (1941)
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QSAR for the cytotoxicity of 2-alkyl or 2,6-dialkyl, 4-X-phenols: The nature of the radical reaction
Selassie, Cynthia D.,Verma, Rajeshwar P.,Kapur, Sanjay,Shusterman, Alan J.,Hansch, Corwin
, p. 1112 - 1117 (2002)
In a continuation of studies on the radical mediated toxicity of phenols to leukemia cells, a set of di- and tri-substituted phenols with mostly alkyl substituents in the ortho position were examined. These analogs are similar in structure to the commercial antioxidants BHA and BHT. A QSAR analysis of their growth inhibitory constants led to the formulation of this simple but unusual equation based on 18 congeners: log 1/C = -0.47Es-2 + 2.42RR + 2.43; r3 = 0.934 ES-2 is the Taft steric parameter for the larger of the two ortho substituents while ER is Otsu's radical parameter, which was originally defined to correlate radical reactions.
Selective catalytic conversion of guaiacol to phenols over a molybdenum carbide catalyst
Ma, Rui,Cui, Kai,Yang, Le,Ma, Xiaolei,Li, Yongdan
supporting information, p. 10299 - 10301 (2015/06/25)
An activated carbon supported α-molybdenum carbide catalyst (α-MoC1-x/AC) showed remarkable activity in the selective deoxygenation of guaiacol to substituted mono-phenols in low carbon number alcohol solvents. Combined selectivities of up to 85% for phenol and alkylphenols were obtained at 340°C for α-MoC1-x/AC at 87% conversion in supercritical ethanol. The reaction occurs via consecutive demethylation followed by a dehydroxylation route instead of a direct demethoxygenation pathway.
