Synthesis of Methyl Substituted 6-Hydroxychromans, Model Compounds of Tocopherols.

Nilsson, Jonas; Sievertsson, Hans; Selander, Hans; Smidsrød, Olav

doi:10.3891/acta.chem.scand.22-3160

Cited by 59 publications

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“…2,2‐Dimethyl‐6‐hydroxychroman ( 2 ) was synthesized following a procedure reported by Nilsson et al . as depicted in Scheme . Hydroquinone ( 1 ) was treated with 2‐methyl‐3‐buten‐2‐ol in aqueous formic acid (85%) at 80°C for 6 h to afford hydroxyl chroman 2 in 30% yield after purification using column chromatography.…”

Section: Resultssupporting

confidence: 53%

“…The direct (one step) synthesis of 2,2‐dimethylchromans is usually achieved by acid or base‐catalyzed condensation reaction of phenolic precursors with prenylsynthons such as allylic alcohols, isoprene, dienes, and halides, and others . In the present work, we have used 2‐methyl‐3‐buten‐2‐ol as prenylsynthon for construction of 2,2‐dimethylchroman ring.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Evaluation of 2,2‐Dimethylchroman Derivatives as Inhibitors of ICAM‐1 Expression on Human Endothelial Cells

Dhawan

Balwani

Prasad

et al. 2014

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).We herein report the synthesis of novel 2,2-dimethylchroman analogs and their effect on the modulation of tumor necrosis factor-a-induced expression of intercellular adhesion molecule-1 in human endothelial cells. These compounds were found to be potent inhibitors of tumor necrosis factor-a-induced expression of intercellular adhesion molecule-1 on human endothelial cells at very low concentration. The structure-activity relationship of these compounds has been studied. The IC 50 and maximum tolerable dose value of the lead compound 7d (X═NH, R═4Cl) of this study was found to be 9.5 and 150 mM, respectively. The present results indicate that our novel compound is potentially effective and therefore could be useful for further pharmaceutical studies.

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Section: Resultssupporting

confidence: 53%

Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of 2,2‐Dimethylchroman Derivatives as Inhibitors of ICAM‐1 Expression on Human Endothelial Cells

Dhawan

Balwani

Prasad

et al. 2014

Journal of Heterocyclic Chem

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“…Briefly, 5-ethoxymethyl-2,2, 7,8-tetramethyl-6-hydroxychroman (6), 5-propoxymethyl-2,2,7,8-tetramethyl-6-hydroxychroman (7), 5-buthoxymethyl-2,2,7,8-tetramethyl-6-hydroxychroman (8), and 5-pentyloxymethyl-2,2,7,8-tetramethyl-6-hydroxychroman (9) were prepared by reactions of 2,2,5,7,8-pentamethyl-6-hydroxychroman and the corresponding alcohols using t-butylhydroperoxide according to published methods [14]. 2,2,5,7,8-Pentamethyl-6-hydroxychroman was prepared according to the method of Nilsson et al [15]. Tocols (tocol (5), 5,7-dimethyltocol (10), 5,7-diethyltocol (11), 5,7-diisopropyltocol (12), 7-t-butyl-5-methyltocol (13), 8-t-butyl-5-methyltocol (14), and 7-t-butyl-5-isopropyltocol (15)) were synthesized by condensation of isophytol with the corresponding alkylhydroquinones, as reported in a previous paper [11].…”

Section: Experimental D-␣- D-␤- D-␥ - and D-␦-tocsmentioning

confidence: 99%

Why is the order reversed? peroxyl‐scavenging activity and fats‐and‐oils protecting activity of vitamin E

Mukai

Noborio

Nagaoka

2005

Int J of Chemical Kinetics

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The orders of relative tocopherol biopotency, scavenging activity of lipid peroxyl radicals, and quenching activity of singlet oxygen are as follows: α-tocopherol > β-tocopherol ≥ γ-tocopherol > δ-tocopherol. However, the reverse is the case for the activity to protect fats and oils from oxidation: α-tocopherol < β-tocopherol < γ-tocopherol < δ-tocopherol. The reason for this reverse has been studied by measuring weight gains of solutions including methyl linoleate and various antioxidants at daily intervals. Antioxidant activity is expressed as an induction period in days. Induction periods are compared with the second-order rate constants for scavenging of an aroxyl radical by the antioxidants. A plot of the logarithm of the secondorder rate constant vs. the induction period is found to give a good linear fit, and the slope is negative. From these results, it is considered that the larger the peroxyl-radical-scavenging activity of a tocopherol, the more favorable the production of the tocopheroxyl radical, and thus the more efficient the oxidation of fats and oils by the tocopheroxyl radical. This is not the case for tocopherols in vivo, because vitamin C and ubiquinol reduce tocopheroxyl radicals formed from tocopherols. C 2005 Wiley Periodicals, Inc. Int J Chem Kinet 37: [605][606][607][608][609][610] 2005

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“…Endothelial cell growth factor (ECGF) was isolated from newborn-bovine brains by the method of Lobb and Fett (7). 2,2,5,7,8-Pentamethylchroman-6-ol was synthesized by the method of Nilsson et al (8). Linoleic acid hydroperoxide (13-hydroperoxy-9,11-octadecadienoic acid) was prepared as described previously (9).…”

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confidence: 99%

Protective effect of vitamin E on linoleic acid hydroperoxide‐induced injury to human endothelial cells

Kaneko

Nakano

Matsuo

1991

Lipids

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The protective effects of vitamin E (alpha-tocopherol) and its model compounds, which act as antioxidants, on linoleic acid hydroperoxide-induced injury to human umbilical vein endothelial cells were examined. When incubated at 50 microM with endothelial cells at 37 degrees C for 24 hr, alpha-tocopherol protected the cells from injury, and 2,2,5,7,8-pentamethylchroman-6-ol showed a similar protective effect. Trolox C, a water-soluble vitamin E model compound, had no protective effect. Tocol, a poor antioxidant, proved toxic. During preincubation, alpha-tocopherol was incorporated into the cells at 16.6 nmol/mg protein, while the pentamethylchromanol was incorporated at 0.5 nmol/mg protein; Trolox C was not incorporated at all. The results suggest that agents having both high antioxidant activity and lipophilicity can protect endothelial cells from linoleic acid hydroperoxide-induced injury.

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Synthesis of Methyl Substituted 6-Hydroxychromans, Model Compounds of Tocopherols.

Cited by 59 publications

References 0 publications

Synthesis and Evaluation of 2,2‐Dimethylchroman Derivatives as Inhibitors of ICAM‐1 Expression on Human Endothelial Cells

Synthesis and Evaluation of 2,2‐Dimethylchroman Derivatives as Inhibitors of ICAM‐1 Expression on Human Endothelial Cells

Why is the order reversed? peroxyl‐scavenging activity and fats‐and‐oils protecting activity of vitamin E

Protective effect of vitamin E on linoleic acid hydroperoxide‐induced injury to human endothelial cells

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