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Jean-marie Aubry - One of the best experts on this subject based on the ideXlab platform.
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Asymmetric Iodoetherification of Isosorbide-Derived Glycals: A Regio- and Stereoselective Access to a Variety of O-Substituted Isosorbide Derivatives
Proceedings, 2019Co-Authors: Christophe Berini, Aurélie Lavergne, Valérie Molinier, Stéphane Lebrun, Jean-marie Aubry, Eric DeniauAbstract:Isosorbide is a competitive starting material for various valuable derivatives by functionalization and/or substitution since it is a renewable and carbon neutral material that is produced on an industrial scale from sorbitol. A set of O-alkyl- or O-arylated beta-iodo ethers has been synthesized from Isosorbide. The key step was the iodoetherification of Isosorbide-derived glycals with a variety of oxygenated nucleophiles in the presence of N-iodosuccinimide. trans-Iodo ethers and acetate were obtained in good yields and the removal of iodide affords Isosorbide derivatives. The usefulness of this new approach is illustrated by the synthesis of a surfactant having a dimer of Isosorbide as hydrophilic group and by the preparation of a structurally unusual bicyclic anhydro carbohydrate.
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iodoetherification of Isosorbide derived glycals access to a variety of o alkyl or o aryl Isosorbide derivatives
European Journal of Organic Chemistry, 2013Co-Authors: Christophe Berini, Aurélie Lavergne, Valérie Molinier, Eric Deniau, Frédéric Capet, Jean-marie AubryAbstract:A set of O-alkylated or O-arylated β-iodo ethers has been synthesized from Isosorbide. Isosorbide is a competitive starting material for various valuable derivatives by functionalization and/or substitution since it is a renewable and carbon neutral material that is produced on an industrial scale from sorbitol. The key step was the iodoetherification of Isosorbide-derived glycals with a variety of oxygenated nucleophiles in the presence of N-iodosuccinimide. trans-Iodo ethers and acetate were obtained in good yields and the removal of iodide affords Isosorbide derivatives. The usefulness of this new approach is illustrated by the synthesis of a surfactant having a dimer of Isosorbide as hydrophilic group and by the preparation of a structurally unusual bicyclic anhydro carbohydrate.
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Iodoetherification of Isosorbide‐Derived Glycals: Access to a Variety of O‐Alkyl or O‐Aryl Isosorbide Derivatives
European Journal of Organic Chemistry, 2013Co-Authors: Christophe Berini, Aurélie Lavergne, Valérie Molinier, Eric Deniau, Frédéric Capet, Jean-marie AubryAbstract:A set of O-alkylated or O-arylated β-iodo ethers has been synthesized from Isosorbide. Isosorbide is a competitive starting material for various valuable derivatives by functionalization and/or substitution since it is a renewable and carbon neutral material that is produced on an industrial scale from sorbitol. The key step was the iodoetherification of Isosorbide-derived glycals with a variety of oxygenated nucleophiles in the presence of N-iodosuccinimide. trans-Iodo ethers and acetate were obtained in good yields and the removal of iodide affords Isosorbide derivatives. The usefulness of this new approach is illustrated by the synthesis of a surfactant having a dimer of Isosorbide as hydrophilic group and by the preparation of a structurally unusual bicyclic anhydro carbohydrate.
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Aqueous phase behavior of Isosorbide-based non-ionic surfactants
Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2012Co-Authors: Aurélie Lavergne, Valérie Molinier, Ying Zhu, Jean-marie AubryAbstract:Abstract Three non-ionic surfactants have been synthesized from Isosorbide, a readily available molecule from renewable resources. As Isosorbide is a rigid diol, it allows grafting an aliphatic chain on one hydroxyl and various hydrophilic heads on the other one, thus acting as a rigid hydrophilic linker. In this study, the three surfactants possess a dodecyl alkyl chain and triethyleneglycol and glycerol have been coupled to Isosorbide to provide the non-ionic polar groups. The effect of the insertion of an Isosorbide moiety has been evaluated through the study of the aqueous phase behaviors of the compounds and particularly the formation of lyotropic liquid crystal phases.
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Solubilizing and Hydrotropic Properties of Isosorbide Monoalkyl- and Dimethyl-Ethers
Journal of Surfactants and Detergents, 2009Co-Authors: Morgan Durand, Valérie Molinier, Thierry Féron, Jean-marie AubryAbstract:Isosorbide is a diol readily obtained from starch that can be used as a polar building block for the synthesis of derivatives ranging from solvents to surfactants: dimethyl Isosorbide (DMI) is a “sustainable solvent” already on the market, used notably in cosmetic and pharmaceutical formulations; monoalkyl derivatives of Isosorbide are non-ionic hydrotropes that could be potential substitutes to short-chain glycol ethers. The use of these Isosorbide derivatives as bio-sourced alternatives to petroleum-derived products for applications such as compatibilizers in liquid detergent formulations or solubilizing agents in aqueous hard-surface cleaning is discussed in this paper. DMI reveals to have interesting coupling properties for the former applications, whereas the monopentyl ether of Isosorbide (C_5Iso) is a particularly efficient hydrotrope for the latter.
Valérie Molinier - One of the best experts on this subject based on the ideXlab platform.
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Asymmetric Iodoetherification of Isosorbide-Derived Glycals: A Regio- and Stereoselective Access to a Variety of O-Substituted Isosorbide Derivatives
Proceedings, 2019Co-Authors: Christophe Berini, Aurélie Lavergne, Valérie Molinier, Stéphane Lebrun, Jean-marie Aubry, Eric DeniauAbstract:Isosorbide is a competitive starting material for various valuable derivatives by functionalization and/or substitution since it is a renewable and carbon neutral material that is produced on an industrial scale from sorbitol. A set of O-alkyl- or O-arylated beta-iodo ethers has been synthesized from Isosorbide. The key step was the iodoetherification of Isosorbide-derived glycals with a variety of oxygenated nucleophiles in the presence of N-iodosuccinimide. trans-Iodo ethers and acetate were obtained in good yields and the removal of iodide affords Isosorbide derivatives. The usefulness of this new approach is illustrated by the synthesis of a surfactant having a dimer of Isosorbide as hydrophilic group and by the preparation of a structurally unusual bicyclic anhydro carbohydrate.
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iodoetherification of Isosorbide derived glycals access to a variety of o alkyl or o aryl Isosorbide derivatives
European Journal of Organic Chemistry, 2013Co-Authors: Christophe Berini, Aurélie Lavergne, Valérie Molinier, Eric Deniau, Frédéric Capet, Jean-marie AubryAbstract:A set of O-alkylated or O-arylated β-iodo ethers has been synthesized from Isosorbide. Isosorbide is a competitive starting material for various valuable derivatives by functionalization and/or substitution since it is a renewable and carbon neutral material that is produced on an industrial scale from sorbitol. The key step was the iodoetherification of Isosorbide-derived glycals with a variety of oxygenated nucleophiles in the presence of N-iodosuccinimide. trans-Iodo ethers and acetate were obtained in good yields and the removal of iodide affords Isosorbide derivatives. The usefulness of this new approach is illustrated by the synthesis of a surfactant having a dimer of Isosorbide as hydrophilic group and by the preparation of a structurally unusual bicyclic anhydro carbohydrate.
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Iodoetherification of Isosorbide‐Derived Glycals: Access to a Variety of O‐Alkyl or O‐Aryl Isosorbide Derivatives
European Journal of Organic Chemistry, 2013Co-Authors: Christophe Berini, Aurélie Lavergne, Valérie Molinier, Eric Deniau, Frédéric Capet, Jean-marie AubryAbstract:A set of O-alkylated or O-arylated β-iodo ethers has been synthesized from Isosorbide. Isosorbide is a competitive starting material for various valuable derivatives by functionalization and/or substitution since it is a renewable and carbon neutral material that is produced on an industrial scale from sorbitol. The key step was the iodoetherification of Isosorbide-derived glycals with a variety of oxygenated nucleophiles in the presence of N-iodosuccinimide. trans-Iodo ethers and acetate were obtained in good yields and the removal of iodide affords Isosorbide derivatives. The usefulness of this new approach is illustrated by the synthesis of a surfactant having a dimer of Isosorbide as hydrophilic group and by the preparation of a structurally unusual bicyclic anhydro carbohydrate.
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Aqueous phase behavior of Isosorbide-based non-ionic surfactants
Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2012Co-Authors: Aurélie Lavergne, Valérie Molinier, Ying Zhu, Jean-marie AubryAbstract:Abstract Three non-ionic surfactants have been synthesized from Isosorbide, a readily available molecule from renewable resources. As Isosorbide is a rigid diol, it allows grafting an aliphatic chain on one hydroxyl and various hydrophilic heads on the other one, thus acting as a rigid hydrophilic linker. In this study, the three surfactants possess a dodecyl alkyl chain and triethyleneglycol and glycerol have been coupled to Isosorbide to provide the non-ionic polar groups. The effect of the insertion of an Isosorbide moiety has been evaluated through the study of the aqueous phase behaviors of the compounds and particularly the formation of lyotropic liquid crystal phases.
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Solubilizing and Hydrotropic Properties of Isosorbide Monoalkyl- and Dimethyl-Ethers
Journal of Surfactants and Detergents, 2009Co-Authors: Morgan Durand, Valérie Molinier, Thierry Féron, Jean-marie AubryAbstract:Isosorbide is a diol readily obtained from starch that can be used as a polar building block for the synthesis of derivatives ranging from solvents to surfactants: dimethyl Isosorbide (DMI) is a “sustainable solvent” already on the market, used notably in cosmetic and pharmaceutical formulations; monoalkyl derivatives of Isosorbide are non-ionic hydrotropes that could be potential substitutes to short-chain glycol ethers. The use of these Isosorbide derivatives as bio-sourced alternatives to petroleum-derived products for applications such as compatibilizers in liquid detergent formulations or solubilizing agents in aqueous hard-surface cleaning is discussed in this paper. DMI reveals to have interesting coupling properties for the former applications, whereas the monopentyl ether of Isosorbide (C_5Iso) is a particularly efficient hydrotrope for the latter.
Rolf Schröder - One of the best experts on this subject based on the ideXlab platform.
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Comparison of the effect of Isosorbide-5-mononitrate and Isosorbide dinitrate in a slow-release form on exercise-induced myocardial ischemia.
Journal of clinical pharmacology, 1991Co-Authors: Lars Hennig, Dietrich Andresen, Ameneh Hennig, Benny J. Levenson, Thomas Brüggemann, Rolf SchröderAbstract:A randomized, double blind, placebo-controlled crossover study on 20 patients with exercise-induced angina pectoris and reproducible ST-segment depression during exercise-stress test was performed to compare the effect of a single dose of 120 mg of Isosorbide dinitrate in a slow-release form with that of a twice-daily application of 20 mg of Isosorbide-5-mononitrate. Symptom-limited exercise tests were done, and nitrate plasma levels were measured in the subjects 6, 10, and 24 hours after the first administration of the drug. Both drugs produced a highly significant reduction in the size of exercise-induced ST-depressions (P less than .001) 6 and 10 hours after the first administration of Isosorbide dinitrate as well as 6 hours after the first and 4 hours after the second dose of Isosorbide-5-mononitrate. The effect was still significant (P less than .05) 24 hours after the administration of Isosorbide dinitrate in a slow-release form and 18 hours after the second dose of Isosorbide-5-mononitrate. In the case of the drug Isosorbide dinitrate, nitrate plasma levels for its metabolite, Isosorbide-5-mononitrate, were highest 10 hours after first application. In the case of the drug Isosorbide-5-mononitrate, nitrate plasma levels were highest 4 hours after the second dose. Two 20 mg doses of Isosorbide-5-mononitrate and a single dose of 120 mg Isosorbide dinitrate in a slow release form have a comparable effect on the reduction of exercise-induced ST-segment depressions.
Torben Haghfelt - One of the best experts on this subject based on the ideXlab platform.
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Effects of Amlodipine and Isosorbide Dinitrate on Exercise-Induced and Ambulatory Ischemia in Patients with Chronic Stable Angina Pectoris
Cardiovascular Drugs and Therapy, 1997Co-Authors: Rolf Steffensen, Thomas Melchior, Jan Bech, Henrik Nissen, Benedikte Haastrup, Peer Grande, Verner Rasmussen, Jørgen Fischer Hansen, Knud Skagen, Torben HaghfeltAbstract:This study was designed to compare once-daily administration of 5–10 mg amlodipine with two daily doses of 40 mg sustained-release Isosorbide dinitrate in 59 patients with stable angina using a randomized, double-blind, crossover study design. Anginal episodes, nitroglycerin consumption, and possible adverse events were recorded in a diary. A maximal symptom-limited bicycle exercise test and 48-hour ambulatory ECG monitoring were performed at baseline and at the end of each 5-week period of therapy. Exercise time, time to angina, time to ST depression, and maximal ST depression were measured during exercise. During ambulatory monitoring, the number of ischemic episodes and the duration per hour of ST depression were assessed. Amlodipine significantly reduced anginal episodes (P < 0.001) when compared with Isosorbide dinitrate. Furthermore, amlodipine prolonged time to ST depression (P < 0.001) and time to angina (P < 0.05) when compared with Isosorbide dinitrate. The number and duration of ischemic episodes during ambulatory monitoring were significantly reduced with amlodipine when compared with baseline values (P < 0.05), whereas no differences were found between Isosorbide dinitrate and baseline. Adverse events were reported more frequently with Isosorbide dinitrate than with amlodipine (P < 0.02). Amlodipine appears to be more effective and tolerable than sustained-release Isosorbide dinitrate as monotherapy for chronic stable angina.
Jane E Norman - One of the best experts on this subject based on the ideXlab platform.
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the prim study a randomized comparison of prostaglandin e2 gel with the nitric oxide donor Isosorbide mononitrate for cervical ripening before the induction of labor at term
American Journal of Obstetrics and Gynecology, 2004Co-Authors: Inass Osman, John Norrie, Heather Murray, Ian A. Greer, Fiona M Mackenzie, Jane E NormanAbstract:Objective The purpose of this study was to compare the efficacy and safety profile of prostaglandin E 2 with Isosorbide mononitrate for cervical ripening before the induction of labor at term. Study design Primigravid women were assigned randomly to receive either 40 mg of Isosorbide mononitrate or 2 mg of prostaglandin E 2 . Efficacy outcomes were the cervical ripening effect of each agent and the time from treatment initiation to delivery. Safety outcomes were the incidence and frequency of maternal side effects and events that would be potentially hazardous for mother and baby during outpatient cervical ripening. Results Prostaglandin E 2 was more effective than Isosorbide mononitrate in inducing a change in modified Bishop score. Mean duration from treatment initiation to delivery was greater for Isosorbide mononitrate than prostaglandin E 2 . There were no adverse events in the Isosorbide mononitrate group that would contraindicate outpatient treatment. However, in the prostaglandin E 2 group, 7% of the pregnancies had abnormal fetal heart rate patterns ( P = .0002). Maternal satisfaction was significantly higher in the Isosorbide mononitrate group. Conclusion Although Isosorbide mononitrate was less effective, maternal satisfaction was significantly greater. The safety profile of each agent was such that it would be reasonable to give Isosorbide mononitrate, but not prostaglandin E 2 , on an outpatient basis.
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serum profile of Isosorbide mononitrate after vaginal administration in the third trimester
British Journal of Obstetrics and Gynaecology, 2003Co-Authors: Catharine D Bates, Fiona Mackenzie, Antony E Nicoll, Andrew Thomson, Alexander B. Mullen, Jane E NormanAbstract:Vaginally administered nitric oxide donors such as Isosorbide mononitrate have been used to ripen the uterine cervix in pregnancy. The pharmacokinetics of Isosorbide mononitrate following vaginal administration are unknown. Serum levels of Isosorbide mononitrate were determined at baseline and 60, 180 and 360 minutes after vaginal administration of 20 or 40 mg Isosorbide mononitrate to pregnant women scheduled for induction of labour at term. Serum levels of Isosorbide mononitrate continued to rise up to 360 minutes after Isosorbide mononitrate insertion, with mean (SD) final levels of 337 (94) μg/L following Isosorbide mononitrate 40 mg and 144 (47) μg/L following Isosorbide mononitrate 20 mg, P < 0.01.
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a comparison of Isosorbide mononitrate misoprostol and combination therapy for first trimester pre operative cervical ripening a randomised controlled trial
British Journal of Obstetrics and Gynaecology, 2001Co-Authors: Marie Anne Ledingham, Burnett C Lunan, Ian A. Greer, Andrew Thomson, Jane E NormanAbstract:Objective To determine whether a combined therapy with Isosorbide mononitrate (40mg) and misoprostol (400μg) for pre-operative cervical ripening in the first trimester would result in improved clinical effectiveness, and fewer side effects compared with each agent used alone. Design Randomised controlled trial. Setting Glasgow Royal Infirmary. Population Sixty-six primigravid women scheduled for suction termination of pregnancy. Methods Women were randomly assigned to receive before surgery, per vaginam, Isosorbide mononitrate 40 mg (n=22), misoprostol 400 μg (n=22) or both agents together [Isosorbide mononitrate 40 mg and misoprostol 400 μg] (n=22). Main outcome measures 1. To assess the cumulative force required to dilate the cervix to 8 mm; 2. the onset of new symptoms before termination of pregnancy. Results The cervical resistance following combination therapy with Isosorbide mononitrate and misoprostol was not significantly different than following misoprostol alone [24.5N vs 18.5N; median difference (95% CI) 19N (-22 to 49)]. Pre-treatment with misoprostol used alone resulted in a lower cervical resistance than Isosorbide mononitrate alone (18.5Nvs 39N, P=0.04, Mann-Whitney U test). There was no difference in the number of women remaining asymptomatic following either Isosorbide mononitrate or misoprostol or combination therapy [14/22 (64%) vs 11/21 (52%) vs 11/22 (50%), Fisher's exact test]. Conclusions We have not shown any advantage of combining misoprostol with the nitric oxide donor Isosorbide mononitrate compared with misoprostol alone for pre-operative cervical ripening in the first trimester.