72631-67-5Relevant academic research and scientific papers
Isosorbide-based peptidomimetics as inhibitors of hepatitis C virus serine protease
Portela, Aline C.,Barros, Thalita G.,Lima, Camilo H. da S.,Dias, Luiza R.S.,Azevedo, Pedro H.R. de A.,Dantas, Anna Sophia C.L.,Mohana-Borges, Ronaldo,Ventura, Gustavo T.,Pinheiro, Sergio,Muri, Estela M.F.
, p. 3661 - 3665 (2017/07/27)
Hepatitis C infection is a cause of chronic liver diseases such as cirrhosis and carcinoma. The current therapy for hepatitis C has limited efficacy and low tolerance. The HCV encodes a serine protease which is critical for viral replication, and few protease inhibitors are currently on the market. In this paper, we describe the synthesis and screening of novel isosorbide-based peptidomimetic inhibitors, in which the compounds 1d, 1e, and 1i showed significant inhibition of the protease activity in vitro at 100?μM. The compound 1e also showed dose-response (IC50?=?36?±?3?μM) and inhibited the protease mutants D168A and V170A at 100?μM, indicating it as a promising inhibitor of the HCV NS3/4A protease. Our molecular modeling studies suggest that the activity of 1e is associated with a change in the interactions of S2 and S4 subsites, since that the increased flexibility favors a decrease in activity against D168A, whereas the appearance of a hydrophobic cavity in the S4 subsite increase the inhibition against V170A strain.
Iodoetherification of isosorbide-derived glycals: Access to a variety of O-alkyl or O-aryl isosorbide derivatives
Berini, Christophe,Lavergne, Aurelie,Molinier, Valerie,Capet, Frederic,Deniau, Eric,Aubry, Jean-Marie
, p. 1937 - 1949 (2013/05/21)
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. The synthesis of β-iodo ethers by iodoetherification of isosorbide-derived glycals with a variety of oxygenated nucleophiles in the presence of N-iodosuccinimide was achieved. Products were obtained in good to very good yields. The removal of iodide affords isosorbide derivatives that gave access to valuable substrates.
Synthesis of novel chiral monophosphine ligands derived from isomannide and isosorbide. Application to enantioselective hydrogenation of olefins
Ibrahim, Houssein,Bournaud, Chloée,Guillot, Régis,Toffano, Martial,Vo-Thanh, Giang
supporting information; scheme or table, p. 4900 - 4902 (2012/09/21)
A new class of monophosphine ligands has been prepared from natural chirality renewable source, 1,4:3,6-dianhydrohexitol compounds, via a nucleophilic substitution process, or a hydrophosphination reaction involving microwave activation. These ligands have been evaluated for the rhodium-catalyzed enantioselective hydrogenation of olefins giving good conversion and enantioselectivity up to 95% and 96% ee, respectively.
Deoxygenation/dimerization of sugar derivatives with BF3· Et2O-Et3SiH: Synthesis of a β-isonucleoside
Mukherjee, Subhrangshu,Roy, Biswajit G.,Das, Soumendra N.,Mandal, Sukhendu B.
, p. 4929 - 4932,4 (2020/07/31)
Lewis acid-Et3SiH induced deoxygenation of anomeric carbon of sugars generates tetrahydrofuran derivatives, accompanied by hitherto unknown dimeric products. If the reagent addition steps are reversed, tetrahydrofuran derivatives are obtained a
Synthesis of a new class of ligands derived from isosorbide and their application to asymmetric reduction of aromatic ketones by transfer hydrogenation
Huynh, Khanh-Duy,Ibrahim, Houssein,Kolodziej, Emile,Toffano, Martial,Vo-Thanh, Giang
experimental part, p. 2622 - 2631 (2012/01/04)
A new class of β-amino alcohol and diamine ligands has been prepared from isosorbide as a chiral renewable source. The efficiency of these ligands has been evaluated for the metal-catalyzed enantioselective reduction of aromatic ketones by transfer hydrogenation, giving excellent conversion and good enantioselectivity.
New class of chiral ligands derived from isosorbide: First application in asymmetric transfer hydrogenation
Huynh, Khanh-Duy,Ibrahim, Houssein,Toffano, Martial,Vo-Thanh, Giang
experimental part, p. 1542 - 1548 (2010/11/02)
A new class of β-amino alcohol and diamine ligands was prepared from isosorbide as a chiral renewable resource. The original wedge-shaped structure of isosorbide offers an interesting chiral pocket to promote the metal-catalyzed enantioselective reduction of ketones by transfer hydrogenation.
Isosorbide-based cholinesterase inhibitors; replacement of 5-ester groups leading to increased stability
Dillon, Gerald P.,Gaynor, Joanne M.,Khan, Denise,Carolan, Ciaran G.,Ryder, Sheila A.,Marquez, Juan F.,Reidy, Sean,Gilmer, John F.
experimental part, p. 1045 - 1053 (2010/04/26)
Isosorbide-2-carbamate-5-esters are highly potent and selective butyrylcholinesterase inhibitors with potential utility in the treatment of Alzheimer's Disease (AD). They are stable in human plasma but in mouse plasma they undergo hydrolysis at the 5-ester group potentially attenuating in vivo potency. In this paper we explore the role of the 5-position in modulating potency. The focus of the study was to increase metabolic stability while preserving potency and selectivity. Dicarbamates and 5-keto derivatives were markedly less potent than the ester class. The 2-benzylcarbamate-5-benzyl ether was found to be potent (IC50 52 nM) and stable in the presence of mouse plasma and liver homogenate. The compound produces sustained moderate inhibition of mouse butyrylcholinesterase at 1 mg/kg, IP.
Synthesis of novel chiral imidazolium-based ionic liquids derived from isosorbide and their applications in asymmetric aza Diels-Alder reaction
Nguyen Van Buu, Olivier,Aupoix, Audrey,Vo-Thanh, Giang
experimental part, p. 2260 - 2265 (2009/07/18)
A novel family of chiral imidazolium-based ionic liquids containing a chiral moiety and a free hydroxyl function has been designed and synthesized using isosorbide as a biorenewable substrate. These chiral ionic liquids were found to catalyze the aza Diels-Alder reaction to give good yields and moderate diastereoselectivities. Chiral ionic liquids are recycled while their efficiency is preserved.
Chiral ionic liquids derived from isosorbide: Synthesis, properties and applications in asymmetric synthesis
Van Buu, Olivier Nguyen,Aupoix, Audrey,Hong, Nhung Doan Thi,Vo-Thanh, Giang
scheme or table, p. 2060 - 2072 (2009/12/25)
A novel class of chiral ammonium and imidazolium-based ionic liquids has been designed and synthesized using isosorbide as a biorenewable substrate. These chiral ionic liquids were found to catalyze the aza Diels-Alder reaction to give good yields and moderate diastereoselectivitives.
The synthesis and applications of asymmetric phase-transfer catalysts derived from isomannide and isosorbide
Kumar, Sanjeev,Ramachandran, Uma
, p. 4141 - 4148 (2007/10/03)
We report herein the synthesis of various derivatives of isomannide and isosorbide. Alkylation on N-(diphenylmethylene)glycine tert-butyl ester show the new catalysts to be effective phase-transfer catalysts with moderately good enantioselectivity. The ef
