29655-46-7Relevant academic research and scientific papers
Insulin Analogues with Altered Insulin Receptor Isoform Binding Specificities and Enhanced Aggregation Stabilities
Chrudinova, Martina,Halamova, Tereza,Jiracek, Jiri,Kurochka, Andrii,Mitrova, Katarina,Mrzilkova, Karolina,Panikova, Terezie,Picha, Jan,Selicharova, Irena,Zakova, Lenka
supporting information, p. 14848 - 14859 (2021/10/20)
Insulin is a lifesaver for millions of diabetic patients. There is a need for new insulin analogues with more physiological profiles and analogues that will be thermally more stable than human insulin. Here, we describe the chemical engineering of 48 insulin analogues that were designed to have changed binding specificities toward isoforms A and B of the insulin receptor (IR-A and IR-B). We systematically modified insulin at the C-terminus of the B-chain, at the N-terminus of the A-chain, and at A14 and A18 positions. We discovered an insulin analogue that has Cα-carboxyamidated Glu at B31 and Ala at B29 and that has a more than 3-fold-enhanced binding specificity in favor of the "metabolic"IR-B isoform. The analogue is more resistant to the formation of insulin fibrils at 37 °C and is also more efficient in mice than human insulin. Therefore, [AlaB29,GluB31,amideB31]-insulin may be interesting for further clinical evaluation.
Ammonium Chloride-Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation
Lan, Chunling Blue,Auclair, Karine
supporting information, p. 5135 - 5146 (2021/10/19)
Monosubstituted ureas are important scaffolds in organic chemistry. They appear in various biologically active compounds and serve as versatile precursors in synthesis. Monosubstituted ureas were originally prepared using toxic and hazardous phosgene equivalents. Modern methods include transamidation of urea and nucleophilic addition to cyanate salts, both of which suffer from a narrow substrate scope due to the need for a strong acid and prolonged reaction times. We hereby report that ammonium chloride can promote the reaction between amines and potassium cyanate to generate monosubstituted ureas in water. This method proceeds rapidly under microwave irradiation and tolerates a broad range of functional groups. Unlike previous strategies, it is compatible with other nucleophiles, acid-labile moieties, and most of the common protecting groups. The products precipitate out of solution, allowing facile isolation without column chromatography.
Chemical Synthesis of the Trisaccharide Epitope of Phenolic Glycolipid-1 Surface Antigen from Mycobacterium leprae
Luo, Wan-Yue,Lu, Bin,Zhou, Rong-Ye,Hu, Xiao,Wang, Jin
, p. 10973 - 10979 (2020/09/23)
PGL-1 epitope 1 bearing a p-aminoethylphenol group was efficiently synthesized by using linear synthetic routes. A method for efficient synthesis of oligosaccharides containing rhamnose rings was developed. The chemistry is flexible and could be used for
triAZOLOtriAZINE DERIVATIVES AS A2A RECEPTOR ANTAGONISTS
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Page/Page column 52, (2020/01/24)
The present invention provides triazolotriazine derivatives of formula (1) as A2A receptor antagonists. Compounds of formula (1) and pharmaceutical compositions including the compounds can be used for the treatment of disorders related to A2A receptor hyperfunctioning, such as certain types cancers. Compounds of formula (1) and methods of preparing the compounds are disclosed in the invention.
GLYCOPOLYMERS SEQUESTERING CARBOHYDRATE-BINDING PROTEINS
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Page/Page column 98; 99, (2018/10/19)
The invention relates to polymers comprising carbohydrate ligands and moieties, respectively, that bind to carbohydrate-binding proteins (CBPs), as well as to these carbohydrate ligands, and to their use in diagnosis and therapy of diseases that are assoc
N-Urethane protection of amines and amino acids in an ionic liquid
Di Gioia,Gagliardi,Leggio,Leotta,Romio,Liguori
, p. 63407 - 63420 (2015/08/11)
An efficient, solvent-free protocol for the N-fluorenylmethoxycarbonylation and N-benzyloxycarbonylation of amines is described. The reaction of aliphatic and aromatic amines with FmocOSu and Cbz-Osu in [Bmim][BF4] at room temperature afforded the corresponding N-urethane derivatives in excellent yields and do not require any further purification. The method has been extended to the N-Fmoc and N-Cbz protection of amino acids. Absence of bases, very short reaction times, high yields, selectivity and ease of product separation are some advantages of this protocol.
Synthetic studies towards stachybotrin C
Tumma, Naresh,Jacolot, Maiwenn,Jean, Mickael,Chandrasekhar, Srivari,Van De Weghe, Pierre
supporting information, p. 2919 - 2922 (2013/02/22)
The preparation of racemic des-hydroxy stachybotrin C is described. Different approaches have been studied. Observations made in the course of the synthesis show the efficiency of the intermolecular cyclization between the diethyl acetal 19 and phenol 12 leading to the benzopyran moiety 17. Georg Thieme Verlag KG · Stuttgart · New York.
Synthesis, characterization and biological evaluation of ureidofibrate-like derivatives endowed with peroxisome proliferator-activated receptor activity
Porcelli,Gilardi,Laghezza,Piemontese,Mitro,Azzariti,Altieri,Cervoni,Fracchiolla,Giudici,Guerrini,Lavecchia,Montanari,Di Giovanni,Paradiso,Pochetti,Simone,Tortorella,Crestani,Loiodice
experimental part, p. 37 - 54 (2012/03/09)
A series of ureidofibrate-like derivatives was prepared and assayed for their PPAR functional activity. A calorimetric approach was used to characterize PPARγ-ligand interactions, and docking experiments and X-ray studies were performed to explain the obs
Mild debenzylation of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene as a non-lewis-basic cation scavenger
Okano, Kentaro,Okuyama, Kei-Ichiro,Fukuyama, Tohru,Tokuyama, Hidetoshi
scheme or table, p. 1977 - 1980 (2009/04/07)
Scope and limitations of the debenzylation conditions for aryl benzyl ether, which was developed during our synthetic studies on yatakemycin, were investigated. The chemoselective debenzylation proceeds at low temperature with a combination of BCl3 and pentamethylbenzene as a cation scavenger in the presence of various functional groups.
1,2,4-Triazine Derivatives, Preparation and Use Thereof in Human Therapy
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Page/Page column 19, (2008/12/06)
The invention concerns 3,5-dioxo-(2H,4H)-1,2,4-triazine derivatives of general formula (I), wherein: R1 and R2, identical or different, represent a branched or linear C1-C7 alkyl or alkenyl radical, a C1/s
