845866-13-9Relevant academic research and scientific papers
COMPOSITIONS AND METHODS FOR PROTEIN LABELING, MODIFICATION, ANALYSIS, AND TARGETED DELIVERY
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Paragraph 00240, (2020/01/24)
The invention relates to chemically reactive and/or biologically active compounds, reagents and compositions thereof. More particularly, the invention provides novel reagents that are useful in chemical synthesis, functionalization, delivery, probing and/or analytical measurements of small molecule drugs, proteins, antibodies and other biomolecules. The invention provides novel biologically active agents useful as diagnostics or therapeutics, and related composition and methods of uses thereof.
Organocatalyzed Decarboxylative Trichloromethylation of Morita–Baylis–Hillman Adducts in Batch and Continuous Flow
Enevoldsen, Martin V.,Overgaard, Jacob,Pedersen, Maja S.,Lindhardt, Anders T.
supporting information, p. 1204 - 1208 (2018/02/06)
Two protocols for the organocatalyzed decarboxylative trichloromethylation of Morita–Baylis–Hillman (MBH) substrates have been developed. Applying sodium trichloroacetate, as the trichloromethyl anion precursor, in combination with an organocatalyst and a
A versatile approach to noncoded β-hydroxy-α-amino esters and α-amino acids/esters from morita-baylis-hillman adducts
Ullah, Hamid,Ferreira, Andr V.,Bendassolli, Jos A.,Rodrigues, Manoel T.,Formiga, Andr Luiz B.,Coelho, Fernando
, p. 113 - 123 (2015/02/02)
A simple and straightforward approach to the diastereoselective synthesis of noncoded β-hydroxy-α-amino esters from Morita-Baylis-Hillman (MBH) adducts is described. The strategy is based on a one-pot sequence involving an oxidative cleavage of the double bond of silylated Morita-Baylis-Hillman adducts, followed by the reaction with hydroxylamine hydrochloride/pyridine to form oximes. The stereoselective reduction of the oximes with the mixture MoCl5·nH2O/NaBH3CN led to the corresponding anti-β-hydroxy-α-amino esters in four steps in good overall yield and with diastereoselectivity higher than 95%. A slight modification of the synthetic approach has allowed for the racemic synthesis of a set of noncoded α-amino esters/acids and DOPA
Synthesis, characterization and antimicrobial activity of some new Baylis-Hillman derived benzothiazolo pyrimidinone derivatives
Gampa, Raghavachary,Chebrolu, Lavanya Devi,Jarapula, Ravi,Vaidya, Jayathirtha Rao,Ghanakota, Venkateshwar Rao,Manda, Sarangapani
, p. 217 - 227 (2015/03/04)
A series of Baylis-Hillman derived 22 new benzothiazolo pyrimidinone derivatives have been synthesized from Baylis-Hillman acetates and 2-amino benzothiazole under neat conditions with high yields. All the newly synthesized compounds have been characteriz
Triazoyl-phenyl linker system enhancing the aqueous solubility of a molecular probe and its efficiency in affinity labeling of a target protein for jasmonate glucoside
Tamura, Satoru,Inomata, Sho,Ebine, Makoto,Genji, Takahisa,Iwakura, Izumi,Mukai, Makoto,Shoji, Mitsuru,Sugai, Takeshi,Ueda, Minoru
supporting information, p. 188 - 193 (2013/02/23)
In methods employing molecular probes to explore the targets of bioactive small molecules, long or rigid linker moieties are thought to be critical factors for efficient tagging of target protein. We previously reported the synthesis of a jasmonate glucoside probe with a highly rigid linker consisting of a triazoyl-phenyl (TAzP) moiety, and this probe demonstrated effective target tagging. Here we compare the TAzP probe with other rigid or flexible probes with respect to target tagging efficiency, hydrophobic parameters, aqueous solubility, and dihedral angles around the biaryl linkage by a combination of empirical and calculation methods. The rigid biaryl linkage of the TAzP probe has a skewed conformation that influences its aqueous solubility. Such features that include rigidness and good aqueous solubility resulted in highly efficient target tagging. These findings provide a promising guideline toward designing of better linkers for improving molecular probe performance.
A general approach to the synthesis of β2-amino acid derivatives via highly efficient catalytic asymmetric hydrogenation of α-aminomethylacrylates
Guo, Yujuan,Shao, Guang,Li, Lanning,Wu, Wenhao,Li, Ruihong,Li, Jingjing,Song, Jian,Qiu, Liqin,Prashad, Mahavir,Kwong, Fuk Yee
experimental part, p. 1539 - 1553 (2010/08/22)
A new strategy was developed for the synthesis of a valuable class of α-aminomethylacrylates via the Baylis-Hillman reaction of different aldehydes with methyl acrylate followed by acetylation of the resulting allylic alcohols and SN2′-type amination of the allylic acetates. Asymmetric hydrogenation of these diverse olefinic precursors using rhodium(Et-Duphos) catalysts provided the corresponding β2-amino acid derivatives with excellent enantioselectivities and exceedingly high reactivities (up to >99.5% ee and S/C=10,000). The first hydrogenation of (Z)-configurated substrates was studied for the synthesis of β2-amino acid derivatives. The high influence of the substrate geometry and steric hindrance on the reactivity and enantioselectivity was also disclosed for this reaction. This protocol provides a highly practical, facile and scalable method for the preparation of optically pure β2- amino acids and their derivatives under mild reaction conditions.
Studies on the reduction of the nitro group in 3-aryl-2-methylene-4-nitro-alkanoates afforded by the Baylis-Hillman adducts: synthesis of 4-aryl-3-methylene-2-pyrrolidinones and 3-(1-alkoxycarbonyl-vinyl)-1H-indole-2-carboxylates
Singh, Vijay,Kanojiya, Sanjeev,Batra, Sanjay
, p. 10100 - 10110 (2007/10/03)
The formation of substituted 2-pyrrolidinones and indoles by the reduction of the secondary nitro group in appropriate 3-aryl-2-methylene-4-nitroalkanoates afforded by Baylis-Hillman chemistry via different reducing agents is described. The 3-aryl-2-methy
Synthesis of methyl (E)-2-nitromethylcinnamates derived from baylis-hillman acetates and conversion into several coumarin derivatives
Hong, Wan Pyo,Lee, Kee-Jung
, p. 33 - 38 (2007/10/03)
Fast and easy access to methyl (E)-2-nitromethylcinnamates, from the corresponding Baylis-Hillman acetates with NaNO2 in DMF is described. Several ortho-chloro-2-nitromethylcinnamates undergo intramolecular aromatic substitution reaction follow
