36650-39-2Relevant articles and documents
Copper(II)-Catalyzed Reactions of α-Keto Thioesters with Azides via C-C and C-S Bond Cleavages: Synthesis of N-Acylureas and Amides
Maity, Rajib,Naskar, Sandip,Das, Indrajit
, p. 2114 - 2124 (2018/02/23)
Cu(II)-catalyzed reaction of α-keto thioesters with trimethylsilyl azide (TMSN3) proceeds with the transformation of the thioester group into urea through C-C and C-S bond cleavages, constituting a practical and straightforward synthesis of N-acylureas. When diphenyl phosphoryl azide (DPPA) is used instead as the azide source in an aqueous environment, primary amides are formed via substitution of the thioester group. The reactions are proposed to proceed through Curtius rearrangement of the initially formed α-keto acyl azide to generate an acyl isocyanate intermediate, which reacts further with an additional amount of azide or water and rearranges to afford the corresponding products. To demonstrate the potentiality of the method, one-step syntheses of pivaloylurea and isovaleroylurea, displaying anticonvulsant activities, have been carried out.
Regio- and diastereoselective synthesis of trans-dihydrofuran-3carboxamides by radical addition of 1,3-dicarbonyl compounds to acrylamides using manganese(III) acetate and determination of exact configuration by X-ray crystallography
Yilmaz, Mehmet,Ustalar, Ash,U?an, Bedriye,Pekel, A. Tar?k
, p. 79 - 91 (2018/05/09)
In this study, we investigated the radical addition of 1,3-dicarbonyl compounds to acrylamide derivatives including phenyl, 2-thienyl and 5-methyl-2-furyl groups mediated by manganese(III) acetate. trans-3-Carboxamide-dihydrofurans were obtained in modarate to good yields, as well as regio- and diastereoselectievly. Structural analyses of these compounds were made by NMR techniques such as HMBC and NOSY spectra. Also, exact configuration and structures of these (7b, 7i and 7j) compounds were determined by X-ray crystallography.
Synthesis and biological evaluation of (E)-cinnamic acid, (E)-2-styrylthiazole and (E)-2-[2-(naphthalen-1-yl)vinyl]thiazole derivatives
Olawode, Emmanuel O.,Tandlich, Roman,Prinsloo, Earl,Isaacs, Michelle,Hoppe, Heinrich,Seldon, Ronnett,Warner, Digby F.,Steenkamp, Vanessa,Kaye, Perry T.
, p. 284 - 296 (2018/03/09)
Cinnamyl- and thiazole-based compounds have been shown to exhibit diverse medicinal properties and a series of twelve (E)-2-styrylthiazole and (E)-2-[(naphthalen-1-yl)vinyl]thiazole derivatives, which are conjugates of both systems and which satisfy the "Lipinski rule of 5", have been synthesised and subjected to in vitro biological screening. While insignificant inhibition (60-98% viability at 10 μM) of HeLa (cervical cancer) cells was noted, all five of the (E)-2-[naphthalen-1- yl)vinyl]thiazole derivatives proved remarkably active against SH-SY5Y (neuroblastoma) cells with IC50 values ranging from 2.09 to 8.64 μM. Two of the seven (E)-2-styrylthiazoles were found to be moderately active (with IC50 values of 10.8 and 11.7 mM), whereas the remaining five analogues exhibit significant proliferation of SH-SY5Y cells (with IC50 values of 180-1000 mM). The results warrant further studies on the effects of styrylthiazoles on the differentiation and extension of SH-SY5Y cells in order to assess their activity in neurological degenerative diseases.
Optimization and Evaluation of 5-Styryl-Oxathiazol-2-one Mycobacterium tuberculosis Proteasome Inhibitors as Potential Antitubercular Agents
Russo, Francesco,Gising, Johan,?kerbladh, Linda,Roos, Annette K.,Naworyta, Agata,Mowbray, Sherry L.,Sokolowski, Anders,Henderson, Ian,Alling, Torey,Bailey, Mai A.,Files, Megan,Parish, Tanya,Karlén, Anders,Larhed, Mats
, p. 342 - 362 (2015/06/30)
This is the first report of 5-styryl-oxathiazol-2-ones as inhibitors of the Mycobacterium tuberculosis (Mtb) proteasome. As part of the study, the structure-activity relationship of oxathiazolones as Mtb proteasome inhibitors has been investigated. Furthermore, the prepared compounds displayed a good selectivity profile for Mtb compared to the human proteasome. The 5-styryl-oxathiazol-2-one inhibitors identified showed little activity against replicating Mtb, but were rapidly bactericidal against nonreplicating bacteria. (E)-5-(4-Chlorostyryl)-1,3,4-oxathiazol-2-one) was most effective, reducing the colony-forming units (CFU)/mL below the detection limit in only seven days at all concentrations tested. The results suggest that this new class of Mtb proteasome inhibitors has the potential to be further developed into novel antitubercular agents for synergistic combination therapies with existing drugs.
ACRYLAMIDE COMPOUNDS AND USE THEREOF FOR INHIBITING APOPTOSIS
-
Paragraph 0037; 0038, (2013/04/10)
The present invention relates to a compound of Formula I, or an isomer, pharmaceutically acceptable salt and solvate thereof; the present invention also relates to a composition comprising a compound of Formula I, or an isomer, pharmaceutically acceptable salt and solvate thereof, and a pharmaceutically acceptable carrier, excipient or diluents. The present invention also relates to use of a compound of Formula I, or an isomer, pharmaceutically acceptable salt and solvate thereof for combating apoptosis, preventing or treating a disease or disorder associated with apoptosis; especially use for protecting cardiomyocyte, preventing or treating a disease or disorder associated with cardiomyocyte apoptosis.
SAR, cardiac myocytes protection activity and 3D-QSAR studies of salubrinal and its potent derivatives
Liu,He,Li,Li,Liu,Zhong,Li
, p. 6072 - 6079 (2013/02/22)
Salubrinal is a selective inhibitor of endoplasmic reticulum (ER) stress and affords remarkable protection to cardiomyocytes. By studying the structure-activity relationship (SAR) of salubrinal, it was found that modification of the quinoline ring terminus and thiourea unit could confer the compound PP1-24 with markedly enhanced cardioprotective activity (EC 50 2 = 0.741, r2 = 0.991).
