1194-57-6Relevant articles and documents
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Fife,T.H.,DeMark,B.R.
, p. 7379 - 7385 (1979)
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Synthesis of benzothiophenones and naphthothiophenone as anticholinesterases
Jung
, p. 5325 - 5327 (2013)
Since AChE and BuChE belong to the same serine hydrolazes, we designed and synthesized compounds 1-6 as anticholinesterases and measured their inhibition poteucies on ChEs. 7-Methoxy-3H-benzo[c]thiophen-1-one 4, 4,6-dibromo-5,7- methoxy-3H-benzo[c]thiophe
Synthesis of Disulfide-Bridged N-Phenyl-N′-(alkyl/aryl/heteroaryl)urea Derivatives and Evaluation of Their Antimicrobial Activities
Dilem Do?an, ?engül,Buran, Sümeyye,G?zde Gündüz, Miyase,?zkul, Ceren,Siva Krishna, Vagolu,Sriram, Dharmarajan
, (2019)
The discoveryof new antimicrobial agents is extremely needed to overcome multidrug-resistant bacterial and tuberculosis infections. In the present study, eight novel substituted urea derivatives (10a–10h) containing disulfide bond were designed, synthesized and screened for their in vitro antimicrobial activities on standard strains of Gram-positive and Gram-negative bacteria as well as on Mycobacterium tuberculosis. According to the obtained results, antibacterial effects of the compounds were found to be considerably better than their antimycobacterial activities along with their weak cytotoxic effects. Molecular docking studies were performed to gain insights into the antibacterial activity mechanism of the synthesized compounds. The interactions and the orientation of compound 10a (1,1′-((disulfanediylbis(methylene))bis(2,1-phenylene))bis(3-phenylurea)) were found to be highly similar to the original ligand within the binding pocket E. faecalis β-ketoacyl acyl carrier protein synthase III (FabH). Finally, a theoretical study was established to predict the physicochemical properties of the compounds.
A convenient synthesis of aromatic thiolactones
Pal,Murty,Mal
, p. 1555 - 1560 (1993)
Hydrolytic decomposition of thiouronium salts A with aqueous NaHCO3 at 80°-90°C directly furnished thiolactones 6-10 in very good yields in one-flask operation.
Flash vacuum thermolysis of 4H-3,1-benzoxathiin-4-thione: UV-photoelectron spectroscopy characterization and quantum chemistry studies
Drewnowski, Tomasz,Chrostowska, Anna,Lesniak, Stanislaw,Dargelos, Alain,Khayar, Said
, p. 766 - 781 (2008)
The mechanism of the reaction of 4H-3,1-benzoxathiin-4-thione (3) under flash vacuum thermolysis conditions has been studied by UV-photoelectron spectra. It was shown that in the first step of the reaction at 400° 3 underwent the Schoenberg - Newman - Kwart rearrangement to give 4H-1,3-benzodithiin-4-one (6). Increasing of the temperature to 650° resulted in the elimination of thioformaldehyde and the formation of benzothiet-2-one (1). Subsequent elevation of the temperature prompted presumably the ring opening of 1 to (6-thioxocyclohexa-2,4-dien-1-ylidene) methanone (7) (at 680°), which at 700° eliminated CO and underwent a Wolff-type ring contraction to give (cyclopenta-2,4-dien-1-ylidene)methanethione (2). UV-Photoelectron spectra were recorded at different steps of the reaction and analyzed considering the theoretical evaluation of ionization potentials.
The Hydrolysis of Phthalide, Thiophthalide, and Methyl o-Methoxybenzoate in Highly Alkaline Media. Curvature in the khyd vs Profile
Kellogg, B. A.,Brown, R. S.,McDonald, R. S.
, p. 4652 - 4658 (1994)
The hydrolyses of phthalide (2a) and thiophthalide (3) have been studied in highly alkaline media, T = 25 deg C, μ = 3 (KCl).For both esters, an upward curvature in the plot of khyd vs is observed, suggestive of the onset of a second order in process in the hydrolysis.Carbonyl 18O-exchange studies indicated that no 18O is lost from the ester recovered from the hydrolysis media at times up to 3t1/2 hydrolysis.Solvent kinetic isotope (skie) studies indicate that for 3, (khyd)H2O/D2O is inverse throughout the entire range of .The lack of 18O-exchange and the inverse nature of the skie on khyd suggest that the curvature in the khyd vs plots is not due to the involvement of two hydroxides in the hydrolytic process.A correlation of the khyd data with the acidity function H- appropriate for highly alkaline media is linear and suggests the involvement of a single hydroxide throughout the entire range.A reinvestigation of the alkaline hydrolysis of methyl o-methoxybenzoate (4) accompanied by 18O-exchange studies failed to detect unambiguous evidence for a bona fide second order in process.
Synthesis of Chiral Selenazolines from N-Acyloxazolidinones via a Selenative Rearrangement of Chiral Cyclic Skeletons
Shibahara, Fumitoshi,Fukunaga, Tomoki,Kubota, Saki,Yoshida, Akihito,Murai, Toshiaki
supporting information, p. 5826 - 5830 (2018/09/25)
A synthetic route to chiral selenazolines from readily available N-acyloxazolidinones via a selenative rearrangement of a chiral cyclic skeleton is reported. The reaction proceeds in the presence of elemental selenium, a hydrochlorosilane, and an amine. A
Theoretical Study, Synthesis, and Reactivity of Five-Membered-Ring Acyl Sulfonium Cations
Rao, K.V. Raghavendra,Caiveau, Nicolas,David, Rolf,Shalayel, Ibrahim,Milet, Anne,Vallée, Yannick
, p. 6125 - 6129 (2015/10/06)
The feasibility of the cyclization of γ-alkylthiobutyric acid derivatives to form previously unknown five-membered-ring acyl sulfonium cations was studied. Experimental results were in good agreement with our DFT calculations that predicted such cyclizations to be easy if starting with acyl iodides and mixed anhydrides of triflic acid. Particularly efficient were the reactions of γ-alkylthiobutyryl fluorides with trimethylsilyl triflate in CDCl3 solution, which led to cyclic acyl sulfonium triflates. In some cases, the observed acyl sulfonium salts were stable enough to be characterized by NMR spectroscopy. They were found to be both alkyl-transfer reagents and acylating agents. They react with amines to form amides. These findings lend some weight to our hypothesis that the acyl sulfonium derived from methionine may have played a major role in the prebiotic synthesis of the first peptides on the primitive Earth. The reaction of trimethylsilyl triflate (Me3SiOTf) with γ-alkylthiobutyryl fluorides leads to previously unknown acyl sulfonium cations. These reactive species react both as alkyl-transfer reagents (e.g., with sulfides) and as acylating reagents (e.g., with amines). Such reactivity suggests that the acyl sulfonium derived from methionine may have been able to do the same in the primitive ocean.
