- Novel substituted benzothiazole and Imidazo[2,1-b][1,3,4]Thiadiazole derivatives: Synthesis, characterization, molecular docking study, and investigation of their in vitro antileishmanial and antibacterial activities
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In this study, we synthesized new imidazo[2,1-b][1,3,4]thiadiazole derivatives containing benzothiazole group. To this end, we firstly obtained the benzo[d]thiazol-2-ylthio/oxy acetonitrile compounds (3a,b), the starting materials, in high yields (82% and 87%, respectively). Then, we synthesized the 2-amino-1, 3,4-thiadiazole derivatives (4a,b) from the reaction of these nitrile derivatives (3a,b) with thiosemicarbazide in trifluoroacetic acid (TFA) (in yields of 83% and 84%). Finally, we synthesized the imidazo[2,1-b][1,3,4]thiadiazole derivatives (5-24) containing benzothiazole group, which are the target compounds, from reactions of 2-amino-1,3,4-thiadiazole derivatives (4a,b) with phenacyl bromide derivatives (in yields of 53%–73%). All of the compounds synthesized were characterized with 1H NMR, 13C NMR, FT-IR, elemental analysis, and mass spectroscopy. Antileishmanial and antibacterial activity tests were applied to the compounds synthesized in the study. It was observed that compound 8 had the highest antileishmanial activity (MIC = 10 000 μg/mL). Also, compounds 7 and 17 were found to be effective at the highest concentration studied (MIC = 20 000 μg/mL). In terms of antibacterial activity, compounds 4b and 7 were found to be the most effective compounds against Escherichia coli (MIC = 625 μg/mL). Theoretical calculations were performed to support the experimental results. To this end, we performed Molecular Docking studies to determine whether or not the compounds (4a, 4b, 7 and 13) optimized with Gaussian09 using the DFT/B3LYP/6-31G(d,p) theory, which is a quantum chemical calculation, could be an inhibitor agent for the 2eg7 Escherichia coli protein structure. Also, we investigated the relationship between the calculated HOMO values of these four ligands and docking studies.
- Er, Mustafa,?zer, Arif,Direkel, ?ahin,Karakurt, Tuncay,Tahtaci, Hakan
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- Trisubstituted Highly Activated Benzo[ d]thiazol-2-yl-sulfone-Containing Olefins as Building Blocks in Organic Synthesis
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In this paper, we report the formation of highly electrophilic 1,1-deactivated olefins, their use as novel synthetic building blocks, and their transformation to structurally diverse molecular scaffolds. Synthesis of 1,1-deactivated olefins substituted with a BT-sulfonyl group and a carbonyl or nitrile, respectively, consists of unusual Ti(OPri)4-mediated Knoevenagel-type condensation and proceed in good to excellent yields. Generated olefins can be further transformed in a highly stereoselective manner and in good yields to various polyfunctionalized heterocycles and acyclic molecular scaffolds. Overall, the obtained structures are accessed in two to four steps starting from the (mostly) commercially available aldehydes. In addition, the presence of the BT-sulfonyl group in prepared structures allows for further chemoselective functionalization/post-synthetic transformations to provide structurally diverse final compounds.
- Baar, Lubomír V.,J.-Y. D. Bon, David,Ková?, Ond?ej,Pospí?il, Ji?í,Roiser, Lukas,Waser, Mario,Zále?ák, Franti?ek
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p. 7192 - 7206
(2020/06/27)
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- Synthesis and E/Z configuration determination of novel derivatives of 3-Aryl-2-(benzothiazol-2′-ylthio) acrylonitrile, 3-(benzothiazol-2′- ylthio)-4-(furan-2′ ′-yl)-3-buten-2-one and 2-(1-(Furan-2′ ′-yl)-3′-oxobut-1′ ′-en-2-ylthio)-3-phenylquinazolin- 4(3H)-one
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Knoevenagel condensation of 2-(benzothiazol-2-ylthio) acetonitrile (2) with either furan-2-carbaldehyde or thiophene-2-carbaldehydes leads to E-isomers 4a-b exclusively, while the condensation of the compound 2 with benzaldehyde or parasubstituted benzaldehydes with an electron-donating group afforded E/Z mixtures 4c-e with preferentially formation of the E-isomer. Condensation of furan-2-carbaldehyde (3a) with either 1-(benzothiazol-2′-ylthio) propan-2-one (5) or 2-(2′-oxo propylthio)-3-phenylquinazolin- 4(3H)-one (9) leads exclusively to the Z-isomers of 6 and 10, respectively. The structures of the newly synthesized compounds were elucidated by elemental analyses, 1H-NMR and 13C-NMR spectra, COSY, HSQC, HMBC, NOE, MS and X-ray crystallographic investigations.
- Al-Omran, Fatima,Mohareb, Rafat M.,El-Khair, Adel Abou
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experimental part
p. 6129 - 6147
(2011/09/20)
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- Fluoro-Julia olefination as a mild, high-yielding route to α-fluoro acrylonitriles
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(Chemical Equation Presented) Synthesis of a novel, stable reagent (1,3-benzothiazol-2-ylsulfonyl)fluoroacetonitrile from readily synthesized ethyl α-(1,3-benzothiazol-2-ylsulfanyl)-α-fluoroacetate is reported. Aldehydes undergo condensations with (1,3-be
- Del Solar, Maria,Ghosh, Arun K.,Zajc, Barbara
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supporting information; experimental part
p. 8206 - 8211
(2009/04/11)
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- Electrolytic Partial Fluorination of Organic Compounds. 24.1 Highly Regioselective Anodic Monofluorination of 2-Benzothiazolyl and 5-Chloro-2-benzothiazolyl Sulfides
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Electrochemical fluorination of 2-benzothiazolyl and 5-chloro-2-benzothiazolyl sulfides was successfully carried out using Et4NF·3HF as a supporting electrolyte and fluoride ion source in dimethoxyethane to provide the corresponding α-monofluorinated sulfides in good yields. Fluorination took place selectively at the position α to the sulfur atom of the sulfides, and the heterocyclic moieties were not fluorinated at all.
- Hou, Yankun,Higashiya, Seiichiro,Fuchigami, Toshio
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p. 9173 - 9176
(2007/10/03)
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- Synthesis of 2-Thioxo-3-benzothiazolineacetonitrile and Related Products
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Attempts to thermally rearrange 2-benzothiazolylthioacetonitrile (1) to the titled compound 8 failed.The reaction of 3-chloromethyl-2-benzothiazolinethione with potassium cyanide in dimethylformamide (DMF) or dimethylsulfoxide (DMSO) at 25-30 deg C afforded 8 in 98percent yield.Whereas replacing the DMF or DMSO solvent with acetone furnished the unexpected sulfide 9 in 92percent yield.Substituting 3-chloromethyl-2-benzoxazolinethione as the electrophile in the same reaction gave the sulfide 10 in 95percent yield.Possible mechanisms and supporting nmr data are discussed.
- D'Amico, John J.,Suba, Lydia,Ruminski, Peter G.
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p. 1479 - 1482
(2007/10/02)
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- Thio and sulfonyl glyoxylnitrileoxime phosphates and phosphonates
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Compounds of the formula EQU1 in which R is lower alkyl; R1 is lower alkyl or lower alkoxy; X is thio or sulfonyl; R2 is alkyl, benzothiazolo, benzyl, naphthyl, benzodiazolo-1,3, thiazolo, phenyl or substituted phenyl wherein said substituents are chloro, bromo, methyl or methoxy and the use of these compounds as insecticides.
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