6285-57-0Relevant articles and documents
Synthesis of Some New 3-(2'-Benzothiazolyl)-4(3H)-quinazolinones as Antifungal Agents
Lakhan, Ram,Ral, Babban J.
, p. 501 - 502 (1986)
Five new 2-methyl-3--4(3H)-quinazolinones have been synthesized.Three of them were tested for their antifungal activity against agricultural fungi by the food poison technique and the activity was compared with that of Dithan M-45.
Synthesis, Spectral Characteristics, and Biological Activity of 1,3-Oxazepines and 1,3-Oxazepanes Derived from 6-Nitrobenzothiazol-2-amine
Abbas, S. K.,Abbas, Z. F.,Hanoon, H. D.,Hussein, K. A.,Radhi, S. M.
, p. 327 - 331 (2020)
Abstract: 1,3-Oxazepine and 1,3-oxazepane derivatives of 6-nitrobenzothiazol-2-amine were synthesized, and their spectral and antibacterial properties were studied. The condensation of 6-nitrobenzothiazol-2-amine with aromatic aldehydes gave the corresponding Schiff bases, whose subsequent intermolecular cyclization with maleic and succinic anhydrides led to the target 1,3-oxazepine and 1,3-oxazepane derivatives. The compositions and structures of the synthesized compounds were established by elemental analysis and FTIR and 1H NMR spectroscopy. 2-(4-Hydroxy-3-methoxyphenyl)-3-(6-nitrobenzothiazol-2-yl)-1,3-oxazepane-4,7-dione and 2-(4-iso-propylphenyl)-3-(6-nitrobenzothiazol-2-yl)-1,3-oxazepane-4,7-dione showed the highest antibacterial activity against the gram-positive bacteria Klebsiellapneumonia and Bacillussubtilis, and the gram-negative bacteria Staphylococcusaureus provide to be highly sensitive to 2-(4-hydroxy-3-methoxyphenyl)-3-(6-nitrobenzothiazol-2-yl)-1,3-oxazepane-4,7-dione.
An efficient one-pot synthesis of 2-aminobenzothiazoles from substituted anilines using benzyltrimethylammonium dichloroiodate and ammonium thiocyanate in DMSO:H2O
Dass, Reuben,Peterson, Matt A.
supporting information, (2021/10/04)
Treatment of a variety of substituted anilines with benzyltrimethylammonium dichloroiodate (1.2 equiv) and ammonium thiocyanate (1.0 equiv) in DMSO:H2O (9:1) at 70 °C gave the corresponding 2-aminobenzothiazoles in excellent isolated yields (75–97%; ave. yield for all substrates = 90%). The reaction worked well for 2(4)-mono-, 2,4-di-, or 3,4,5-tri-substituted anilines, and a wide range of both electron donating groups (MeO, HO, CF3O, Me) and electron withdrawing groups (NO2, CN, CO2Et, CO2H, Cl, F) were well tolerated. This method provides a useful alternative to other methods that are either less efficient (requiring 3–7 fold equivalents of reagents) or utilize highly toxic and corrosive liquid Br2 as the oxidizing agent.
Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles
Chen, Xiran,Fu, Lianrong,Hao, Xin-Qi,Shi, Linlin,Song, Mao-Ping,Zhu, Xinju,Zhu, Yu-Shen
supporting information, (2021/09/09)
A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles
Condensation of 2-Amino-1,3-thiazole Salts and Benzo Analogs with Trifluoroacetylacetone
Shulga,Simurova,Shulga
, p. 364 - 368 (2021/04/13)
Abstract: The condensation of 2-amino-1,3-thiazolium perchlorates and their benzo analogs with trifluoro-acetyl-acetone in acetic acid afforded the corresponding [1,3]thiazolo[3,2-a]pyrimidinium, pyrimido[2,1-b][1,3]benzothiazolium, and naphtho[2′,1′:4,5][1,3]thiazolo[3,2-a]pyrimidinium salts as a single isomer in which the trifluoromethyl group is located in the γ-position with respect to the bridgehead nitrogen atom. The structure of the synthesized compounds was confirmed by 1H NMR spectra and elemental analyses.
Synthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide
Akhtar, Md Jawaid,Debnath, Biplab,Grover, Gourav,Nath, Rajarshi,Pathania, Shelly,Shahar Yar, M.
, (2020/12/25)
A series of N-(substituted benzothiazole-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a-i) and substituted-[3-((5-phenyl-1,3,4-oxadiazole-2-yl)imino)indolene-2-one] (5a-f) were designed, synthesized fulfilling the structural requirement of pharmacophore and evaluated for anticonvulsant activities using maximal electroshock test (MES), subcutaneous pentylenetetrazole (scPTZ) seizures and neurotoxicity by motor impairment model in mice. The most active compoundN-(5-chlorobenzo[d]thiazol-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a) has shown significant anticonvulsant activity against both MES and scPTZ screens and emerged as most effective anticonvulsant compound with median dose of 35.7 mg/kg (MES ED50), 88.15 mg/kg (scPTZ ED50) and toxic dose (TD50) was found to be > 500mg/kg. In silico studies including molecular docking study was carried to establish the molecular interaction of potent compound (4a) in both Na+ channel and GABAA receptors. The prediction of pharmacokinetic parameters and distance mapping of compounds were also performed to establish the drug likeness property.
Synthesis of new benzothiazole derivatives bearing thiadiazole as monoamine oxidase inhibitors
Acar ?evik, Ulviye,Osmaniye, Derya,Sa?lik, Begüm N.,Levent, Serkan,K. ?avu?o?lu, Betül,Karaduman, Abdullah B.,D. ?zkay, ümide,?zkay, Yusuf,Kaplancikli, Zafer A.,Turan, Gülhan
, p. 2225 - 2233 (2020/03/04)
Monoamine oxidases (MAO) are enzymes that catalyze the oxidative deamination of monoamines such as dopamine, noradrenaline, adrenaline, and serotonin. Recent studies have shown that numerous benzothiazole derivatives exhibit hMAO inhibitory activity in the micromolar concentration range. In this study, a novel series of benzothiazole-thiadiazole (5a-5l) was synthesized and characterized their chemical structures by 1H-NMR, 13C-NMR, and Mass spectroscopy. These compounds were evaluated as inhibitors for types A and B MAO enzymes. Compounds 5f and 5l were the most active derivatives in the series with an IC50 values of 0.107 ± 0.003 and 0.128 ± 0.004, respectively. Furthermore, cytotoxicity of compounds 5f and 5l were investigated and found as non-cytotoxic.
Benzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17Β-HSD10 with implications to Alzheimer’s disease treatment
Aitken, Laura,Benek, Ondrej,Chribek, Matej,Dolezal, Rafael,Gunn-Moore, Frank,Hrabinova, Martina,Hroch, Lukas,Jun, Daniel,Kralova, Vendula,Kuca, Kamil,Lycka, Antonin,Musilek, Kamil,Prchal, Lukas,Schmidt, Monika,Vinklarova, Lucie,Zemanova, Lucie
, (2020/03/26)
Human 17β-hydroxysteroid dehydrogenase type 10 is a multifunctional protein involved in many enzymatic and structural processes within mitochondria. This enzyme was suggested to be involved in several neurological diseases, e.g., mental retardation, Parkinson’s disease, or Alzheimer’s disease, in which it was shown to interact with the amyloid-beta peptide. We prepared approximately 60 new compounds based on a benzothiazolyl scaffold and evaluated their inhibitory ability and mechanism of action. The most potent inhibitors contained 3-chloro and 4-hydroxy substitution on the phenyl ring moiety, a small substituent at position 6 on the benzothiazole moiety, and the two moieties were connected via a urea linker (4at, 4bb, and 4bg). These compounds exhibited IC50 values of 1–2 μM and showed an uncompetitive mechanism of action with respect to the substrate, acetoacetyl-CoA. These uncompetitive benzothiazolyl inhibitors of 17β-hydroxysteroid dehydrogenase type 10 are promising compounds for potential drugs for neurodegenerative diseases that warrant further research and development.
1-Aryl-3-(4-methoxybenzyl)ureas as potentially irreversible glycogen synthase kinase 3 inhibitors: Synthesis and biological evaluation
Venter, Jana,Perez, Concepción,van Otterlo, Willem A.L.,Martínez, Ana,Blackie, Margaret A.L.
, p. 1597 - 1600 (2019/05/02)
Glycogen synthase kinase 3 (GSK-3)has become known for its multifactorial involvement in the pathogenesis of Alzheimer's disease. In this study, a benzothiazole- and benzimidazole set of 1-aryl-3-(4-methoxybenzyl)ureas were synthesised as proposed Cys199-targeted covalent inhibitors of GSK-3β, through the incorporation of an electrophilic warhead onto their ring scaffolds. The nitrile-substituted benzimidazolylurea 2b (IC50 = 0.086 ± 0.023 μM)and halomethylketone-substituted benzimidazolylurea 9b (IC50 = 0.13 ± 0.060 μM)displayed high GSK-3β inhibitory activity, in comparison to reference inhibitor AR-A014418 (1, IC50 = 0.072 ± 0.043)in our assay. The results suggest further investigation of 2b and 9b as potential covalent inhibitors of GSK-3β, since a targeted interaction might provide improved kinase-selectivity.
Design, synthesis and biological evaluation of some 2-(6-nitrobenzo[d]thiazol-2-ylthio)-N-benzyl-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide derivatives as selective DprE1 inhibitors
Gawad, Jineetkumar,Bonde, Chandrakant
, p. 2696 - 2708 (2019/08/12)
Tuberculosis (TB) is an infectious disease and caused by various strains of mycobacteria. In the present study, pharmacophore model was developed using single ligand by ligand-based drug discovery approach. The key features responsible for DprE1 inhibitory activity were taken into consideration for developing pharmacophore. After the virtual screening, top 1000 hits were further subjected to docking study using GLIDE module, Schr?dinger. Docking studies have shown promising interaction with amino residues with better glide score. Ligand-based drug design approach yielded a series of 15, 2-(6-nitrobenzo[d]thiazol-2-ylthio)-N-benzyl-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide derivatives. All synthesized derivatives were characterized using NMR, mass, CHN analysis. The synthesized compounds were screened for In vitro antitubercular activity against Mycobacterium tuberculosis (H37Rv). Four compounds, 5g (MIC-1.01 μM); 5i (MIC-0.91 μM); 5k (MIC-0.82 μM); and 5o (MIC-1.04 μM) has shown promising activity compared to MIC of standard isoniazid (INH) and DprE1 enzyme inhibition was compared to BTZ043. Two halogen-substituted compounds have exhibited drastic enzyme inhibition.
