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2-hydroxy-benzoic anilide compounds and derivatives, compositions thereof, and methods for treating metabolic diseases and cancer through uncoupling mitochondria.

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Reference:
Thiazole | C3H10622NS – PubChem,
Thiazole | chemical compound | Britannica

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A series of benzothiazole linked phenylpyridopyrimidinones (8a-g) and their diones (9a-g) have been designed, synthesized and evaluated for their anticancer activity. Among the series one of the conjugate 8b showed significant cytotoxicity against human cervical cancer cell line ME-180 with IC 50 value of 4.01 muM. This compound was tested on the cell cycle perturbations and DNA damage. Flow cytometry analysis revealed that the compound 8b showed drastic cell cycle perturbations due to concentration dependent increase in the sub-G0 phase in ME-180 cell line. DNA fragmentation and Hoechst staining reveals that this compound induced cell death by apoptosis. Further caspase-3 and loss of mitochondrial membrane potential suggested that the compound induces cell death by apoptosis.

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Reference:
Thiazole | C3H10564NS – PubChem,
Thiazole | chemical compound | Britannica

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Background: Epilepsy affects approximately 50 million people globally. It is generally characterized by periodic seizures of unpredictable nature, though a variety of anticonvulsant drugs are available but the major drawback is undesirable side effects. Here an effort is being made to utilise the beneficial effect of benzothiazoles and oxadiazoles as potent anticonvulsants and there is an anticipation of synergistic effect from the hybrid molecule. Methods: Here a series of new hybrid molecules containing oxadiazole and benzothiazole pharmacophore were synthesised using appropriate synthetic route and characterised by IR, 1H NMR, 13C NMR, mass and elemental analysis. The synthesised compounds were examined for their maximal electroshock seizure (MES) and subcutaneous pentylene tetrazole (Sc PTZ) induced seizure and neurotoxicity screens. Those found potent were also evaluated for their CNS depressant effect. Results: Among the compounds tested 4m N-(6-fluro-1,3-benzothiazol-2-yl)-2-{[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamide and 4n N-(6-Chloro-1,3-benzothiazol-2-yl)-2-{[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl} acetamide showed protection from seizures in both the animal models at dose level of 30 mg/kg after 0.5 hr and at 100 mg/kg after 4 hr period indicating that the compound is potent and long acting. These compounds also exhibited lesser CNS depression and neurotoxicity. Conclusion: Among the synthesized compounds 4m and 4n possessed significant anticonvulsant activity without any neurotoxicity and CNS depressant effects. Thus the hybrid benzothiazolyl acetamide derivatives containing oxadizole scaffold provided a new opportunity for possible modification and future exploitation to get the safer and effective anticvulsant agents.

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Reference:
Thiazole | C3H10522NS – PubChem,
Thiazole | chemical compound | Britannica

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The ethyl 2-(6-substituted benzo[d]thiazol-2-ylamino)-2-oxoacetate derivatives (OX 1-9) were prepared using a one-step reaction. The in vitro inhibitory activity of the compounds against protein tyrosine phosphatase 1B (PTP-1B) was evaluated. Compounds OX-(1, 6 and 7) were rapid reversible (mixed-type) inhibitors of PTP-1B with IC50 values in the low micro-molar range. The most active compounds OX-(1, 6 and 7) were docked into the crystal structure of PTP-1B. Docking results indicate potential hydrogen bond interactions between the oxamate group in all compounds and the catalytic amino acid residues Arg221 and Ser216. The compounds were evaluated for their in vivo hypoglycemic activity, showing significant lowering of plasma glucose concentration in acute normoglycemic model and oral glucose tolerance test similarly at the effect exerted for hypoglycemic drug glibenclamide.

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Reference:
Thiazole | C3H10416NS – PubChem,
Thiazole | chemical compound | Britannica

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Catalyst-free autocatalyzed dehydrative N-alkylation reactions of 2-aminobenzothiazoles, 2-aminopyrimidines, and 2-aminopyrazine with primary and secondary alcohols have been achieved for efficient, practical, and green synthesis of the versatile heteroaryl amine derivatives. These reactions were interestingly induced by structure-dependent tautomeric equilibria of the heteroaryl amines via MPV-O transfer hydrogenation of the imino tautomers by alcohols to give aldehydes as the key initiating step.

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Reference:
Thiazole | C3H10512NS – PubChem,
Thiazole | chemical compound | Britannica

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The acid dissociation constants of some 4- and/or 6-substituted 2-aminobenzothiazole and 4-substituted thiazole derivatives were determined spectroscopically. With the exception of a few, the first protonation was found to occur on the amino group. In some molecules where prototropic tautomerism is possible, a change-over in the protonation mechanism was observed. The first protonation under these circumstances was found to occur on the imino nitrogen atom. The second protonation takes place on the thiazole ring nitrogen atom.

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Reference:
Thiazole | C3H10423NS – PubChem,
Thiazole | chemical compound | Britannica

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The 2-arylsulfonylaminobenzothiazole derivatives 1-27 were prepared using a one step reaction. The in vitro inhibitory activity of the compounds against protein tyrosine phosphatase 1B (PTP-1B) was evaluated. Compounds 4 and 16 are rapid reversible (mixed-type) inhibitors of PTP-1B with IC50 values in the low micromolar range. The most active compounds (4 and 16) were docked into the crystal structure of PTP-1B. Docking results indicate potential hydrogen bond interactions between the nitro group in both compounds and the catalytic amino acid residues Arg 221 and Ser 216. Both compounds were evaluated for their in vivo antihyperglycemic activity in a type 2 diabetes mellitus rat model, showing significant lowering of plasma glucose concentration, during the 7 h post-intragastric administration.

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Reference:
Thiazole | C3H10424NS – PubChem,
Thiazole | chemical compound | Britannica

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Compounds of the Formula I: STR1 useful in the treatment of thrombin and trypsin related disorders.

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Reference:
Thiazole | C3H10507NS – PubChem,
Thiazole | chemical compound | Britannica

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Synthesis of beta-fluorophenethylamines was accomplished in three steps with an overall yield of 50%. Condensation of beta-fluorophenethylamine hydrochloride with thiocarbonylimidazole derivative derived from halopyridyl amines in dimethylformamide furnished the desired thiourea compounds as crystalline solids. Several of the beta-fluorophenethyl thiourea compounds inhibited HIV-1 reverse transcriptase (RT) at nanomolar to low micromolar concentrations.

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Reference:
Thiazole | C3H10427NS – PubChem,
Thiazole | chemical compound | Britannica

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The efficient, highly convenient synthesis of polysubstituted pyridine derivatives was established via the reaction of N-(benzothiazol-2-yl)-2-cyanoacetamides with an assortment of arylidene malononitriles and arylidene ethyl cyanoacetates in the presence of l-proline as an efficient organocatalyst for this type of ultrasonic-mediated Michael addition. The mechanistic pathway and factors affecting this reaction were also established. The main characteristics of this procedure are high yields, use of a cost-effective catalyst, and easy work-up and purification.

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Reference:
Thiazole | C3H10417NS – PubChem,
Thiazole | chemical compound | Britannica