2-Amino-6-nitrobenzothiazole

Anticonvulsant activity, organotypic hippocampal neuroprotection assay and in-silico sodium channel blocking potential of 2-amino-6-nitrobenzothiazole derived semicarbazones.[Pubmed:28946193]

Biomed Pharmacother. 2017 Nov;95:1451-1460.

Epilepsy is one of the dreadful neurodegenerative disorder characterized by recurrent, unprovoked seizures. Currently available antiepileptic drugs are still associated with enormous side effects resulting in search of newer, more effective and safer agents. In view of this, we have investigated anticonvulsant activity of 2-Amino-6-nitrobenzothiazole derived semicarbazones (7-32) in various in-vivo animal seizure models viz. maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) and 6Hz psychomotor seizure model. Neurotoxicity was estimated by rotarod test. The compounds were also assessed for their neuroprotective potential from excitotoxic insult using organotypic hippocampal slice culture neuroprotection assay. Several compounds exhibited excellent anticonvulsant activity in MES and scPTZ models compared to reference drugs, phenytoin and levetiracetam. The results of kainic acid (KA) - induced neuroprotection assay indicated that compounds 26 and 24 were found to be most potent with IC50 of 99.54+/-1.27 and 101.00+/-1.20muM respectively. Both the compounds attenuated KA-mediated cell death in organotypic hippocampal slice cultures. Some of the compounds were found to be good antidepressants, better than the reference drug citalopram, when analyzed in forced swim test. Since semicarbazones exhibited profile resembling phenytoin, an attempt was made to screen them against human neuronal sodium channel isoform (hNav1.2) by performing computational molecular docking using AutoDock 4.2. Compound 30, 1-(5-Chloro-2-oxoindolin-3-ylidene)-4-(6-nitrobenzothiazol-2-yl)semicarbazide emerged as lead candidate possessing excellent in-vivo MES activity and high binding affinity computationally, better than the reference drug phenytoin and also exhibited neuroprotection from excitotoxic insult in KA-induced neuroprotection assay (IC50=126.80+/-1.24muM). However, some of the active compounds were neurotoxic at their anticonvulsant doses. Further optimization studies are needed to reduce toxicity and develop them as novel therapeutic agents for epilepsy.

Bismuth film electrode at a silver solid amalgam substrate as a new tool for voltammetric determination of electrochemically reducible organic compounds.[Pubmed:23182576]

Talanta. 2012 Dec 15;102:68-74.

New type of bismuth film electrode prepared by electrodeposition of bismuth film on a silver solid amalgam substrate (BiF-AgSAE) was tested as a sensor for voltammetric determination of electrochemically reducible organic substances using 2-Amino-6-nitrobenzothiazole (ANBT) as a model analyte. Using the optimized conditions (a 9:1 (v/v) mixture of aqueous Britton-Robinson buffer solution (pH 10.0) and methanol), the limits of quantification are 0.16 mumol L(-1) for direct current voltammetry (DCV) and 0.22 mumol L(-1) for differential pulse voltammetry (DPV). The obtained calibration dependences are linear in the concentration range from 0.2 to 100 mumol L(-1) and the practical applicability of the newly developed electrode for the direct determination of ANBT in tap and mineral water model samples was confirmed in the concentration range from 0.2 to 10 mumol L(-1).