20358-00-3

Usage

Chemical Properties

Colorless to light yellow solid

InChI:InChI=1/C7H5ClN2S/c8-4-1-2-6-5(3-4)10-7(9)11-6/h1-3H,(H2,9,10)

Upstream product

• 108-42-9 3-chloro-aniline 
• 1147550-11-5 ammonium thiocyanate 
• 2786-51-8 5-chlorobenzo[d]thiazole 
• 3425-46-5 potassium selenocyanate 
• 506-68-3 bromocyane 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 5331-91-9 5-chloro-2-mercaptobenzothiazole 
• 141-85-5 3-chloroaniline hydrochloride 
• 1391365-04-0 N₁-(9H-fluoren-9-ylmethyloxycarbonyl)-N₂-(3-chlorophenyl)thiourea 
• 333-20-0 potassium thioacyanate 
• 6828-35-9 5-chloro-2-iodoaniline 
• 17356-08-0 thiourea 
• 4947-89-1 1-(3-chlorophenyl)-2-thiourea 
• 6803-43-6 4-chloro-2-nitro-phenyl thiocyanate 

Downstream Products

• 35412-19-2 N-(5-chlorobenzo[d]thiazol-2-yl)benzamide 
• 1457-46-1 3-phenylrhodanine 
• 117844-40-3 N,N'-Bis-(5-chloro-benzothiazol-2-yl)-hydrazine; hydrobromide 
• 77203-70-4 2,4-Dibromo-6-{[(E)-5-chloro-benzothiazol-2-ylimino]-methyl}-phenol 
• 104497-70-3 2-(5-Chlorobenzothiazolyl)hydrazonobutyl-1-aminophenyl-1,3-dione 
• 77203-65-7 4-Bromo-2-{[(E)-5-chloro-benzothiazol-2-ylimino]-methyl}-phenol 
• 110704-19-3 5-chloro-2-(chloromethyl)-1,3-benzothiazole 
• 1251838-05-7 N-(5-chloro-1,3-benzothiazol-2-yl)-1,1'-biphenyl-4-carboxamide 
• 1207835-47-9 6-chloro-2-[4-(dimethylamino)phenyl]-N-(2-methoxyethyl)imidazo[2,1-b][1,3]benzothiazol-3-amine 
• 1207835-46-8 6-chloro-2-[4-(dimethylamino)phenyl]-N-(3-methoxypropyl)-imidazo[2,1-b][1,3]benzothiazol-3-amine 
• 2941-56-2 2-bromo-5-chlorobenzothiazole 
• 1259288-43-1 C₁₇H₁₂ClN₅OS 
• 1259288-41-9 4-[(5-chloro-benzothiazol-2-yl)-hydrazono]-2-(2,4-dinitro-phenyl)-5-methyl-2,4-dihydro-pyrazol-3-one 
• 1313371-63-9 4-amino-5-(2-cyclohexylethyl)-3-[N-(6-chlorobenzothiazole-2-yl)acetamido]thio-4H-1,2,4-triazole 

Relevant academic research and scientific papers

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles

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

Synthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide

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.

Benzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17Β-HSD10 with implications to Alzheimer’s disease treatment

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.

Chagas Disease Drug Discovery: Multiparametric Lead Optimization against Trypanosoma cruzi in Acylaminobenzothiazole Series

Acylaminobenzothiazole hits were identified as potential inhibitors of Trypanosoma cruzi replication, a parasite responsible for Chagas disease. We selected compound 1 for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.63 μM) and its human metabolic stability (human clearance = 9.57 mL/min/g). A total of 39 analogues of 1 were synthesized and tested in vitro. We established a multiparametric structure-activity relationship, allowing optimization of antiparasite activity, physicochemical parameters, and ADME properties. We identified compound 50 as an advanced lead with an improved anti-T. cruzi activity in vitro (IC50 = 0.079 μM) and an enhanced metabolic stability (human clearance = 0.41 mL/min/g) and opportunity for the oral route of administration. After tolerability assessment, 50 demonstrated a promising in vivo efficacy.

ANTIBIOTIC COMPOUNDS, PHARMACEUTICAL FORMULATIONS THEREOF AND METHODS AND USES THEREFOR

The present invention relates to compounds of formula (I) wherein G1 to G8 are as defined herein. The compounds are PK inhibitors and as such represent a new approach to treating pathogenic infections, including multidrug resistant pathogens. Disclosed herein are the compounds of formula (I), pharmaceutical compositions comprising the compounds of formula (I) and their use in the treatment of antimicrobial infection. (Formula (1))

Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists

Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by assessment of active derivatives on STZ-induced diabetic model. It was observed that nine of twenty novel piperine analogues (5b, 6a-h), showed significantly higher antidiabetic activity in comparison with rosiglitazone (standard). Furthermore, these active derivatives were evaluated for their action as PPAR-γ agonists demonstrating their mechanism of action. The effects on body weight, lipid peroxidation, and hepatotoxicity after administration with active derivatives were also studied to further establish these derivatives as lead molecules for treatment of diabetes with lesser side-effects.

Efficient and facile protocol for one-pot synthesis of 2-amino-substituted benzothiazoles catalyzed by nano-BF3/SiO2 under mild conditions

Abstract: A highly efficient and simple protocol for the preparation of 2-aminobenzothiazoles through the reaction of potassium thiocyanate and substituted anilines in the presence of nano-BF3/SiO2 as a reusable heterogeneous catalyst is described. In this method, all of the 2-amino-substituted benzothiazoles were obtained in high to excellent yields and short reaction times under mild conditions. The structures of the resulting products were characterized and confirmed by melting point, FT-IR, 1H NMR and 13C NMR techniques. Graphical Abstract: A highly efficient and simple protocol for the preparation of 2-aminobenzothiazoles by reaction of potassium thiocyanate and substituted anilines in the presence of nano-BF3/SiO2 as a reusable heterogeneous catalyst is described.[Figure not available: see fulltext.]

Design, synthesis and anticonvulsant evaluation of N-(benzo[d]thiazol-2- ylcarbamoyl)-2-methyl-4-oxoquinazoline-3(4H)-carbothioamide derivatives: A hybrid pharmacophore approach

Novel N-(benzo[d]thiazol-2-ylcarbamoyl)-2-methyl-4-oxoquinazoline-3(4H)- carbothioamide derivatives were synthesized and evaluation of their anticonvulsant effects was done using various models of experimental epilepsy. Initial anticonvulsant activities of the compounds were investigated using intraperitoneal (i.p.) maximal electroshock shock (MES), subcutaneous pentylenetetrazole (scPTZ) seizure models in mice. The quantitative assessment after oral administration in rats showed that the most active was 2-methyl-4-oxo-N-(6-(trifluoromethoxy)benzo[d]thiazol-2-ylcarbamoyl) quinazoline-3(4H)-carbothioamide (SA 24) with ED50 values of 82.5 μmol/kg (MES) and 510.5 μmol/kg (scPTZ). This molecule was more potent than phenytoin and ethosuximide which were used as reference antiepileptic drugs. To explain the possible mechanism for anticonvulsant action, some of the selected active compounds were subjected to GABA (γ-amino butyric acid) assay and AMPA ((S)-2-amino-3-(3-hydroxyl-5-methyl-4-isoxazolyl) propionic acid) induced seizure test.

Discovery of benzothiazole guanidines as novel inhibitors of thrombin and trypsin IV

In a project to find novel neutral P1 fragments for the synthesis of thrombin inhibitors with improved pharmacokinetic properties, fragments containing a benzothiazole guanidine scaffold were identified as weak thrombin inhibitors. WaterLOGSY (Water-Ligan

COMPOUNDS FOR THE INHIBITION OF CELLULAR PROLIFERATION

Compositions and methods for inhibiting translation are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, (4) disorders associated with viral infections, and/or (5) non-proliferative metabolic disorders such as type II diabetes where inhibition of translation initiation is beneficial using the compounds disclosed herein.