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| Other Sizes |
| Targets |
Benzothiazole derivatives target a diverse array of molecular targets. They have shown promise as GPR183 antagonists for inflammatory bowel disease, as strong inhibitors of phosphoinositide 3-kinase γ (PI3Kγ) linked to inflammatory and autoimmune diseases, and as RIPK1 inhibitors for cell death-related disorders. Benzothiazole derivatives also target Hsp90, TRPC3/6, androgen receptors, glutathione peroxidase, and kinases including SCD and CLK in cancer. They modulate EGFR, JAK/STAT, ERK/MAPK, and PI3K/Akt/mTOR pathways.
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| ln Vitro |
Benzothiazole derivatives exhibit potent in vitro anticancer activity. Compound 7m showed significant anticancer activity with IC50 values of 2.32±0.03 µM against MCF-7, 3.57±0.05 µM against PC-3, and 2.93±0.05 µM against HeLa cancer cell lines. Compound 7d demonstrated antiproliferative effects with IC50 values of 10.83 μM (MCF-7), 12.68 μM (HeLa), and 106.75 μM (HUVEC). Benzothiazole derivatives also exhibit antimicrobial, anti-inflammatory, and antiviral activities.
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| ln Vivo |
In vivo activity of benzothiazole derivatives has been demonstrated, with some showing enhanced in vivo efficacy through optimal structural alterations. Benzothiazole-based DHFR inhibitors have shown promise in bacterial infections. Compounds targeting HSV-1, HCV, USP7, NS3/4A, and SARS-CoV-2 have been identified. Further in vivo studies are needed to fully characterize the therapeutic potential of specific benzothiazole derivatives.
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| Enzyme Assay |
In vitro enzyme assays for benzothiazole derivatives involve measuring their inhibition of various targets, including kinases, PI3Kγ, RIPK1, and DHFR. The assays typically use purified recombinant enzymes and measure enzymatic activity in the presence of the compound. IC50 values are determined from dose-response curves. Binding affinity can be assessed using surface plasmon resonance or isothermal titration calorimetry.
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| Cell Assay |
In vitro cellular assays for benzothiazole derivatives involve treating cancer cell lines (e.g., MCF-7, HeLa, PC-3, A549) with varying concentrations of the compound. Cell viability is assessed using MTT or other assays. Apoptosis is evaluated by Annexin V staining, caspase activity assays, or DNA fragmentation analysis. Antimicrobial activity is assessed using standard bacterial and fungal growth inhibition assays.
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| Animal Protocol |
In vivo animal experiments for benzothiazole derivatives would typically involve administering the compound to tumor-bearing mouse models for anticancer studies, or to models of inflammatory or infectious diseases. Efficacy is evaluated by measuring tumor growth inhibition, inflammatory markers, or pathogen load. The compound's pharmacokinetic properties and safety profile are also assessed in these studies.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for benzothiazole derivatives vary depending on the specific compound. Many benzothiazole-based compounds have been developed as orally active drugs. Their absorption, distribution, metabolism, and excretion properties are influenced by the substituents on the benzothiazole scaffold. The heterocyclic framework allows interaction with a variety of molecular targets.
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| Toxicity/Toxicokinetics |
Toxicity Data
LC (Rats) > 1,400 mg/m³/6h Non-human Toxicity Values Mouse intravenous LD50 = 95 mg/kg Benzothiazole and its derivatives have been extensively studied for their pharmacological actions. Some derivatives have shown potential as anti-necroptotic agents by protecting cells against necroptosis through RIPK1 inhibition. Benzothiazole scaffolds have been investigated for the synthesis of agents targeting neurodegenerative diseases. The compound is a versatile scaffold in drug discovery. |
| References |
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| Additional Infomation |
Benzothiazole is an organic heterobicyclic compound, a fused product of benzene and thiazole, and the parent compound of benzothiazoles. It is both a plant metabolite and an exogenous substance and environmental pollutant. Benzothiazole has been reported to exist in tea plants (Camellia sinensis), Gymnodinium nagasakiense, and other organisms with relevant data. Benzothiazole is a metabolite of Saccharomyces cerevisiae, or is produced by Saccharomyces cerevisiae.
Benzothiazole (CAS#: 95-16-9) has the molecular formula C7H5NS and a molecular weight of 135.19. It is a heterocyclic compound consisting of a benzene ring fused to a thiazole ring. Benzothiazole-based compounds exhibit a wide range of biological activities, including anticancer, antimicrobial, anti-inflammatory, antiviral, antimalarial, antitubercular, antidiabetic, and neuroprotective activities. The compound is a valuable scaffold in drug discovery. |
| Molecular Formula |
C7H5NS
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|---|---|
| Molecular Weight |
135.18
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| Exact Mass |
135.014
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| CAS # |
95-16-9
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| Related CAS # |
Benzothiazole-d4;194423-51-3
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| PubChem CID |
7222
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
227.0±9.0 °C at 760 mmHg
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| Melting Point |
2 °C(lit.)
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| Flash Point |
96.6±7.6 °C
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| Vapour Pressure |
0.1±0.4 mmHg at 25°C
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| Index of Refraction |
1.689
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| LogP |
2.01
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
9
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| Complexity |
105
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| Defined Atom Stereocenter Count |
0
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| SMILES |
N1C2C(=CC=CC=2)SC=1
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| InChi Key |
IOJUPLGTWVMSFF-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H
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| Chemical Name |
1,3-benzothiazole
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : 110 mg/mL (813.73 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.75 mg/mL (20.34 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.75 mg/mL (20.34 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.75 mg/mL (20.34 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.3975 mL | 36.9877 mL | 73.9754 mL | |
| 5 mM | 1.4795 mL | 7.3975 mL | 14.7951 mL | |
| 10 mM | 0.7398 mL | 3.6988 mL | 7.3975 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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