24044-91-5

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
(Benzothiazol-2-ylsulfanyl)-acetic acid hydrazide is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals due to its unique structure and functional groups, which can be further modified to create a wide range of active compounds.
Used in Anti-Tuberculosis Applications:
(Benzothiazol-2-ylsulfanyl)-acetic acid hydrazide has demonstrated potential as an anti-tuberculosis agent, making it a candidate for the development of new treatments against this infectious disease.
Used in Antimicrobial and Anti-Fungal Applications:
(Benzothiazol-2-ylsulfanyl)-acetic acid hydrazide has shown antimicrobial and antifungal properties, indicating its use in applications that require the inhibition of microbial growth, such as in medical and environmental settings.
Used in Corrosion Inhibition:
It has been studied for its potential use as a corrosion inhibitor, suggesting that it could be employed in industrial applications to protect materials from corrosion and extend their lifespan.
Used in Organic Synthesis as a Reagent:
(Benzothiazol-2-ylsulfanyl)-acetic acid hydrazide is also used as a reagent in organic synthesis, highlighting its versatility in facilitating various chemical reactions and the creation of diverse chemical compounds.

InChI:InChI=1/C9H9N3OS2/c10-12-8(13)5-14-9-11-6-3-1-2-4-7(6)15-9/h1-4H,5,10H2,(H,12,13)

Upstream product

• 24044-88-0 ethyl 2-(benzo[d]thiazol-2-ylthio)acetate 
• 24044-87-9 methyl (1,3-benzothiazol-2-ylsulfanyl)acetate 
• 149-30-4 2-Mercaptobenzothiazole 
• 6295-57-4 2-benzthiazole thioacetic acid 
• 137-07-5 2-amino-benzenethiol 
• 80357-75-1 2-[(benzothiazol-2-yl)thio] acetyl chloride 

Downstream Products

• 154017-15-9 (2-benzothiazolylthio)acetic acid (3-pyridilmethylene)hydrazide 
• 140935-41-7 2-(Benzothiazol-2-ylsulfanyl)-N-{4-[1-(4-chloro-phenyl)-meth-(Z)-ylidene]-2-methyl-5-oxo-4,5-dihydro-imidazol-1-yl}-acetamide 
• 140935-48-4 2-(Benzothiazol-2-ylsulfanyl)-N-{4-[1-(4-hydroxy-phenyl)-meth-(Z)-ylidene]-5-oxo-2-phenyl-4,5-dihydro-imidazol-1-yl}-acetamide 
• 140935-42-8 2-(Benzothiazol-2-ylsulfanyl)-N-{2-methyl-4-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-5-oxo-4,5-dihydro-imidazol-1-yl}-acetamide 
• 140935-44-0 2-(Benzothiazol-2-ylsulfanyl)-N-{2-methyl-4-[1-(4-nitro-phenyl)-meth-(Z)-ylidene]-5-oxo-4,5-dihydro-imidazol-1-yl}-acetamide 
• 140935-49-5 2-(Benzothiazol-2-ylsulfanyl)-N-{4-[1-(2-chloro-phenyl)-meth-(Z)-ylidene]-5-oxo-2-phenyl-4,5-dihydro-imidazol-1-yl}-acetamide 
• 140935-47-3 2-(Benzothiazol-2-ylsulfanyl)-N-{4-[1-(3,4-dimethoxy-phenyl)-meth-(Z)-ylidene]-5-oxo-2-phenyl-4,5-dihydro-imidazol-1-yl}-acetamide 
• 127152-56-1 (Benzothiazol-2-ylsulfanyl)-acetic acid [1-(4-chloro-phenyl)-meth-(E)-ylidene]-hydrazide 
• 94768-91-9 (2-benzothiazolylthio)acetylhydrazone of m-nitrobenzaldehyde 
• 94768-90-8 (Benzothiazol-2-ylsulfanyl)-acetic acid [1-(4-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide 
• 24044-93-7 benzothiazol-2-ylsulfanyl-acetic acid (2-hydroxy-benzylidene)-hydrazide 
• 112779-66-5 (Benzothiazol-2-ylsulfanyl)-acetic acid [1-(2-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide 
• 128991-13-9 (Benzothiazol-2-ylsulfanyl)-acetic acid [1-(3-hydroxy-4-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide 
• 140935-50-8 2-(Benzothiazol-2-ylsulfanyl)-N-{4-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-5-oxo-2-phenyl-4,5-dihydro-imidazol-1-yl}-acetamide 

Relevant academic research and scientific papers

Synthesis and biological evaluation of benzothiazol-based 1,3,4-oxadiazole derivatives as amyloid β-targeted compounds against Alzheimer’s disease

Abstract: A series of new benzothiazol-based 1,3,4-oxadiazole derivatives were synthesized and evaluated for their neuroprotective effects against Aβ25–35-induced toxicity in SH-SY5Y cells. The bioassay results indicated that most of the tested compounds exhibited promising neuroprotective activity. In particular, compound 2-[[[5-[(4-bromophenylmethyl)thio]-1,3,4-oxadiazol-2-yl]methyl]thio]benzothiazole showed the most potent activity (95.7% of cell viability at 10?μM), better than the positive control EGCG (90.7% of cell viability at 10?μM). Furthermore, compounds 2-[[[5-[(2-bromophenylmethyl)thio]-1,3,4-oxadiazol-2-yl]methyl]thio]benzothiazole, 2-[[[5-[(4-bromo-2-fluorophenylmethylyl)thio]-1,3,4-oxadiazol-2-yl]methyl]thio]benzothiazole, and 2-[[[5-[(4-methoxyphenylmethyl)thio]-1,3,4-oxadiazol-2-yl]methyl]thio]benzothiazole displayed neuroprotective activity similar to EGCG (87.7, 89.1, and 87.7% of cell viability, respectively, at 10?μM). The preliminary SARs analysis indicated that benzene ring is the key factor for the neuroprotective activity and the bromo atom substituted at 4-position of the benzene ring favors the neuroprotective activity. In addition, the fluoro group in the benzene ring appears not beneficial for the neuroprotective activity. Graphical abstract: [Figure not available: see fulltext.].

Developing a scaffold for urease inhibition based on benzothiazoles: Synthesis, docking analysis, and therapeutic potential

The synthesis, in silico molecular docking, and in vitro urease inhibition studies of a novel series of benzothiazole derivatives are reported. The title compounds in the two series, namely, 2-({5-[(benzothiazol-2-ylthio)methyl]-1,3,4-oxadiazol-2-yl}thio)-1-(4-substituted-phenyl)ethan-1-one and 2-(benzothiazol-2-ylthio)-1-(4-substituted-phenyl)ethan-1-one oxime, were synthesized by the reaction of benzo[d]thiazole-2-thiol with different kinds of intermediates in several steps using both conventional and microwave techniques. All compounds were found to have an excellent degree of urease-inhibitory potential ranging between 16.16 ± 0.54 and 105.32 ± 2.10 μM when compared with the standard inhibitor acetohydroxamic acid with IC50 = 320.70 ± 4.24 μM. The structure–activity relationship was established in detail. The binding interactions of the compounds with the enzyme were confirmed through molecular docking. Further, 100 -ns molecular dynamics simulations were performed to investigate the stability and structural perturbations experienced by the most potent compound over the urease active site.

Design, modification of phyllanthone derivatives as anti-diabetic and cytotoxic agents

Twelve benzylidene derivatives, one Baeyer-Villiger oxidative, six imine derivatives were successfully designed and synthesised from phyllanthone. In the search for potential new anti-diabetic agents, phyllanthone along with its benzylidene and oxidation analogues were evaluated for enzyme inhibition against α-glucosidase. In the benzylidene series, most analogues displayed stronger activity than the mother compound. Compound 1c revealed the strongest activity, outperforming the acarbose positive control with an IC50 value of 19.59 μM. Phyllanthone and its derivatives were then tested for cytotoxic activity against the K562 cell line. The imine analogues displayed the most powerful cytotoxic activity with 3cand 3d having IC50 values of 57.55 and 68.02 μM, respectively.

Synthesis, α-glucosidase inhibition, and molecular docking studies of novel N-substituted hydrazide derivatives of atranorin as antidiabetic agents

A series of novel N-substituted hydrazide derivatives were synthesized by reacting atranorin, a compound with a natural depside structure (1), with a range of hydrazines. The natural product and 12 new analogues (2–13) were investigated for inhibition of α-glucosidase. The N-substituted hydrazide derivatives showed more potent inhibition than the original. The experimental results were confirmed by docking analysis. This study suggests that these compounds are promising molecules for diabetes therapy. Molecular dynamics simulations were carried out with compound 2 demonstrating the best docking model using Gromac during simulation up to 20 ns to explore the stability of the complex ligand-protein. Furthermore, the activity of all synthetic compounds 2–13 against a normal cell line HEK293, used for assessing their cytotoxicity, was evaluated.

Synthesis and anticancer activity of some novel benzothiazole-thiazolidine derivatives

Sixteen new 2-(benzothiazol-2-ylthio)-N′-(3-substituted-4-(3,4-substitutedphenyl)thiazol-2(3H)-ylidene)acetohydrazide derivatives (4a-4p) were synthesized. The structures of the synthesized compounds were elucidated using FT-IR, 1H-NMR, 13C-NMR, and HRMS spectral data. Anticancer activity of the compounds 4a-4p against C6 (rat brain glioma) and A549 (human lung adenocarcinoma) cell lines was evaluated by using MTT, inhibition of DNA synthesis, and flow cytometric analysis assays. According to MTT assay, 4a and 4d were found to be the most active compounds against C6 cell line with an IC50 value of 0.03?mM. Moreover, IC50 values of 4a (0.2 mM) and 4d (0.1 mM) against NIH3T3 (mouse embryo fibroblast cell line) were higher than their IC50 values (0.03 mM) against C6 cell line. Accordingly, selectivity of compound 4a against C6 cell line was two-fold higher than that of compound 4d. Flow cytometry analysis showed that these compounds display anticancer activity by inducing apoptosis. As a result, compound 4a has a remarkable anticancer activity and a good selectivity towards C6 cell lines.

Synthesis of novel benzazole derivatives and evaluation of their antidepressant-like activities with possible underlying mechanisms

Novel benzazole derivative compounds 4a–4h were obtained by the reaction of corresponding 2-(benzazol-2-ylthio)acetohydrazide and appropriate 4-substituted benzaldehydes. The chemical structures of the synthesized compounds were elucidated by FT-IR, 1H-NMR, 13C-NMR and LCMS spectroscopic methods. Antidepressant-like effects of the compounds were evaluated by tail suspension test (TST) and modified forced swimming tests (MFST). Moreover, locomotor activities of the animals were assessed by an activity cage apparatus. In the series, compounds 4a, 4b, 4e and 4f (at 50 mg/kg) significantly decreased the immobility time of mice in both of the TST and MFST. The same compounds prolonged the swimming time of animals in MFST without any change in the climbing duration. These data indicated that compounds 4a, 4b, 4e and 4f possess significant antidepressant-like activities. Moreover, pre-treatments with p-chloro-phenylalanine methyl ester (an inhibitor of serotonin synthesis), NAN-190 (a 5-HT1A antagonist), ketanserin (a 5-HT2A/2C antagonist), and ondansetron (a 5-HT3 antagonist) reversed the exhibited pharmacological effects. Results of the mechanistic studies suggested the involvement of serotonergic system and contributions of 5-HT1A, 5-HT2A/2C and 5-HT3 receptors to the antidepressant-like effects of compounds 4a, 4b, 4e and 4f. Furthermore, unchanged locomotor activity of mice following the administrations of these four derivatives confirmed that the presented antidepressant-like effects are specific.

Binding characterization, synthesis and biological evaluation of RXRα antagonists targeting the coactivator binding site

Previously we identified the first retinoid X receptor-alpha (RXRα) modulators that regulate the RXRα biological function via binding to the coregulator-binding site. Here we report the characterization of the interactions between the hit molecule and RXRα through computational modeling, mutagenesis, SAR and biological evaluation. In addition, we reported studies of additional new compounds and identified a molecule that mediated the NF-κB pathway by inhibiting the TNFα-induced IκBα degradation and p65 nuclear translocation.

Acylhydrazone derivatives as potential anticancer agents: Synthesis, bio-evaluation and mechanism of action

A series of novel acylhydrazone derivatives were designed, synthesized and evaluated for their potential cytotoxic effects against human cancer cell lines. The preliminary results indicated that some of the obtained compounds (such as 8b, 13c) exhibited good to moderate cytotoxic activities against human HepG2, Huh-7, and BCG-823 cell lines. Especially, compounds 8c and 8e presented obviously selective cytotoxic activities against Huh-7 in vitro (8c, IC50 = 7.74 ± 2.18 μg/mL; 8e, IC50 = 4.46 ± 1.05 μg/mL) compared to 5-FU (IC50 = 10.41 ± 3.41 μg/mL). The highly potential compounds to induce apoptosis in HepG2 cells were analyzed by flow cytometry, and the apoptotic effects of compounds 8b and 13c were further evaluated using Annexin V-FITC/propidium iodide dual staining assay.

Rational design and synthesis of benzothiazolo-isatins for antimicrobial and cytotoxic activities

In search of novel antimicrobial agents, a series new isatin derivatives 3a-p and 5a-p have been synthesized by condensation of isatins with 2-mercaptobenzothiazole acetic acid hydrazide and 2-hydrazinobenzothiazole respectively. Compounds synthesized have been evaluated for antibacterial and antifungal activity against various strains of bacteria and fungi as well as screened for their cytotoxic activity against HeLa and HBL-100 cell lines by MTT method. Some of the compounds 3k, 5j and 5o show significant antibacterial and antifungal activities when compared with standard drugs. Amongst them, compound 3k has been found to be relatively more effective and it is also observed that its action is against all the four strains of bacteria tested. Compound 5j shows noticeable degree of inhibition, specifically against gram-positive strains B. subtilis and S. aureus with average zone of inhibition 23 mm and 34 mm respectively. Compound 3a shows good antifungal action against both C. albicans and A. niger with average zone of inhibition 10 mm each . The compound 3g is found to be most significant with IC50 values of 154.59 μM and 261.99 μM against HeLa and HBL-100 cell lines, respectively.

Design, synthesis, and anticonvulsant evaluation of some novel 1, 3 benzothiazol-2-yl hydrazones/acetohydrazones

A series of 2-[2-(substituted)hydrazinyl]-1,3-benzothiazole and 2-(1,3-benzothiazol-2-ylsulfanyl)-N′-(substituted)acetohydrazide were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity of the titled compounds was assessed using the 6 Hz psychomotor seizure test. The most active compound of the series was 2-(1,3-benzothiazol-2-ylsulfanyl)-N′-[4-(4-bromophenoxy)benzylidene] acetohydrazide BT 15, which showed 75% protection (3/4, 1.0 h) and 50% protection (2/4, 0.5 h) at a dose of 100 mg/kg in mice. A computational study was carried out for calculation of pharmacophore pattern and prediction of pharmacokinetic properties. Titled compounds have also exhibited good binding properties with epilepsy molecular targets such as GABA (A) alpha-1, glutamate, GABA (A) delta receptors and Na/H exchanger, in Lamarckian genetic algorithmbased flexible docking studies. Springer Science+Business Media, LLC 2011.