28891-34-1

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Benzothiazole-2-carbohydrazide is used as an antibacterial agent for its potential to combat bacterial infections. Its unique chemical structure allows it to target and inhibit bacterial growth, making it a valuable component in the development of new antimicrobial drugs.
Used in Chemical Research:
1,3-Benzothiazole-2-carbohydrazide serves as a key intermediate in the synthesis of more complex chemical structures. Its versatile nature and reactivity make it a valuable building block for creating novel compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.
Used in Medicinal Chemistry Studies:
The presence of the benzothiazole group in 1,3-Benzothiazole-2-carbohydrazide makes it an interesting subject for studies in medicinal chemistry. Researchers explore its potential interactions with biological targets, such as enzymes and receptors, to develop new therapeutic agents with improved efficacy and selectivity.

InChI:InChI=1/C8H7N3OS/c9-11-7(12)8-10-5-3-1-2-4-6(5)13-8/h1-4H,9H2,(H,11,12)

Upstream product

• 32137-76-1 benzothiazole-2-carboxylic acid ethyl ester 
• 137-07-5 2-amino-benzenethiol 

Downstream Products

• 3622-04-6 2-carboxybenzothiazole 
• 87802-07-1 benzothiazole-2-carboxylic acid methyl ester 
• 32137-76-1 benzothiazole-2-carboxylic acid ethyl ester 
• 1628297-57-3 N-4-[octyloxy(phenoxy)]-salicylidene-N'-(benzothiazolyl)hydrazine 
• 57711-05-4 (5-benzothiazol-2-yl-[1,3,4]oxadiazol-2-yl)-(4-chloro-phenyl)-amine 
• 57711-11-2 (5-benzothiazol-2-yl-[1,3,4]thiadiazol-2-yl)-phenyl-amine 
• 57711-04-3 (5-benzothiazol-2-yl-[1,3,4]oxadiazol-2-yl)-phenyl-amine 
• 58328-17-9 2-(2-acetylimino-5-benzothiazol-2-yl-[1,3,4]thiadiazol-3-yl)-1-(4-nitro-phenyl)-ethanone 
• 58328-16-8 2-(2-acetylimino-5-benzothiazol-2-yl-[1,3,4]thiadiazol-3-yl)-1-phenyl-ethanone 
• 58328-21-5 N-(5-benzothiazol-2-yl-[1,3,4]thiadiazol-2-yl)-N-(2-oxo-2-phenyl-ethyl)-acetamide 
• 55439-45-7 2-(benzo[d]thiazol-2-yl)-5-phenyl-1,3,4-oxadiazole 
• 55439-47-9 2-benzothiazolyl-5-(4-nitrophenyl)-1,3,4-oxadiazole 
• 55439-48-0 2-(benzo[d]thiazol-2-yl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole 
• 55439-46-8 2-(benzo[d]thiazol-2-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole 

Relevant academic research and scientific papers

Novel hybrids of benzothiazole-1,3,4-oxadiazole-4-thiazolidinone: Synthesis, in silico ADME study, molecular docking and in vivo anti-diabetic assessment

A series of new benzothiazole-1,3,4-oxadiazole-4-thiazolidinone hybrid analogs (Tz1-Tz28) were synthesized in search of potential anti-diabetic agents. Molecular docking study was conducted with binding pocket of peroxisome proliferator activated receptor-gamma to elucidate the binding interactions of newly synthesized targets. Seven selected compounds with best docking scores were further screened for in vivo anti-hyperglycemic efficacy by oral glucose tolerance test in non-diabetic rats and on streptozotocin induced diabetic rat models. All the tested compounds demonstrated excellent to moderate reduction in blood glucose levels. Three of the compounds (Tz21, Tz7 and Tz10) showed excellent anti-diabetic effect by reducing concentration of glucose to 157.15 ± 1.79 mg/dL, 154.39 ± 1.71 mg/dL, 167.36 ± 2.45 mg/dL, respectively better than the standard drug, pioglitazone, 178.32 ± 1.88 mg/dL. Moreover, three derivatives Tz21, Tz4 and Tz24 with IC50 values of 0.21 ± 0.01 μM, 9.03 ± 0.12 μM and 11.96 ± 0.40 μM respectively also showed better inhibitory activities on alpha-glucosidase even more than the standard acarbose (IC50 = 18.5 ± 0.20 μM), indicating Tz21 has the highest inhibitory effect among the seven tested derivatives. Prediction of Drug like properties using molinspiration online software suggests that all the synthesized compounds have potential of becoming the orally active molecules. Thus, these novel hybrids could serve as potential candidates to become leads for the development of new drugs eliciting anti-hyperglycemic effect orally.

Discovery of Novel Triazolothiadiazines as Fungicidal Leads Targeting Pyruvate Kinase

Pyruvate kinase (PK) was discovered as a potent new target for novel fungicide development. A series of novel triazolothiadiazine derivatives were rationally designed and synthesized by a ring expansion strategy and computer-aided pesticide design using the 3D structure of Rhizoctonia solani PK (RsPK) obtained by homology modeling as a receptor and our previously discovered lead YZK-C22 as a ligand. The in vitro bioassay results indicated that compounds 4g, 6h, 6m, 6n, 6o, and 6p exhibited good activity against R. solani with the EC50 values falling between 10.99 and 72.76 μM. Especially, 6m showed similar potency to YZK-C22 (10.99 vs 11.97 μM of the EC50 value, respectively). The in vivo bioassay results suggested that 6m against R. solani at a concentration of 200 μg/mL displayed a numerically higher inhibition than YZK-C22 (70 vs 60%, respectively). A field experiment validated that 6m at an application rate of 120 g ai/ha showed comparable efficacy against R. solani to thifluzamide at an application rate of 80 g ai/ha (77.80 vs 84.5%, respectively). Enzymatic inhibition suggested that the potency of 6m was about twofold lower than that of YZK-C22 (67.30 vs 32.64 μM of IC50, respectively). Fluorescence quenching studies validated that RsPK was quenched by both 6m and YZK-C22, implying that they both might act at the same target site of PK. A possible binding conformation of 6m in the RsPK active site was depicted by molecular docking. Our studies suggest that 6m could be a fungicidal lead targeting PK.

Targeting EGFR tyrosine kinase: Synthesis, in vitro antitumor evaluation, and molecular modeling studies of benzothiazole-based derivatives

New benzothiazole-based derivatives were synthesized in the present work with the aim of evaluating their antitumor activity. They were in vitro tested against hepatocellular carcinoma (HepG2), colorectal carcinoma (HCT-116), mammary gland cancer (MCF-7), prostate cancer (PC-3), and epithelioid carcinoma (HeLa). The results of the in vitro antitumor evaluation revealed that the most active compounds were 39, 40, 51, 56, and 61 exhibiting IC50 values comparable to the reference drug lapatinib. The most active compounds were further subjected to EGFR inhibitory activity assay to rationalize their potency mode. Notably, the most active antitumor compounds 39 and 40 represented the most potent inhibitors to EGFR with IC50 values of 24.58 and 30.42 nM respectively in comparison with 17.38 nM for lapatinib as a standard drug. Molecular modeling studies were also conducted for the synthesized compounds, including docking into EGFR active site and surface mapping. Results proved the superior binding of the hydrazone derivatives 39 and 40 with EGFR suggesting them as good candidates for targeted antitumor therapy through EGFR kinase inhibition.

Synthesis and Antiproliferative Activity of New N-Acylhydrazone Derivatives Containing Benzothiazole and Indole Based Moiety

Through a structure-based molecular hybridization strategy, a series of new N-acylhydrazone derivatives containing the benzothiazole and indole based moiety were designed, synthesized and screened for in vitro antiproliferative activity against Hep G2 cancer cell line. One compound (7a) exhibited excellent antiproliferative activity with IC50 values of 0.78 μM against Hep G2. In addition, C-5 substitutions of the indole ring of target compounds might be crucial for their cytotoxic activities. Additionally, the relative configuration of target compounds was confirmed as the E isomer. Further chemical manipulation of derivative 7a can make it possible to obtain new potential antitumor agents.

OXADIAZOLE AND PHENOL DERIVATIVES AS ANTIBACTERIAL AND/OR HERBICIDAL AGENTS

Antimicrobial resistance is rising at an alarming rate. The methylerythritol phosphate (MEP) pathway is a metabolic pathway that produces the isoprenoids isopentyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). Notably, the MEP pathway is present in bacteria and not mammals, which made the enzymes of the MEP pathway attractive targets for discovering new anti-infective agents due to reduced chances of off-target interactions leading to side effects. The biophysical properties of 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase (IspD) and 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase (IspE) were determined to aid discovery of novel inhibitors. Thermal shift screening was used as an initial filter to narrow down a library of compounds with thermal shifts greater than 1° C., which could indicate binding to the IspD and IspE enzymes. Follow-up studies were performed using isothermal titration calorimetry and enzymatic inhibition assays. Results from these studies have revealed compounds with high micromolar inhibition of both IspD from Escherichia coli and IspE from Burkholderia thailandensis. The hit compounds are used for future development of more potent IspD and IspE inhibitors.

Design, synthesis, topoisomerase I & II inhibitory activity, antiproliferative activity, and structure-activity relationship study of pyrazoline derivatives: An ATP-competitive human topoisomerase IIα catalytic inhibitor

A series of pyrazoline derivatives (5) were synthesized in 92-96% yields from chalcones (3) and hydrazides (4). Subsequently, topo-I and IIα-mediated relaxation and antiproliferative activity assays were evaluated for 5. Among the tested compounds, 5h had

Novel pyrazoline derivatives and the use thereof

The present invention relates to a novel pyrazoline derivative compound, a pharmaceutically acceptable salt thereof, and a pharmaceutical composition for preventing or treating cancer, containing the pyrazoline derivative compound or the pharmaceutically

NOVEL NK-3 RECEPTOR SELECTIVE ANTAGONIST COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN NK-3 RECEPTORS MEDIATED DISORDERS

The present invention is directed to novel compounds of formula I and their use as therapeutic compounds.

OXADIAZOLE DERIVATIVES AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS

Oxadiazole derivatives of formula (I) where ring A is a bicyclic or tricyclic system. Claimed compounds are active on nicotinic acetylcholine receptors (nAChRs), and are useful to treat neurological, psychiatric, and gastrointestinal disorders, as well as sepsis and obesity.