3042-01-1

Usage

Uses

Used in Pharmaceutical Industry:
THIAZOLO(2 3-B)BENZIMIDAZOLE-3(2H)-ONE is used as a potential drug target for the treatment of various diseases. Its unique structure and pharmacological activities make it a promising candidate for the development of new therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, THIAZOLO(2 3-B)BENZIMIDAZOLE-3(2H)-ONE serves as a valuable building block. Its incorporation into more complex molecular structures can lead to the creation of novel compounds with diverse applications.
Used in Drug Discovery:
THIAZOLO(2 3-B)BENZIMIDAZOLE-3(2H)-ONE is also utilized in drug discovery processes, where its properties are explored for potential medicinal uses. This can involve screening for activity against specific biological targets or for general pharmacological effects that could be beneficial in treating certain conditions.
Overall, THIAZOLO(2 3-B)BENZIMIDAZOLE-3(2H)-ONE is a versatile molecule with a broad range of potential applications, particularly in the pharmaceutical and chemical industries, where its unique structure and properties are being harnessed for the development of new drugs and synthetic compounds.

InChI:InChI=1/C9H6N2OS/c12-8-5-13-9-10-6-3-1-2-4-7(6)11(8)9/h1-4H,5H2

Upstream product

• 3042-00-0 2-(1H-benzimidazol-2-ylthio)acetic acid 
• 5429-62-9 ethyl 2-(1H-benzo[d]imidazol-2-ylthio)acetate 
• 79-08-3 bromoacetic acid 
• 134469-07-1 Benzimidazol-2-thiol 
• 95-54-5 1,2-diamino-benzene 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 79-11-8 chloroacetic acid 
• 16458-64-3 3-Hydroxy-2,3-dihydro-thiazolo<3,2-a>benzimidazol 
• 108-24-7 acetic anhydride 

Downstream Products

• 41777-02-0 2-trans-cinnamylidene-benz[4,5]imidazo[2,1-b]thiazol-3-one 
• 41776-81-2 12-(4-Nitro-benzyliden)-1-thia-3,10-diazatricyclo<4-9,2-10>-dodecen(2)-aren-(4)-on-(11) 
• 41887-58-5 2-benzylidenethiazolo<3,2-a>benzimidazol-3(2H)-one 
• 41776-82-3 2-(2-hydroxybenzylidene)thiazolo<3,2-a>benzimidazol-3(2H)-one 
• 88498-93-5 2-(p-hydroxy-m-methoxybenzylidene)thiazolo<3,2-a>benzimidazol-3(2H)-one 
• 23983-04-2 2-(4-dimethylaminobenzylidene)thiazolo<3,2-a>benzimidazol-3(2H)-one 
• 21578-54-1 benzo[4,5]imidazo[2,1-b]thiazole-2,3-dione 2-[(4-nitro-phenyl)-hydrazone] 
• 21578-53-0 2-phenylazathiazolo<3,2-a>benzimidazol-3(2H)-one 
• 3042-05-5 benzo[4,5]imidazo[2,1-b]thiazole-2,3-dione 2-({4-[bis-(2-chloro-ethyl)-amino]-phenyl}-hydrazone) 
• 59490-63-0 N-(3-oxo-benzo[4,5]imidazo[2,1-b]thiazol-2-ylidenemethyl)-N-phenyl-acetamide 
• 59490-64-1 N-[3-(3-oxo-benzo[4,5]imidazo[2,1-b]thiazol-2-ylidene)-propenyl]-N-phenyl-acetamide 
• 23983-06-4 2-(4-chlorobenzylidene)thiazolo<3,2-a>benzimidazol-3(2H)-one 
• 23983-05-3 2-(2-chlorobenzylidene)thiazolo<3,2-a>benzimidazol-3(2H)-one 
• 23983-08-6 2-(m-Nitro-benzyliden)-thiazolo<3,2-a>benzimidazol-3-on 

Relevant academic research and scientific papers

Novel thiazolidinone/thiazolo[3,2-a] benzimidazolone-isatin conjugates as apoptotic anti-proliferative agents towards breast cancer: One-pot synthesis and in vitro biological evaluation

In connection with our research program on the development of new isatin-based anticancer candidates, herein we report the synthesis of two novel series of thiazolidinone-isatin conjugates (4a–n) and thiazolo[3,2-a]benzimidazolone-isatin conjugates (7a–d), and in vitro evaluation of their antiproliferative activity towards two breast cancer cell lines; triple negative MDA-MB-231, and MCF-7. Compounds 4m and 7b emerged as the most active congeners against MDA-MB-231 cells (IC50 = 7.6 ± 0.5 and 13.2 ± 1.1 μM, respectively). Compounds 4m and 7b were able to provoke apoptosis in MDA-MB-231 cells, evidenced by the up-regulation of Bax and down-regulation of Bcl-2, besides boosting caspase-3 levels. Hybrid 4m induced a fourfold increase in the percentage of cells at Sub-G1, with concurrent arrest in G2-M phase by 2.5-folds. Furthermore, hybrid 4m resulted in a sixfold increase in the percentage of annexin V-FITC positive apoptotic MDA-MB-231 cells as compared with the control. Moreover, the cytotoxic activities of the active conjugates were assessed towards two nontumorigenic cell lines (breast MCF-10A and lung WI-38) where both conjugates 4m and 7b displayed mean tumor selectivity index: 9.6 and 13.9, respectively. Finally, several ADME descriptors were predicted for the active conjugates via a theoretical kinetic study.

Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist

Abstract: The present work describes the design, synthesis, molecular docking, biological evaluation, and assessment of structure–activity relationship of new derivatives based upon the molecular skeleton of the drug pioglitazone, a compound which is currently used for the management of type 2 diabetes mellitus. Pioglitazone has several side effects such as weight gain, edema, congestive heart failure, and bladder cancer. Therefore, there is a strong demand for identification of new lead candidates in the treatment of type 2 diabetes mellitus. A series of 24 compounds were prepared and evaluated for their peroxisome proliferator-activated receptor-γ (PPARγ) binding affinity assay and the IC50 values were determined. Among these compounds, six compounds exhibited promising IC50 values as compared to standard drugs pioglitazone and rosiglitazone. Furthermore, in order to confirm the target of these molecules, molecular docking study was carried out with peroxisome proliferator-activated receptor-γ (PPARγ) protein. Molecular modeling studies suggested that these compounds appropriately interact in the active sites of receptor. Graphical abstract: [Figure not available: see fulltext.].

Tautomerism and isomerism in some antitrichinellosis active benzimidazoles: Morphological study in polarized light, quantum chemical computations

The morphology of the crystal structure of some antitrichinellosis active benzimidazole derivatives including (1H-benzimidazol-2-ylthio)acetic acids, [1,3]thiazolo[3,2-a]benzimidazol-3(2H)-ones, 1H-benzimidazol-2-ylthioacetylpiperazines and starting 2-mercapto benzimidazoles, was studied by the use of Polarized Light Microscopy (PLM). Characterization of the crystal phase was complimented by Differential scanning calorimetry analysis (DSC) and spectroscopic data. DFT computations were performed in order to investigate the prototropic tautomerism and the geometry of the molecule of the synthesized compounds. One distinct type of crystal structure for each one of 5 or 6-methyl-(1H-benzimidazol-2-ylthio)acetic acid 6 was observed by PLM – dendritic and needle-shaped formations. Compound 14, containing a methyl substituent in the benzimidazole ring crystallized also into two phases; while for the unsubstituted compound 13 a separation of phases does not take place. The influence of the both solvents - chloroform and ethanol on the phase separation and the formation of the crystalline structure of compound 14 was investigated. The morphological study showed that the cyclization of 6 in the presence of acetic anhydride in pyridine medium led to a mixture of 6-methyl-[1,3]tiazolo[3,2-a]benzimidazol-3(2H)-one (10a) and 7-methyl-[1,3]thiazolo[3,2-a]-benzimidazole-3(2H)-one (10b), which crystallized in the form of fibrils and spherulites respectively. It was found that a difference in the crystal structures of substituted and unsubstituted benzimidazol-2-thiones, respectively benzimidazol-2-thiol derivatives exists, which may be due not only to the thiol-thione tautomerism but to the prototropic properties of the hydrogen atom in first position of the ring. The calculation results indicated that the thione form is more stable than the thiol tautomer by 51–55 kJ mol?1. But at the same time ΔG for the two thiol tautomers is below 0.5 kJ mol?1. In solid phase the 5(6)-substituted-1H-benzimidazol-2-thiols crystallized in two different crystal structures while the unsubstituted 1H-benzimidazol-2-thiol possess one type of crystal structure.

New compounds having skin whitening activity and medical use thereof

The present invention refers to skin whitening which inhibit activity of compound and medical use thereof relates to, the present invention according to compounds are tyrosinase inhibitors have fine skin whitening activity pharmaceutical composition for skin whitening, health food or cosmetic composition can be used.

A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions

A rapid and efficient one pot solvent/scavenger-free protocol for the synthesis of 2-iminothiazolidin-4-ones has been developed. Interestingly, the regio/stereoselective synthesis affords the regioisomeric (Z)-3-alkyl/aryl-2-(2- phenylcyclohex-2-enylimino

Synthesis and biological evaluation of novel thiazolidinone derivatives as potential anti-inflammatory agents

The modulation of pro-inflammatory cytokines provides a target for controlling inflammatory diseases and attracts much attention in current anti-inflammatory drug development. Here, four series of thiazolidinone derivatives were synthesized and screened for anti-inflammatory activities. A majority of these compounds showed excellent inhibition on the expression of TNF-α and IL-6 in LPS-stimulated macrophages. Discussions are given regarding the structure-activity relationships. Compounds 12d and 12h inhibited LPS-induced TNF-α and IL-6 release in a dose-dependent manner. Furthermore, 12d exhibited a significant protection against LPS-induced septic death in mouse model. Together, these data present a series of new thiazolidinones with potential therapeutic effects in acute inflammatory diseases and they could be important leads in the continuing anti-inflammatory drug research.

Antihelminthic activity of some newly synthesized 5(6)-(un)substituted-1H-benzimidazol-2-ylthioacetylpiperazine derivatives

Piperazine derivatives of 5(6)-substituted-(1H-benzimidazol-2-ylthio)acetic acids were synthesized by using two methods and studied for antihelminthic activity. The antiparasitic screening showed that compounds 18-24 exhibited higher activity against Trichinella spiralis in vitro in comparison to methyl 5-(propylthio)-1H-benzimidazol-2-yl-carbamate (albendazole). Most active were compounds 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-1H-benzimidazo le 21 and 2-{[2-oxo-2-(4-benzhydrylpiperazin-1-yl)ethyl]thio}-5(6)-methyl-1(H)-ben zimidazole 19 as well as 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-5(6)-methyl-1( H)-benzimidazole 23 with efficacy of 96.0%, 98.4% and 100%, respectively. The tested derivatives 15-19 and 20-23 were less active against Syphacia obvelata in vivo than albendazole and exhibited the same efficacy as piperazine, but in twice lower concentration.Compounds 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-1H-benzimidazo le 21, 1,4-bis[(5(6)-methyl-1(H)-benzimidazol-2-ylthio)acetyl]piperazine 17 and 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-5(6)-methyl-1( H)-benzimidazole 23 had higher efficacies of 73%, 76%, and 77%, respectively.

Synthesis and antitrichinellosis activity of some 2-substituted-[1,3] thiazolo[3,2-a]benzimidazol-3(2H)-ones

Some new thiazolo[3,2-a]benzimidazolone derivatives were synthesized using two methods. The structures of the synthesized compounds were proved by means of IR, 1H NMR and mass spectral data. Ab initio computations were performed in order to determine the electronic structure and geometry of the investigated molecules and to compare it to the geometry of albendazole. Biologically, experiments in vitro and in vivo were accomplished in order to identify the efficacy of the obtained thiazolobenzimidazolones against Trichinella spiralis. The effectiveness of compounds 4a-c in the intestinal phase of trichinellosis was 100% and in the muscle phase were 88% and 80% at a concentration of 100 mg/kg mw for the compounds 4a and 4c. The results of the hepatotoxicity test showed that the compounds 4a and 4b possess hepatotoxicity comparable to that of albendazole.

Synthesis of New 2-Substituted Benzylidenethiazolobenzimidazol-3(2H)-ones and Their Biological Activity

2-Substituted benzylidenethiazolobenzimidazol-3(2H)-ones (I-XIV) have been synthesized and found to possess anticonvulsant activity (0-60percent).These compounds also inhibit rat brain monoamine oxidase (MAO) (33.70-98.30percent) and succinate dehydrogenase (SDH) (25.72-78.95percent) in vitro of concentrations 4E-4 M and 6E-4 M, respectively.Structure-activity relationship has been dicussed.