3042-01-1

Basic information

• Product Name: THIAZOLO(2 3-B)BENZIMIDAZOLE-3(2H)-ONE
• Synonyms: Thiazolo[3,2-a]benzimidazol-3(2H)-one (7CI,8CI,9CI);[1,3]thiazolo[3,2-a]benzimidazol-1-one;1-thiazolo[3,2-a]benzimidazolone;thiazolo[3,2-a]benzimidazol-1-one
• CAS NO: 3042-01-1
• Molecular Formula: C₉H₆N₂OS
• Molecular Weight: 190.22174
• Product Categories: BENZIMIDAZOLE
• Mol File: 3042-01-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 180-184 °C(lit.)
• Boiling Point: 391.5°Cat760mmHg
• Flash Point: 190.6°C
• Appearance: /
• Density: 1.59g/cm³
• Vapor Pressure: 2.45E-06mmHg at 25°C
• Refractive Index: 1.823
• CAS DataBase Reference: THIAZOLO(2 3-B)BENZIMIDAZOLE-3(2H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: THIAZOLO(2 3-B)BENZIMIDAZOLE-3(2H)-ONE(3042-01-1)
• EPA Substance Registry System: THIAZOLO(2 3-B)BENZIMIDAZOLE-3(2H)-ONE(3042-01-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3042-01-1(Hazardous Substances Data)

Usage

General Description

THIAZOLO(2 3-B)BENZIMIDAZOLE-3(2H)-ONE is a chemical compound with the molecular formula C9H6N2OS. It is a heterocyclic compound containing a thiazole ring fused to a benzimidazole ring, and a ketone group at the 3-position. THIAZOLO(2 3-B)BENZIMIDAZOLE-3(2H)-ONE has been studied for its potential pharmacological activities, including as a possible drug target for the treatment of various diseases. It has also been investigated for its potential use as a building block in organic synthesis and drug discovery. The chemical structure and properties of THIAZOLO(2 3-B)BENZIMIDAZOLE-3(2H)-ONE make it an interesting molecule for further research and potential applications in various fields.

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

Downstream Products

• 88498-94-6 2-(3,4-dimethoxy-2-nitrobenzylidene)thiazolo<3,2-a>benzimidazol-3(2H)-one 
• 30065-11-3 2-tolylazathiazolo<3,2-a>benzimidazol-3(2H)-one 
• 30065-13-5 2-(p-chlorophenyl)azothiazolo<3,2-a>benzimidazol-3(2H)-one 
• 86317-25-1 2-(p-methoxyphenyl)azothiazolo<3,2-a>benzimidazol-3-(2H)-one 
• 41776-77-6 2-(3-chlorobenzylidene)thiazolo<3,2-a>benzimidazol-3(2H)-one 
• 41776-83-4 2-(3-hydroxybenzylidene)thiazolo<3,2-a>benzimidazol-3(2H)-one 
• 30065-12-4 2-m-Tolylazo-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 88498-95-7 2-(3,4-dichlorobenzylidene)thiazolo<3,2-a>benzimidazol-3(2H)-one 
• 86317-26-2 2-(m-nitrophenyl)azothiazolo<3,2-a>benzimidazol-3(2H)-one 
• 21541-32-2 1-(2-thioxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethanone 
• 72740-46-6 2-anilinomethylene-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 72740-47-7 2-(4-nitro-anilinomethylene)-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 72740-48-8 2-(4-propionyloxy-anilinomethylene)-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 72740-49-9 4-[(3-oxo-benzo[4,5]imidazo[2,1-b]thiazol-2-ylidenemethyl)-amino]-benzenesulfonamide 

Relevant articles and documents

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.

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.

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