133687-93-1

Basic information

• Product Name: 5-TRIFLUOROMETHYL-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE
• Synonyms: 6-(Trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one;5-(trifluoromethyl)benzimidazol-2(3H)-one;5-TRIFLUOROMETHYL-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE;5-TRIFLUOROMETHYLBENZIMIDAZOLONE;5-Trifluoromethylbenzimidazone;5-(TRIFLUOROMETHYL)-1,3-DIHYDRO-2H-BENZIMIDAZOL-2-ONE;5-(trifluoroMethyl)-1H-benzo[d]iMidazol-2(3H)-one;5-TrifluoroMethyl-1,3-dihydrobenzoiMidazol-2-one
• CAS NO: 133687-93-1
• Molecular Formula: C₈H₅F₃N₂O
• Molecular Weight: 202.13
• Mol File: 133687-93-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-TRIFLUOROMETHYL-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-TRIFLUOROMETHYL-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE(133687-93-1)
• EPA Substance Registry System: 5-TRIFLUOROMETHYL-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE(133687-93-1)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN2811
• Hazardous Substances Data: 133687-93-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5-TRIFLUOROMETHYL-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE is used as an intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs with potential therapeutic benefits.
Used in Antitumor Applications:
In the field of oncology, 5-TRIFLUOROMETHYL-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE is used as an antitumor agent. Its potential as a cancer treatment has been investigated due to its biological activities, such as the ability to inhibit certain enzymes that play a role in tumor growth and progression.
Used in Medicinal Chemistry Research:
5-TRIFLUOROMETHYL-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE is utilized in medicinal chemistry research to explore its potential as a lead compound for the development of new therapeutic agents. Its unique structure and pharmacological properties make it a valuable asset in the search for innovative treatments for various diseases and conditions.

Upstream product

• 530-62-1 1,1'-carbonyldiimidazole 
• 368-71-8 4-(trifluoromethyl)-1,2-phenylenediamine 
• 124-38-9 carbon dioxide 
• 400-98-6 4-trifluoromethyl-2-nitroaniline 

Downstream Products

• 86604-86-6 2-chloro-6-(trifluoromethyl)-1H-benzo[d]imidazole 
• 1453097-16-9 3-methyl-4-(phenylmethyl)-1-(5-trifluoromethyl-1H-benzimidazol-2-yl)-1H-pyrazol-5-ol 
• 1073558-69-6 3-(3,4-dichlorophenyl)-8-[5-(trifluoromethyl)-1H-benzimidazol-2-yl]-1-oxa-3,8-diazaspiro-[4.5]decan-2-one 
• 1073558-62-9 3-phenyl-8-[5-(trifluoromethyl)-1H-benzimidazol-2-yl]-1-oxa-3,8-diazaspiro-[4.5]decan-2-one 
• 1351534-16-1 (2R)-2-[2-chloro-5-[[3-(6-chlorobenzisoxazol-3-yl)-2-oxo-6-trifluoromethylbenzimidazol-1-yl]methyl]phenoxy]propanoic acid 
• 1351534-14-9 (2R)-2-[2-chloro-5-[[3-(4-tert-butylphenyl)-2-oxo-6-trifluoromethylbenzimidazol-1-yl]methyl]phenoxy]propanoic acid 
• 1351534-13-8 (2R)-2-[2-chloro-5-[[3-(4-chlorobenzoyl)-2-oxo-6-trifluoromethylbenzimidazol-1-yl]methyl]phenoxy]propanoic acid 
• 1351534-12-7 (2R)-2-[2-chloro-5-[[3-(4-chlorobenzyl)-2-oxo-6-trifluoromethylbenzimidazol-1-yl]methyl]phenoxy]propanoic acid 
• 1351534-01-4 1-(4-tert-butylphenyl)-5-trifluoromethylbenzimidazole-2-one 
• 877681-21-5 1-(4-chlorobenzoyl)-5-trifluoromethylbenzimidazole-2-one 
• 877681-20-4 1-(4-chlorobenzyl)-5-trifluoromethylbenzimidazole-2-one 
• 86604-86-6 2-chloro-5-(trifluoromethyl)-1H-1,3-benzimidazole 
• 161468-73-1 2,3-Dihydro-2-oxo-3-(phenylmethyl)-6-(trifluoromethyl)-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester 
• 161468-74-2 2,3-Dihydro-2-oxo-3-(phenylmethyl)-5-(trifluoromethyl)-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester 

Relevant articles and documents

DBU-based ionic-liquid-catalyzed carbonylation of o-phenylenediamines with CO2 to 2-benzimidazolones under solvent-free conditions

Herein, a new route was presented to synthesize 2-benzimidazolones via the carbonylation of o-phenylenediamines with CO2 catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-based ionic liquids under solvent-free conditions. DBU acetate ([DBUH][OAc]) displayed high efficiency for catalyzing the reactions of CO2 with o-phenylenediamines, and a series of benzimidazolones were obtained in high yields. It was demonstrated that [DBUH][OAc] could serve as a bifunctional catalyst for these reactions with the cation activating CO2 and the anion activating o-phenylenediamines. This protocol provides an effective and environmentally friendly alternative route for production of benzimidazolones, and extends the chemical utilization of CO2 in organic synthesis as well.

Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source

A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.

ISOINDOLINES AS HDAC INHIBITORS

The present disclosure relates to inhibitors of zinc-dependent histone deacetylases (HDACs), having the formula: (I) wherein Z, X1, X2, Y1, Y2, Y3, L, Z, and R are described herein.

Discovery of a Selective Aurora A Kinase Inhibitor by Virtual Screening

Here we report the discovery of a selective inhibitor of Aurora A, a key regulator of cell division and potential anticancer target. We used the atom category extended ligand overlap score (xLOS), a 3D ligand-based virtual screening method recently developed in our group, to select 437 shape and pharmacophore analogs of reference kinase inhibitors. Biochemical screening uncovered two inhibitor series with scaffolds unprecedented among kinase inhibitors. One of them was successfully optimized by structure-based design to a potent Aurora A inhibitor (IC50 = 2 nM) with very high kinome selectivity for Aurora kinases. This inhibitor locks Aurora A in an inactive conformation and disrupts binding to its activator protein TPX2, which impairs Aurora A localization at the mitotic spindle and induces cell division defects. This phenotype can be rescued by inhibitor-resistant Aurora A mutants. The inhibitor furthermore does not induce Aurora B specific effects in cells.

NOVEL BENZIMIDAZOLE DERIVATIVE AND USE THEREOF

The present invention aims to provide a compound capable of inhibiting PCA-1 that can be a target for a novel treatment method of various diseases, and pharmaceutical use of the compound. A compound represented by the formula (I): wherein each symbol is a

Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs

A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5- methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H-pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects.

ORGANIC COMPOUND, CHARGE-TRANSPORTING MATERIAL, COMPOSITION FOR CHARGE-TRANSPORTING MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE

An organic compound having excellent heat resistance, an excellent amorphous nature, an excellent ability to transport charges, highly excited singlet and triplet states, and excellent solubility in an organic solvent is an organic compound represented by Formula (I): wherein Ar1 represents an optionally-substituted aromatic hydrocarbon group, an optionally-substituted aromatic heterocyclic group, or an optionally-substituted alkyl group; Ar2 represents an optionally-substituted aromatic hydrocarbon group or an optionally-substituted aromatic heterocyclic group; R1 and R2 each represent a hydrogen atom or a substituent, and R1 and R2 may be bonded to each other to form a ring; and Q is represented by Formula (I-1) or (I-2): wherein Ar3 to Ar5 each represent an optionally-substituted aromatic hydrocarbon group or an optionally-substituted aromatic heterocyclic group, and Ar3 and Ar4 may be bonded to each other to form a ring.

BENZIMIDAZOLES WITH A HETERO SPIRO-DECANE RESIDUE AS NPY-Y5 ANTAGONISTS

The present invention relates to compounds of formula (I), or a pharmaceutically acceptable salts, solvates, stereoisomers thereof, formula (I), R1 may be C1-C4 alkyl, aryl or heteroaryl, which may be substituted by one or more: halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, cyano; R2 may be halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, cyano, nitro; or aryl, heteroaryl or heterocycle, which may be substituted by one or more: halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, cyano; or R2 may correspond to -0-R3; R3 is a 6-membered aromatic carbocyclic ring which may contain 1 or 2 nitrogen X is carbon or oxygen; Z is carbon or nitrogen; G is a fused 6-membered aromatic carbocyclic ring which may contain 1 or 2 nitrogen; m may be 0 or an integer ranging from 1 to 4; processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as NPY- Y5 receptor antagonists.

Design of potent, orally available antagonists of the transient receptor potential vanilloid 1. Structure-activity relationships of 2-piperazin-1-yl-1H- benzimidazoles

The vanilloid receptor-1 (VR1 or TRPV1) is a membrane-bound, nonselective cation channel that is predominantly expressed by peripheral neurons sensing painful stimuli. TRPV1 antagonists produce antihyperalgesic effects in animal models of inflammatory and neuropathic pain. Herein, we describe the synthesis and the structure-activity relationships of a series of 2-(4-pyridin-2- ylpiperazin-1-yl)-1H-benzo-[d]imidazoles as novel TRPV1 antagonists. Compound 46ad was among the most potent analogues in this series. This compound was orally bioavailable in rats and was efficacious in blocking capsaicin-induced flinch in rats in a dose-dependent manner. Compound 46ad also reversed thermal hyperalgesia in a model of inflammatory pain, which was induced by complete Freund's adjuvant (CFA).

BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR LIGANDS

Compounds of formula (I) are useful in the treatment of vanilloid-receptor-meditated diseases, such as inflammatory or neuropathic pain and diseases involving sensory nerve function such as asthma, rheumatoid arthritis, osteoarthritis, inflammatory bowel disorders, urinary incontinence, migraine and psoriasis.