146366-01-0

Basic information

• Product Name: 2H-Benzimidazol-2-one,5-fluoro-1,3-dihydro-1-(1-methylethyl)-(9CI)
• Synonyms: 2H-Benzimidazol-2-one,5-fluoro-1,3-dihydro-1-(1-methylethyl)-(9CI);5-fluoro-1-isopropyl-1,3-dihydro-2H-benzo[d]imidazol-2-one
• CAS NO: 146366-01-0
• Molecular Formula: C₁₀H₁₁FN₂O
• Molecular Weight: 194.2055432
• Product Categories: BENZIMIDAZOLE
• Mol File: 146366-01-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-Benzimidazol-2-one,5-fluoro-1,3-dihydro-1-(1-methylethyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Benzimidazol-2-one,5-fluoro-1,3-dihydro-1-(1-methylethyl)-(9CI)(146366-01-0)
• EPA Substance Registry System: 2H-Benzimidazol-2-one,5-fluoro-1,3-dihydro-1-(1-methylethyl)-(9CI)(146366-01-0)

Safety Data

• Hazardous Substances Data: 146366-01-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2H-Benzimidazol-2-one,5-fluoro-1,3-dihydro-1-(1-methylethyl)-(9CI) is used as a pharmaceutical compound for its potential anti-inflammatory, antiviral, and anticancer properties. Its unique structure allows it to be a candidate for drug development, offering new therapeutic options for various medical conditions.
Used in Drug Synthesis:
In the pharmaceutical industry, 2H-Benzimidazol-2-one,5-fluoro-1,3-dihydro-1-(1-methylethyl)-(9CI) is also used as a precursor in the synthesis of other drugs. Its chemical properties and structural features make it a valuable building block for creating new and effective medications.

Upstream product

• 364-78-3 2-nitro-4-fluoroaniline 
• 146366-00-9 4-Fluoro-N-(1-methylethyl)-2-nitrobenzenamine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 153877-87-3 4-fluoro-N¹-isopropyl-benzene-1,2-diamine 

Downstream Products

• 240143-39-9 1,3-dihydro-5-fluoro-1-(1-methylethyl)-6-nitro-2H-benzimidazol-2-one 
• 1057215-55-0 C₁₈H₁₉FN₂O₃ 
• 1400655-35-7 4-nitrophenyl 6-fluoro-3-isopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate 
• 240143-21-9 6-fluoro-3-isopropyl-5-nitro-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid [2-(4-methyl-piperazin-1-yl)-ethyl]-amide 
• 240143-58-2 6-fluoro-3-isopropyl-5-nitro-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid (2-chloro-ethyl)-amide 

Relevant articles and documents

1- Or 3-(3-amino-2-hydroxy-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2- ones: Potent, selective, and orally efficacious norepinephrine reuptake inhibitors

Sequential structural modifications of the aryloxypropanamine template (e.g., atomoxetine, 2) led to a novel series of 1-(3-amino-2-hydroxy-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors (NRIs). In general, this series of compounds potently blocked the human norepinephrine transporter (hNET) while exhibiting selectivity at hNET against both the human serotonin (hSERT) and dopamine transporters (hDAT). Numerous compounds (e.g., 19-22) had low nonamolar hNET potency with IC 50 values of 7-10 nM and excellent selectivity (>500 fold) at hNET over hSERT and hDAT. Several compounds, such as 20 and 22, were tested in a telemetric rat model of ovariectomized-induced thermoregulatory dysfunction and were efficacious at oral doses of 3 mg/kg in reducing the tail skin temperature. In addition, compound 20 was also studied in the rat hot plate and spinal nerve ligation (SNL) models of acute and neuropathic pain, respectively, and was orally efficacious at doses of 3-10 mg/kg.

2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxamides with selective affinity for the 5-HT4 receptor: Synthesis and structure-affinity and structure-activity relationships of a new series of partial agonist and antagonist derivatives

A series of 2,3-dihydro-2-oxo-1H-benzimidazole-l-carboxamide derivatives bearing a piperazine moiety was synthesized. Their in vitro 5-HT4, 5-HT3, and D2 receptors affinities were evaluated by radioligand binding assay. For selected compounds functional studies at the 5-HT4 receptor were made by using precontracted (by carbachol) preparations of rat esophageal tunica muscularis mucosae (TMM). The influence of the 3-substituent of the benzimidazole ring, the 4-substituent of the piperazine moiety, and the alkylene spacer was studied. Compounds with an ethyl or a cyclopropyl substituent in the 3-position of the benzimidazole ring showed moderate to high affinity (K(i) = 6.7-75.4 nM) for the 5-HT4 receptor with selectivity over 5-HT3 and D2 receptors and moderate antagonist activity (pK(b) = 6.19- 7.73). Compounds with an isopropyl substituent in the 3-benzimidazole position exhibited moderate and selective 5-HT4 affinity (K(i) ≥ 38.9 nM) and a partial agonist activity (5a, i.a. = 0.94) higher than that of the reference compound BIMU 8 (i.a. = 0.70). This reversal of the pharmacological activity due only to a small structural difference might confirm the existence of two binding sites on the 5-HT4 receptor. In the alkylene spacer, a two-methylene chain is favorable to optimize the affinity and the antagonist or the partial agonist activity. In the ethyl and cyclopropyl series, 5-HT4 antagonist activity seems to be unrelated to the size of the 4-substituent of the piperazine moiety, whereas a methyl group is optimal for high partial agonist activity in the isopropyl series; however, the presence of a butyl substituent is a favorable pattern for 5-HT4 antagonism and even causes a reversal of the pharmacological profile in the isopropyl series (5h, pK(b) = 7.94). N-Butyl quaternization of 5a led to an improvement in affinity for the 5-HT4 receptor and maintained the high partial agonist activity (5r, K(i) = 66.3 nM, i.a. = 0.93).

Piperidine derivatives, their preparation and their therapeutic application

A compound which is a piperidine derivative of general formula (I) STR1 in which R 1 represents a hydrogen atom, a linear or branched (C 1-6)alkyl group or a cyclo(C 3-8)alkyl group, X represents an oxygen atom, a sulphur atom or a group of general formul