202859-73-2

Basic information

• Product Name: 1-Cyclopropyl-1,3-dihydro-2H-benzimidazol-2-one
• Synonyms: 2H-BENZIMIDAZOL-2-ONE, 1-CYCLOPROPYL-1,3-DIHYDRO-;1-CYCLOPROPYL-1,3-DIHYDRO-2H-BENZIMIDAZOL-2-ONE;2H-Benzimidazol-2-one,1-cyclopropyl-1,3-dihydro-(9CI);1-Cyclopropyl-1,3-dihydro-2H-Benzimidazol-2;1-Cyclopropyl-1H-benzo[d]imidazol-2(3H)-one;1-cyclopropyl-1,3-dihydro-2H-benzo[d]imidazol-2-one
• CAS NO: 202859-73-2
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• Product Categories: BENZIMIDAZOLE
• Mol File: 202859-73-2.mol

Chemical Properties

• Appearance: /
• Density: 1.35 g/cm³
• Refractive Index: 1.669
• CAS DataBase Reference: 1-Cyclopropyl-1,3-dihydro-2H-benzimidazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclopropyl-1,3-dihydro-2H-benzimidazol-2-one(202859-73-2)
• EPA Substance Registry System: 1-Cyclopropyl-1,3-dihydro-2H-benzimidazol-2-one(202859-73-2)

Safety Data

• Hazardous Substances Data: 202859-73-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Cyclopropyl-1,3-dihydro-2H-benzimidazol-2-one is used as a pharmaceutical candidate for its potential therapeutic applications. Its unique chemical structure and pharmacological properties make it a valuable target for the development of new drugs to treat a range of diseases and conditions.
Used in Medicinal Chemistry Research:
1-Cyclopropyl-1,3-dihydro-2H-benzimidazol-2-one is utilized as a subject of medicinal chemistry research to explore its potential applications and optimize its properties for specific therapeutic uses. Further studies are necessary to fully understand its properties, mechanism of action, and potential applications in the treatment of various diseases.

InChI:InChI=1/C10H10N2O/c13-10-11-8-3-1-2-4-9(8)12(10)7-5-6-7/h1-4,7H,5-6H2,(H,11,13)

Upstream product

• 1493-27-2 ortho-nitrofluorobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 55432-23-0 cyclopropyl-(2-nitro-phenyl)-amine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 118482-03-4 N¹-cyclopropylbenzene-1,2-diamine 
• 57-13-6 urea 

Downstream Products

• 1352950-41-4 2-((8-(3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid 
• 1352950-42-5 tert-butyl 2-((8-(3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate 
• 1352950-32-3 tert-butyl 3-((8-(3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate 
• 1352950-30-1 tert-butyl 2-((8-(3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate 
• 1352949-77-9 tert-butyl 3-((8-(3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate 
• 929565-03-7 1-cyclopropyl-3-[(1R)-3-(chloro)-1-phenylpropyl]-1,3-dihydro-2H-benzimidazol-2-one 
• 929565-00-4 1-cyclopropyl-3-[(1S)-3-(chloro)-1-phenylpropyl]-1,3-dihydro-2H-benzimidazol-2-one 

Relevant articles and documents

PYRIMIDINE OR PYRIDINE COMPOUNDS, PREPARATION METHOD THEREFOR AND PHARMACEUTICAL USES THEREOF

The present invention disclosed a class of pyrimidine or pyridine compounds, pharmaceutically acceptable salts, stereoisomers, prodrugs and solvates thereof, preparation method therefor and pharmaceutical compositions and pharmaceutical uses thereof. The compounds can inhibit the variants of EGFR (Epidermis Growth Factor Receptor) proteinases, and therefore can inhibit the growth of a variety of tumor cells effectively. The compounds can be used to prepare antitumor drugs, used for the treatment, combined therapy or prevention of various different cancers. The compounds can overcome the drug resistance induced by the existing first-generation EGFR inhibitors such as gefitinib, erlotinib and so on. Particularly, the compounds can be used to prepare drugs for treating or preventing diseases, disturbances, disorders or conditions mediated by epidermis growth factor receptor variants (such as L858R activated mutants, Exon19 deletion activated mutants and T790M resistant mutants).

QUINAZOLINE BASED RESPIRATORY SYNCYTIAL VIRUS INHIBITORS

Compounds of Formula (I), wherein R1, R2, R3, R4 and n are defined herein, are useful as inhibitors of RSV.

RESPIRATORY SYNCYTIAL VIRUS INHIBITORS

Compounds of Formula (I): wherein R1, R2 and R3 are defined herein, are useful as inhibitors of RSV.

AZABENZIMIDAZOLES AS RESPIRATORY SYNCYTIAL VIRUS ANTIVIRAL AGENTS

A compound satisfying formula I, a prodrug, N-oxide, addition salt, quaternary metal complex, or a stereochemically isomeric form thereof; (formula I) compositions contain these compounds as active ingredient and processes for preparing these compounds and compositions.

Synthesis and activity of novel 1- or 3-(3-amino-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors

A series of novel 1- or 3-(3-amino-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors was discovered. Several compounds such as 15 and 20 showed good hNET potency. Compounds 15 and 20 also displayed excellent selectivity at hNET that appeared superior to those of reboxetine and atomoxetine (4 and 5).

Substituted propylamine derivatives and methods of their use

The present invention is directed to substituted propylamine derivatives of formula I: or a pharmaceutically acceptable salt thereof, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions ameliorated by monoamine reuptake including, inter alia, vasomotor symptoms (VMS), sexual dysfunction, gastrointestinal and genitourinary disorders, chronic fatigue syndrome, fibromylagia syndrome, nervous system disorders, and combinations thereof, particularly those conditions selected from the group consisting of major depressive disorder, vasomotor symptoms, stress and urge urinary incontinence, fibromyalgia, pain, diabetic neuropathy, and combinations thereof.

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).

New 2-piperazinylbenzimidazole derivatives as 5-HT3 antagonists. Synthesis and pharmacological evaluation

A series of 2-piperazinylbenzimidazole derivatives were prepared and evaluated as 5-HT3 receptor antagonists. Their 5-HT3 receptor affinities were evaluated by radioligand binding assays, and their abilities to inhibit the 5-HT-induced Bezold-Jarisch reflex in anesthetized rats were determined. Compound 7e (lerisetron, pK(i) = 9.2) exhibited higher affinity for the 5- HT3 receptor than did tropisetron and granisetron, while compound 7q (pK(i) = 7.5) had very low affinity for this receptor, showing that substitution on the N1 atom of the benzimidazole ring is essential for affinity and activity. The effect of substitution on the aromatic ring of benzimidazole by several substituents in different positions is also discussed. A strong correlation between the 5-HT3 antagonistic activity of the studied compounds and the position of substitution on the aromatic ring was established. Thus, while the 4-methoxy derivative 7m showed weak affinity for the 5-HT3 receptor (pK(i) = 6.7), the 7-methoxy derivative 7n exhibited the highest affinity (pK(i) = 9.4). Compounds 7e and 7n are now under further investigation as drugs for the treatment of nausea and emesis evoked by cancer chemotherapy and radiation.

Pharmacological profile of a novel series of NK1, antagonists. In vitro and in vivo potency of benzimidazolone derivatives

By low throughput examination of our chemical library, compound 7 was selected as a lead NK1, antagonist with a K(i) of 7.1 nM. Modifications of its structure led to the finding that the in vitro potency could be markedly enhanced by disubstituting the anilino phenyl ring as in compounds 13 or 22. Human binding data correlated rather well with results obtained with in vitro animal smooth muscle preparations. Several agents proved to possess antinociceptive properties as exemplified in the hot-plate test in mice; compound 13 was the most active with ED50 of 0.001 and 0.3 mg/kg after iv and po administration respectively. Furthermore, antagonist 71 was found to be a potent inhibitor of SP-induced bronchoconstriction in guinea-pigs with an ED50 between 0.1 and 0.03 mg/kg iv. Furthermore, upon oral administration, 71 was observed to be active in a model of SP-induced bronchial hypersensitivity in mice, with an ID50 of around 3 mg/kg.