390811-95-7

Usage

Uses

Used in Pharmaceutical Industry:
1-CYCLOHEXYL-2-(3-FURANYL)-1H-BENZIMIDAZOLE-5-CARBOXYLIC ACID is used as a potential active pharmaceutical ingredient for its potential antiparasitic, antiviral, and anticancer properties. The presence of diverse functional groups in its structure allows for versatile interactions with biological targets, making it a candidate for the development of new therapeutic agents.
Used in Drug Discovery:
In the field of drug discovery, 1-CYCLOHEXYL-2-(3-FURANYL)-1H-BENZIMIDAZOLE-5-CARBOXYLIC ACID serves as a lead compound for further optimization and research. Its unique molecular architecture may be modified to enhance its pharmacological properties, such as potency, selectivity, and bioavailability, leading to the creation of more effective drugs.
Used in Medicinal Chemistry Research:
1-CYCLOHEXYL-2-(3-FURANYL)-1H-BENZIMIDAZOLE-5-CARBOXYLIC ACID is utilized as a subject of study in medicinal chemistry to explore its structure-activity relationships. Understanding how its molecular features contribute to its biological activity can inform the design of novel and improved benzimidazole-based drugs.

InChI:InChI=1/C18H18N2O3/c21-18(22)12-6-7-16-15(10-12)19-17(13-8-9-23-11-13)20(16)14-4-2-1-3-5-14/h6-11,14H,1-5H2,(H,21,22)

Upstream product

• 16588-16-2 ethyl 4-chloro-3-nitrobenzoate 
• 108-91-8 cyclohexylamine 
• 87815-77-8 4-cyclohexylamino-3-nitrobenzoic acid ethyl ester 
• 347174-05-4 3-Amino-4-cyclohexylamino benzoic acid ethyl ester 
• 498-60-2 furan-3-carboxaldehyde 
• 871930-30-2 1-cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acid ethyl ester 

Downstream Products

• 390809-69-5 2-[(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carbonyl)-amino]-3-(5-hydroxy-1H-indol-3-yl)-propionic acid methyl ester 
• 390812-38-1 2-[(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carbonyl)-amino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 871929-76-9 1-cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acid amide 
• 871928-52-8 1-cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acid [2-(4-chlorophenyl)oxoethyl]amide 
• 1208255-92-8 C₂₉H₃₈N₄O₄ 
• 1254322-59-2 C₂HF₃O₂*C₂₉H₂₈N₄O₅ 
• 1254322-63-8 C₂HF₃O₂*C₃₀H₃₀N₄O₅ 
• 1254322-64-9 C₂HF₃O₂*C₃₀H₃₀N₄O₅ 
• 1254322-73-0 C₂₅H₂₉N₃O₄ 

Relevant academic research and scientific papers

Development of safe one-pot synthesis of N-1- and C-2-substituted benzimidazole via reductive cyclization of o-nitroarylamine using Na 2S2O4

We report that the reductive cyclization of o-nitroarylamine with aldehyde using sodium dithionite (Na2S2O4) could be accelerated by addition of H2O, which made it possible to control the heat release of the reaction by semibatch-type operation. Safety evaluation was performed using DSC, ARSST, in situ IR analysis, and Multimax.

Non-nucleoside benzimidazole-based allosteric inhibitors of the hepatitis C virus NS5B polymerase: Inhibition of subgenomic hepatitis C virus RNA replicons in huh-7 cells

A previously disclosed series of non-nucleoside allosteric inhibitors of the NS5B polymerase of the hepatitis C virus (HCV) was optimized to yield novel compounds with improved physicochemical properties and activity in cell-based assays. Replacement of ionizable carboxylic acids with neutral substituents in lead compounds produced inhibitors with cellular permeability and antiviral activity in a cell-based assay of subgenomic HCV RNA replication (replicon EC50 as low as 1.7 μM. The improvement in potency in this ex vivo model of HCV RNA replication validates, in part, the mechanism by which this class of allosteric benzimidazole derivatives inhibits the polymerase and represents a significant step forward in the discovery of novel HCV therapeutics.

Viral polymerase inhibitors

A compound of the formula I: wherein: X is CH or N; Y is O or S; Z is OH, NH2, NMeR3, NHR3; OR3 or 5- or 6-membered heterocycle, having 1 to 4 heteroatoms selected from 0, N and S, said heterocycle being optionally substituted with from 1 to 4 substituents; A is N, COR7 or CR5, wherein R5 is H, halogen, or (C1-6) alkyl and R7 is H or (C1-6 alkyl), with the proviso that X and A are not both N; R6 is H, halogen, (C1-6 alkyl) or OR7, wherein R7 is H or (C1-6 alkyl); R1 is selected from the group consisting of 5- or 6-membered heterocycle having 1 to 4 heteroatoms selected from O, N, and S, phenyl, phenyl(C1-3)alkyl, (C2-6)alkenyl, phenyl(C2-6)alkenyl, (C3-6)cycloalkyl, (C1-6)alkyl, CF3, 9- or 10-membered heterobicycle having 1 to 4 heteroatoms selected from O, N and S, wherein said heterocycle, phenyl, phenyl(C2-6)alkenyl and phenyl(C1-3)alkyl), alkenyl, cycloalkyl, (C1-6)alkyl, and heterobicycle are all optionally substituted with from 1 to 4 substituents R2 is selected from (C1-6)alkyl, (C3-7)cycloalkyl, (C3-7)cycloalkyl(C1-3)alkyl, (C6-10)bicycloalkyl, adamantyl, phenyl, and pyridyl, all of which is optionally substituted with from1 to 4 substituents; R3 is selected from H, (C1-6)alkyl, (C3-6)cycloalkyl, (C36)cycloalkyl(C1-6)alkyl, (C6-10)aryl, (C6-10)aryl(C1-6)alkyl, (C2-6)alkenyl, (C3-6)cycloalkyl(C2-6)alkenyl, (C6-10)aryl(C2-6)alkenyl, N{(C1-6)alkyl}2, NHCOO(C1-6)alkyl(C6-10)aryl, NHCO(C6-10)aryl, (C1-6)alkyl-5- or 10-atom heterocycle, having 1 to 4 heteroatoms selected from O, N and S, and 5- or 10-atom heterocycle having 1 to 4 heteroatoms selected from O, N and S; wherein said alkyl, cycloalkyl, aryl, alkenyl and heterocycle are all optionally substituted with from 1 to 4 substituents; n is zero or 1; or a detectable derivative or salt thereof. The compounds of the invention may be used as inhibitors of hepatitis C virus replication. The invention further provides a method for treating or preventing hepatitis C virus infection.