1865-09-4

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 1519, 1974 DOI: 10.1021/jo00924a014

InChI:InChI=1/C10H10N2O2/c1-2-12-8-6-4-3-5-7(8)11-9(12)10(13)14/h3-6H,2H2,1H3,(H,13,14)

Upstream product

• 480-96-6 benzofurazan oxide 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 2849-93-6 2-benzimidazolecarboxylic acid 
• 64-17-5 ethanol 
• 62-53-3 aniline 
• 95-54-5 1,2-diamino-benzene 
• 95-92-1 oxalic acid diethyl ester 
• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 3624-90-6 N-tosyl-1,2-diaminobenzene 
• 1330785-75-5 ethyl 2-(2-(4-methylphenylsulfonamido)phenylimino)acetate 
• 144167-25-9 α-amino-α-carbethoxy-N-phenylnitrone 
• 5436-00-0 benzimidazole-2-carboxylic acid hydrazide 
• 148-79-8 thiabendazole 
• 144167-33-9 3-carbethoxy-2-phenyl-Δ³-1,2,4-oxadiazolin-5-one 

Downstream Products

• 4856-97-7 2-(Hydroxymethyl)benzimidazole 

Relevant academic research and scientific papers

An efficient one-pot two catalyst system in the construction of 2-substituted benzimidazoles: Synthesis of benzimidazo[1,2-c]quinazolines

The benzimidazole core is a common moiety in a large number of natural products and pharmacologically active small molecules. The synthesis of novel benzimidazole derivatives remains a main focus in medicinal research. In continuation of the efforts towards Ce(iii) catalysts for organic transformations, we observed for the first time the activity of the iodide ion and copper cation in activating CeCl3·7H2O in the selective formation of prototypical 2-substituted benzimidazoles. The one-pot CeCl3·7H2O-CuI catalytic system procedure includes the cyclo-dehydrogenation of aniline Schiff's bases, generated in situ from the condensation of 1,2-phenylenediamine and aldehydes, followed by the oxidation with iodine, which works as a hydrogen sponge. Mild reaction conditions, good to excellent yields, and clean reactions make the procedure a useful contribution to the synthesis of biologically active fused heterocycles containing benzimidazoquinazolines.

Discovery of heterocyclic carbohydrazide derivatives as novel selective fatty acid amide hydrolase inhibitors: design, synthesis and anti-neuroinflammatory evaluation

Fatty acid amide hydrolase (FAAH) is a promising target for the development of drugs to treat pain, inflammation, and other central nervous system disorders. Herein, a series of novel heterocyclic carbohydrazide derivatives were firstly designed by the classic scaffold-hopping strategy. Then, multi-steps synthesis and human FAAH enzyme inhibiting activity assays were conducted. Among them, compound 26 showed strong inhibition against human FAAH with IC50 of 2.8 μM. Corresponding docking studies revealed that the acyl hydrazide group of compound 26 well-occupied the acyl-chain binding pocket. It also exhibited high selectivity towards FAAH when comparing with CES2 and MAGL. Additionally, compound 26 effectively suppressed the LPS-induced neuroinflammation of microglial cells (BV2) via the reduction of interleukin-1β and tumor necrosis factor-α. Our results provided significative lead compounds for the further discovery of novel selective and safe FAAH inhibitors with potent anti-neuroinflammation activity.

ADENOSINE RECEPTOR BINDING COMPOUNDS

The present invention relates to pharmaceutical compounds and compositions of Formula (I) and methods of treatment using the compounds and compositions, especially for the treatment and/or prevention of a proliferation disorder, such as cancer. Compounds of Formula (I) as further described herein are shown modulators of the adenosine A2A receptor and exhibit antiproliferative activity. Accordingly, these compounds are useful to treat proliferative disorders such as cancer, and other adenosine receptor-related conditions including an inflammatory disease, renal disease, diabetes, vascular disease, lung disease, or an autoimmune disease.

Formation of Amidinyl Radicals via Visible-Light-Promoted Reduction of N-Phenyl Amidoxime Esters and Application to the Synthesis of 2-Substituted Benzimidazoles

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Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus

Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus.

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A series of new nitrogen heterocyclic compounds containing sulfur-ether (8a-8f) and Schiff-base (9a-9q) functionalities were synthesized by the reaction of the pharmaceutical lead compound containing both benzimidazole and 1,2,4-triazole rings. The compounds were characterized by 1H NMR, 13C NMR, FT-IR, HR-MS, and ESI-MS.

Palladium-catalyzed intramolecular sulfonamidation/oxidation of imines: Access to multifunctional benzimidazoles

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