68502-46-5

Upstream product

• 14719-83-6 methyl 3-nitro-4-chlorobenzoate 
• 100-46-9 benzylamine 
• 3987-92-6 methyl 4-amino-3-nitrobenzoate 
• 100-39-0 benzyl bromide 
• 329-59-9 4-fluoro-3-nitro-benzoic acid methyl ester 
• 186581-53-3 diazomethane 
• 453-71-4 3-nitro-4-fluorobenzoic acid 
• 96-99-1 4-chloro-3-nitrobenzoate 
• 1588-83-6 4-amino-3-nitrobenzoic acid 

Downstream Products

• 1024351-30-1 C₂₂H₁₇ClN₂O₂ 
• 951558-74-0 1-benzyl-1H-benzotriazole-5-carboxylic acid methyl ester 
• 185428-95-9 1-benzyl-1H-benzimidazole-5-carboxylic acid methyl ester 
• 1646359-33-2 1-benzyl-2-oxo-3-methyl-2,3-dihydro-1H-benzimidazole-5-carboxylic acid methyl ester 
• 1239608-92-4 methyl 6-benzyl-3,3-dimethyl-1-oxo-12-phenyl-1,2,3,4,6,12-hexahydrobenzo[4,5]imidazo[2,1-b]quinazoline-9-carboxylate 

Relevant academic research and scientific papers

Discovery of a Potent FLT3 Inhibitor (LT-850-166) with the Capacity of Overcoming a Variety of FLT3 Mutations

Secondary mutations of FLT3 have become the main mechanism of FLT3 inhibitor resistance that presents a significant clinical challenge. Herein, a series of pyrazole-3-amine derivatives were synthesized and optimized to overcome the common secondary resistance mutations of FLT3. The structure-activity relationship and molecular dynamics simulation studies illustrated that the ribose region of FLT3 could be occupied to help address the obstacle of secondary mutations. Among those derivatives, compound 67 exhibited potent and selective inhibitory activities against FLT3-ITD-positive acute myeloid leukemia (AML) cells and possessed equivalent potency against transformed BaF3 cells with a variety of secondary mutations. Besides, cellular mechanism assays demonstrated that 67 strongly inhibited phosphorylation of FLT3 and its downstream signaling factors, as well as induced cell cycle arrest and apoptosis in MV4-11 cells. In the MV4-11 xenograft models, 67 exhibited potent antitumor potency without obvious toxicity. Taken together, these results demonstrated that 67 might be a drug candidate for the treatment of FLT3-ITD-positive AML.

Diversity-Oriented Synthesis of Coumarin-Linked Benzimidazoles via a One-Pot, Three-Step, Intramolecular Knoevenagel Cyclization

Diversity-oriented synthesis of coumarin-linked benzimidazoles from N-(2-aminophenyl)-2-cyanoacetamide was achieved via a one-pot, three-step sequential reaction in excellent yields. In situ intramolecular cyclization of the cyanoacetamide afforded benzimidazoles which subsequently underwent a Knoevenagel condensation of the 2-cyanomethylbenzimidazoles with salicylaldehydes promoted by triethylamine to reach the target compounds. An important intermediate, 2-(2-imino-2H-chromen-3-yl)-1H-benzimidazole was characterized by X-ray analysis and further hydrolyzed to 2-(coumarin-3-yl)benzimidazole in acidic condition. Among the synthesized compounds, some were found to be promising inhibitors of porcine kidney d-amino acid oxidase (pkDAO).

3D-Printed Polypropylene Continuous-Flow Column Reactors: Exploration of Reactor Utility in SNAr Reactions and the Synthesis of Bicyclic and Tetracyclic Heterocycles

3D printing has the potential to transform the way in which chemical reactions are carried out due to its low-cost, ease-of-use as a technology and its capacity to expedite the development of iteratively enhanced prototypes. In this present study, we developed a novel, low-cost polypropylene (PP) column reactor that was incorporated into an existing continuous-flow reactor for the synthesis of heterocycles. The utility and solvent resistance of the printed devices were explored in SNAr reactions to produce substituted aniline derivatives and in the synthesis of bicyclic and tetracyclic heterocycles. Using this approach, a range of heterocyclic compounds was synthesised including the core structure of the natural product (±)-γ-lycorane and structurally complex compounds based on the tetracyclic core of the erythrina alkaloids.

A Novel Mechanistic Study on Ultrasound-Assisted, One-Pot Synthesis of Functionalized Benzimidazo[2,1-b]quinazolin-1(1H)-ones

Ultrasound-assisted synthesis of benzimidazo[2,1-b]quinazolin-1(1H)-ones was achieved via piperidine-catalyzed three-component reaction of 2-aminobenzimidazoles, an aromatic aldehyde, and 1,3-dione in aqueous isopropanol. This mechanism was first suspected following our identification of unusual reaction intermediates in a one-pot reaction. An unprecedented coupling reaction, it involved a nucleophilic attack by 2-aminobenzimidazole on in situ generated Michael adduct, followed by electrocyclic ring formation reaction. In contrast to the commonly accepted mechanism, that the direct reaction of 2-amino benzimidazole with a Knoevenagel adduct cannot deliver target compounds.

Synthesis and bioevaluation of pyrazole-benzimidazolone hybrids as novel human 4-Hydroxyphenylpyruvate dioxygenase inhibitors

4-Hydroxyphenylpyruvate dioxygenase (HPPD), an essential enzyme in tyrosine catabolism, is an important target for treating type I tyrosinemia. Inhibition of HPPD can effectively alleviate the symptoms of type I tyrosinemia. However, only one commercial H

GPR40 RECEPTOR AGONIST, METHODS OF PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to a novel compound having GPR40 receptor agonist activity that promotes insulin secretion and inhibits blood sugar rise after glucose loading, and is thereby useful for the treatment of diabetes and complications thereof, the preparation method thereof and pharmaceutical composition containing them as an active ingredient.

Hydrogen-bonded sheet structures in methyl 4-(4-chloroanilino)-3- nitrobenzoate and methyl 1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole-5- carboxylate

In methyl 4-(4-chloroanilino)-3-nitrobenzoate, C14H11ClN 2O4, (I), there is an intramolecular N - H...O hydrogen bond and the intramolecular distances provide evidence for electronic polarization of the o-quinonoid type. The molecules are linked into sheets built from N - H...O, C - H...O and C - H...π(arene) hydrogen bonds, together with an aromatic π-π stacking interaction. The molecules of methyl 1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate, C22H 17ClN2O2, (II), are also linked into sheets, this time by a combination of C - H...π(arene) hydrogen bonds and aromatic π-π stacking interactions.

Benzoic acid and pyridine derivatives as inhibitors of Trypanosoma cruzi trans-sialidase

Benzoic acid and pyridine derivatives inhibit recombinant trans-sialidase from Trypanosoma cruzi with I50 values between 0.4 and 1 mM. The best compounds, 4-acetylamino-3-hydroxymethylbenzoic acid and 5-acetylamino-6-aminopyridine-2-carboxylic

Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups

A series of benzimidazole-5-carboxylic acid alkyl ester derivatives carrying amide or amidine substituted methyl or phenyl groups at the position C-2 were synthesised and evaluated for antibacterial and antifungal activities against S. aureus, methicillin

An improved synthesis of N-substituted-2-nitroanilines

The reaction of 2-chloronitrobenzene with substituted amines/ anilines in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) gives N-substituted-2-nitroanilines in good to excellent yields (>75-90%).