53691-91-1

Usage

InChI:InChI=1/C15H12ClNO/c16-13-7-9-14(10-8-13)17-15(18)11-6-12-4-2-1-3-5-12/h1-11H,(H,17,18)/b11-6+

Upstream product

• 102-92-1 cinnamoyl chloride 
• 106-47-8 4-chloro-aniline 
• 26112-94-7 1-(3-phenylpropenoyl)-1H-benzotriazole 
• 621-79-4 cinnamamide 
• 944551-28-4 3-(4-chlorophenyl)-1-phenylprop-2-yn-1-ol 
• 873-73-4 4-n-chlorophenylacetylene 
• 100-42-5 styrene 
• 100-00-5 4-chlorobenzonitrile 
• 13939-06-5 molybdenum hexacarbonyl 
• 100-52-7 benzaldehyde 
• 621-82-9 Cinnamic acid 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 645-45-4 hydrocinnamic acid chloride 

Downstream Products

• 1810-67-9 6-chloroquinolin-2(1H)-oney 
• 1810-72-6 2,6-dichloroquinoline 
• 1568113-64-3 C₁₆H₁₁ClF₃NO 
• 1453188-38-9 1-benzyl-6-chloro-4-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 1453188-48-1 2-(4-chlorophenyl)-5-phenyl-1,2,4,5-tetrahydro-2-benzazepin-3-one 
• 1453188-61-8 8-methyl-2-(4-chlorophenyl)-5-phenyl-1,2,4,5-tetrahydro-2-benzazepin-3-one 
• 1453188-59-4 6-methyl-2-(4-chlorophenyl)-5-phenyl-1,2,4,5-tetrahydro-2-benzazepin-3-one 
• 1453188-42-5 1-(4-methylbenzyl)-6-chloro-4-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 1453188-58-3 2-(4-chlorophenyl)-7-methyl-5-phenyl-1,2,4,5-tetrahydro-2-benzazepin-3-one 
• 902757-75-9 (E)-3-benzylidene-5-chloro-1,3-dihydro-indol-2-one 
• 387342-89-4 (Z)-3-benzylidene-5-chloroindolin-2-one 

Relevant academic research and scientific papers

Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand

Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.

Design of enamides as new selective monoamine oxidase-B inhibitors

Objectives: To develop of new class of selective and reversible MAO-B inhibitors from enamides. Methods: Syntheses of the titled derivatives (AD1–AD11) were achieved by reacting cinnamoyl chloride and various primary and secondary amines in basic medium. All eleven compounds were investigated for in vitro inhibitory activities against recombinant human MAO-A and MAO-B. The reversibilities of lead compound inhibitions were analysed by dialysis. MTT assays of lead compounds were performed using normal VERO cell lines. Key findings: Compounds AD3 and AD9 exhibited the greatest inhibitory activity against MAO-B with IC50 values of 0.11 and 0.10?μm, respectively, and were followed by AD2 and AD1 (0.51 and 0.71?μm, respectively). Most of the compounds weakly inhibited MAO-A, with the exceptions AD9 and AD7, which had IC50 values of 4.21 and 5.95?μm, respectively. AD3 had the highest selectivity index (SI) value for MAO-B (>363.6) and was followed by AD9 (SI 42.1). AD3 and AD9 were found to be competitive inhibitors of MAO-B with Ki values of 0.044?±?0.0036 and 0.039?±?0.0047?μm, respectively. Reversibility experiments showed AD3 and AD9 were reversible inhibitors of MAO-B; dialysis restored the activity of MAO-B to the reference level. MTT assays revealed AD3 and AD9 were non-toxic to normal VERO cell lines with IC50 values of 153.96 and 194.04?μg/ml, respectively. Computational studies provided hypothetical binding modes for AD3 and AD9 in the binding cavities of MAO-A and MAO-B. Conclusions: These results encourage further studies on the enamide scaffold as potential drug candidates for the treatment of Alzheimer's and Parkinson's diseases.

Direct Amidation of Carboxylic Acids with Nitroarenes

N-Aryl amides are an important class of compounds in pharmaceutical and agrochemical chemistry. Rapid and low-cost synthesis of N-aryl amides remains in high demand. Herein, we disclose an operationally simple process to access N-aryl amides directly from readily available nitroarenes and carboxylic acids as coupling substrates. This method involves the in situ activation of carboxylic acids to acyloxyphosphonium salt for one-pot amidation, without the need for isolation of the corresponding synthetic intermediates. Furthermore, the ease of preparation and workup allow the quick and efficient synthesis of a wide range of N-aryl amides, including several amide-based druglike and agrochemical molecules.

Palladium-Catalyzed Carbonylative Synthesis of α,β-Unsaturated Amides from Styrenes and Nitroarenes

A procedure on palladium-catalyzed selective aminocarbonylation of styrenes with nitroarenes for the synthesis of α,β-unsaturated amides has been developed. A range of substituted α,β-unsaturated amides were synthesized in moderate to good yields. Interestingly, nitroarenes act as both a nitrogen source and oxidant, and Mo(CO)6 acts as a solid CO source and reductant in this catalytic system.

6-Cyano Analogues of Bedaquiline as Less Lipophilic and Potentially Safer Diarylquinolines for Tuberculosis

Bedaquiline (1) is a new drug for tuberculosis and the first of the diarylquinoline class. It demonstrates excellent efficacy against TB but induces phospholipidosis at high doses, has a long terminal elimination half-life (due to its high lipophilicity), and exhibits potent hERG channel inhibition, resulting in clinical QTc interval prolongation. A number of structural ring A analogues of bedaquiline have been prepared and evaluated for their anti-M.tb activity (MIC90), with a view to their possible application as less lipophilic second generation compounds. It was previously observed that a range of 6-substituted analogues of 1 demonstrated a positive correlation between potency (MIC90) toward M.tb and drug lipophilicity. Contrary to this trend, we discovered, by virtue of a clogP/M.tb score, that a 6-cyano (CN) substituent provides a substantial reduction in lipophilicity with only modest effects on MIC values, suggesting this substituent as a useful tool in the search for effective and safer analogues of 1.

Synthesis of Cinnamanilide Derivatives and Their Antioxidant and Antimicrobial Activity

The amide derivatives of cinnamic acid were synthesized and their antimicrobial and antioxidant activities were investigated. The investigation of antimicrobial potentials of the compounds demonstrated a strong activity against 21 bacterial strains comprising Gram-positive and Gram-negative bacteria. Compounds 2a, 2b, and 3b showed strong antimicrobial activity against all microorganisms with the pMIC value ranging from 2.45 to 3.68. Compounds 2a, 3a, and 3b demonstrated strong antioxidant activity with % inhibition of the DPPH radical of 51% (±1.14), 41% (±1.01), and 50% (±1.23), respectively. These findings indicate that the amide derivatives of the cinnamic acid possess strong antibacterial and antioxidant activities.

TMSCl-mediated synthesis of α,β-unsaturated amides via C-C bond cleavage and C-N bond formation of propargyl alcohols with trimethylsilyl azide

A new method with high efficiency for the synthesis of α,β- unsaturated amides from the easily prepared propargyl alcohols and TMSN 3 using TMSCl as an acid promoter is developed. A wide variety of α,β-unsaturated amides were produced in moderate to excellent yields. Mechanistic studies indicate that this transformation involves TMSCl-mediated allenylazide intermediate formation, C-C bond cleavage, and C-N bond formation. Significantly, this reaction shows good functional group compatibility and high regioselectivity, with a relatively short reaction time and inexpensive reagents.

A novel one-step synthesis of benzo[b]furo[3,2-b]pyridines having an amino group at the 4-position from benzo[b]furo[3,2-d][1,3]oxazine

A novel one-step synthesis of benzo[b]furo[3,2-b]pyridines having an amino group at the 4-position from benzo[b]furo[3,2-d][1,3]oxazine by treatment of various amines is described.

Sulfated tungstate: A highly efficient catalyst for transamidation of carboxamides with amines

An environmentally benign protocol for the transamidation of carboxamides with amines using sulfated tungstate, as a heterogeneous catalyst, has been developed. The method has been successfully applied to the synthesis of a wide range of aromatic and aliphatic amides and phthalimides. Efficient transformation, mild reaction conditions, easy product isolation and the potential reusability of the catalyst are attractive features.

Preparation of esters and amides from carboxylic acids and N-formylation of amines promoted by 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)

A new method is described for the preparation of esters and amides promoted by TAPC from carboxylic acids using a solvent-free grinding technique. The solvent-free N-formylation of amines is also reported.