6757-32-0

Upstream product

• 110-89-4 piperidine 
• 6908-41-4 4-(methoxycarbonyl)benzyl alcohol 
• 1357155-90-8 3-((4-methoxycarbonyl)phenyl) propiolic acid 
• 1013-92-9 di(piperidin-1-yl)methanethione 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 201230-82-2 carbon monoxide 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 619-44-3 methyl 4-iodobenzoate 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 1571-08-0 methyl 4-formylbenzoate 
• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 

Downstream Products

• 210961-92-5 4-(piperidine-1-carbonyl)benzoic acid 
• 35278-95-6 N,N-piperidyl-1-p-tolylmethanamine 
• 68453-37-2 4-(piperidinomethyl)benzoic acid methyl ester 

Relevant academic research and scientific papers

Discovery of Novel Thiophene-arylamide Derivatives as DprE1 Inhibitors with Potent Antimycobacterial Activities

In this study, we report the design and synthesis of a series of novel thiophene-arylamide compounds derived from the noncovalent decaprenylphosphoryl-β-d-ribose 2′-epimerase (DprE1) inhibitor TCA1 through a structure-based scaffold hopping strategy. Systematic optimization of the two side chains flanking the thiophene core led to new lead compounds bearing a thiophene-arylamide scaffold with potent antimycobacterial activity and low cytotoxicity. Compounds 23j, 24f, 25a, and 25b exhibited potent in vitro activity against both drug-susceptible (minimum inhibitory concentration (MIC) = 0.02-0.12 μg/mL) and drug-resistant (MIC = 0.031-0.24 μg/mL) tuberculosis strains while retaining potent DprE1 inhibition (half maximal inhibitory concentration (IC50) = 0.2-0.9 μg/mL) and good intracellular antimycobacterial activity. In addition, these compounds showed good hepatocyte stability and low inhibition of the human ether-à-go-go related gene (hERG) channel. The representative compound 25a with acceptable pharmacokinetic property demonstrated significant bactericidal activity in an acute mouse model of tuberculosis. Moreover, the molecular docking study of template compound 23j provides new insight into the discovery of novel antitubercular agents targeting DprE1.

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

Palladium-Catalyzed Desulfurative Amide Formation from Thioureas and Arylboronic Acids

The development of the reactivity on carbene complexes would lead to the creation of novel synthetic strategies. We discovered herein the Pd-catalyzed desulfurative amide formation involved Suzuki-Miyaura coupling reaction, notably the Pd complex was generated in situ from thioureas, Ag salt and Pd catalyst. Silver salt was essential for the construction of this type of carbenes from available and stable thioureas and well participated in the catalytic cycle. We report a method for the synthesis of arylamides from arylboronic acids, which greatly enriched the application of thiourea chemistry and expanded the application of the Suzuki-Miyaura coupling.

Cobalt-catalyzed aminocarbonylation of (hetero)aryl halides promoted by visible light

The catalytic aminocarbonylation of (hetero)aryl halides is widely applied in the synthesis of amides but relies heavily on the use of precious metal catalysis. Herein, we report an aminocarbonylation of (hetero)aryl halides using a simple cobalt catalyst under visible light irradiation. The reaction extends to the use of (hetero)aryl chlorides and is successful with a broad range of amine nucleophiles. Mechanistic investigations are consistent with a reaction proceeding via intermolecular charge transfer involving a donor-acceptor complex of the substrate and cobaltate catalyst.

Diaryl 2- amide-substituted thiophene imide ester compound as well as preparation method and application thereof (by machine translation)

The invention also discloses a 2 - synthesis method thereof, and an application of the compound as an antibacterial agent, in the phthisis-caused by the bacterium, in particular to the, mycobacterium-induced infectious disease (especially (Tuberculosis,TB), mycobacterium- induced mycobacterium, tuberculosis), and (I) the invention, specifically relates to a pharmaceutical composition containing the compound of the present invention or, a R pharmaceutical composition comprising the compound of the present invention. 1 , R2 , R3 , R4 , R5 As described Y in the present invention. as described in the specification, the present invention is directed, to the preparation of novel compounds, having an anti-mycobacterial activity as potential, new drug (s) for the treatment (TB) or preventative treatment of infectious diseases, consisting of M. tuberculosis, in particular phthisis- caused by tubercular mycobacteria, while being useful in overcoming the problems associated with drug resistance. (by machine translation)

Discovery and Structural Optimization of 4-(Aminomethyl)benzamides as Potent Entry Inhibitors of Ebola and Marburg Virus Infections

The recent Ebola epidemics in West Africa underscore the great need for effective and practical therapies for future Ebola virus outbreaks. We have discovered a new series of remarkably potent small molecule inhibitors of Ebola virus entry. These 4-(aminomethyl)benzamide-based inhibitors are also effective against Marburg virus. Synthetic routes to these compounds allowed for the preparation of a wide variety of structures, including a conformationally restrained subset of indolines (compounds 41-50). Compounds 20, 23, 32, 33, and 35 are superior inhibitors of Ebola (Mayinga) and Marburg (Angola) infectious viruses. Representative compounds (20, 32, and 35) have shown good metabolic stability in plasma and liver microsomes (rat and human), and 32 did not inhibit CYP3A4 nor CYP2C9. These 4-(aminomethyl)benzamides are suitable for further optimization as inhibitors of filovirus entry, with the potential to be developed as therapeutic agents for the treatment and control of Ebola virus infections.

Versatile Heterogeneous Palladium Catalysts for Diverse Carbonylation Reactions under Atmospheric Carbon Monoxide Pressure

Herein, we report a versatile carbonylation protocol using heterogeneous Pd0 nanoparticles supported on the metal–organic frameworks (MOFs) MIL-88B-NH2 (Fe/Cr). The synthesis of a vast array of carbonyls, which includes amides, esters, carboxylic acids, and α-ketoamides, was achieved through mono- and dicarbonylation reactions. The selectivity could be controlled simply by tuning the reaction conditions. Superior activity and selectivity were recorded in some cases compared to that achieved with commercial Pd/C. However, the utility of an elaborate catalyst support is questionable and important reactivity and recyclability issues are discussed.

Metal-Free Decarboxylative Trichlorination of Alkynyl Carboxylic Acids: Synthesis of Trichloromethyl Ketones

2,2,2-Trichloroacetophenone derivatives were synthesized via decarboxylative trichlorination from arylpropiolic acids and trichloroisocyanuric acid (TCCA). The reaction was performed in the presence of water at room temperature, and the desired products were obtained in good yields. The reaction showed good functional group tolerance towards halide, cyano, nitro, ketone, ester and aldehyde groups. In addition, the 2,2,2-trichloroacetophenone derivatives were readily transformed into esters, amides, and hydrazides. Based on experiments with H218O (water-18O), we proposed a cationic reaction pathway as the mechanism and suggested two different pathways for producing aryl- and alkyl-substituted propiolic acids. (Figure presented.).

Straightforward α-Amino Nitrile Synthesis Through Mo(CO)6-Catalyzed Reductive Functionalization of Carboxamides

The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)6 together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of α-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of α-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.

An efficient and mild oxidative amidation of aldehydes using B(C6F5)3 as a catalyst and biological evaluation of the products as potential antimicrobial agents

A mild and efficient protocol for oxidative amidation of diverse aldehydes with amines was developed using 3 mol% tris(pentafluorophenyl)borane and tert-butyl hydroperoxide to generate the corresponding amides in good to excellent yields. This method has significant advantages such as short reaction time, low toxicity, low catalyst loading, and being environmentally friendly and an operationally simple procedure. Acid labile protecting groups such as acyl and Boc displayed tolerance under the present catalytic system. Applicability in large scale synthesis of amides is an added advantage of the protocol. Moreover, direct amidation of aldehydes using substituted N-benzylanilines for the synthesis of corresponding amides was devised using the present catalytic system. Compounds 3n and 3o displayed promising antimicrobial activity against Staphylococcus aureus (Gram positive) with MIC ranging from 0.4-0.7 μg mL?1 and against Escherichia coli (Gram negative) with MIC 0.7-1.2 μg mL?1 with reference to the standard drug Ciprofloxacin.