59512-29-7Relevant academic research and scientific papers
Asymmetric Markovnikov Hydroaminocarbonylation of Alkenes Enabled by Palladium-Monodentate Phosphoramidite Catalysis
Yao, Ya-Hong,Yang, Hui-Yi,Chen, Ming,Wu, Fei,Xu, Xing-Xing,Guan, Zheng-Hui
supporting information, p. 85 - 91 (2021/01/12)
A palladium-catalyzed asymmetric Markovnikov hydroaminocarbonylation of alkenes with anilines has been developed for the atom-economical synthesis of 2-substituted propanamides bearing an α-stereocenter. A novel phosphoramidite ligand L16 was discovered which exhibited very high reactivity and selectivity in the reaction. This asymmetric Markovnikov hydroaminocarbonylation employs readily available starting materials and tolerates a wide range of functional groups, thus providing a facile and straightforward method for the regio- and enantioselective synthesis of 2-substituted propanamides under ambient conditions. Mechanistic studies revealed that the reaction proceeds through a palladium hydride pathway.
CAL-B-mediated efficient synthesis of a set of valuable amides by direct amidation of phenoxy- and aryl-propionic acids
Benamara, Nourelhouda,Merabet-Khelassi, Mounia,Aribi-Zouioueche, Louisa,Riant, Olivier
, p. 4045 - 4053 (2021/04/21)
An efficient, easy and sustainable amidation of a set of non-activated carboxylic acids with anilines, assisted by CAL-B, as biodegradable catalyst, is reported. The enzymatic amidation reactions are performed on set of nonsteroidal anti-inflammatory drugs (NSAIDs), phenoxypropionic acid and protected-prolines by direct condensation of one equivalent of carboxylic acids and two equivalents of anilines derivatives in heptane after 72?h of reaction at 80?°C. The obtained carboxylic amides are recovered with isolated chemical yields varied between moderate and excellent. Fourteen from them are reported for the first time, and an X-ray crystal is obtained for: N-(4-iodophenyl)-2-(4-isobutylphenyl)propanamide 1d.
Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages
Wang, Shi-Meng,Zhao, Chuang,Zhang, Xu,Qin, Hua-Li
supporting information, p. 4087 - 4101 (2019/04/30)
The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.
Dexibuprofen amide derivatives as potential anticancer agents: Synthesis, in silico docking, bioevaluation, and molecular dynamic simulation
Ashraf, Zaman,Mahmood, Tariq,Hassan, Mubashir,Afzal, Samina,Rafique, Hummera,Afzal, Khurram,Latip, Jalifah
, p. 1643 - 1657 (2019/06/11)
Background: The amide derivatives of nonsteroidal anti-inflammatory drugs have been reported to possess antitumor activity. The present work describes the synthesis of dexibuprofen amide analogues (4a–j) as potential anticancer agents. Methods: The title amides (4a–j) were obtained by simple nucleophilic substitution reaction of dexibuprofen acid chloride with substituted amines in good yield and chemical structures were confirmed by FTIR,1H NMR,13C NMR and mass spectral data. Results: The brine shrimp lethality assay results showed that all of the synthesized compounds are non-toxic to shrimp larvae. The inhibitory effects on tumor growth were evaluated and it was observed that N-(2,5-dichlorophenyl)-2-(4-isobutylphenyl) propionamide (4e) and N-(2-chlorophenyl)-2-(4-isobutylphenyl) propionamide (4g) exhibited excellent antitumor activity compared to all other derivatives. The compound 4e bearing 2,5-dichloro substituted phenyl ring and 4g possesses 2-chloro substituted phenyl ring exhibited 100% inhibition of the tumor growth. The anticancer activity was evaluated against breast carcinoma cell line (MCF-7) and it was observed that derivative 4e exhibited excellent growth inhibition of cancer cells with IC50 value of 0.01±0.002 μm, which is better than the standard drugs. The docking studies against breast cancer type 1 susceptibility protein BRCA1 (PDBID 3K0H) exhibited good binding affinities, which are in good agreement with the wet lab results. The compounds 4e and 4g showed the binding energy values of ?6.39 and ?6.34 Kcal/mol, respectively. The molecular dynamic (MD) simulation was also carried out to evaluate the residual flexibility of the best docking complexes of compounds 4e and 4g. The MD simulation analysis assured that the 4e formed a more stable complex with the target protein than the 4g. The synthesized amide derivatives exhibited were devoid of gastrointestinal side effects and no cytotoxic effects against human normal epithelial breast cell line (MCF-12A) were found. Conclusion: Based upon our wet lab and dry lab findings we propose that dexibuprofen analogue 4e may serve as a lead structure for the design of more potent anticancer drugs.
Synthesis of ibuprofen derivatives with improved antibacterial activity
Kiran, Shumaila,Kamal, Shagufta,Aslam, Nosheen,Hussain, Abdullah Ijaz,Ghaffar, Abdul,Bibi, Ismat,Kamal, Amna,Munir, Bushra,Sultan, Neelam
, p. 3259 - 3262 (2015/12/05)
A new series of ibuprofen derivatives i.e., (S)-ibuprofen amide, (S)-4-(2-(4-isobutylphenyl)propanamido)benzoic acid, (S)-3-(4- isobutylphenyl)butan-2-one compound with morpholine, (S)-2-(4-isobutylphenyl)-N-(4-nitrophenyl)propanamide and (S)-3-hydroxy-5- (2-(4-isobutylphenyl)propylamino benzoic acid have been synthesized by treating commercially available 2-(4-isobutyl-phenyl)propionic acid (ibuprofen) with thionyl chloride to get 2-(4-isobutyl-phenyl)propionyl chloride. Acid chloride was further reacted with different amines to get ibuprofen amides. The structures of all these compounds were confirmed on the basis of their analytical and spectral data. FTIR and elemental analysis were performed to characterize the synthesized compounds. Chemical stability studies revealed that amide derivatives were chemically stable at pH 1.2-6.8. Disc diffusion and micro-dilution assays were used to evaluate the antibacterial potential of synthesized ibuprofen derivatives against Gram positive i.e., Bacillus subtilis and Gram negative strains i.e., Escherichia coli. The amide derivatives of ibuprofen exhibited stronger inhibitory effect against tested bacteria than ester derivatives. MIC values of all derivatives were in the range of 2-20 mg/mL. Results suggested that amide derivative of ibuprofen has more potential as antimicrobial agent it may find its application against infectious diseases.
NEW CHIRAL STATIONARY PHASES FOR CHROMATOGRAPHY BASED ON AROMATIC ALLYL AMINES
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Page/Page column 16-17, (2009/10/22)
New chiral stationary phases (CSPs) based on chiral selectors covalently bound on a solid support were prepared. Chiral selectors were obtained from enantiomerically pure aromatic amines and 3,5-dinitrobenzoic acid and then linked to the support surface through the allylic double bond. Such obtained materials allow enantioseparation of racemates or enantiomerically enriched compounds. These chiral stationary phases can be used as fillings in chromatographic columns for enantiomer separation of naproxen type drugs and other similar non-steroidal anti-inflammatory drugs (NSAID) by means of high performance liquid chromatography on both the analytical and preparative scale.
2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors
Allegretti, Marcello,Bertini, Riccardo,Cesta, Maria Candida,Bizzarri, Cinzia,Di Bitondo, Rosa,Di Cioccio, Vito,Galliera, Emanuela,Berdini, Valerio,Topai, Alessandra,Zampella, Giuseppe,Russo, Vincenzo,Di Bello, Nicoletta,Nano, Giuseppe,Nicolini, Luca,Locati, Massimo,Fantucci, Piercarlo,Florio, Saverio,Colotta, Francesco
, p. 4312 - 4331 (2007/10/03)
The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM) G-protein-coupled receptors CXC chemokine receptor 1 (CXCR1) and CXC chemokine receptor 2 (CXCR2). (R)-Ketoprofen (1) was previously reported to be a potent and specific noncompetitive inhibitor of CXCLS-induced human PMNs chemotaxis. We report here molecular modeling studies showing a putative interaction site of 1 in the TM region of CXCR1. The binding model was confirmed by alanine scanning mutagenesis and photoaffinity labeling experiments. The molecular model driven medicinal chemistry optimization of 1 led to a new class of potent and specific inhibitors of CXCL8 biological activity. Among these, repertaxin (13) was selected as a clinical candidate drug for prevention of post-ischemia reperfusion injury.
