- Hexagonal Boron Nitride Supported N-Heterocyclic Carbene-Palladium(II): A New, Efficient and Recyclable Heterogeneous Catalyst for Suzuki–Miyaura Cross-Coupling Reaction
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Abstract: In this study, a new stable and powerful hexagonal boron nitride supported N-heterocyclic carbene-palladium(II) complex (h-BN@NHC-Pd) heterogeneous catalyst was designed and synthesized. The structure of the h-BN@NHC-Pd heterogeneous catalyst was characterized by various techniques such as Fourier transform infrared spectra (FT-IR), ultraviolet–visible spectroscopy (UV–Visible), inductively coupled plasma-optical emission spectroscopy (ICP-OES), energy-dispersive X-ray spectroscopy (EDS), field-emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), X-ray powder diffraction (XRD), thermogravimetric analysis (TGA) and Brunauer–Emmett–Teller surface area analysis (BET). Then catalytic activity of h-BN@NHC-Pd heterogeneous catalyst was studied in the Suzuki–Miyaura cross-coupling reactions between aryl halides and arylboronic acids in aqueous medium at room temperature. The effects of varying solvents, bases, temperature, time and catalytic ratios on the performance of the Suzuki–Miyaura cross-coupling reaction were investigated. Moreover, h-BN@NHC-Pd heterogeneous catalyst could be easily recovered through simple filtration or centrifugation method and could be reused five times without significant loss of its catalytic efficiency. Furthermore, stability of the h-BN@NHC-Pd heterogeneous catalyst after recycling was confirmed through FESEM and FT-IR techniques. The h-BN@NHC-Pd heterogeneous catalyst shows remarkable advantages such as simplicity of operation, excellent yields, short reaction times, heterogeneous nature, easily separable and high stability without leaching. Graphic Abstract: A new stable and powerful hexagonal boron nitride supported N-heterocyclic carbene-palladium(II) complex (h-BN@NHC-Pd) heterogeneous catalyst was designed, synthesized, characterized and catalytic activity was studied in the Suzuki–Miyaura cross-coupling reactions. [Figure not available: see fulltext.]
- Antony, Arnet Maria,Kandathil, Vishal,Kempasiddaiah, Manjunatha,Sasidhar,Patil, Shivaputra A.,Patil, Siddappa A.
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p. 1293 - 1308
(2020/10/06)
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- DNA as a bioligand supported on magnetite for grafting palladium nanoparticles for cross-coupling reaction
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The utilization of deoxyribonucleic acid (DNA) in nanotechnology is a promising area of research wherein the distinct properties of DNA are exploited for the design and development of new materials and applications. The biodegradability and natural profusion of DNA makes it highly suitable for use in various fields. In this report, we have treated DNA as a bioligand, supported on functionalized magnetite for the grafting of palladium (Pd) nanoparticles to make Pd-DNA bio-nanocatalyst. The Pd-DNA was subjected to Fourier-transform infrared spectroscopy, field-emission scanning electron microscopy, transmission electron microscopy, X-ray powder diffraction, Brunauer–Emmett–Teller, energy dispersive X-ray spectroscopy, vibrating sample magnetometry, X-ray photoelectron spectroscopy, and inductively coupled plasma optical emission spectrometry analysis. The prepared Pd-DNA was found to be highly efficient in catalyzing Suzuki–Miyaura cross-coupling reaction with excellent yields when compared with commercially available palladium-based catalysts. Also, the Pd-DNA could be easily recovered from the reaction mass using an external magnet and recycled up to six times without substantial loss of activity. Furthermore, Felbinac, a non-inflammatory drug, was synthesized in quantitative yields using the Pd-DNA bio-nanocatalyst.
- Kandathil, Vishal,Kempasiddaiah, Manjunatha,Nataraj, Sanna Kotrappanavar,Patil, Siddappa A.,Somappa, Sasidhar Balappa
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- Potent, Selective, Water Soluble, Brain-Permeable EP2 Receptor Antagonist for Use in Central Nervous System Disease Models
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Activation of prostanoid EP2 receptor exacerbates neuroinflammatory and neurodegenerative pathology in central nervous system diseases such as epilepsy, Alzheimer's disease, and cerebral aneurysms. A selective and brain-permeable EP2 antagonist will be useful to attenuate the inflammatory consequences of EP2 activation and to reduce the severity of these chronic diseases. We recently developed a brain-permeable EP2 antagonist 1 (TG6-10-1), which displayed anti-inflammatory and neuroprotective actions in rodent models of status epilepticus. However, this compound exhibited moderate selectivity to EP2, a short plasma half-life in rodents (1.7 h) and low aqueous solubility (27 μM), limiting its use in animal models of chronic disease. With lead-optimization studies, we have developed several novel EP2 antagonists with improved water solubility, brain penetration, high EP2 potency, and selectivity. These novel inhibitors suppress inflammatory gene expression induced by EP2 receptor activation in a microglial cell line, reinforcing the use of EP2 antagonists as anti-inflammatory agents.
- Amaradhi, Radhika,Banik, Avijit,Mohammed, Shabber,Patro, Vidyavathi,Rojas, Asheebo,Wang, Wenyi,Motati, Damoder Reddy,Dingledine, Ray,Ganesh, Thota
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p. 1032 - 1050
(2020/03/10)
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- PROSTAGLANDIN RECEPTOR EP2 ANTAGONISTS, DERIVATIVES, AND USES RELATED THERETO
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The disclosure relates to Prostaglandin receptor EP2 antagonists, derivatives, compositions, and methods related thereto. In certain embodiments, the disclosure relates to methods of treating or preventing conditions and diseases in which EP2 receptor activation has a physiological role, such as but not limited to, brain injury, inflammatory diseases, epilepsy, neuroinflamation after a seizure, pain, endometriosis, cancer, rheumatoid arthritis, skin inflammation, vascular inflammation, colitis, and neurological disorders by administering a pharmaceutical composition comprising a compound disclosed herein to a subject in need thereof.
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Page/Page column 57; 62
(2020/10/09)
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- Discovery of a Potent Thiazolidine Free Fatty Acid Receptor 2 Agonist with Favorable Pharmacokinetic Properties
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Free fatty acid receptor 2 (FFA2/GPR43) is a receptor for short-chain fatty acids reported to be involved in regulation of metabolism, appetite, fat accumulation, and inflammatory responses and is a potential target for treatment of various inflammatory and metabolic diseases. By bioisosteric replacement of the central pyrrolidine core of a previously disclosed FFA2 agonist with a synthetically more tractable thiazolidine, we were able to rapidly synthesize and screen analogues modified at both the 2- and 3-positions on the thiazolidine core. Herein, we report SAR exploration of thiazolidine FFA2 agonists and the identification of 31 (TUG-1375), a compound with significantly increased potency (7-fold in a cAMP assay) and reduced lipophilicity (50-fold reduced clogP) relative to the pyrrolidine lead structure. The compound has high solubility, high chemical, microsomal, and hepatocyte stability, and favorable pharmacokinetic properties and was confirmed to induce human neutrophil mobilization and to inhibit lipolysis in murine adipocytes.
- Hansen, Anders H?jgaard,Sergeev, Eugenia,Bolognini, Daniele,Sprenger, Richard R.,Ekberg, Jeppe Hvidtfeldt,Ejsing, Christer S.,McKenzie, Christine J.,Rexen Ulven, Elisabeth,Milligan, Graeme,Ulven, Trond
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supporting information
p. 9534 - 9550
(2018/10/24)
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- Method for synthesizing biphenylcarboxylic acid compound by using Suzuki coupling reaction
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The invention provides a method for synthesizing a biphenylcarboxylic acid compound by using the Suzuki coupling reaction. According to the method, brominated aromatic hydrocarbon and arylboronic acidare used as raw materials, and water-soluble fullerene nanopalladium is used as a catalyst; and the equation of the Suzuki coupling reaction is as described in the specification. In the equation, R1and R2 represent substituents at different positions, may be acceptor or donor substituents, and may be monosubstitutents or polysubstitutent; and R1 and R2 may be identical or different groups. The water-soluble fullerene nanopalladium catalyst is cheap, easily available and environmentally friendly, and has high catalytic activity and stable properties. When the catalyst is used for catalysis ofthe Suzuki coupling reaction, conditions are mild, anhydrous anaerobic treatment and high-temperature treatment are not needed, and cost is low. The method can be applied to the industrial synthesisof non-steroidal anti-inflammatory drugs such as diphenylacetic acid and diflunisal.
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Paragraph 0027
(2018/09/21)
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- An efficient water-soluble surfactant-type palladium catalyst for Suzuki cross-coupling reactions in pure water at room temperature
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A palladium catalyst based on a bidentate phosphine-type zwitterionic surfactant as a ligand exhibited an excellent catalytic activity in the Suzuki-Miyaura cross coupling reactions. This novel method allowed the reaction of aryl halides with arylboronic acids to occur in pure water at room temperature, forming a variety of biaryls in good to high yields. Heterobiaryls were also efficiently assembled even in the presence of water-insoluble heteroaryl halides as substrates. In addition, such a coupling protocol was successfully used in the iterative diarylation of 2,5-dibromopyridine in one-pot.
- Qiu, Pei,Zhao, Jing Yang,Shi, Xu,Duan, Xin Hong
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supporting information
p. 6568 - 6572
(2016/08/10)
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- COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING INFLAMMATORY DISEASES
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The present invention is directed to compounds of formula (I), useful in treating and/or preventing inflammatory diseases.
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Page/Page column 185
(2015/06/11)
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- PYRROLIDINE OR THIAZOLIDINE CARBOXYLIC ACID DERIVATIVES, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERSAS AS AGONISTS OF G- PROTEIN COUPLED RECEPTOR 43 (GPR43)
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The present invention is directed to novel compounds of formula (I) and their use in treating and/or preventing metabolic diseases.
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Page/Page column 201
(2011/07/07)
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- The 1,3-diaminobenzene-derived aminophosphine palladium pincer complex {C6H3[NHP(piperidinyl)2]2Pd(Cl)} - A highly active Suzuki-Miyaura catalyst with excellent functional group tolerance
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The rapidly prepared 1,3-diaminobenzenederived aminophosphine pincer complex {C6H3 [NHP(piperidinyl)2] 2Pd(Cl)} (1) is an effective Suzuki catalyst with excellent functional group tolerance. Side-product formations, such as homocoupling, debromation or protodeboration have only rarely been detected and if so, were in all cases below the 5% level. The presented reaction protocol is universally applicable. Experimental observations indicate that palladium nanoparticles are the catalytically active form of 1.
- Bolliger, Jeanne L.,Frech, Christian M.
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experimental part
p. 1075 - 1080
(2010/06/17)
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- SAR and biological evaluation of SEN12333/WAY-317538: Novel alpha 7 nicotinic acetylcholine receptor agonist
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Alpha 7 nicotinic acetylcholine receptor (α7 nAChR) agonists are promising therapeutic candidates for the treatment of cognitive impairment associated with a variety of disorders including Alzheimer's disease and schizophrenia. Alpha 7 nAChRs are expressed in brain regions associated with cognitive function, regulate cholinergic neurotransmission and have been shown to be down regulated in both schizophrenia and Alzheimer's disease. Herein we report a novel, potent small molecule agonist of the alpha 7 nAChR, SEN12333/WAY-317538. This compound is a selective agonist of the α7 nAChR with excellent in vitro and in vivo profiles, excellent brain penetration and oral bioavailability, and demonstrates in vivo efficacy in multiple behavioural cognition models. The SAR and biological evaluation of this series of compounds are discussed.
- Haydar, Simon N.,Ghiron, Chiara,Bettinetti, Laura,Bothmann, Hendrick,Comery, Thomas A.,Dunlop, John,La Rosa, Salvatore,Micco, Iolanda,Pollastrini, Martina,Quinn, Joanna,Roncarati, Renza,Scali, Carla,Valacchi, Michela,Varrone, Maurizio,Zanaletti, Riccardo
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experimental part
p. 5247 - 5258
(2009/12/01)
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- An improved protocol for ligandless Suzuki-Miyaura coupling in water
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Using a reverse order of addition of reagents, PdCl2 and Pd(OAc)2 are efficient catalysts for the Suzuki-Miyaura reactions in water. The ligandless and mild conditions, the high stability of the catalytic system, short reaction time and good to excellent yields are important features of this protocol.
- Korolev, Dmitrii N.,Bumagin, Nikolay A.
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p. 4225 - 4229
(2007/10/03)
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- MODULATORS OF ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTORS AND THERAPEUTIC USES THEREOF
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The present invention relates to compounds with α7 nAChR agonistic activity, processes for their preparation, pharmaceutical compositions containing the same and the use thereof for the treatment of neurological, psychiatric, cognitive, immunological and inflammatory disorders.
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Page/Page column 21-22
(2010/02/15)
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- INDANE DERIVATES AS MUSCARINIC RECEPTOR AGONISTS
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The present invention relates to compounds of Formula I: I which are agonists of the M-1 muscarinic receptor.
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- MUSCARINIC AGONISTS
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The present invention relates to compounds of Formula (I): which are agonists of the M-1 muscarinic receptor.
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- MUSCARINIC AGONISTS
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The present invention relates to compounds of Formula (I): which are agonists of the M-1 muscarinic receptor.
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- Biphenyl vasopressin agonists
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A compound of the formulae (I) or (II): wherein: Y is a moiety selected from NR or —(CH2)n; wherein R is hydrogen or (C1-C6) lower alkyl, and n is 1; represents: (1) a phenyl ring optionally substituted with one
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- N-acylsulfonamide apoptosis promoters
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N-Benzoyl arylsulfonamides having the formula are BCL-Xl inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-Xl inhibiting compositions and methods of promoting apoptosis in a mammal.
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- N-Acylsulfonamide apoptosis promoters
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N-Benzoyl arylsulfonamides having the formula Are BCL-X1 inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-X1 inhibiting compositions and methods of promoting apoptosis in a mammal.
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- An easily prepared, air and moisture stable, resin-bound palladium catalyst for Suzuki cross-coupling reactions
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An air and moisture stable polymer supported palladium catalyst easily prepared from a commercial available thiourea resin Deloxan THP was found to enable Suzuki cross-coupling reactions to be carried out in high yields and convenient manner.
- Zhang, Tony Y.,Allen, Matthew J.
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p. 5813 - 5816
(2007/10/03)
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- Identification and initial structure-activity relationships of a novel class of nonpeptide inhibitors of blood coagulation factor Xa
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The discovery and some of the basic structure-activity relationships of a series of novel nonpeptide inhibitors of blood coagulation Factor Xa is described. These inhibitors are functionalized β-alanines, exemplified by 2a. Docking experiments placing 2a in the active site of Factor Xa implied that the most expeditious route to enhancing in vitro potency was to modify the group occupying the S3 site of the enzyme. Increasing the hydrophobic contacts between the inhibitor and the enzyme in this region led to 8, which has served as the prototype for this series. In addition, an enantioselective synthesis of these substituted β-alanines was also developed.
- Klein, Scott I.,Czekaj, Mark,Gardner, Charles J.,Guertin, Kevin R.,Cheney, Daniel L.,Spada, Alfred P.,Bolton, Scott A.,Brown, Karen,Colussi, Dennis,Heran, Christopher L.,Morgan, Suzanne R.,Leadley, Robert J.,Dunwiddie, Christopher T.,Perrone, Mark H.,Chu, Valeria
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p. 437 - 450
(2007/10/03)
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- NMR-based discovery of lead inhibitors that block DNA binding of the human papillomavirus E2 protein
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The E2 protein is required for the replication of human papillomaviruses (HPVs), which are responsible for anogenital warts and cervical carcinomas. Using an NMR-based screen we tested compounds for binding to the DNA-binding domain of the HPV-E2 protein. Three classes of compounds were identified which bound to two distinct sites on the protein. Biphenyl and biphenyl ether compounds containing a carboxylic acid bind to a site near the DNA recognition helix and inhibit the binding of E2 to DNA. Benzophenone- containing compounds which lack a carboxylic acid group bind to the β- barrel formed by the dimer interface and exhibit negligible effects on the binding of E2 to DNA. Structure-activity relationships from the biphenyl and biphenyl ether compounds were combined to produce a compound [5-(3'- (3'',5''-dichlorophenoxy)-phenyl)-2,4-pentadienoic acid] with an IC50 value of approximately 10 μM. This compound represents a useful lead for the development of antiviral agents that interfere with HPV replication and further illustrates the usefulness of the SAR by NMR method in the drug discovery process.
- Hajduk, Philip J.,Dinges, Jürgen,Miknis, Gregory F.,Merlock, Megan,Middleton, Tim,Kempf, Dale J.,Egan, David A.,Walter, Karl A.,Robins, Terry S.,Shuker, Suzy B.,Holzman, Thomas F.,Fesik, Stephen W.
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p. 3144 - 3150
(2007/10/03)
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- The Effects of Substituents on the Rate of Saponification of Biphenyl-4-carboxylates
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Second-order rate constants have been measured for the saponification of methyl 2'-, 3'-, and 4'-substituted biphenyl-4-carboxylates at several temperatures in 85percent (w/w) methanol-water and activation parameters have been calculated.The Hammett equation applies very well to the saponification of 3'- and 4'-substituted biphenyl-4-carboxylates with ?-constants evaluated by the FMMF method.The effect of 2'-substituents is understandable in terms of ?-electron steric effects.
- Ananthakrishnanadar, Ponnambalanad.,Kannan, Nagarathnam
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