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An amidation/cyclization approach to the synthesis of N-hydroxyquinolinones and their biological evaluation as potential anti-plasmodial, anti-bacterial, and iron(II)-chelating agents

A 26-member library of novel N-hydroxyquinolinone derivatives was synthesized by a one-pot Buchwald-type palladium catalyzed amidation and condensation sequence. The design of these rare scaffolds was inspired from N-hydroxypyridones and 2-quinolinones classes of compounds which have been shown to have rich biological activities. The synthesized compounds were evaluated for their anti-plasmodial and anti-bacterial properties. In addition, these compounds were screened for their iron(II)-chelation properties. Notably, four of these compounds exhibited anti-plasmodial activities comparable to that of the natural product cordypyridone B.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Discovery of 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex

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(S)-4-(Difluoromethyl)-5-(4-(3-methylmorpholino)-6-morpholino-1,3,5-triazin-2-yl)pyridin-2-amine (PQR530), a Potent, Orally Bioavailable, and Brain-Penetrable Dual Inhibitor of Class i PI3K and mTOR Kinase

The phosphoinositide 3-kinase (PI3K)/mechanistic target of rapamycin (mTOR) pathway is frequently overactivated in cancer, and drives cell growth, proliferation, survival, and metastasis. Here, we report a structure-activity relationship study, which led to the discovery of a drug-like adenosine 5?-triphosphate-site PI3K/mTOR kinase inhibitor: (S)-4-(difluoromethyl)-5-(4-(3-methylmorpholino)-6-morpholino-1,3,5-triazin-2-yl)pyridin-2-amine (PQR530, compound 6), which qualifies as a clinical candidate due to its potency and specificity for PI3K and mTOR kinases, and its pharmacokinetic properties, including brain penetration. Compound 6 showed excellent selectivity over a wide panel of kinases and an excellent selectivity against unrelated receptor enzymes and ion channels. Moreover, compound 6 prevented cell growth in a cancer cell line panel. The preclinical in vivo characterization of compound 6 in an OVCAR-3 xenograft model demonstrated good oral bioavailability, excellent brain penetration, and efficacy. Initial toxicity studies in rats and dogs qualify 6 for further development as a therapeutic agent in oncology.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Low band gap polymers based on 1,4-dialkoxybenzene, thiophene, bithiophene donors and the benzothiadiazole acceptor

Four new copolymers of 1,4-dialkoxybenzene, thiophene, bithiophene and benzothiadiazole have been prepared and investigated for optical properties and in photovoltaic devices. The structures were chosen to show the effect of successively introducing an acceptor moiety, longer alkoxy side chains and finally, substituting thiophene for bithiophene. The absorption spectra and IPCE showed that these are low band gap polymers that can harvest light in the visible spectrum (400 to 700 nm) and that photoelectrons are generated in the whole range. The photovoltaic devices produced short circuit current densities (Jsc) of 2.6 to 4.6 mA/cm2 under AM1.5 G illumination. The open circuit voltage (Voc) was 0.56 to 0.64 V and the efficiencies (eta) of 0.8% to 2.2% depending on the structure.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, Recommanded Product: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 72287-26-4, Name is [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), molecular formula is C34H28Cl2FeP2Pd

1,2,4,5-Tetra([5]trovacenyl)benzene: An organometallic tetraradical displaying pronounced electro- and magnetocommunication

The organometallic tetraradical 1,2,4,5-[(eta7-C 7H7)V(eta5-C5H4)] 4C6H2 has been prepared and structurally characterized. The isotropic EPR spectrum displays 29 a(51V) hyperfine lines, the intensity distribution slightly deviating from binomial. Exchange coupling therefore approaches the strong exchange limit, J ortho ? Jmeta ? Jpara, ?50 a( 51V) with a(51V) = 0.0067 cm-1. According to magnetic susceptometry, the interaction is antiferromagnetic. While redox splittings deltaE1/2, are resolved for the four reduction steps this is not the case for oxidation. The Royal Society of Chemistry 2005.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Bipolar type indolocarbazole host for green phosphorescent organic light-emitting diodes

A bipolar host designed using indolocarbazole as a bipolar moiety was developed by coupling two indolocarbazole moieties via a phenyl linker. The indolocarbazole derived hosts could carry holes and electrons in the emitting layer, functioning as bipolar hosts in the green phosphorescent organic light-emitting diodes. The linker based molecular design was superior to the directly coupled molecular design to match carrier balance for high quantum efficiency in the green phosphorescent devices.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Brief introduction of Pd2(DBA)3

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A new, robust, and nonradioactive approach for exploring N-myristoylation

Myristoyl-CoA (CoA): protein N-myristoyltransferase (NMT) catalyzes protein modification through covalent attachment of a C14 fatty acid (myristic acid) to the N-terminal glycine of proteins, thus promoting protein-protein and protein- membrane interactions. NMT is essential for the viability of numerous human pathogens and is also up-regulated in several tumors. Here we describe a new, nonradioactive, ELISA-based method for measuring NMT activity. After the NMT-catalyzed reaction between a FLAG-tagged peptide and azido-dodecanoyl-CoA (analog of myristoyl-CoA), the resulting azido-dodecanoyl-peptide-FLAG was coupled to phosphine- biotin by Staudinger ligation, captured by plate-bound anti-FLAG antibodies and detected by streptavidin-peroxidase. The assay was validated with negative controls (including inhibitors), corroborated by HPLC analysis, and demonstrated to function with fresh or frozen tissues. Recombinant murine NMT1 and NMT2 were characterized using this new method. This versatile assay is applicable for exploring recombinant NMTs with regard to their activity, substrate specificity, and possible inhibitors as well as for measuring NMT-activity in tissues. Copyright

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Zerovalent palladium and platinum complexes of aminomethylphosphines. Crystal structure of the palladium(0) dibenzylideneacetone complex >

Tris(dibenzylideneacetone)dipalladium and bis(dibenzylideneacetone)platinum react with N, N-bis(dicyclohexylphosphinomethyl)methylamine, (Cy2PCH2)2NMe (Cy = cyclohexyl), and with N, N-bis(diphenylphosphinomethyl)methylamine, (Ph2PCH2)2NMe (Ph = phenyl), to give the complexes > (M = Pd or Pt, dba = dibenzylideneacetone), R = Cy or Ph.The zerovalent platinum complex > can be obtained by hydrazine hydrate reduction of a mixture of > and triphenylphosphine or oneof cis- and (Cy2PCH2)2NMe.Thecrystal structure of > has been determined and some reactions of the complexes are reported.Keywords: Palladium; Platinum; Aminomethylphosphines; Dibenzylideneacetone; Crystal structure

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Luminescence properties of carborane-containing distyrylaromatic systems

A set of distyrylbenzene, distyrylbiphenyl and distyrylanthracene end-substituted with carborane clusters is introduced herein. All these compounds have been prepared from the corresponding styrene-containing carborane derivatives via Heck coupling reaction. High regioselectivity has been achieved yielding exclusively E isomers. All compounds have been fully characterized and the crystal structure of the distyrylbiphenyl end-substituted with Methyl-o-carborane was analyzed by X-ray diffraction. The absorption properties of compounds were elucidated by TD-DFT calculations, highlighting the importance of the aromatic core and pi-conjugation. It is worth noting that the luminescence properties of these systems depend on the aromatic core; in solution, benzene and biphenyl derivatives showed higher fluorescence emission than the anthracene ones and the presence of the carborane clusters does not induce any major change in fluorescence as compared to the pristine non-carborane containing partners. Nevertheless, all compounds exhibited low fluorescence quantum yields in aggregation state, which gives clear evidence of considerable intermolecular interactions between aggregates that could be the reason of the fluorescence quenching.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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USE OF SUBSTITUTED 2 PHENYLBENZIMIDAZOLES AS MEDICAMENTS

The present invention relates to the use of a substituted 2-phenylbenzimidazole of formula I wherein R1, R2, R3, R 4, R5 and m have the meanings given in the claims, for the preparation of a medicament for the treatment or prevention of diseases involving glucagon receptors, as well as new compounds of formula I wherein R1 is a group of formula

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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2,6-Bis(2-benzimidazolyl)pyridine receptor for urea recognition

The use of 2,6-bis(2-benzimidazolyl)pyridine as a neutral receptor enables the formation of highly stable supramolecular complexes with urea via self-assembly and which were characterized by spectroscopy and X-ray diffraction analysis. This receptor utilizes the imine nitrogen located on its outer core in addition to the cavity to form hydrogen-bonded adducts with high binding affinity, thus providing a unique design for chemical and biological recognition.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method