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Design and synthesis of a novel DNA-encoded chemical library using Diels-Alder cycloadditions

DNA-encoded chemical libraries are increasingly being employed for the identification of binding molecules to protein targets of pharmaceutical relevance. Here, we describe the synthesis and characterization of a DNA-encoded chemical library, consisting of 4000 compounds generated by Diels-Alder cycloaddition reactions. The compounds were encoded with unique DNA fragments which were generated through a stepwise assembly process and serve as amplifiable bar codes for the identification and relative quantification of library members.

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P-chirogenic silylphosphine-boranes: Synthesis and phospha-Michael reactions

Chiral and achiral silylphosphine-boranes were prepared in high yields by reaction of phosphide boranes with halogenosilanes. Their reaction at room temperature with Michael acceptors afforded 1,4-addition products as silylenol ether or ketone derivatives in good to excellent yields. In the case of the 2,3-dihalogeno-maleimides, the double addition of silylphosphine-borane led to the corresponding trans-diphosphine-boranes in 86% yield. Noteworthy, the reaction of Pchirogenic silylphosphine-boranes with enones afforded the phospha-Michael adducts without racemization at the P-center. While the silylphosphine-boranes have been scarcely described so far, these compounds demonstrate their great interest for the synthesis of chiral and achiral functionalized organophosphorus compounds.

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Archives for Chemistry Experiments of 1081-17-0

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Related Products of 1081-17-0, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 1081-17-0, molcular formula is C11H9NO3, introducing its new discovery.

Flavonoid glycosides and isoquinolinone alkaloids from Corydalis bungeana

The whole plant of Corydalis bungeana (Papaveraceae) yielded several flavonol O-glycosides together with two isoquinolinone alkaloids. Two flavonol O-glycosides identified as the 3-O-alpha-arabinopyranosyl(1? ? 6?)-beta-glucopyranoside 7-O-beta-glucopyranosides of kaempferol and quercetin were isolated from the whole plant of Corydalis bungeana Turcz. together with eight known flavonol O-glycosides. Two isoquinolinone alkaloids were also obtained from the same source, including the new derivative, 6,7-methylenedioxy-2-(6-acetyl-2,3-methylenedioxybenzyl)-1(2H)-isoquinolinone. The structures were determined by spectroscopic methods (NMR and high-resolution MS).

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Application of 1081-17-0, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.1081-17-0, Name is 1-(4-Methoxyphenyl)-1H-pyrrole-2,5-dione, molecular formula is C11H9NO3. In a article£¬once mentioned of 1081-17-0

1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae)

The NMR signal assignments of a series of structurally divergent benzylisoquinolines isolated from Fumaria officinalis L. (Fumariaceae, Papaverales), namely adlumine, corlumine, corydamine, cryptopine, fumarophycine, O-methylfumarophycine, hydrastine, parfumine, protopine and sinactine, are presented. Copyright

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Distrubution and excretion of protopine in rats by RP-HPLC method

AIM: To study the distrubution and excretion of protopine in rats. METHODS: Reversed phase high performance liquid chromatographic method (RP-HPLC) was developed for determining the level of protopine in rats. The analytical column were packed with 5 mum C18. The mobile phase was a mixture of methanol, water and 10% acetic acid (80: 20: 2), in which the pH was modulated to 5.6 with 15% ammonia. Protopine biological samples were isolated well, in which two extraction with ether under basical condition and an extraction with 0.02 mol ¡¤ L-1 sulfuric acid were performed, respectively. The content of protopine in the biological sample was measured by an UV detector at 285 nm. The distrubution and excetion of protopine have been investigated in rats after intravenous administration 10 mg ¡¤ kg-1. RESULTS: Protopine distrubuted in many tissues after iv a dose of 10 mg ¡¤ kg-1. The higher level of protopine was found in lung, kidney, spleen and brain, and the highest was observed in lung at 5, 15 minutes after administration. However the top level tissue was testicle at 3 h, which may be due to small blood circulation. The excretion of the parent compound in urine was 36.87% of dose, but the excretion of the parent compound in feces and bile was less than 1% of dose. Plasma protein binding was less than 5%. CONCLUSION: The distrubution of protopine is extensive and the parent compoud was mainly excreted by urine and plasma protein binding was low.

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Discovery of 1-(4-Methoxyphenyl)-1H-pyrrole-2,5-dione

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ALKALOIDS FROM Papaver atlanticum BALL AND Papaver glaucum BOISS. et HAUSKN.

In addition to the alkaloids previously found in the aerial part of P. atlanticum BALL, viz. protopine, rhoeadine (predominant constituents), rhoeagenine, stylopine, cryptopine, sanguinarine, magnoflorine and papaverrubines A, B, E and D, we have now isolated the tertiary bases isothebaine, scoulerine, corytuberine and a new quaternary alkaloid 13beta-hydroxy-N-methylstylopinium hydroxide (I). The presence of papaverrubine B and muramine was also detected (TLC). The contents of the bases in the roots of P. atlanticum were found similar to those in the aerial part.Magnoflorine was isolated from the roots in a considerable yield.The dominant alkaloids isolated from P. glaucum BOISS. et HAUSKN. were glaudine and glaucamine; they were accompanied by protopine, papaverrubine B and traces of sanguinarine, coptisine and papaverrubine C.Magnoflorine and corytuberine have been isolated from this species for the first time and the presence of allocryptopine, cryptopine, corydine, isocorydine and papaverrubines D and H has been demonstrated.

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ALKALOIDS FROM PLATYCAPNOS SPICATA

Two new phenanthrene alkaloids, N-methylsecoglaucine and thalicthuberine N-oxide, were isolated from aerial parts of Platycapnos spicata along with the known alkaloids: dehydronantenine, dehydroglaucine, (+)-glaucine, (+)-nantenine, (+)-domesticine, (+)-thalicmidine, (+)-isodomesticine, (+)-N-methyllaurotetanine, (+)-predicetrine, O-methylateroline, oxonantenine, corunine, pontevedrine, thalicthuberine and protopine.The structures of all the isolated alkaloids were established by spectroscopic methods and, in the case of the new alkaloids, corroborated by syntheses. Key Word Index – Platycapnos spicata; Fumariaceae; isoquinoline alkaloids; phenanthrene alkaloids; N-methylsecoglaucine; thalicthuberine N-oxide.

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Final Thoughts on Chemistry for 1-(4-Methoxyphenyl)-1H-pyrrole-2,5-dione

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In vitro antiplasmodial, antiamoebic, and cytotoxic activities of some monomeric isoquinoline alkaloids

Twenty-one alkaloids have been assessed for activities against Plasmodium falciparum (multidrug-resistant strain K1) in vitro; 18 of these are reported for the first time. Two protoberberine alkaloids, dehydrodiscretine and berberine, were found to have antiplasmodial IC50 values less than 1 muM, while seven alkaloids – allocrytopine, columbamine, dehydroocoteine, jatrorrhizine, norcorydine, thalifendine, and ushinsunine – had values between 1 and 10 muM. These results are discussed in the context of structure-activity relationships. Compounds were also assessed for antiamoebic and cytotoxic activities, but none was significantly active except for berberine, which was moderately cytotoxic.

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Ex vivo anticholinesterase activity of benzoic acid derivatives.

p-Aminobenzoic acid (p-ABA) derivatives were evaluated as acetylcholinesterase inhibitors (AChEIs). Finding a correlation between AChE activity with the partition coefficient (log P) and the highest occupied molecular orbital (HOMO) energy of the compounds.

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Electrophysiological effects of protopine in cardiac myocytes: Inhibition of multiple cation channel currents

1. Protopine (Pro) from Corydalis tubers has been shown to have multiple actions on cardiovascular system, including anti-arrhythmic, anti-hypertensive and negative inotropic effects. Although it was thought that Pro exerts its actions through blocking Ca2+ currents, the electrophysiological profile of Pro is unclear. The aim of this study is to elucidate the ionic mechanisms of Pro effects in the heart. 2. In single isolated ventricular myocytes from guinea-pig, extracellular application of Pro markedly and reversibly abbreviates action potential duration, and decreases the rate of upstroke (dV/dt)(max), amplitude and overshoot of action potential in a dose-dependent manner. Additionally, it produces a slight, but significant hyperpolarization of the resting membrane potential. 3. Pro at 25, 50 and 100 muM reduces L-type Ca2+ current (I(Ca,L)) amplitude to 89.1, 61.9 and 45.8% of control, respectively, and significantly slows the decay kinetics of I(Ca,L) at higher concentration. The steady state inactivation of I(Ca,L) is shifted negatively by 5.9-7.0 mV (at 50-100 muM Pro), whereas the voltage-dependent activation of I(Ca,L) remains unchanged. In contrast, Pro at 100 muM has no evident effects on T-type Ca2+ current (I(Ca,T)). 4. In the presence of Pro, both the inward rectifier (I(K1)) and delayed rectifier (I(K)) potassium currents are variably inhibited, depending on Pro concentrations. 5. Sodium current (I(Na)), recorded in low [Na+](o) (40 mM) solution, is more potently suppressed by Pro. At 25 muM, Pro significantly attenuated I(Na) at most of the test voltages (-60 ~ + 40 mV, with a 53% reduction at -30 mV. 6. Thus, Pro is not a selective Ca2+ channel antagonist. Rather, it acts as a promiscuous inhibitor of cation channel currents including I(Ca,L), I(K), I(K1) as well as I(Na). These findings may provide some mechanistic explanations for the therapeutic actions of Pro in the heart.

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