P-nitrophenylacetic Acid Research Articles

Study on electrochemical reduction mechanism of p-nitrophenylacetic acid prepared by electrocarboxylation

The direct carboxylation of organic halides under CO2 atmosphere by electrochemical reduction is an effective way to realize the value utilization of waste (CO2), and has great potential in green organic synthesis. P-nitrophenylacetic acid is a chemical raw material in great demand, which can be used not only in medicine and other organic synthesis intermediates but also in biochemical research. In this paper, the electrochemical reduction mechanism of p-nitrobenzyl bromide (PNBB) in N2 and CO2 atmosphere was investigated by cyclic voltammetry (CV), in-situ FT-IR spectroelectrochemistry, and bulk electrolysis experiments. Under N2 conditions, the electrochemical behavior of PNBB in aprotic acetonitrile solvent is a 1-electron irreversible transfer process. However, in the presence of CO2, it is a completely irreversible 2-electron transfer process. The electrolytic products were analyzed by 1H NMR, 13C NMR and MS. The results showed that the electrolytic products were 1,2-bis(4-nitrophenyl) ethane and p-nitrophenylacetic acid under N2 and CO2 conditions, respectively. The successful preparation of p-nitrophenylacetic acid provides more possibilities for the “green” synthesis of helpful chemical products from organic halides.

Insights into the In-vivo Antiplasmodial Activity of Trisdimethylamino Pyrimidine Derivative in Plasmodium berghei: Infected Mouse Model

Aims: To evaluate the antiplasmodial activity of a trisdimethylamino pyrimidine derivative synthesized by indirect methylation of p-nitrophenylacetic acid via a substituted amine or amide derivative against Plasmodium berghei NK65 strain in an in vivo Plasmodium berghei-Infected mouse model.
 Methodology: Plasmodium berghei-parasitized suppressive model in Albino mice was adopted for the antiplasmodial activity evaluation. The schizontocidal activity of the compound was evaluated by a 4-day suppressive test. All the treatments (test sample, standard control and blank) were administered intraperitoneally to the mice. Parameters such as rectal temperature, packed cell volume, survival time and parasitemia were measured.
 Results: The 10, 20 and 40 mg/kg doses of 2, 4, 6-trisdimethylamino-5-(4´-nitrophenyl) pyrimidine elicited a statistically significant reduction (p < 0.01) in parasitemia level in treated mice. The 40 mg/kg dose caused 97.19% suppression of parasitemia and a mean survival time of 22 days compared with 97.64% and 24 days respectively in the standard control group (artemether-lumefantrine combination, 5 mg/kg). All the treatments restored the packed cell volume to the baseline (~39.8%). A dose-dependent decrease in the rectal temperature was observed in all the treatment groups. However, only the 10 and 20 mg/kg doses of 2, 4, 6-trisdimethylamino-5-(4´-nitrophenyl) pyrimidine caused a significant decrease (p < 0.01) compared with the control.
 Conclusion: The strong suppression of Plasmodium berghei in the mice treated with 2, 4, 6-trisdimethylamino-5-(4´-nitrophenyl) pyrimidine has further provided insights into the potential of the compound as a lead in the discovery of antimalarial agents.

STIMULATION OF GROWTH AND OIL PRODUCTION IN CUMIN PLANT

A pot experiment was carried out during two successive seasons (2017/ 2018 and 2018/2019) at Medicinal and Aromatic Plants Research Department in Dokki. The aim of this work was to study the effect of foliar application of phenylalanine (Phe) and p -nitro phenylacetic acid (PNPAA) each of them alone at (0, 50,100 and 150 ppm) on cumin (Cuminum cyminum L.) plant growth, fruits yield, volatile oil production and its major chemical constituents. In general results indicated that, the foliar application of phenylalanine or p-nitrophenylacetic acid significantly increased vegetative growth expressed as (plant height, number of branches per plant) and produced higher fruits yield (g)/plant as well as volatile oil percentage and oil yield compared with control in the two seasons. Moreover, the highest values were obtained from phenylalanine or p-nitrophenylacetic acid at 150 ppm. Cumin plants showed more effective response to p-nitrophenylacetic acid (PNPAA) than phenylalanine (Phe). As for GLC analysis, the results showed that in general the highest percentage of p -menth-1-en7-ol and cumin aldehyde (p -isopropylbenzaldehyde) the main constituents in the volatile oil achieved with the treatment p-nitrophenylacetic acid at 150 ppm. The high concentration of phenylalanine and p-nitrophenylacetic acid (150 ppm) had significant increments in total phenols, total flavonoids and antioxidant activity compared with control. There was a significant increase in phenylalanine ammonia-lyase (PAL) activity compared to control. Also, there was an increment in IAA, GA3 and low level of ABA. It was observed that p -nitrophenylacetic acid (150 ppm) was superior to phenylalanine (150 ppm) in all afore mentioned characters

Fast Immobilization of Human Carbonic Anhydrase II on Ni-Based Metal-Organic Framework Nanorods with High Catalytic Performance

Carbonic anhydrase (CA) has received considerable attention for its ability to capture carbon dioxide efficiently. This study reports a simple strategy for immobilizing recombinant carbonic anhydrase II from human (hCA II) on Ni-based MOFs (Ni-BTC) nanorods, which was readily achieved in a one-pot immobilization of His-tagged hCA II (His-hCA II). Consequently, His-hCA II from cell lysate could obtain an activity recovery of 99% under optimal conditions. After storing for 10 days, the immobilized His-hCA II maintained 40% activity while the free enzyme lost 91% activity. Furthermore, during the hydrolysis of p-nitrophenyl acetic acid, immobilized His-hCA II exhibited excellent reusability and still retained more than 65% of the original activity after eight cycles. In addition, we also found that Ni-BTC had no fixation effect on proteins without histidine-tag. These results show that the Ni-BTC MOFs have a great potential with high efficiency for and specific binding of immobilized enzymes.

Synthesis of A New Class of Pyridazin-3-one and 2-Amino-5-arylazopyridine Derivatives and Their Utility in the Synthesis of Fused Azines

A general route for the synthesis of a novel class of pyridazin-3-one derivatives 3 by the reaction in acetic anhydride between 3-oxo-2-arylhydrazonopropanals 1 and some active methylene compounds like p-nitrophenylacetic acid and cyanoacetic acid was established. Under these conditions the pyridazin-3-one derivatives 3 were formed as the sole isolable products in excellent yield. The 6-acetyl-3-oxopyridazine derivative 3l was reacted with DMF-DMA to afford the corresponding enaminone derivative 4, which reacts with a variety of aminoazoles to afford the corresponding azolo[1,5-a]pyrimidine derivatives 5–7. Also, in order to explore the viability and generality of a recently uncovered reaction between 3-oxo-2-arylhydrazonopropanals and active methylene compounds, a variety of 2-amino-6-aryl-5-arylazo-3-aroylpyridines 16–19 were prepared by reacting 3-oxo-2-arylhydrazonopropanals with miscellaneous active methylene compounds like 3-oxo-3-phenylpropionitrile, hetaroylacetonitriles and cyanoacetamides. These 2-aminopyridine derivatives undergo smooth reactions with cyanoacetic acid that led to the formation in high yield of a new class of 1,8-naphthyridine derivatives 24. The structures of all new substances prepared in this investigation were determined by the different analytical spectroscopic methods, in addition to the X-ray crystallographic analysis.

2 : 1 Co-crystals of p-nitrophenylacetic acid with three isomeric n-pyridinealdazines, n = 2, 3 and 4, featuring the {… HOCO … N(py)} heterosynthon

Abstract Crystal and molecular structures of 2 : 1 co-crystals formed between p-nitrophenylacetic acid and three isomeric n-pyridinealdazines, n = 2(1), 3(2) and 4(3), are described in which the carboxylic acid is always in a general position and the respective n-pyridinealdazine is located about a centre of inversion. A common feature of the supramolecular aggregation is the formation of three-molecule aggregates sustained by the {… HOCO … N(py)} heterosynthon, further vindicating this as a most reliable synthon for co-crystal design. Molecules are assembled into three-dimensional architectures by C–H … O interactions coupled with C–H … π (1) or π … π (2 and 3) contacts.

Synthesis of Novel Fluorescent 2-{4-[1-(Pyridine-2-yl)-1H-pyrazol-3-yl] phenyl}-2H-naphtho [1,2-d] [1,2,3] triazolyl Derivatives and Evaluation of Their Thermal and Photophysical Properties

Novel 2-{4-[1-(pyridine-2-yl)-1H-pyrazol-3-yl] phenyl}-2H-naphtho [1,2-d] [1,2,3] triazolyl fluorescent derivatives were synthesized from p-nitrophenylacetic acid and 2-hydrazino pyridine through Vilsmeier–Haack and diazotization reactions. Photophysical properties were evaluated, and results show that compounds have good fluorescence quantum yields. Thermal analysis showed that they are reasonably stable. The structures of the compounds were confirmed by FT-IR, 1H NMR, 13C NMR, and mass spectral and elemental analysis.

Self-assembly and nonlinear optical properties of a synthetic dipeptide

The self-assembly propensities and nonlinear optical properties of synthetic dipeptides are illustrated. The single crystal X-ray diffraction study of dipeptide 1 containing a p-nitrophenylalanine moiety reveals that the peptide adopts a supramolecular antiparallel β-sheet structure using hydrogen bonding, as well as π–π stacking interactions, in the solid state and the peptide exhibits nonlocal thermal nonlinear refraction due to the thermal lensing effect. The heat dissipation in the dipeptide 1 was a slow process with a millisecond to microsecond time scale. However the peptide 2 containing a p-nitrophenylacetic acid moiety adopts a parallel β-sheet structure and has no thermal lensing effect.

Acylation of Heteroaromatic Amines: Facile and Efficient Synthesis of a New Class of 1,2,3-Triazolo[4,5-b]pyridine and Pyrazolo[4,3-b]pyridine Derivatives

1,2,3-Triazolo[4,5-b]pyridines and pyrazolo[4,3-b]pyridines can be readily prepared via cyanoacetylation reactions of 5-amino-1,2,3-triazoles 1a,b and 4-amino- pyrazole 2 followed by subsequent cyclization of the formed cyanoacetamides. Reactions of amines 1a,b with a mixture of p-nitrophenylacetic acid and acetic anhydride under microwave irradiation conditions afforded the corresponding amides 15a,b that underwent cyclization to form 1,2,3-triazolo[4,5-b]pyridines 16a,b upon heating in DMF solutions containing sodium acetate. Reactions of 1a,b with active methylene compounds, including 17a-c, in the presence of zeolites as catalyst also afforded 1,2,3-triazolo[4,5-b]pyridine derivatives 20a-f via the intermediacy of triazole derivatives 19 and not 18.

Activity‐Based Fingerprinting of Proteases

Activity‐Based Fingerprinting of Proteases

Synthesis of14C-labeled and tritiated AMPA potentiator LY450108

Asymmetric synthesis of AMPA potentiator LY450108-[14C] containing 14C-label attached to the chiral center of the molecule, was accomplished based on Evans' chiral oxazolidinone auxiliary method. Diastereoselective methylation of p-nitrophenylacetic acid derivative was used as a key step. The auxiliary was reductively removed, and the resulting primary alcohol was converted into the corresponding amine. Its sulfonylation, reduction of the aromatic nitro group, and acylation with 3,5-difluorobenzoyl chloride led to the final product. The synthesis of tritiated LY450108 is also detailed. Copyright © 2005 John Wiley & Sons, Ltd.

Reduction of methemoglobin via electron transfer from photoreduced flavin: restoration of O2-binding of concentrated hemoglobin solution coencapsulated in phospholipid vesicles.

Ferric methemoglobin is reduced to its ferrous form by photoirradiation either by direct photoexcitation of the heme portion to induce electron transfer from the surrounding media (Sakai at al. (2000) Biochemistry 39, 14595-14602) or by an indirect electron transfer from a photochemically reduced electron mediator such as flavin. In this research, we studied the mechanism and optimal condition that facilitates photoreduction of flavin mononucleotide (FMN) to FMNH(2) by irradiation of visible light, and the succeeding reduction of concentrated metHb in phospholipid vesicles to restore its O(2) binding ability. Visible light irradiation (435 nm) of a metHb solution containing FMN and an electron donor such as EDTA showed a significantly fast reduction to ferrous Hb with a quantum yield (Phi) of 0.17, that is higher than the method of direct photoexcitation of heme (Phi = 0.006). Electron transfer from a donor molecule to metHb via FMN was completed within 30 ns. Native-PAGE and IEF electrophoresis indicated no chemical modification of the surface of the reduced Hb. Coencapsulation of concentrated Hb solution (35 g/dL) and the FMN/EDTA system in vesicles covered with a phospholipid bilayer membrane (Hb-vesicles, HbV, diameter: 250 nm) facilitated the metHb photoreduction even under aerobic conditions, and the reduced HbV restored the reversible O(2) binding property. A concentrated HbV suspension ([Hb] = 8 g/dL) was sandwiched with two glass plates to form a liquid layer with the thickness of about 10 microm (close to capillary diameter in tissue, 5 microm), and visible light irradiation (221 mW/cm(2)) completed 100% metHb photoreduction within 20 s. The photoreduced FMNH(2) reacted with O(2) to produce H(2)O(2), which was detected by the fluorescence measurement of the reaction of H(2)O(2) and p-nitrophenylacetic acid. However, the amount of H(2)O(2) generated during the photoreduction of HbV was significantly reduced in comparison with the homogeneous Hb solution, indicating that the photoreduced FMNH(2) was effectively consumed during the metHb reduction in a highly concentrated condition inside the HbV nanoparticles.

Biosynthesis of the antibiotic obafluorin from D-[U-13C]glucose and p-aminophenylalanine in Pseudomonas fluorescens

The separate units which are used to construct the antibiotic obafluorin 1 in Pseudomonas fluorescens are defined by the results of D-[U-13C]glucose incorporation. A key intermediate in the biosynthesis of 1 is established to be L-p-aminophenylalanine 8; L-phenylalanine and L-p-nitrophenylalanine are very poor precursors. Results similar to those for obafluorin are obtained for p-nitrophenylacetic acid 20 which along with the derivative 4 and 2-(4-nitrophenyl)ethanol 21 are identified as new metabolites of P. fluorescens. Deuteriated samples of 20, 22 and 23 are not precursors for obafluorin 1. [2,3-3H3]-p-Aminophenylalanine 18 is incorporated into 1 with complete loss of deuterium from C-2 but retention of the deuterium present in both diastereotopic positions on C-3.

ChemInform Abstract: Crystallographic Studies and Physicochemical Properties of π‐Electron Compounds. Part 17. The Structure of p‐Nitrophenylacetic Acid

ChemInformVolume 21, Issue 26 Physical Organic Chemistry ChemInform Abstract: Crystallographic Studies and Physicochemical Properties of π-Electron Compounds. Part 17. The Structure of p-Nitrophenylacetic Acid S. J. GRABOWSKI, S. J. GRABOWSKI Inst. Chem., Warsaw Univ., 15-443 Bialystok, Pol.Search for more papers by this authorT. M. KRYGOWSKI, T. M. KRYGOWSKI Inst. Chem., Warsaw Univ., 15-443 Bialystok, Pol.Search for more papers by this authorG. + HAEFELINGER, G. + HAEFELINGER Inst. Chem., Warsaw Univ., 15-443 Bialystok, Pol.Search for more papers by this authorG. RITTER, G. RITTER Inst. Chem., Warsaw Univ., 15-443 Bialystok, Pol.Search for more papers by this author S. J. GRABOWSKI, S. J. GRABOWSKI Inst. Chem., Warsaw Univ., 15-443 Bialystok, Pol.Search for more papers by this authorT. M. KRYGOWSKI, T. M. KRYGOWSKI Inst. Chem., Warsaw Univ., 15-443 Bialystok, Pol.Search for more papers by this authorG. + HAEFELINGER, G. + HAEFELINGER Inst. Chem., Warsaw Univ., 15-443 Bialystok, Pol.Search for more papers by this authorG. RITTER, G. RITTER Inst. Chem., Warsaw Univ., 15-443 Bialystok, Pol.Search for more papers by this author First published: June 26, 1990 https://doi.org/10.1002/chin.199026051Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume21, Issue26June 26, 1990 RelatedInformation

Crystallographic studies and physicochemical properties of π-electron compounds. XVII. The structure of p-nitrophenylacetic acid

C 8 H 7 NO 4 cristallise dans Pbca avec a=15,096, b=7,1500, c=15,923 A, Z=8; affinement jusqu'a R=0,065. Les molecules forment des dimeres cycliques centrosymetriques par pont hydrogene (O..O=2,613 A). Le deplacement entre les plans COOH, pas tout a fait coplanaires est de d=0,093 A. Ce deplacement resulte des forces de cohesion du cristal. Pour l'expliquer, un modele de calcul STO-3G a ete employe avec diverses valeurs de d pour des dimeres de l'acide formique. Lorsque d augmente jusqu'a 0,2 A, l'energie du dimere varie peu. Aucun desordre n'est observe dans le groupe carboxylique

The biosynthesis of the pseudomonas antibiotic obafluorin from p-aminophenylalanine and glycine (glyoxylate)

DL-[2,3- 2H 3]- p-Aminophenylalanine is incorporated into obafluorin (1) with retention of C-3 deuterium and loss of deuterium from C-2. Labelled samples of p-nitrophenylacetic acid, p-aminophenylacetic acid and the N-acetylcysteamine thioester of the latter are not incorporated into obafluorin. Results of experiments with [2- 13C]-, [1- 13C]-, and [2- 2H 2]-glycine show that glyoxylic acid is specifically the source of C-1 and C-2 of the antibiotic. A mechanism is proposed for the biosynthesis of the unit (2) in obafluorin (1).

The biosynthesis of the antibiotic obafluorin from p-aminophenylalanine in Pseudomonas fluorescens

Abstract The separate units which are used to construct the unique β-lactone antibiotic obafluorin (1) in Pseudomonas fluorescens are defined by the results of [U-13C]glucose incorporation. A key intermediate in the biosynthesis of (1) is established to be L-p-aminophenylalanine (7); L-p-nitrophenylalanine (8) is a relatively insignificant precursor. Similar results were obtained for p-nitrophenylacetic acid (9) which is also a metabolite of Ps. fluorescens. L-phenylalanine is an insignificant precursor for obafluorin (1).

ｐ‐ニトロフェニル酢酸とｍ‐ニトロベンズアルデヒドとのＫｎｏｅｖｅｎａｇｅｌ縮合に及ぼすアミン触媒の効果

The Knoevenagel condensation of p-nitrophenylacetic acid [1] with m-nitrobenzaldehyde [2] was carried out in the presence of amines such as piperidine, diethylamine, triethylamine, pyrrolidine, morpholine, N-ethylmorpholine, etc. trans-3, 4'-Dinitrostilbene [3], 1-(m-nitrophenyl)-2-(p-nitrophenyl)ethanol [4], and α-(p-nitrophenyl)-m-nitrocinnamic acid [5] were isolated. The {[3]+[5]}/[4] ratio varied greatly with the amine used, because of its steric hindrance. [3] also was obtained by the dehydration of [4] with small amounts of concentrated sulfuric acid in 96% yield and by the decarboxylation of [5] with pyrrolidine in 90% yield. A probable reaction pathway was discussed.

Cis- and trans-4-aminocyclohexylacetic acids and their diethylenimido(thio)phosphoryl derivatives

1. The stereospecific hydrogenation of p-nitrophenylacetic acid was run on Raney Ni catalyst to give chiefly the trans isomer of 4-aminocyclohexylacetic acid. The cis and trans isomers were separated as the hydrochlorides. 2. We synthesized the N-phthalyl, N-dichloro(thio)phosphoryl, N-diethylenimido(thio)phosphoryl, and N-tetramethyldiamido(thio)phosphoryl derivatives of cis- and trans-4-aminocyclohexylacetic acid.

Isolation and Identification of Free Compounds with SH Group in Rice Embryo

By means of paper chromatography, polarography and the p-nitrophenyl acetic acid(p-NPA) method, free cystine, cysteine, oxidized glutathione, reduced glutathione and vitamin B1 were isolated from rice embryo and identified. The reduced glutathione and cysteine which were isolated from rice embryo decomposed p-NPA, but the islated cystine, oxidized glutathione and vitamin B1 did not decomposed p-NPA. Cystine, oxidized glutathione, reduced glutathione and vitamin B1 which were determined polarographically and by the p-NPA method were 1, 71, 15 and 7mg percent respectively.