Hydroxy Phenyl Research Articles

Anisalidine derivatives as corrosion inhibitors of copper in acidic media

The corrosion inhibitory properties on copper in acidic media by anisalidine derivatives viz. N-(4-nitro phenyl) p-anisalidine (SB1), N-(4-chloro phenyl) p-anisalidine (SB2), N-(4-phenyl) p-anisalidine (SB3), N-(4-methoxy phenyl) p-anisalidine (SB4), N-(4-hydroxy phenyl) p-anisalidine (SB5) have been studied using mass loss method, Langmuir adsorption isotherm and surface analysis by Atomic Force Microscopy (AFM). The inhibition efficiency increases up to 98.99% with increasing additive concentration it may be due to adsorption of the additive molecules on the copper surface.

Therapeutic activity of N‐(2‐hydroxy phenyl) acetamide: a novel anti‐arthritic agent on pro‐inflammatory cytokines production and suppression of Toll‐like receptors (TLR‐2 and TLR‐4) in adjuvant‐induced arthritic rats

Toll‐like receptors (TLRs) are key recognition structures of immune system and emerged as potential contributors to the inflammation observed in human and rodent models of arthritis. In addition, the pro‐inflammatory cytokines IL‐1β and TNF‐α play an important role in aggravating the disease process. Present study aims to investigate the effect of N‐(2‐hydroxy phenyl)‐acetamide (NA‐2) on modulation of TLRs in the development of adjuvant‐induced arthritis. Arthritis was induced by heat‐killed MT H37Ra. Treatment of NA‐2 (5 mg/kg) was started on the day of arthritis induction. Body weights, paw volume and nociception measurements were done to monitor the progression of the disease. TLR‐2 and TLR‐4 mRNAs were analyzed in 48‐h cultured splenocytes and the supernatants were used to determine IL‐1β and TNF‐α. A significant increase in body weights with a parallel decrease in paw edema and nociception was observed in NA‐2 treated animals. Remission of the clinical signs was associated with improved histology. NA‐2 treatment significantly decreased the level of IL‐1β (p < 0.003) and TNF‐α (p < 0.001). Likewise, NA‐2 also reduced the expression of TLRs mRNA. Our findings suggest that NA‐2 affects AIA in a pleiotropic manner, suppressing TLRs‐mediated joint inflammation and thus it might have a therapeutic potential for arthritis

Evaluation of the potential impact of Cu competition on the performance of o,o‐FeEDDHA in soil applications

SummaryFerric ethylene diamine‐N,N′‐bis(hydroxy phenyl acetic acid) (FeEDDHA)‐based iron (Fe) fertilizers are commonly applied to plants grown on calcareous soils and comprise a mixture of FeEDDHA components. Upon application to the soil, the pore water concentrations of the active ingredients racemic and meso o,o‐FeEDDHA show a gradual decline unrelated to plant uptake or biodegradation. In the present study, the potential of soil copper (Cu) to reduce the effectiveness of FeEDDHA‐based fertilizers in calcareous soils by displacing Fe from o,o‐FeEDDHA has been evaluated through modelling and experiments. Predictions with mechanistic multi‐surface models show that there is a thermodynamic basis for assuming that under equilibrium conditions a certain fraction of o,o‐EDDHA ligands in soil solution can be chelated to Cu, in particular for meso o,o‐EDDHA. The large affinity of o,o‐CuEDDHA for binding to the soil solid phase, demonstrated in a batch interaction experiment, greatly increases the potential impact of Cu competition on the o,o‐FeEDDHA solution concentration; for a given quantity of o,o‐CuEDDHA in soil solution, a much larger quantity of o,o‐CuEDDHA is adsorbed to the solid phase. Finally, evidence for the actual displacement of Fe from o,o‐FeEDDHA by Cu was found in a soil incubation study. With these results, the boundary conditions are met for explaining the observed gradual decline in o,o‐FeEDDHA concentration with Cu competition.

Scalable synthesis of the unusual amino acid segment (ADMOA unit) of marine anti-inflammatory peptide: solomonamide A.

The most abundantly available hexose sugar, d-glucose has been converted to protected 4-amino(2'amino-4'-hydroxy phenyl)-3,5-dihydroxy-2-methyl-6-oxo hexanoic acid (protected ADMOA, 3), the unusual amino acid present in marine natural product solomonamide A in gram quantities involving easy to operate chemical transformations.

Biological Activity and Phytochemical Study of Scutellaria platystegia.

This study aimed to determine biological activity and phytochemical study of Scutellaria platystegia (family Labiatae). Methanolic (MeOH) extract of aerial parts of S. platystegia and SPE fractions of methanolic extract (specially 20% and 40% methanolic fractions), growing in East-Azarbaijan province of Iran were found to have radical scavenging activity by DPPH (2, 2-diphenyl -1- pycryl hydrazyl) assay. Dichloromethane (DCM) extract of this plant exhibited animalarial activity by cell free method providing IC50 at 1.1876 mg/mL. Crude extracts did not exhibit any toxicity assessed by brine shrimp lethality assay. Phytochemical study of methanolic extract by using reverse phase HPLC method and NMR instrument for isolation and identification of pure compounds respectively, yielded 2-(4- hydroxy phenyl) ethyl-O-β-D- glucopyranoside from 10% and apigenin 7-O-glucoside, verbascoside and martynoside from 40% SPE fraction. Occurance of verbascoside and martynoside as biochemical markers appeared to be widespread in this genus. Antioxidant and antimalarial activity of MeOH and DCM extracts, respectively, as well as no general toxicity of them could provide a basis for further in-vitro and in-vivo studies and clinical trials to develop new therapeutical alternatives.

Estradiol receptors mediate estradiol-induced inhibition of mitochondrialCa2+ efflux in rat caudate nucleus and brain stem

Our earlier studies found that in vitro estradiol modulates mitochondrial Ca2+ transport in discrete brain regions. The present study examined the role of estradiol receptors (ERs) in estradiol-induced inhibition of Ca^{2+} efflux from synaptosomal mitochondria isolated from rat caudate nuclei and brain stems. Radioactively labeled CaCl_2 (0.6?0.75 µCi ^45CaCl_{2}) was used for Ca^{2+} transport monitoring. The results revealed that in the presence of ER antagonist 7\alpha,17AŸ-[9[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]estra-1,3,5(10)-triene-3,17-diol (ICI 182,780) (1 µmol/L), the inhibitory effect of estradiol on mitochondrial Ca^{2+} efflux was more than 60% decreased, suggesting the involvement of ER in this mode of estradiol neuromodulatory action. When particular contributions of ER\alpha and ERAŸ were tested, it was found that ERAŸ agonist 2,3-bis(4-hydroxy phenyl)-propionitrile (10 nmol/L) inhibited Ca^{2+} efflux more than 20%, while the inhibition with ER\alpha agonist 4,4?,4??-(4-propyl-[1H]-pyrazole-1,3,5-triyl)trisphenol (10 nmol/L) was about 10%, both compared to the control. Both agonists demonstrated attenuation of Ca^{2+} efflux decrease in the presence of mitochondrial Na^{+}/Ca^{2+} exchanger antagonist 7-chloro-5-(2-chlorophenyl)-1,5-dihyhdro-4,1-benzothiazepin-2(3H)-one (10 µmol/L), showing interference with the inhibitory action of that agent. Our results strongly indicate ERs as the mediators of estradiol-induced mitochondrial Ca^{2+} efflux inhibition in rat caudate nucleus and brain stem synaptosomes.

Immobilization of a novel synthesized Schiff base on the surface of a gold electrode for the electrochemical study of adrenaline

A self-assembled monolayer of 2-[({2-[(2-{[(Z)-1-(2-hydroxy phenyl) methylidene] amino} phenyl) disulfanyl] phenyl} imino) methyl] phenol was fabricated on a bare gold electrode (SITP-Au SAM electrode).

Expression of toll-like receptor (TLR4) in splenocytes and its inhibition by N-(2-hydroxy phenyl) acetamide in adjuvant induce arthritic rat model (AIA)

Expression of toll-like receptor (TLR4) in splenocytes and its inhibition by N-(2-hydroxy phenyl) acetamide in adjuvant induce arthritic rat model (AIA)

N-(2-hydroxy phenyl) acetamide induces apoptosis of brain cancer cells by increasing Bax/Bcl-2 ratio

N-(2-hydroxy phenyl) acetamide induces apoptosis of brain cancer cells by increasing Bax/Bcl-2 ratio

Comparison of Field Management Strategies for Preventing Iron Deficiency Chlorosis in Soybean

Iron deficiency chlorosis (IDC) is a serious management issue for soybean [Glycine max (L.) Merr.] grown on calcareous soils. Strip trials were established on calcareous Mollisols to study the effects of Fe‐ethylene diamine‐N,N′‐bis (hydroxy phenyl) acetic acid (EDDHA) in‐furrow (IF‐Fe) and of an oat (Avena sativa L.) companion crop on two soybean varieties either tolerant or susceptible to IDC. The severity of IDC varied from low to severe within sites. The susceptible variety produced the highest yield in the absence of IDC. In‐furrow Fe increased the yield of a variety susceptible to IDC under moderate to severe IDC. The oat companion crop increased yield consistently for the susceptible variety under severe IDC and sometimes reduced yield when oat grew beyond 25 cm in height. The tolerant variety without IDC management produced yields similar to those of the susceptible variety with IF‐Fe or an oat companion crop. Oat reduced trifoliate nitrate N and Fe concentration regardless of IDC severity. Trifoliate Fe concentration lowered with IF‐Fe, but only when oat was not planted. Grain protein and oil concentration were affected by variety, but were not affected by IDC management. Soil test factors such as soil organic matter (SOM), pH, electrical conductivity (EC), or diethylene triamine phentaacetic acid Fe (Fe‐DTPA) were poor predictors of the severity of IDC. Variety selection is the most important strategy for lessening the severity of IDC. In‐furrow application of Fe‐EDDHA provides a solution for mitigating moderate to severe IDC and provides less risk than an oat companion crop.

Type 1 Tyrosinemia with Hypophosphatemic Rickets: A Case Report

Background: Tyrosinemia type 1 is an autosomal recessive metabolic disorder, which typically affects liver and kidneys. It is caused by a defect in fumarylacetoacetate hydrolase or fumarylacetoacetase (FAH) enzyme, the final enzyme in the tyrosine degradation pathway. The disease typically manifests as early onset type in early infancy with acute hepatic crisis with hepatomegaly and bleeding tendency. In 1992, a new drug orfadin (NTBC, Nitisinone) which is a potent inhibitor of 4 hydroxy phenyl pyrovate dioxygenase has revolutionized the treatment of tyrosinemia type 1 and is now the mainstry of therapy. Case presentation: Our case was a girl in midchidhood period with profound rickets and slowly progressing liver disease who presented with difficulty walking and weakness of muscles. She had an elevated serum tyrosine and urinary succinylacetone, which confirmed the diagnosis of tyrosinemia type 1 and after treatment with NTBC significant remission, was achieved.

Design, synthesis, and structure–activity relationships of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety as potent antitumor agents

A series of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety were designed and synthesized and their cytotoxic activities against five cancer cell lines (NCI-H226, SK-N-SH, HT29, MKN45, and MDA-MB-231) were screened in vitro. Most of them showed moderate to excellent activity against all the tested cell lines. Among them, compounds 15g (procaspase-3 EC50 = 1.42 μM) and 16b (procaspase-3 EC50 = 0.25 μM) exhibited excellent antitumor activity with IC50 values ranging from 0.14 μM to 0.98 μM against all cancer cell lines, which were 1.8–8.7 times more active than the first procaspase activating compound (PAC-1) (procaspase-3 EC50 = 4.08 μM). The structure–activity relationship (SAR) analyses indicated that the introduction of a lipophilic group (a benzyloxy or heteroaryloxy group) at the 4-position of the 2-hydroxy phenyl ring was beneficial to antitumor activity, and the presence of substituents containing nitrogen that are positively charged at physiological pH could also improve antitumor activity. It was also confirmed that the steric effect of the 4-position substituent of the benzyloxy group had a significant influence on cytotoxic activity.

Electron beam curing of functionalized N-(4-hydroxy phenyl)maleimide monomers

Electron beam (E-beam) curing by different total radiation doses (100, 200, 300 and 400 kGy at 10 kGy per pass) of functionalized maleimides (20%) [ N-(4-acryloyloxy phenyl)maleimide, N-(4-methacryloyloxy phenyl)maleimide and N-(4-cyanato phenyl)maleimide] is carried out using N-vinyl-2-pyrrolidone as the reactive diluent (80%). The swelling studies indicate the presence of highly cross-linked structure in the polymer derived from cyanate-functionalized maleimide cured using 400 kGy electron beam (E-beam) irradiation. The thermal stabilities of all the polymers are studied using thermogravimetric analyzer. The materials cured using the highest radiation dose (400 kGy) are found to have better thermal stability compared to other materials cured using lower doses (100, 200 and 300 kGy at 10 kGy per pass). The degradation kinetic studies using the Vyazovkin method showed that the activation energies for the thermal degradation of polymeric materials got by E-beam irradiation of the monomers at 400 kGy are higher. Of all the materials investigated, liquid composition having N-(4-cyanato phenyl)maleimide (20%) and N-vinyl-2-pyrrolidone (80%) cured by E-beam radiation (400 kGy) showed better thermal stability.

N-(2-hydroxy phenyl) acetamide: a novel suppressor of Toll-like receptors (TLR-2 and TLR-4) in adjuvant-induced arthritic rats.

Toll-like receptors (TLRs) are key recognition structures of immune system and recently emerged as potential contributors to the inflammation observed in human and rodent models of arthritis. Present study aims to investigate the effect of N-(2-hydroxy phenyl)-acetamide (NA-2) on modulation of TLRs in the development of adjuvant-induced arthritis. Arthritis was induced by intradermal administration of heat-killed Mycobacterium tuberculosis H37Ra. The treatment of NA-2 (5 mg/kg) and indomethacin (5 mg/kg) was started in their respective group on the day of arthritis induction. Body weights, paw volume measurements, and nociception sensation (Plantar test) were done on alternate days to monitor the progression of the disease until arthritis score of four was observed in arthritic control group. Along with the clinical signs, histopathology of knee joints was also performed. The splenocytes cultures were prepared from each group; TLR-2 and TLR-4 mRNAs were analyzed in 48-h cultured splenocytes using RT-PCR; and the supernatants were used to determine IL-1β and TNF-α by ELISA. A significant reversal of deficit seen in body weights of the arthritic control group was observed in NA-2-treated animals with a parallel decrease in paw edema and transmission of nociception. Remission of the clinical signs and nociception was associated with improved histology. Compared with arthritic control, NA-2 treatment significantly decreased the level of IL-1β (p < 0.003) and TNF-α (p < 0.001) in the supernatants of cultured splenocytes. Likewise, NA-2 also reduced the expression of TLRs mRNA. Our findings suggest that NA-2 affects AIA in a pleiotropic manner, suppressing TLRs-mediated joint inflammation and related symptoms.

Enhanced optoelectronics properties of europium(III) complexes with β-diketone and nitrogen heterocyclic ligands

Preparation and photoluminescence behavior of six new europium complexes with β-diketone 1-(2-hydroxy phenyl)-3-phenylpropane-1,3-dione (HPPP) and bathophenanthroline (batho), 2,2′-bipyridyl (bipy), 2,2′-biquinoline (biq), neocuproin (neo) and 1,10-phenanthroline (phen) are reported in solid state. The ligand (HPPP) and complexes Eu(HPPP)3·H2O (1), Eu(HPPP)3·phen (2), Eu(HPPP)3·batho (3), Eu(HPPP)3·bipy (4), Eu(HPPP)3·biq (5) and Eu(HPPP)3·neo (6) were characterized by means of elemental analysis, infrared spectroscopy, proton nuclear magnetic resonance (1H-NMR). The optical properties, thermal stability and crystalline nature were investigated by photoluminescence spectroscopy, thermogravimetric analysis and XRD respectively. The emission spectra show narrow intense emission band of central europium (III) metal ion that arise from the high intense 5D0 → 7F0 transition. The introduction of ancillary ligands like batho, bipy, biq, neo, phen enlarged the π-conjugation system in complexes as a result higher luminescence intensity, longer life time (τ) and higher quantum efficiency (η) observed in europium ternary complexes in comparison to Eu(HPPP)3·H2O (1). Based on the emission spectra, the luminescence decay curve was measured which indicated that the transfer of energy from HPPP ligand to the europium metal is more efficient in complexes 2–6 than complex 1.

Synthesis, physicochemical characterization, and biological activity of nanocomplexes of iron(III) of 3(2′-hydroxyphenyl)-5-(4-substituted phenyl) pyrazolines and dithiophosphoric acid

Complexes of iron(III) with dithiophosphoric acid and 3(2′-hydroxy phenyl)-5-(4-substituted phenyl) pyrazolines, [Fe(C6O14O2PS2)2(C15H12N2OX)], and [Fe(C6O14O2PS2)(C15H12N2OX)2], where (C6O14O2PS2H) = dithiophosphoric acid, (C15H13N2OX) = deprotonated 3(2′-hydroxy phenyl)-5-(4-substituted phenyl)pyrazolines (X = H, CH3, OCH3, Cl), have been synthesized. These complexes have been physicochemically characterized by elemental analysis (C, H, N, S, Cl, and Fe), magnetic moment data, thermogravimetric analysis, molar conductance, cyclic voltammetry, and spectral analysis (UV–visible, IR, and Fast atom bombardment mass spectrometry). Scanning electron microscopy, TEM, and PXRD have been carried out for powdered samples, which show nanometric particles of these derivatives. Antibacterial and antifungal potential of free pyrazoline and iron(III) complexes have been evaluated.

Natural bond orbital analysis, electronic structure and vibrational spectral analysis of N-(4-hydroxyl phenyl) acetamide: A density functional theory

The Fourier transform infrared (FT-IR) and FT-Raman spectra of N-(4-hydroxy phenyl) acetamide (N4HPA) of painkiller agent were recorded in the region 4000–450cm−1 and 4000–50cm−1 respectively. Density functional theory (DFT) has been used to calculate the optimized geometrical parameter, atomic charges, and vibrational wavenumbers and intensity of the vibrational bands. The computed vibrational wave numbers were compared with the FT-IR and FT-Raman experimental data. The computational calculations at DFT/B3LYP level with 6-31G(d,p), 6-31++G(d,p), 6-311G(d,p) and 6-311++G(d,p) basis sets. The complete vibrational assignments were performed on the basis of the potential energy distribution (PED) of the vibrational modes calculated using Vibrational energy distribution analysis (VEDA 4) program. The oscillator’s strength calculated by TD-DFT and N4HPA is approach complement with the experimental findings. The NMR chemical shifts 13C and 1H were recorded and calculated using the gauge independent atomic orbital (GIAO) method. The molecular electrostatic potential (MESP) and electron density surfaces of the molecule were constructed. The Natural charges and intermolecular contacts have been interpreted using Natural Bond orbital (NBO) analysis the HOMO–LUMO energy gap has been calculated. The thermodynamic properties like entropy, heat capacity and zero vibrational energy have been calculated.

Assessment of the antioxidant and antiradicalic capacities in vitro of different phenolic derivatives

Introduction: The antioxidant and radical scavenging properties of some of the hydroxy phenyl derivatives such as 4-Hydroxybenzoic acid (1), 3-Hydroxy-4-methoxycinnamic acid (2), 3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2- enoic acid (Sinapic acid) (3), 4-Hydroxy-3,5-dimethoxybenzoic acid (4), 3,4-Dihydroxycinnamic acid (Caffeic acid) (5) and 5-Isopropyl-2-methylphenol (6), which are naturally present in fruits and vegetables, were investigated. Methods: The following analysis were conducted: The total antioxidant activity via the ferric thiocyanate method; 2,2’-azinobis-(3-ethylbenzothiazole-6-sulphonate) (ABTS) radical scavenging activity; superoxide anion radical (O2•-) scavenging activity; the total reduction power through potassium ferricyanide reduction method; Cupric ions (Cu2+) reduction capacity through Cuprac method; hydrogen peroxide scavenging activity and chelating activity of ferrous ions (Fe2+). Furthermore, α-tocopherol, butylatedhydroxyanisole (BHA) and quercetin were used as the reference antioxidant compounds. Results: In the comparison of initial states and the products, it’s observed that at the 50th hour the linoleic acid emulsion at 30 μg/mL concentration inhibited the lipid peroxidation by 85%, 60.7%, 69%, 45.4%, 80.4% and 31%, respectively. On the other hand, it’s observed that the linoleic acid emulsion of α-tocopherol, (BHA) and quercetin inhibited the lipid peroxidation by 62.65%, 35.84% and 34.82% respectively, at the same concentration. Conclusions: It’s found as a result of our studies that some of the phenolic compounds such as 4-Hydroxybenzoic acid (1), 3-Hydroxy-4-methoxycinnamic acid (2), 3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid (3), 4-Hydroxy-3,5- dimethoxybenzoic acid (4), 3,4-Dihydroxycinnamic acid (5) and 5-Isopropyl-2-methylphenol (6) which are naturally present in foods. They have higher total antioxidant activity, radical scavenging and metal chelating activities than the widely used powerful antioxidant compounds such as BHA, Quercetin and α-tocopherol.

Extraction process optimization of polyphenols from Indian Citrus sinensis – as novel antiglycative agents in the management of diabetes mellitus

BackgroundDiabetes mellitus is a chronic metabolic disorder characterized by increased blood glucose level. It has become an epidemic disease in the 21st century where, India leads the world with largest number of diabetic subjects. Non-enzymatic glycosylation (glycation) is severe form of diabetes, occurs between reducing sugar and proteins which results in the formation of advanced glycation end products (AGEs) that leads to the other complicated secondary disorders. In this context, Mangifera indica (Mango), Syzygium cumini (Jambul), Vitis vinifera (Grapes), Citrus sinensis (Orange), Artocarpus heterophyllus (Jackfruit), Manilkara zapota (Sapodilla) seeds were evaluated for their antiglyation activity. Attempts were made to isolate the polyphenols in the seeds that have recorded the maximum activity.MethodsDifferent extraction methods (shake flask, centrifugation and pressurized hot water) using various extractants (organic solvents, hot water and pressurized hot water) were adopted to investigate the in vitro antiglycation activity. Central composite (CCD) design based Response Surface Methodology (RSM) was espoused to optimize the extraction process of polyphenols from the fruit seeds that have recorded poor antiglycation activity. The PTLC analysis was performed to isolate the polyphenols (Flavonoids and phenolic acids) and LC-PDA-MS analysis was done for structure prediction.ResultsPressurized hot water extraction of Artocarpus heterophyllus (87.52%) and Citrus sinensis seeds (74.79%) was found to possess high and low antiglycation activity, respectively. The RSM mediated optimization process adopted for the Citrus sinensis seeds have revealed that 1:15 solvent ratio (hexane to heptane), 6 minutes and 1:20 solid to liquid ratio as the optimal conditions for the extraction of polyphenols with a maximum antiglycation activity (89.79%). The LC-PDA-MS analysis of preparative thin layer chromatography (PTLC) eluates of Artocarpus heterophyllus seed has showed the presence of compounds like quercetin (301.2), 4-hydroxy phenyl acetic acid (149.0), rhamnosyl-di-hexosyl quercetin sulphate (857.6), quercetin-3-O-xyloside (428.2), rutin (613.4), diosmetin (298.1) and luteolin (283.0).ConclusionThe Artocarpus heterophyllus was observed to possess a significant antiglycation activity and the activity of Citrus sinensis was improved after the optimization process, which proved that both the seeds may be used as a traditional medicine in the management of chronic diabetes mellitus.

Spirocyclic 2,5-dihydro-1H-imidazole 1-oxyl radicals with a mesogenic substituent on C4. Synthesis and crystal structure

Stable spirocyclic 2,5-dihydro-1H-imidazole 1-oxyl radicals containing a mesogenic fragment were synthesized on the basis of 1-[4-hydroxy(alkoxy)phenyl]-2-hydroxyamino-2-methylpropan-1-ones. The crystalline structure of two aminoxyl radicals was determined by X-ray analysis.