Phenoxy Phenyl Research Articles

1-(4-Methoxyphenyl)-3-(3-phenoxyphenyl) prop-2-en-1-one: A Diphenyl Chalcone Derivative with Potent Antitumor Activity Via Up-Regulation of p21 Gene

Background and Aim: Cancer is a disease of complex aetiology and is characterised by uncontrolled growth of abnormal cells. It is a major worldwide health problem. Many natural and synthetic chalcone or their derivatives showed anticancer activities. The aim of the present study is to evaluate the anticancer activity of novel chalcone derivatives and also to establish possible mechanism of action. Materials and Methods: A series of chalcones 3-(3-phenoxyphenyl)-1-phenylprop-2-en-1-one (2a); 1-(4-chlorophenyl)-3-(3-phenoxyphenyl) prop-2-en-1-one (2b); 1-(4-fluorophenyl)-3-(3-phenoxyphenyl) prop-2-en-1-one (2c); 1-(4-Nitro-phenyl)-3-(3-phenoxy-phenyl)prop-2-en-1-one (2d); 1-(4-methoxyphenyl)-3-(3-phenoxyphenyl) prop-2-en-1-one(2e) were evaluated for the cytotoxic activity both in vitro and in vivo. The in vivo antitumor activity of these compounds was estimated on Daltons Ascites Lymphoma induced solid tumor model. The effect of promising compound was further analysed by flow cytometer and RT- PCR analysis. Results and Conclusion: 1-(4-methoxyphenyl)-3-(3-phenoxyphenyl) prop-2-en-1-one and 1-(4- chlorophenyl)-3-(3-phenoxyphenyl) prop-2-en-1-one was showed in vitro cytotoxic activity, DNA damage and antiproliferative activity. DLA induced solid tumor model suggested that 1-(4-methoxyphenyl)-3-(3- phenoxy phenyl) prop-2-en-1-one significantly reduced the tumor volume, increase the percentage tumor inhibition and reverse the haematological parameters. Flow cytometry analysis concluded that the compound induces cell cycle arrest at G0/G1 phase due to the over expression of p21. 1-(4-methoxyphenyl)-3-(3- phenoxy phenyl) prop-2-en-1-one may be a potential agent for cancer treatment.

Synthesis and Characterization of New Organosoluble and Thermally Stable Aromatic Polyamides Containing Flexible Ether, Ketone, and Methylene Linkages

AbstractA new aromatic diacid monomer, namely, 1,4‐phenylene‐bis‐[[4′‐(4″‐carboxy methylene) phenoxy phenyl] methanone] (PBCPPM) is successfully synthesized and characterized by physical constant, FT‐IR, NMR (1H and 13C) spectroscopy, and mass spectrometry. Synthesis of new series of polyamides with high thermal stability and improved solubility are performed by Yamazaki's direct phosphorylative polycondensation method from new PBCPPM with different aromatic diamines. The inherent viscosity of these polyamides is in the range 0.47–0.81 dL g−1. All these polyamides are amorphous or partly crystalline and reveal good solubility in polar aprotic solvents and exhibit glass transition temperatures between 201 and 232 °C. Initial decomposition temperatures are in the range 300–367 °C and T10 is in the range of 376–414 °C indicating good thermal stability of these polyamides. The present observations suggest that these polyamides can find potential applications as high performance polymers.

New water soluble phenoxy phenyl diazenyl benzoic acid substituted phthalocyanine derivatives: Synthesis, antioxidant activities, atypical aggregation behavior and electronic properties

Novel substituted phthalonitrile derivatives were obtained by the reaction of 2-(4-hydroxyphenylazo)benzoic acid and 4,5-dichloro-1,2-dicyanobenzene, or 4-nitrophthalonitrile. Peripherally phenoxy phenyl diazenyl benzoic acid substituted zinc (II) phthalocyanine complexes, and their sodium salts were synthesized and characterized for the first time. The newly synthesized phthalocyanine complexes show excellent solubility in water. The aggregation investigations carried out in different concentrations indicate that phenoxy phenyl diazenyl benzoic acid-substituted phthalocyanine compounds do not have any aggregation behavior for the concentration range of 7.00 × 10−5–4.38 × 10−6 M in DMF. The antioxidant activities of DMF solution of compounds were analyzed through radical scavenging, and chelating ability to Fe2+ cation. Additionally, new compounds did not show any antibacterial activity against some selected bacteria cultures. Moreover, the ground-state geometries of the complexes were optimized using density functional theory (DFT) methods at B3LYP/6-31G(d,p) level in order to obtain information about the 3D geometries and electronic structure.

Soil and Glass Surface Photodegradation of Etofenprox under Simulated California Rice Growing Conditions

Photolysis is an important degradation process to consider when evaluating a pesticide's persistence in a rice field environment. To simulate both nonflooded and flooded California rice field conditions, the photolytic degradation of etofenprox, an ether pyrethroid, was characterized on an air-dried rice soil and a flooded rice soil surface by determination of its half-life (t(1/2)), dissipation rate constant (k) and identification and quantitation of degradation products using LC/MS/MS. Photodegradation was also characterized on a glass surface alone to rule out confounding soil factors. Measured photolytic dissipation rates were used as input parameters into a multimedia environmental fate model to predict etofenprox persistence in a rice field environment. Photolytic degradation proceeded at a faster rate (0.23/day, t(1/2) = 3.0 days) on the flooded soil surface compared to the air-dried surface (0.039/day, t(1/2) = 18 days). Etofenprox degradation occurred relatively quickly on the glass surface (3.1/day, t(1/2) = 0.23 days or 5.5 h) compared to both flooded and air-dried soil layers. Oxidation of the ether moiety to the ester was the major product on all surfaces (max % yield range = 0.2 ± 0.1% to 9.3 ± 2.3%). The hydroxylation product at the 4' position of the phenoxy phenyl ring was detected on all surfaces (max % yield range = 0.2 ± 0.1% to 4.1 ± 1.0%). The air-dried soil surface did not contain detectable residues of the ester cleavage product, whereas it was quantitated on the flooded soil (max % yield = 0.6 ± 0.3%) and glass surface (max % yield = 3.6 ± 0.6%). Dissipation of the insecticide in dark controls was significantly different (p < 0.05) compared to the light-exposed surfaces indicating that degradation was by photolysis. Laboratory studies and fate model predictions suggest photolysis will be an important process in the overall degradation of etofenprox in a rice field environment.

Aerobic versus Anaerobic Microbial Degradation of Etofenprox in a California Rice Field Soil

The microbial degradation of etofenprox, an ether pyrethroid, was characterized under anaerobic (flooded) and aerobic (nonflooded) California rice field soil conditions by determination of its half-life (t1/2) and dissipation rate constant (k) and identification and quantification of degradation products at both 22 and 40 °C using LC-MS/MS. The overall anaerobic t1/2 at 22 °C ranged from 49.1 to 100 days (k=-0.0141 to -0.0069 days(-1)) compared to 27.0 days (k=-0.0257 days(-1)) at 40 °C, whereas under aerobic conditions the overall t1/2 was 27.5 days (k=-0.0252 days(-1)) at 22 °C compared to 10.1-26.5 days (k=-0.0686 to -0.0262 days(-1)) at 40 °C. The biphasic dissipation profiles were also fit to a first-order model to determine the t1/2 and k for both the fast and slow kinetic regions of the dissipation curves. Hydroxylation at the 4'-position of the phenoxy phenyl ring was the major metabolic process under anaerobic conditions for both 22 °C (maximum% yield of applied etofenprox mass=1.3±0.7%) and 40 °C (max % yield=1.2±0.8%). Oxidation of the ether moiety to the ester was the major metabolite under aerobic conditions at 22 °C (max% yield=0.5±0.1%), but at 40 °C increased amounts of the hydroxylated form were produced (max% yield=0.7±0.2%, compared to 0.3±0.1% for the ester). The hydrolytic product of the ester, 3-phenoxybenzoic acid (3-PBA), was not detected in any samples. Sterilized control soils showed little etofenprox degradation over the 56-day incubation period. Thus, the microbial population in a flooded soil was able to transform and contribute to the overall dissipation of etofenprox. The simulated summer temperature extreme (40 °C) increased the overall degradation.

Probing effects of alternately‐embedded phenoxy phenyl lateral groups on properties of novel aromatic poly(ether‐urea)s

AbstractA new class of alternate aromatic poly(ether‐urea)s having bulky phenoxy phenyl lateral groups was prepared by the reaction of 2,2′‐bis[(p‐phenoxy phenyl)]‐4,4′‐diaminodiphenyl ether (PPAPE) with two diisocyanates, isophorone diisocyanate and 2,4‐tolylene diisocyanate. The limited viscosity values as well as Mn and Mw values of the resulting polymers were determined. The resulting poly(ether‐urea)s could be easily cast into optically‐transparent, flexible, and light color films. The cut‐off wavelength values and the percentage of transmittance at 800 nm were found to be at about 415 nm and 85%, respectively. PPAPE‐derived poly(ether‐urea)s showed a low‐crystallinity and had excellent solubility in polar organic solvents. Tonset, Tg, Td5%, and Td10% values of the PPAPE‐derived polymers measured from their DSC and TGA thermograms were up to 270, 280, 315, and 340°C, respectively. Surface morphology of the resulted poly(ether‐urea)s were also evaluated by their scanning electron microscopy images. Excellent organo‐solubility, satisfactory film quality, moderate Tg values, and good thermal stability make this class of poly (ether‐urea)s promising high‐performance polymeric materials. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010

Synthesis and characterization of fluorine and nitrile containing polyimides

AbstractA series of polyimides were synthesized from new diamine, Bis [4,4′‐amino‐5,5′ trifluoromethyl phenoxy‐(hexafluoro isopropylidine) phenoxy phenyl] benzonitrile [BATFB] and various aromatic tetracarboxylic anhydrides by thermal and chemical imidization routes. The BATFB was synthesized in two steps by nucleophilic displacement reaction of 2,6‐dichloro benzonitrile, 4,4′‐(hexafluoro isopropylidine) diphenol and 2‐amino‐5‐fluoro benzotrifluoride in the presence of anhydrous potassium carbonate in N,N′‐dimethyl acetamide (DMAc) and the structure was confirmed by FTIR spectroscopy and CHNSO analyzer. The polymers were characterized by FTIR spectroscopy and thermal analysis were performed by differential scanning calorimetry and thermogravimetric analysis methods. The prepared polyimides had glass transition temperatures between 230 and 290°C and their 10% weight loss were recorded in the range 550–590°C in N2 atmosphere. Majority of polymers are found to be soluble in most of the organic solvents such as DMSO, DMF, DMAc, m‐cresol, and THF even at room temperature and few becomes soluble on heating. The prepared polyimides showed water uptake values 0.34–0.54 wt % at room temperature. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 101: 3455–3461, 2006

Synthesis and chiral recognition ability of O-phenyl ethylphosphonothioic acid with a conformationally flexible phenoxy group for CH/π interaction

Enantiopure O-phenyl ethylphosphonothioic acid 1 was easily obtained by the enantioseparation of racemic 1, which was prepared from commercially available phosphorothioic trichloride in four steps. Enantiopure 1 was found to show an excellent chiral recognition ability for various 1-arylethylamine derivatives during the diastereomeric salt formation. In particular, enantiopure 1 was able to recognize the chirality of o- and m-substituted 1-arylethylamine derivatives, of which the chirality is generally difficult to establish by conventional resolving agents. X-ray crystallographic analyses of the less-soluble diastereomeric salts revealed that the conformation of the phenoxy group in enantiopure 1 could change in the diastereomeric salt crystals and that the excellent chiral recognition ability of enantiopure 1 resulted from the effective CH/π interaction of the phenoxy phenyl group.

New amorphous electron-transporting materials based on Tris-benzimidazoles for all wet-process OLED devices

New amorphous electron-transporting materials 1,3,5-tris[1-(phenoxy phenyl)- 1H-benzimidazol-2-yl]benzene ( 6a and 6b) were synthesized by dehydration reaction of corresponding triamides and fully characterized. Compounds 6a and 6b showed high thermal stability ( T g = 108 to 110 °C) and good solubility in common organic solvents, such as acetone, 2-methoxyetanol, tetrahydrofuran, chloroform, and 2-butanone. Pinhole-free transparent films were obtained by spin-casting the 2-butanone solution. 6a and 6b were fabricated as electron-transporting layer by spin-casting on a hole-transporting layer that was deposited by spin-cast beforehand and was insoluble in 2-butanone. Both devices showed no emission, but carrier transporting property was observed (400 mA/cm 2). The device showed a blue emission (35 cd/m 2) from 9,10-diphenylanthracene (DPA) when 10 wt.% DPA was mixed into the 6b layer.

A benzopyran derivative substituted at position 3.

In (E)-3-[[(diphenoxyphosphoryl)methylhydrazono]methyl]-4H-1-benzopyran-4-one, C(23)H(19)N(2)O(5)P, the benzopyran-methylhydrazone moiety is planar and the two phenoxy phenyl rings are inclined at angles of 21.29 (6) and 89.33 (5) degrees. Weak C[bond]H...O and C[bond]H...N intramolecular interactions exert some influence on the planarity and orientation of that moiety.

Do thyroid hormones function in insects?

Earlier work demonstrated that phenoxy–phenyl compounds such as fenoxycarb and thyroxine mimicked the effects of JH III in causing a reduction in volume of the follicle cells of Locusta migratoria. While these compounds were only moderately effective, a derivative of thyroxine, 3,3′,5-triiodothyronine (T3) was as effective as JH III, and T3 has been shown to bind to the same membrane receptor and activate the same pathway as JH III. The current paper shows that other thyroxine derivatives vary in activity. 3,3′,5′-Triiodothyronine (reverse T3) is inactive. 3,5-Diiodothyronine (T2) is more active than JH III, while its relatives (iodines at 3′,5′ or at 3,3′) are inactive. When follicles are exposed in vitro to rhodamine conjugated T3, the fluorescent compound can be seen to enter the cells and accumulate there: this process is inhibited by cycloheximide or by a temperature of 0°C. The accumulation is antagonised by JH III but not JH I (which does not bind to the JH III membrane receptor) and by an antiserum raised against the putative membrane receptor protein. The action of T3, but not T2, is inhibited by 6- n-propyl-2-thiouracil or by aurothioglucose, both known to inhibit deiodinases. The activity of T3, but not of T2, increases with time of exposure to the follicle cells. These facts suggest that T3 enters the cells by receptor mediated endocytosis and is converted to a more active compound. Immunoreactivity to T3, but not thyroxine, can be detected in the haemolymph of locusts, and the titre varies slightly with the gonotrophic cycle. The food shows immunoreactivity for both thyroxine and T3. These findings suggest that thyroid hormones are ingested by locusts and have the potential to be used as hormonal signals in the control of egg production.

Fenoxycarb and thyroid hormones have JH-like effects on the follicle cells of Locusta migratoria in vitro.

Earlier work had shown that JH acts on the membrane of the follicle cell of Locusta migratoria, bringing about a rapid reduction in volume which can be detected in vitro by measuring the increase in optical path difference using quantitative interference microscopy. The juvenoid fenoxycarb, a phenoxyphenyl derivative, is unrelated in structure to the juvenile hormones (which are derivatives of farnesoic acid), but it also caused a reduction in volume of the cells in vitro as measured by an increase in the optical path difference. The vertebrate hormone thyroxine, and thyronine, the non-iodinated derivative of thyroxine, also phenoxy phenyl compounds, evoked a response like fenoxycarb. The effect of thyroxine was abolished by ouabain, which inhibits Na+/K+ ATPase, the effector molecule for JH, and inhibited by ethoxyzolamide which inhibits the binding of JH to a putative membrane receptor. Triiodothyronine, the effective vertebrate hormone, acted at a lower threshold and optimum concentration, and had a greater magnitude of effect than the other compounds tested. These facts suggest that these phenoxyphenyl compounds are JH agonists and that the membrane receptor for JH may resemble a possible membrane receptor for thyroxine.

Fenoxycarb and thyroid hormones have JH‐like effects on the follicle cells of Locusta migratoria in vitro

Earlier work had shown that JH acts on the membrane of the follicle cell of Locusta migratoria, bringing about a rapid reduction in volume which can be detected in vitro by measuring the increase in optical path difference using quantitative interference microscopy. The juvenoid fenoxycarb, a phenoxyphenyl derivative, is unrelated in structure to the juvenile hormones (which are derivatives of farnesoic acid), but it also caused a reduction in volume of the cells in vitro as measured by an increase in the optical path difference. The vertebrate hormone thyroxine, and thyronine, the non-iodinated derivative of thyroxine, also phenoxy phenyl compounds, evoked a response like fenoxycarb. The effect of thyroxine was abolished by ouabain, which inhibits Na+/K+ ATPase, the effector molecule for JH, and inhibited by ethoxyzolamide which inhibits the binding of JH to a putative membrane receptor. Triiodothyronine, the effective vertebrate hormone, acted at a lower threshold and optimum concentration, and had a greater magnitude of effect than the other compounds tested. These facts suggest that these phenoxyphenyl compounds are JH agonists and that the membrane receptor for JH may resemble a possible membrane receptor for thyroxine. © 1996 Wiley-Liss, Inc.