Design, synthesis and pharmacological profile of (−)-verbenone hydrazones

AbstractA series of novel (−)-verbenone hydrazones was designed and synthesized via condensation of terpenoid with hydrazides derived from phenoxyacetic acid. The structure of target compounds was confirmed by 1H-NMR and 13C-NMR analysis, Raman and FT-IR spectroscopy, electrospray ionization method and fast atom bombardment (FAB) mass spectrometry. Thermal properties of (−)-verbenone hydrazones 3a–3e were estimated by differential scanning calorimetry and their purity by HPLC coupled to mass spectrometry. Verbenone hydrazones were revealed to exist as Z/E geometrical isomers about C═N bond and cis/trans amide conformers. Verbenone derivatives were estimated as potential anticonvulsant agents after their oral administration against pentylenetetrazole and maximal electroshock-induced seizures in mice. Analgesic effect of hydrazones was studied by topical application on models of allyl isothiocyanate and capsaicin-induced pain. The present findings indicate that verbenone hydrazones contribute to seizure protection both at short (6 h) and long (24 h) time periods by blocking chemical- and electroshock-induced convulsions. Binding of compounds 3a–3e to TRPA1/TRPV1 ion channels was suggested as a feasible mechanism explaining their significant analgesic activity.

Download Full-text

(2S,5R)-2-Isopropyl-5-methylcyclohexanone Hydrazones

Molbank ◽

10.3390/m1062 ◽

2019 ◽

Vol 2019 (2) ◽

pp. M1062 ◽

Cited By ~ 1

Author(s):

Mariia Nesterkina ◽

Dmytro Barbalat ◽

Ivan Zheltvay ◽

Ildar Rakipov ◽

Mehmet Atakay ◽

...

Keyword(s):

Mass Spectrometry ◽

Differential Scanning Calorimetry ◽

Acetic Acid ◽

Glacial Acetic Acid ◽

Catalytic Amount ◽

Phenoxyacetic Acid ◽

Scanning Calorimetry ◽

Geometrical Isomers ◽

Esi Mass Spectrometry ◽

Amide Conformers

Hydrazones were obtained in 76–78% yield via condensation of (2S,5R)-2-isopropyl-5-methylcyclohexanone with 4-R-phenoxyacetic acid hydrazides in the presence of a catalytic amount of glacial acetic acid. The structure of the target compounds has been established by FTIR-ATR, Raman, 1H-NMR and 13C-NMR spectral analysis and EI/FAB/ESI mass spectrometry. Thermal properties of hydrazones 3a–3e were elucidated by differential scanning calorimetry (DSC) and their purity by HPLC coupled to mass spectrometry. Synthesized compounds were found to exist as Z/E geometrical isomers about C=N bond and cis/trans amide conformers.

Download Full-text

Liquid crystalline polyureas with oligo(ethylene glycol) sequences

e-Polymers ◽

10.1515/epoly.2010.10.1.1425 ◽

2010 ◽

Vol 10 (1) ◽

Author(s):

Shahram Mehdipour-Ataei ◽

Leila Akbarian-Feizi

Keyword(s):

Liquid Crystalline ◽

Spectroscopic Method ◽

Polymerization Reaction ◽

X Ray Diffraction ◽

Subsequent Reaction ◽

Scanning Calorimetry ◽

Polar Solvents ◽

X Ray ◽

H Nmr ◽

Ft Ir

AbstractA diamine monomer containing ester, amide and ether functional groups was prepared and its polymerization reaction with different diisocyanates to give main chain poly(ester amide ether urea)s was investigated. The monomer was synthesized via reaction of terephthaloyl chloride with 4-hydroxybenzoic acid and subsequent reaction of the resulted diacid with 1,8-diamino-3,6-dioxaoctane. The polymers were characterized by FT-IR and 1H-NMR spectroscopic method and elemental analysis. The resulting polymers exhibited excellent solubility in polar solvents. Crystallinity of the resulted polymers was evaluated by wide-angle X-ray diffraction (WXRD) method, and they exhibited semi-crystalline patterns. The glass transition temperatures (Tg) of the polymers determined by differential scanning calorimetry (DSC) and dynamic mechanical thermal analysis (DMTA) were in the range of 88-112 °C. The temperatures for 10% weight loss (T10) from their thermogravimetric analysis (TGA) curves were found to be in the range of 297-312 °C in air. Also the prepared polyureas showed liquid crystalline character.

Download Full-text

Design, synthesis, molecular modelling and in vitro screening of monoamine oxidase inhibitory activities of novel quinazolyl hydrazine derivatives

Royal Society Open Science ◽

10.1098/rsos.200050 ◽

2020 ◽

Vol 7 (4) ◽

pp. 200050

Author(s):

Adel Amer ◽

Abdelrahman H. Hegazi ◽

Mohammed Khalil Alshekh ◽

Hany E. A. Ahmed ◽

Saied M. Soliman ◽

...

Keyword(s):

Mass Spectrometry ◽

Monoamine Oxidase ◽

In Vitro Screening ◽

Phenyl Substituent ◽

Design Synthesis ◽

Mao B ◽

Mao A ◽

Ft Ir ◽

Inhibitory Activities

A new series of N'-substituted benzylidene-2-(4-oxo-2-phenyl-1,4-dihydroquinazolin-3(2H)-yl)acetohydrazide ( 5a–5h ) has been synthesized, characterized by FT-IR, NMR spectroscopy and mass spectrometry and tested against human monoamine oxidase (MAO) A and B. Only (4-hydroxy-3-methoxybenzylidene) substituted compounds gave submicromolar inhibition of MAO-A and MAO-B. Changing the phenyl substituent to methyl on the unsaturated quinazoline ring ( 12a–12d ) decreased inhibition, but a less flexible linker ( 14a–14d ) resulted in selective micromolar inhibition of hMAO-B providing insight for ongoing design.

Download Full-text

Cationic copolymerization of 1,3-pentadiene with α-pinene

Journal of Polymer Engineering ◽

10.1515/polyeng-2014-0062 ◽

2014 ◽

Vol 34 (7) ◽

pp. 583-589 ◽

Cited By ~ 1

Author(s):

Ai-Yuan Li ◽

Xiang-Dong Sun ◽

Hui-Bo Zhang ◽

Yong-Chun Zhang ◽

Bin Wang ◽

...

Keyword(s):

Average Molecular Weight ◽

Gel Permeation Chromatography ◽

Polymerization Temperature ◽

Scanning Calorimetry ◽

Gardner Color ◽

H Nmr ◽

Cationic Copolymerization ◽

Ft Ir ◽

Better Than ◽

C Nmr

Abstract The cationic copolymerization of 1,3-pentadiene (PD) with α-pinene (AP) initiated by aluminum trichloride (AlCl3) was carried out in N-pentane solvent. The effects of the polymerization temperature and the comonomer composition on the yield of the copolymer, softening point, Gardner color scale and number-average molecular weight (Mn) are discussed. The performance of the copolymer was better than that of AP homopolymer (PAP) and PD homopolymer (PPD). The structure of the copolymer was characterized by Fourier transform infrared spectroscopy (FT-IR), 1H-nuclear magnetic resonance (1H-NMR), 13C-NMR, differential scanning calorimetry (DSC) and gel permeation chromatography (GPC). In addition, the reactivity ratios for AP (M1) and PD (M2) determined by the Kelen-Tudos method from low-conversion data are r1=0.58 and r2=5.92, respectively.

Download Full-text

Synthesis of a Cationic Polyacrylamide under UV Initiation and Its Flocculation in Estrone Removal

International Journal of Polymer Science ◽

10.1155/2018/8230965 ◽

2018 ◽

Vol 2018 ◽

pp. 1-11 ◽

Cited By ~ 2

Author(s):

Jiaoxia Sun ◽

Xiqin Ma ◽

Xiang Li ◽

Jianxin Fan ◽

Qingkong Chen ◽

...

Keyword(s):

Ammonium Chloride ◽

Removal Rate ◽

Phenyl Group ◽

Resonance Spectroscopy ◽

Scanning Calorimetry ◽

Floc Size ◽

Cationic Polyacrylamide ◽

H Nmr ◽

Ft Ir ◽

Dsc Analyses

A ternary cationic polyacrylamide (CPAM) with the hydrophobic characteristic was prepared through ultraviolet- (UV-) initiated polymerization technique for the estrone (E1) environmental estrogen separation and removal. The monomers of acrylamide (AM), acryloyloxyethyl-trimethyl ammonium chloride (DAC), and acryloyloxyethyl dimethylbenzyl ammonium chloride (AODBAC) were used to synthesize the ternary copolymer (PADA). Fourier transform infrared spectroscopy (FT-IR), 1H nuclear magnetic resonance spectroscopy (1H NMR), thermogravimetry/differential scanning calorimetry (TG/DSC), and scanning electron microscopy (SEM) were employed to characterize the structure, thermal decomposition property, and morphology of the polymers, respectively. FT-IR and 1H NMR results indicated the successful formation of the polymers. Besides, with the introduction of hydrophobic groups (phenyl group), an irregular and porous surface morphology and a favorable thermal stability of the PADA were observed by SEM and TG/DSC analyses, respectively. At the optimal condition (pH = 7, flocculant dosage = 4.0 mg/L and E1 concentration = 0.75 mg/L), an excellent E1 flocculation performance (E1 removal rate: 90.1%, floc size: 18.3 μm, and flocculation kinetics: 22.69×10-4 s−1) was acquired by using the efficient flocculant PADA-3 (cationic degree = 40%, and intrinsic viscosity = 6.30 dL·g−1). The zeta potential and floc size analyses were used to analyze the possible flocculation mechanism for the E1 removal. Results indicated that the charge neutralization, adsorption, and birding effects were dominant in the E1 removal progress.

Download Full-text

SYNTHESIS AND CHARACTERIZATION OF NEW THERMOTROPIC LIQUID CRYSTALLINE POLYURETHANES WITH BIPHENYL MOIETY

International Journal of Modern Physics B ◽

10.1142/s0217979206041562 ◽

2006 ◽

Vol 20 (25n27) ◽

pp. 4487-4492 ◽

Cited By ~ 1

Author(s):

JONG BACK LEE ◽

SANG PILL LEE ◽

JIN KYUNG LEE

Keyword(s):

Liquid Crystalline ◽

Gravimetric Analysis ◽

Scanning Calorimetry ◽

Infrared Study ◽

H Nmr ◽

X Ray Scattering ◽

Phase Transition Temperatures ◽

No Weight Loss ◽

Ft Ir ◽

Tolylene Diisocyanate

A new series of thermotropic polyurethanes containing biphenyl units was synthesized by polyaddition reaction of diisocyanates such as 2,6-tolylene diisocyanate, 2,5-tolylene diisocyanate, 2,4-tolylene diisocyanate, and 1,4-phenylene diisocyanate, with 4,4□-bis(9-hydroxynonoxy)biphenyl (BP9). Structures of the monomer and the corresponding polymers were identified using FT-IR and 1 H NMR spectroscopic methods. BP9 exhibited a smectic type mesophase, however, nematic phase was found for all synthesized liquid crystalline polyurethanes except for 1,4-phenylene diisocyanate/BP9 based polyurethane. Their phase transition temperatures and thermal stability were investigated by differential scanning calorimetry (DSC), optical polarizing microscopy, and X-ray scattering. The infrared study indicated that the hydrogen bonding among urethane linkages attributed to the mesomorphism. Thermal gravimetric analysis (TGA) of synthesized polyurethanes showed that no weight loss of the polymers observed up to 280°C.

Download Full-text

Halogenated sunflower oil as a precursor for synthesis of polysulfide polymer

e-Polymers ◽

10.1515/epoly-2015-0152 ◽

2016 ◽

Vol 16 (1) ◽

pp. 33-39 ◽

Cited By ~ 10

Author(s):

Samira Moqadam ◽

Mehdi Salami-Kalajahi

Keyword(s):

Sunflower Oil ◽

Proton Nuclear Magnetic Resonance ◽

Gravimetric Analysis ◽

Scanning Calorimetry ◽

X Ray ◽

H Nmr ◽

Ft Ir ◽

Harsh Conditions ◽

Thermal Stability Of ◽

Polysulfide Polymer

AbstractPolysulfide polymers usually are prepared by the reaction of different dihalide compounds with disodium polysulfides. In this field, dihalides are expensive and produced from halogenation of organic compounds by different methods with harsh conditions. To overcome this problem, in this work, sunflower oil as polyunsaturated oil was used as precursor to produce polyhalide compound. In this field, double bonds of oil were applied as functional groups to halogenate the sunflower via benzoyl peroxide-catalyzed reaction with hydrochloric acid. Also, Na2S3 was synthesized via the reaction between sulfur and sodium hydroxide. Then, halogenated oil was reacted with Na2S3 to produce sunflower oil-based polysulfide polymer. Fourier transform infrared spectroscopy (FT-IR) and proton nuclear magnetic resonance (1H NMR) were used to characterize the structure of sunflower oil and synthesized polysulfide polymer. The content of halogenation was also obtained via energy-dispersive X-ray spectroscopy (EDX). Thermal stability of synthesized polymer was determined by means of thermal gravimetric analysis (TGA) and glass transition temperature was investigated by differential scanning calorimetry (DSC).

Download Full-text

Preparation and characterization of tetrachlorocobaltates(II) of α,ω-alkylenediammonium. Magnetic and thermal properties. Crystal structure of [NH3(CH2)5NH3]CoCl4

Acta Crystallographica Section B Structural Science ◽

10.1107/s0108768199005698 ◽

1999 ◽

Vol 55 (6) ◽

pp. 947-952 ◽

Cited By ~ 21

Author(s):

J. J. Criado ◽

A. Jiménez-Sánchez ◽

F. H. Cano ◽

R. Sáez-Puche ◽

E. Rodríguez-Fernández

Keyword(s):

Crystal Structure ◽

Mass Spectrometry ◽

Thermal Analysis ◽

Magnetic Susceptibility ◽

Ground State ◽

Monoclinic Space Group ◽

Visible Spectroscopy ◽

Scanning Calorimetry ◽

Ft Ir

Tetrachlorocobaltates(II) of diprotonated α,ω-diaminoalkanes with the formula [NH3(CH2) n NH3]CoCl4, where n = 5 (cadaverine; 1,5-pentanediammonium tetrachlorocobaltate), 8 (1,8-octanediammonium tetrachlorocobaltate) and 10 (1,10-decanediammonium tetrachlorocobaltate), were prepared. The compounds were studied by mass spectrometry, FT-IR and visible spectroscopy, magnetic susceptibility techniques and thermal analysis. The compounds contain the tetrahedral tetrachlorocobaltate(II) ion and the corresponding diprotonated diamine (cadaverine, 1,8-octamethylenediamine and 1,10-decamethylenediamine). The compound corresponding to cadaverine crystallizes in the monoclinic space group P21/c, with lattice parameters a = 7.1633 (7), b = 15.940 (3), c = 11.137 (2) Å, β = 98.44 (1)° and Z = 4. Its crystal structure contains slightly distorted tetrahedral CoCl_4^{2-} ions: the largest difference in Co—Cl bond lengths is 0.029 Å and the largest difference in Cl—Co—Cl angles is 7.76°. The compound also contains diprotonated cadaverine ions. An extensive hydrogen-bonding network connects these ions. The slightly positive deviations of the magnetic susceptibility from the Curie–Weiss law are in agreement with the 4 A 2 ground state for the tetrachlorocobaltate anion. The compounds with eight and ten C atoms show phase transitions in the solid state and a greater complexity is observed in their differential scanning calorimetry curves. Unfortunately, no suitable single crystals of these could be obtained.

Download Full-text

Synthesis and Characterization of Triethanolamine Borate

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.709.28 ◽

2013 ◽

Vol 709 ◽

pp. 28-31

Author(s):

Cheng Xue Wang ◽

Tian Tian Liang ◽

Chun Qiao Wei

Keyword(s):

Mass Spectrometry ◽

Differential Scanning Calorimetry ◽

Synthesis And Characterization ◽

Spectroscopy Analysis ◽

Scanning Calorimetry ◽

Reaction Conditions ◽

Different Types ◽

Ft Ir ◽

Ft Ir Spectroscopy

Starting with boric acid and triethanolamine , the effect of the different types of the water-carrying agent on the yield was invested, and influences of dosage of water-carrying agent ,the mole ratio of reactants, reaction time on yield were discussed, the optimized reaction conditions were confirmed. The structure of the product was described by Fourier transform-infrared (FT-IR) spectroscopy, NMR Spectroscopy analysis, mass spectrometry (MS) and thermodynamic properties was analyzed by differential scanning calorimetry (DSC) and thermogravimetry (TG).

Download Full-text

Green anionic polymerization of vinyl acetate using Maghnite-Na+ (Algerian MMT): synthesis characterization and reactional mechanism

Discover Chemical Engineering ◽

10.1007/s43938-021-00005-8 ◽

2021 ◽

Vol 1 (1) ◽

Author(s):

Badia Imene Cherifi ◽

Mohammed Belbachir ◽

Abdelkader Rahmouni

Keyword(s):

Vinyl Acetate ◽

Polymerization Reaction ◽

Resonance Spectroscopy ◽

X Ray Diffraction ◽

Scanning Calorimetry ◽

H Nmr ◽

Simple Filtration ◽

Renewable Material ◽

Ft Ir ◽

C Nmr

AbstractIn this work, the green polymerization of vinyl acetate is carried out by a new method which consists in the use of clay called Maghnite-Na+ as an ecological catalyst, non-toxic, inexpensive and recyclable by simple filtration. X-ray diffraction (XRD) showed that Maghnite-Na+ is successfully obtained after cationic treatment (sodium) on raw Maghnite. It is an effective alternative to replace toxic catalysts such as benzoyl peroxide (BPO) and Azobisisobutyronitrile (AIBN) which are mostly used during the synthesis of polyvinyl acetate (PVAc) making the polymerization reaction less problematic for the environment. The synthesis reaction is less energetic by the use of recycled polyurethane as container for the reaction mixture and which is considered as a renewable material and a good thermal insulator which maintains the temperature at 0 °C for 6 h. The reaction in bulk is also preferred to avoid the use of a solvent and therefore to stay in the context of green chemistry. In these conditions, the structure of obtained polymer is established by Nuclear Magnetic Resonance Spectroscopy 1H NMR and 13C NMR. Infrared spectroscopy (FT-IR) is also used to confirm the structure of PVAc. Thermogravimetric analysis (TGA) showed that it is thermally stable and it starts to degrade from 330 °C while Differential Scanning calorimetry (DSC) shows that this polymer has a glass transition temperature (Tg = 50 °C). The composition in PVAc/Maghnite-Na+ (7 wt% of catalyst) is the most tensile resistant with a force of 182 N and a maximum stress of 73.16 MPa, the most flexible (E = 955 MPa) and the most ductile (εr = 768%).

Download Full-text