Novel Heterocyclic Hybrids Based on 2-Pyrazoline: Synthesis and Assessment of Anti-Inflammatory and Analgesic Activities

2019 ◽  
Vol 16 (6) ◽  
pp. 921-930 ◽  
Author(s):  
Ahmed A.O. Abeed ◽  
Gehad A.A. Jaleel ◽  
Mohamed S.K. Youssef
Keyword(s):  
Acute Toxicity ◽  
1H Nmr ◽  
13C Nmr ◽  
High Performance ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
Inflammatory Activity ◽  
Necrosis Factor Alpha ◽  
Anti Inflammatory

Aim and Objective: A series of new 2-pyrazoline analogues were synthesized. The structures of the synthesized compounds were elucidated by the analytical and spectroscopic data. Some selected compounds were screened for the anti-inflammatory activity by using animal model of carrageenan-induced paw edema in mice. Additionally, the analgesic and acute toxicity of these compounds were evaluated and exhibited reasonable results. The anti-oxidant and anti-inflammatory effects of these compounds were established by measuring the contents of malondialdehyde (MDA), reduced glutathione (GSH), nitric oxide (NO), and tumor necrosis factor alpha (TNF-α) in the edema paw tissue. Materials and Methods: All chemicals and reagents used in current study were of analytical grade. Melting points were determined using APP. Digital ST 15 melting point apparatus and are uncorrected. FT-IR spectra were recorded on a Pye-Unicam SP3-100 spectrophotometer in KBr pellet. All 1H and 13C NMR spectra were recorded on AVANCE-III (400 MHz) High Performance FT-NMR Spectrometer Brucker (Switzerland) and some 1H NMR spectra were recorded on Varian EM-360L NMR Spectrophotometer (60 MHz) (USA) in CDCl3 or DMSO-d6 as solvent. Chemical shifts are reported in δ units and the coupling constants (J) are reported in hertz. C, H, N and S analyses were performed with a Vario EL C, H, N, S Analyzer. Carrageenan (product number C1013) was obtained from Sigma-Aldrich (USA). Results: The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR, and elemental analyses. The results of pharmacological activity revealed that compounds 5, 6, 7, and 15 could be recognized as potential multi-potent anti-inflammatory. Conclusion: A simple and suitable method for the synthesis of new pharmacophore was reported. We have designed nineteen heterocycles related to pyrazoline ring, and evaluated eleven of them for their antiinflammatory, analgesic and acute toxicity activities. Compounds 5, 6, 7, and 15 proved to be the interesting compounds, they have high anti-inflammatory activity. However, all the selected compounds show remarkable analgesic activity.

The Electron Effect of Aromatic Group: Control Conformation of 2-Aromatic Cyclododecanone Derivatives

2020 ◽  
Vol 24 (10) ◽  
pp. 1139-1147
Author(s):  
Yang Mingyan ◽  
Wang Daoquan ◽  
Wang Mingan
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Nmr Spectra ◽  
Coupling Constants ◽  
The Other ◽  
Repulsive Interaction ◽  
X Ray Diffraction ◽  
X Ray ◽  
Electron Effect ◽  
Group Control

2-Phenylcyclododecanone and 2-cyclohexylcyclododecanone derivatives were synthesized and characterized by 1H NMR, 13C NMR, HR-ESI-MS and X-ray diffraction. Their preferred conformations were analyzed by the coupling constants in the 1H NMR spectra and X-ray diffraction, which showed the skeleton ring of these derivatives containing [3333]-2-one conformation, and the phenyl groups were located at the side-exo position of [3333]-2-one conformation due to the strong π-π repulsive interaction between the π- electron of benzene ring and π-electron of carbonyl group. The cyclohexyl groups were located at the corner-syn or the side-exo position of [3333]-2-one conformation depending on the hindrance of the other substituted groups. The π-π electron effect played a crucial role in efficiently controlling the preferred conformation of 2-aromatic cyclododecanone and the other 2-aromatic macrocyclic derivatives with the similar preferred square and rectangular conformations.

scholarly journals Synthesis, Characterization and Evaluation of Anti-inflammatory Activity of Novel Indoline Derivatives

2016 ◽  
Vol 12 (12) ◽  
pp. 4557-4563
Author(s):  
Dhinesh kumar Manoharan
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Protein Denaturation ◽  
Inflammatory Activity ◽  
Potent Inhibition ◽  
Ft Ir ◽  
Anti Inflammatory

Series of indoline derivatives were synthesized using N-(4-aminophenyl) indoline-1-carbothiamide as a precursor. The structures of synthesized compounds were confirmed by   FT-IR, 1H-NMR, 13C-NMR and LC-MS. The in vitro anti-inflammatory activity of synthesized indoline derivatives were examined by standard anti-denaturation assay. The compounds 4a (IC50 = 62.2 µg/ml) and 4b (IC50 = 60.7 µg/ml) showed potent inhibition on protein denaturation. The compounds 5a (IC50 = 97.8 µg/ml) exhibits moderate inhibition on protein denaturation

scholarly journals Chemical constituents of Pseudobrickellia brasiliensis leaves(Spreng.) R.M. King & H. Rob. (Asteraceae)

2016 ◽  
Vol 18 (2) ◽  
pp. 408-414 ◽  
Author(s):  
M.L.L. DE AMORIM ◽  
W.M. GODINHO ◽  
F.C. ARCHANJO ◽  
C.F.F. GRAEL
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Chemical Constituents ◽  
Inflammatory Activity ◽  
Anti Inflammatory

ABSTRACT Pseudobrickelliabrasiliensisis aspecies endemic toBrazil, popularlyknown as “arnica”/ “arnica-do-campo”/ “arnica-do-mato” and used for itsanalgesicand anti-inflammatoryproperties. The objective of this research was thephytochemical studyof the essential oilandhexaneandethyl acetateextracts of the leaves of this species. The essential oilwasextracted byhydrodistillation using a Clevengerapparatusand was analyzed byGC/MS, 25components were identified, with a predominance ofmonoterpenes. The extractswere subjected toclassicalchromatographyand the fractionswere analyzed byGC/MS, 1D 1H-NMR, 13C-NMR and 13C-NMR-DEPT 135.α-amyrin, α-amyrin acetate, β-amyrin, β-amyrin acetate, lupeol, lupeolacetate, pseudotaraxasterol andtaraxasterol (triterpenes), andkaurenoicacid (diterpene) were identified.Theseterpenesarechemo-taxonomicallyrelated to theEupatorieaetribe(Asteraceae) and may be responsible for the anti-inflammatory activity attributed to the plant.

gNMR simulated 1H and proton-coupled 13C NMR spectra of substituted 3-nitropyridines. GIAO/DFT calculated values of proton and carbon chemical shifts and coupling constants

2006 ◽  
Vol 787 (1-3) ◽  
pp. 131-147 ◽  
Author(s):  
Alan R. Katritzky ◽  
Novruz G. Akhmedov ◽  
Alâattin Güven ◽  
Jacek Doskocz ◽  
Rena G. Akhmedova ◽  
...  
Keyword(s):  
13C Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
13C Nmr Spectra

scholarly journals Synthesis, Characterization and Anti-inflammatory Activity of (2E)-3-(2-Bromo-6-hydroxy-4-methoxyphenyl)-1-(naphthalene-2-yl)prop-2-en-1-one

2020 ◽  
Vol 32 (3) ◽  
pp. 561-564
Author(s):  
Dileep Kumar M. Guruswamy ◽  
Shankar Jayarama
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Stair Climbing ◽  
Inflammatory Activity ◽  
Spectral Studies ◽  
Albino Rats ◽  
Paw Edema ◽  
Standard Drug ◽  
Edema Model ◽  
Anti Inflammatory

(2E)-3-(2-Bromo-6-hydroxy-4-methoxyphenyl)-1-(naphthalene-2-yl)prop-2-en-1-one (d1) was synthesized by the Claisen-Schmidt condensation method and characterized by 1H NMR, 13C NMR spectral studies. The anti-inflammatory activity was conducted in Swiss albino rats for paw edema model. Edema was actuated with 1 % carrageenan to every one of the animals following 1 h of the oral medicines. Paw thickness was checked at t = 1, 2, 3, 4, 5 and 24 h. Stair climbing score and motility score were surveyed at t = 24 h. Compound d1 signicant decline in paw thickness at p < 0.001 diminished by 32 % in paw thickness. The compound d1 signicantly expanded the stair climbing and motility score. This study suggested that the compound d1 exhibits remarkable anti-inflammatory activity when compared with that of the standard drug.

15N, 13C, and 1H NMR spectra of acylated ureas and thioureas

1987 ◽  
Vol 52 (10) ◽  
pp. 2474-2481 ◽  
Author(s):  
Josef Jirman ◽  
Antonín Lyčka
Keyword(s):  
1H Nmr ◽  
Electron Acceptor ◽  
Sulfur Atom ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
1H Nmr Spectra ◽  
Coupling Constants ◽  
Nmr Chemical Shifts ◽  
H Nmr ◽  
Better Than

A series of 1-acylated and 1,3-diacylated (acyl = acetyl or benzoyl) ureas and thioureas have been prepared and their proton-coupled and proton-decoupled 15N, 13C, and 1H NMR spectra have been measured. All the signals have been assigned. The 15N NMR chemical shifts in 1-acylated ureas and thioureas are shifted downfield as compared with δ(15N) of urea and thiourea, resp. This shift is greater for N-1 than for N-3 nitrogen atoms in both the series. When comparing acylureas and acylthioureas it is obvious from the Δδ(15N) differences that the CS group is better than CO group in transferring the electron-acceptor effect of acyl group. The proton-coupled 15N NMR spectra of the acylureas dissolved in hexadeuteriodimethyl sulphoxide exhibit a doublet of NH group and a triplet of NH2 group at 25 °C. At the same conditions the acylthioureas exhibit a doublet of NH group, the NH2 group signal being split into a doublet of doublets with different coupling constants 1J(15N, H). The greater one of these coupling constants is due to the s-trans proton with respect to the sulfur atom of the thiourea.

13C and 1H NMR spectra of all methyl O-benzoyl-β-D-xylopyranosides. nonadditivity of acylation effects on 13C chemical shifts in deutoriochloroform solutions

1983 ◽  
Vol 48 (3) ◽  
pp. 877-888 ◽  
Author(s):  
Eva Petráková ◽  
Jan Schraml
Keyword(s):  
1H Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
Conformational Heterogeneity ◽  
Additivity Rule ◽  
Homonuclear Decoupling ◽  
First Order ◽  
H Nmr ◽  
C Nmr

All methyl O-benzoyl-β-D-xylopyranosides have been prepared and their 1H and 13C NMR spectra measured in deuteriochloroform solutions. The 1H NMR spectra were analysed to the first order and assigned with the aid of homonuclear decoupling. The 13C chemical shifts were assigned through heteronuclear selective decouling experiments. Some of the 13C chemical shifts observed in di- and tri-O-benzoyl derivatives differ considerably from those calculated according to the direct additivity rule from the shifts in the mono derivatives. It is shown that the nonadditivity is due to a conformational heterogeneity of the series of investigated compounds dissolved in deuteriochloroform. The heterogeneity is evidenced by the vicinal 1H-1H coupling constants and by 13 chemical shifts of C(1) methoxyl carbon atoms.

Nonanalogousness of 1,3,5-trithianes to other cyclic systems. Chemical shifts and coupling constants in 13C NMR spectra.

1976 ◽  
Vol 17 (20) ◽  
pp. 1685-1686
Author(s):  
Kazutaka Arai ◽  
Michio Fukunaga ◽  
Hiizu Iwamura ◽  
Michinori Ōki
Keyword(s):  
13C Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
13C Nmr Spectra ◽  
Cyclic Systems

scholarly journals Synthesis and HPLC Enantioseparation of Derivatives of the 3-hydroxyphenylethanone

2012 ◽  
Vol 59 (2) ◽  
pp. 15-27
Author(s):  
R. Čižmáriková ◽  
A. Némethy ◽  
J. Valentová ◽  
K. Hroboňová ◽  
K. Bruchatá
Keyword(s):  
High Performance Liquid Chromatography ◽  
Liquid Chromatography ◽  
1H Nmr ◽  
13C Nmr ◽  
High Performance ◽  
Nmr Spectra ◽  
Stationary Phases ◽  
13C Nmr Spectra ◽  
Basic Part ◽  
Derivatives Of

AbstractWithin the framework of the study of the synthesis and high-performance liquid chromatography (HPLC) enantioseparation the series of 9 derivatives of 3-hydroxyphenylethanone was prepared by a well-tried method. The structure of the prepared compounds was confirmed on the basis of interpretation of the IR, UV, 1H NMR and 13C NMR spectra. An enantioseparation of prepared compounds was performed using HPLC on a native teicoplanin (Chirobiotic T) and the amylose tris (3,5-dimethylphenylcarbamate) (Chiralpak AD) chiral stationary phases, which is more suitable for the enantioseparation of all prepared compounds especially with heterocycles in the basic part of a molecule.

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