13C NMR DEPT Research Articles

Novel chalcone-based crown ethers: synthesis, characterization, antioxidant activity, biological evaluations, and wastewater remediation.

Macrocycles play a pivotal and indispensable role within the realms of both medicine and industry. In the course of our research endeavors, we have successfully synthesized five distinct macrocyclic chalcone entities, each showcasing remarkable biological and anti-oxidative properties. Furthermore, these compounds exhibit exceptional promise as potent agents for the removal of dyes in wastewater treatment processes. The synthesis of these key constituents was achieved through the judicious application of the Robinson ether synthesis and Claisen-Schmidt condensation reactions. The structures of compounds 1a-f and 2a-e were characterized by using analytical techniques such as FTIR, 1H NMR, 13C NMR, and DEPT 13C NMR spectroscopy. These macrocycles also underwent in vitro assessments to measure their antibacterial activity using the agar well diffusion method. The results revealed that the macrocyclics were more sensitive to Gram-positive than Gram-negative bacteria. For example, compound 2d exhibited an inhibition zone of 20 mm at 150 ppm. The antioxidant activity as determined via the DPPH method established that all tested compounds showed moderate radical-scavenging ability. Specifically, compound 2e (at 1000 ppm) exhibited antioxidant activity of 79% inhibition of radicals, in comparison to 90% for the standard ascorbic acid. The latter was demonstrated by using methylene blue as an adsorbate under simulated wastewater conditions. Outstandingly, the most effective compounds were 2d and 2c, which achieved removal rates of 96.54% and 92.37%, respectively, for methylene blue dye.

Synthesis and Characterization of New N‐Pyrazol‐5‐yl) amidine Derivatives: X‐Ray Structure Hirshfeld Surface, and DFT Analyses together with Antibacterial and Antifungal Activity Studies

AbstractWe present in this work, the synthesis and characterization of N‐3‐pyrazolyl amidines derivatives obtained in satisfactory yields via one‐pot reaction. New structures of amidines were confirmed by FTIR, 1H NMR, 13C NMR, 13C NMR Dept spectrum and X ray crystallography of N‐benzyl‐N‐(3‐methyl‐1H‐pyrazol‐5‐yl) propanimidamide. In order to determinate the configuration of this amidine we have characterized it using also HRMS, DSC to determine the fusion points, X‐ray crystallography and Hirshfeld Surface analysis. The grown crystal possesses a dielectric behavior and DFT Calculation which has shown linear correlation between theoretical and experimental Hydrogen bond geometry, bond lengths (A°) and Torsion angles of 1 a. The examination of the spectrum and the SEM diagram of amidine 1a allowed us to determine the size of the particles which is of the order of 1.8 μm.All new amidines were screened for their antibacterial and antifungal activities and their phenotypic analysis was performed using the Phenotype Micro Arrays (PMs) tool to determine cellular responses during their respiration process.Amidines had relatively antibacterial activities with an antifungal behavior proving their interface reaction with several microrganisms. Such finding can be useful in medical and agricultural fields. The considered species belong to human's gut flora and soil phytopathogenesis fungi.

One pot and stepwise synthesis of some new azo thiazolidin-4-one derivatives and their biological evaluations.

(2-(2-(benzyloxy)-5-((4-(6-methylbenzo[d]thiazol-2-yl)phenyl)diazenyl)phenyl)-3- substitutedphenylthiazolidin-4-ones derivatives (4a-h) have been synthesized from the reaction of 2-(benzyloxy)-5-((4-(6-methylbenzo[d]thiazol-2-yl) phenyl)diazenyl)benzaldehyde (2) with different substituted aniline, followed by cyclization with mercaptoacetic acid via either a one-pot three-component condensation and stepwise process. The structure of synthesized compounds were elucidated by FT-IR, 1H-NMR, 13C-NMR and DEPT 13C NMR. Finally, the animicrobile activity of these compounds were evaluated by the well diffusion assay against S. aureus Gram-positive and E. coli Gram-negative bacteria.

The anticancer and EGFR-TK/CDK-9 dual inhibitory potentials of new synthetic pyranopyrazole and pyrazolone derivatives: X-ray crystallography, in vitro, and in silico mechanistic investigations

Treatment options for the management of breast cancer are still inadequate. This inadequacy is attributed to the lack of effective targeted medications, often resulting in the recurrence of metastatic disorders. Cumulative evidence suggests that epidermal growth factor receptor (EGFR-TK) and cyclin-dependent kinases-9 (CDK-9) overexpression correlates with worse overall survival in breast cancer patients. Pyranopyrazole and pyrazolone are privileged options for the development of anticancer agents. Inspired by this proven scientific fact, we report here the synthesis of two new series of suggested anticancer molecules incorporating both heterocycles together with their characterization by IR, 1H NMR, 13C NMR, 13C NMR-DEPT, and X-ray diffraction methods. An attempt to get the pyranopyrazole-gold complexes was conducted but unexpectedly yielded benzylidene-2,4-dihydro-3H-pyrazol-3-one instead. This unexpected result was confirmed by X-ray crystallographic analysis. All newly synthesized compounds were assessed for their anti-proliferative activity against two different human breast cancer cells, and the obtained results were compared with the reference drug Staurosporine. The target compounds revealed variable cytotoxicity with IC50 at a low micromolar range with superior selectivity indices. Target enzyme EGFR-TK and CDK-9 assays showed that compounds 22 and 23 effectively inhibited both biological targets with IC50 values of 0.143 and 0.121 µM, respectively. Molecular docking experiments and molecular dynamics simulation were also conducted to further rationalize the in vitro obtained results. Communicated by Ramaswamy H. Sarma

Isolation, Characterization and Antibacterial Activity of ECDY Steroid from Roots of Polycarpaea corymbosa LAM

A new phytoecdysteroid (2- deoxy 20 hydroxy 22 cinnamoyl ecdysone 3, 25 diacetate) was isolated from the roots of Polycarpaea corymbosa Lam (family: caryophyllaceae).The powdered roots were extracted with petroleum ether ( 60-80? C), benzene, ethyl acetate and ethyl alcohol in soxhlet apparatus by simultaneous extraction. The highest yield of benzene extract was chosen for the isolation of ecdysteroid. The white solid pure compound was isolated and tested by TLC and respond positively for Liebermann - burchard reaction. Their structure has been established by UV, IR, 1H, 13C-NMR DEPT -90, DEPT -135 and EI- MS experiments. All the extracts and isolated compound were screened for anti-bacterial activity against B.subtilis, P.vulgaris, E.coli, P.aeruginosa by Kirbybauer method.

Synthesis of sulfonated Sesamum indicum L. seed oil and its application as a fatliquor in leather processing

Fatliquor is an oil-in-water emulsion that improves the physical properties of leather such as tensile strength, flexibility, and softness by lubricating the leather fibres. Sulfonated Sesamum indicum oil was synthesized, characterized, and examined for consideration as a substitute for imported fatliquor in Nigeria. The sulfonation of the oil was confirmed by the significant observations made in the FTIR, 1H NMR, 13C NMR, and 13C NMR DEPT analysis results. A remarkable difference was observed in the physicochemical properties results of both unsulfonated and sulfonated oils. The sulfonated sesame fatliquor was applied onto goatskin and compared with a commercial sulfated fatliquor in the processing of shoe upper leather using standard methods. The average results for tensile strength, double edge tear, elongation, and softness results for the commercial and synthesized fatliquors are as follows: 14.27 N/mm2; 13.77 N/mm2, 50.61 N; 60.11 N, 38.06%; 54.28%, 25.2; 25.0. A comparable level of lubrication of the leather treated with the sulfonated Sesamum indicum oil and that treated with the commercial leather fatliquor was revealed by the Sudan IV stain test as well as scanning electron microscopy analysis results. Experimental analyses, therefore, show that the as-synthesized sulfonated Sesamum indicum oil could be considered as a substitute for imported fatliquor in the leather industry.Graphical abstract

Seeking a Fast Screening Method of the Varietal Origin of Olive Oil: The Usefulness of an NMR-Based Approach.

This work encompasses the use of 1D multinuclear NMR spectroscopy, namely, 1H NMR and 13C NMR DEPT 45, combined with a multivariate statistical analysis to characterize olive oils produced from nine different varieties: Galega Vulgar, Cobrançosa, Cordovil de Serpa, Blanqueta, Madural, Verdeal Alentejana, Arbequina, Picual and Carrasquenha. Thus, the suitability of an NMR-based spectroscopic tool to discriminate olive oils according to their varietal origin is addressed. The results obtained show that the model based on 13C NMR DEPT 45 data has a stronger performance than the model based on 1H NMR data, proving to be promising in the discrimination of the olive oils under study based on their varietal origin, being particularly relevant for olive oils of the Galega Vulgar variety.

Physico-chemical and thermal studies of newly developed phenolic copolymer resin and its antibacterial activities

A new random copolymer derived from 8-hydroxyquinoline, vanillin, 4-hydroxyacetophenone and formaldehyde was synthesized using conventional condensation polymerization. This copolymer further characterized by FT-IR, 1H NMR, 13C NMR, 13C NMR-DEPT, GPC, BET, DSC and TG-DTG. The apparent activation energy of resin by using Friedman methods and Kissinger-Akahira-Sunose (KAS) were 19.8 and 16.3 kJ mol−1, respectively. The three-dimensional diffusion (D3) decomposition mechanisms for the solid state thermal decomposition of copolymer have been observed from the Craido method and master plots. The copolymer resin could be used in the prevention of infections linked to medical devices.

Ferovinolal, a New Humulane from Ferula ovina

The new humulane-type (γ-apiene) ester ferovinone was isolated from roots of Ferula ovina (Boiss.) Boiss. Its structure was elucidated by analyzing PMR and 13C NMR spectra and DEPT, HSQC, COSY, and HMBC experiments and performing an X-ray crystal structure analysis. The molecular structure and absolute configuration of ferovinone were established. Ferovinone adopted the 14,15U78 conformation of the 11-membered humulane macrocycle in which a C8 p-benzoate group occupied a β-equatorial position and the only chiral center had the 8S-configuration.

Structures of Peuceruthen and Peuceruthenin, New Peucedanin-Type Furocoumarins

Extracts of Peucedanum ruthenicum roots contained the known peucedanin-type furocoumarins isoimperatorin, peucedanin, and ostruthin in addition to two new ones, peuceruthen and peuceruthenin. The structures of the new furocoumarins were elucidated by comparing their PMR spectra with those of peucedanin and using 13C NMR and 13C DEPT 135 NMR spectra.

Structural and spectroscopic characterization and DFT studies of 2-amino-1,10-phenanthrolin-1-ium chloride

A versatile synthetic building block, 2-amino-1,10-phenanthrolin-1-ium chloride (L∙HCl) was synthesized and characterized by IR, 1H and 13C NMR DEPT analysis, UV/Vis and single-crystal X-ray diffraction technique. The molecular geometry, vibrational wavenumbers and gauge including atomic orbital (GIAO), 1H and 13C NMR chemical shifts values of the title compound in the ground state were obtained by using density functional theory (DFT/B3LYP) method with 6-311++G(d,p) basis set and compared with the experimental data. Electronic absorption spectrum of the salt was determined using the time-dependent density functional theory (TD-DFT) method at the same level. In the NMR and electronic absorption spectra calculations, the effect of solvent on the theoretical parameters was included using the default model with DMSO as solvent. The obtained theoretical parameters agree well with the experimental findings.

Synthesis And Characterization Of Some New Five Membering Ring Compounds Such As Thiazolidinones and γ -Lactams

This study concerned with the synthesis and characterization of thiazolidinones & γ- lactams , the thiazolidinones compounds are prepared from A mixture of Schiff base (Imine) and thioglycolic acid, γ- lactams compounds are prepared from A mixture of Schiff base (Imine) with phenylsuccinic anhydride in moderate yields (52-71 %). The structures of these thiazolidinones and γ-lactams were established on the basis of the spectral data namely IR, 1H-NMR,13C-NMR, 13C-NMR DEPT , Mass spectra

Developing lipophilic aromatic halogenated fused systems with specific ring orientations, leading to potent anticancer analogs and targeting the c-Src Kinase enzyme

This work presents the combined microwave assisted synthesis, spectroscopic analyses, cytotoxic effects, and molecular docking studies of the chromene fused ring systems with various substituents of the terminal halogenated phenyl ring derivatives of 6-methoxy-4H-benzo [h]chromene (4a-m). The structures of the synthesized compounds were established on the basis of their spectral data, IR, 1H NMR, 13C NMR, 13C NMR-DEPT, and MS data. The target compounds were evaluated for their antitumor activities against three cancer cell lines: MCF-7, HCT-116, and HepG-2, in comparison to Vinblastine and Colchicine as reference drugs with the usage of a MTT colorimetric assay. The most active compounds were subjected to further mechanistic analysis through the assay of the c-Src Kinase inhibition activity. The SAR studies reported that the substitution at the 4-position of the 2-amino-4H-benzo [h]chromene nucleus with specific halogen atoms and lipophilic characters increased the ability of the molecule against the different cell lines. The Molecular Operating Environment (MOE) was used to evaluate the interactions between the ligand and the c-Src Kinase enzyme. Compound 4m, having the 3,5-dibromo-2-methoxyphenyl group attached to the 4H-benzo [h]chromene moiety at the 4-postion, exhibited a promising interaction with the c-Src Kinase, which leads to a strong inhibition of this enzyme.

Membrane Solubilization by Styrene-Maleic Acid Copolymers: Importance of Polymer Length and Comonomer Sequence

Styrene-maleic acid (SMA) copolymers have emerged as a powerful alternative to detergents for the extraction of membrane proteins from cellular membranes. These polymers can solubilize membranes in the form of nanodiscs that are stabilized by the polymer, allowing characterization of membrane proteins in their native environment. However, our understanding of the parameters that determine the efficiency of solubilization or the properties of the resulting nanodiscs is still limited. This is partly due to the heterogeneity of commercially available SMA copolymers, where there are large variations in both the length distribution of the polymers and the comonomer sequence distribution. Here we successfully synthesized a series of copolymers by Reversible Addition-Fragmentation Chain Transfer (RAFT) mediated polymerization in conjunction with repetitive chain extension. These copolymers were found to have a well-defined length, composition and monomer sequence by size exclusion chromatography (SEC) and DEPT 13C NMR, among others. We investigated the solubilizing efficiency of these polymers as well as the properties of the resulting nanodiscs using both lipid model membrane systems and E.coli membranes. Results of these experiments will be shown and the effects of the polymers will be compared with those of commercially available polymers.

A New Hydroxyphenylethyl Hentriacontanoate from Fraxinus syriaca

The new compound 4-hydroxyphenylethyl hentriacontanoate was isolated from the aerial part of Fraxinus syriaca and characterized using PMR and 13C NMR spectral data and DEPT, HSQC, HMBC, and COSY experiments.

New Caurene-Type Diterpenoid Diglycoside from Pulicaria uliginosa

The new caurene-type diterpenoid diglycoside puligiendioside was isolated from Pulicaria uliginosa. Its structure was established using PMR and 13C NMR spectral data and DEPT, HSQC, HMBC, and COSY experiments. The stereochemical features and absolute configuration of asymmetric centers were determined by an X-ray crystal structure analysis. Crystals of the compound contained three water molecules, one of which was disordered over two positions with total population 0.85. Puligiendioside had the structure ent-caur-16-en-15-O-β-xylosyl-19-α-ester-β-glucopyranosyl.

Antimicrobial chemical constituents from endophytic fungus Phoma sp.

ObjectiveTo evaluate the antimicrobial potential of different extracts of the endophytic fungus Phoma sp. and the tentative identification of their active constituents. MethodsThe extract and compounds were screened for antimicrobial activity using the Agar Well Diffusion Method. Four compounds were purified using column chromatography and their structures were assigned using 1H and 13C NMR spectra, DEPT, 2D COSY, HMQC and HMBC experiments. ResultsThe ethyl acetate fraction of Phoma sp. showed good antifungal, antibacterial, and algicidal properties. One new dihydrofuran derivative, named phomafuranol (1), together with three known compounds, phomalacton (2), (3R)-5-hydroxymellein (3) and emodin (4) were isolated from the ethyl acetate fraction of Phoma sp. Preliminary studies indicated that phomalacton (2) displayed strong antibacterial, good antifungal and antialgal activities. Similarly (3R)-5-hydroxymellein (3) and emodin (4) showed good antifungal, antibacterial and algicidal properties. ConclusionsAntimicrobial activities of the ethyl acetate fraction of the endophytic fungus Phoma sp. and isolated compounds clearly demonstrate that Phoma sp. and its active compounds represent a great potential for the food, cosmetic and pharmaceutical industries.

Synthesis, characterization, spectrophotometric and electrochemistry studies, and DNA cleavage of copper(II) complexes of a new azacrown bis-macrocycle and its mono-cyclic analogue

A new azacrown bis-macrocycle (5) and its mono–cyclic analogue (7) were synthesized and characterized by FT-IR, 1H NMR, 13C NMR, DEPT 13C NMR, MS, and elemental analysis. The reaction with copper(II) nitrate yielded the corresponding complexes, formulated as Cu(5)(NO3)2·3H2O (8), and Cu(7)(NO3)2·2.5H2O (9). Also the stoichiometries of the complexes were determined in alcoholic solution and the results show that for both complexes the ratio of ligand to metal was 1:1 in methanol. The redox behavior of both complexes has been studied by cyclic voltammetry in DMF. Cyclic voltamogram of 8 shows quasi-reversible CuII/CuI redox couple whereas 9 shows a reversible CuII/CuI redox couple. Mono- and bis-macrocycle copper(II) complexes (8 and 9 respectively) cleaved plasmid pGS2 DNA by using an oxidative mechanism with 3- mercaptopropionic acid (MPA) as the reductant under aerobic conditions. The bis-macrocycle copper(II) complex 8 showed higher cleavage efficiency than their mono-macrocycle analogue 9 at the same Cu2+ concentration.

Copper(II) and zinc(II) complexes of mono- and tri-linked azacrown macrocycles: Synthesis, characterization, X-ray structure, phosphodiester hydrolysis and DNA cleavage

A new tri-linked azacrown macrocycle (L2) was synthesized from mono macrocycle analogue (L1) by Williamson etherification and characterized by FT-IR, 1H NMR, 13C NMR, DEPT 13C NMR, MS, and elemental analysis. The reaction of copper(II) and zinc(II) salts yielded corresponding complexes and formulated as CuL1Cl2 (1), CuL1(NO3)2·3H2O (2), Cu2L2(NO3)4·4H2O (3), ZnL1(OAc)2 (4) and Zn3L2(OAc)6·3H2O (5). Mono and trinuclear zinc(II) complexes 4 and 5, respectively, have been tested as catalysts for hydrolysis of 2-hydroxylpropyl-4-nitrophenyl phosphate (HNPP). At pH 8.5 the mononuclear complex 4 was found to be inactive. In contrast, trinuclear complex 5 was hydrolyzing phosphodiester and the reaction was up to 35-fold faster than the unpromoted reaction. Mono and dinuclear copper(II) complexes 2 and 3 cleave plasmid pG2 DNA by using an oxidative mechanism under aerobic conditions. Dinuclear copper(II) complex 3 showed a much higher cleavage efficiency than its mononuclear analogue 2 at the same Cu2+ concentration. The X-ray structure of 1 is reported. In this complex, the Cu(II) is bound by three amine nitrogens from the macrocyclic ligand L1 and two chloride anions as distorted trigonal bipyramidal geometry.

Studies on the synthesis, in vitro antitumor activity of 4H-benzo[h]chromene, 7H-benzo[h]chromene[2,3-d]pyrimidine derivatives and structure–activity relationships of the 2-,3- and 2,3-positions

Some 4H-benzo[h]chromene and 7H-benzo[h]chromeno[2,3-d]pyrimidine derivatives were prepared as potential cytotoxic agents. The in vitro cytotoxic activity of the synthesized compounds was investigated in comparison with the well-known anticancer standard drugs Vinblastine, Colchicine, and Doxorubicin using MTT colorimetric assay. It was found that compounds 23, 15, 20, and 21 showed the highest anticancer activity against the three tumor cell lines MCF-7, HCT, and HepG-2, compared with Vinblastine and Colchicine, while compound 23 was the most active against HepG-2 as compared with Doxorubicin. We explored the SAR of 4H-benzo[h]chromenes with modification at the 2-,3- positions and 7H-benzo[h]chromeno[2,3-d]pyrimidine at 2,3-positions. The structure–activity relationship (SAR) study revealed that the antitumor activity on 4H-benzo[h]chromene and 7H-benzo[h]chromeno[2,3-d]pyrimidine derivatives were significantly affected by the lipophilicity (hydrophobic or hydrophilic), of the substituent at 2-,3- and 2,3-positions. Structures of these compounds were established on the basis of spectral data, IR, 1H NMR, 13C NMR, 13C NMR-DEPT, and MS data.