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Papers by CARIDAD NODA PEREZ

New Journal of Chemistry, 2022

Two new isostructural halogenated dihydroquinolinones were synthesized and characterized by singl... more Two new isostructural halogenated dihydroquinolinones were synthesized and characterized by single crystal X-ray diffraction.

Molecules, Apr 7, 2022

This article is an open access article distributed under the terms and conditions of the Creative... more This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY

Journal of Molecular Modeling

Acta Crystallographica Section A Foundations and Advances, 2018

Journal of Molecular Graphics and Modelling, 2010

Glycerol is a byproduct produced in great quantity by biodiesel industries in transesterification... more Glycerol is a byproduct produced in great quantity by biodiesel industries in transesterification reactions. Finding new applications for glycerol is a current concern of many research groups around the world. This work focuses on a theoretical investigation, at the B3LYP/6-31G* level of theory, into the possibility of using aluminum phthalocyanine (AlPc) and magnesium phthalocyanine (MgPc) in the modelling of catalysts to convert glycerol into alcohol, which has wider industrial applicability. According to our calculations there are strong interactions between the O-terminus of glycerol and the central metal atom of AlPc and MgPc. By applying the Fukui function, HSAB theory and analysis of the frontier molecular orbital, it was possible to explain the way in which glycerol interacts with AlPc and MgPc. As a result of these interactions, there is a considerable change in both electronic and geometric parameters of glycerol, which can be used in designing new strategies to convert glycerol into alcohol.

Acta Crystallographica Section A Foundations and Advances, 2017

Sulfonamides are important organic molecules to study regarding their wide range of reported biol... more Sulfonamides are important organic molecules to study regarding their wide range of reported biological activities 1. In this way, hybrid compounds such as sulfonamide chalcones (a fusion of sulfonamide and chalcone moieties) conserve or even increase their biological activities 1-3. The synthesis and structural analysis of a new sulfonamide chalcone (2,5-dichloro-N-{3-[(2E)-3-(4-nitrophenyl)prop-2-enoyl]phenyl}benzene-1-sulfonamide) (SCH) are reported in this work. Single crystal X-ray diffraction of SCH was collected on Bruker APEX II CCD diffractometer. The refinement of the structure (R1 = 5.79% and Goof = 1.068) was made by SHELX suit programs and indicates the centrosymmetric monoclinic space group C2/c, obtained after squeeze by Platon software. Figure 1(a) shows an ortep representation of SCH. The quasi planarity of the chalcone portion is confirmed by the angle of 5.23° formed between the planes of its aromatic rings, whereas the sulfonamide moiety is almost perpendicular to it (85.72°). Hydrogen bonded dimers are linked in a chain by C-H⋯O interaction, involving the nitrobenzene aromatic ring. These chains form a layer associated by interactions around sulfone and nitro groups. Finally, the crystal packing is obtained by stacking these dimeric chains, intercalating chalcone moieties and sulfonamides aromatic rings. The solvent accessible voids were found with 13.2% of unit cell volume, as shown in Figure 1(b). Hirshfeld surface analysis were performed before SQUEEZE and indicates that crystal packing is also stabilized by both π⋯π and C-H⋯π interactions. Figure 1: Ortep representation of ellipsoids at 50% probability level of SCH (a) and its crystal packing (b). Voids are represented by yellow color.

Journal of Molecular Structure, Apr 1, 2020

Increasingly machine learning processes have been applied in the search and development of compou... more Increasingly machine learning processes have been applied in the search and development of compounds that may have specific physicochemical properties to the desired application. This article describes how a machine learning model led us to the synthesis of three dihydroquinoline derivatives with potential application as a pesticide. The synthesized compounds were predicted to be active against the Tobacco mosaic virus (y 90%) and Fusarium oxysporum (y 78%). Regarding a correlation between the pesticide activity and the molecular structure, the new dihydroquinoline derivatives were structurally characterized using spectroscopic techniques and single crystal X-ray diffraction. They crystallized into orthorhombic (I) and monoclinic (II and III) crystal systems with supramolecular arrangements maintained primarily by non-classical CeH/O hydrogen bonds, which form dimers and chains in their molecular packaging. Frontier molecular orbitals and molecular electrostatic potential maps were undertaken using density functional theory in order to study the electronic properties of the observed molecular conformations. Finally, the developed approach is a useful tool on new pesticide investigation when experimental toxicity data are not available.

The Open Medicinal Chemistry Journal, Oct 17, 2022

The aim was to study the elimination and Phase 2 biotransformation of 4'-hydroxy-4-methoxychalcon... more The aim was to study the elimination and Phase 2 biotransformation of 4'-hydroxy-4-methoxychalcone (1) and its bis-Mannich analog (2) in the small intestine of the rat. Background: Earlier studies indicated that chalcones are promising starting points for drug design. Aminomethylation of drugs is considered to improve their delivery into the human body. Objectives: To set up validated HPLC-UV methods to quantitate the investigated chalcones in the rat intestinal perfusates. Comparison of intestinal disappearance and Phase 2 metabolic profile of the 4'-hydroxychalcone (1) and a bis-Mannich analog (2). Methods: Chalcones 1 and 2 were luminally perfused in the small intestine of rats at a concentration of 240 μM and 280 μM, respectively. Analysis of the collected intestinal perfusate samples was performed by a validated HPLC-UV method. Using HPLC-MS, the samples were analyzed for Phase 2 metabolites as well. Results: Elimination kinetics of the two 4'-hydroxychalcones displayed characteristic differences having the nonpolar chalcone 1 higher elimination rate over the 90-minute ex vivo experiments. HPLC-MS analysis of the perfusates indicated the presence of glucuronide, sulfate, and glutathione conjugates in the parent molecules. Intestinal disappearance and sulfation of the bis-Mannich derivative 2 showed characteristic differences compared to 1 Conclusion: The results demonstrate, to the best of our knowledge, for the first time, how the title structural modification of phenolic chalcones affects intestinal elimination and Phase 2 metabolism of the compounds Highlights: Study on ex vivo intestinal elimination of a 4'-hydroxy-4-methoxychalcone and its bis-Mannich analog. Development of validated HPLC-UV methods for quantitation of 4'-hydroxychalcone derivatives in rat intestinal perfusates. HPLC-MS identification of Phase 2 metabolites of 4'-hydroxychalcones in rat intestinal perfusates.

Química Nova, Feb 1, 2007

SIMULTANEOUS SPECTROPHOTOMETRIC DETERMINATION OF PARACETAMOL AND IBUPROFEN IN PHARMACEUTICAL FORM... more SIMULTANEOUS SPECTROPHOTOMETRIC DETERMINATION OF PARACETAMOL AND IBUPROFEN IN PHARMACEUTICAL FORMULATIONS BY MULTIVARIATE CALIBRATION. A simple method was proposed for determination of paracetamol and ibuprofen in tablets, based on UV measurements and partial least squares. The procedure was performed at pH 10.5, in the concentration ranges 3.00-15.00 μg ml-1 (paracetamol) and 2.40-12.00 μg ml-1 (ibuprofen). The model was able to predict paracetamol and ibuprofen in synthetic mixtures with root mean squares errors of prediction of 0.12 and 0.17 μg ml-1 , respectively. Figures of merit (sensitivity, limit of detection and precision) were also estimated. The results achieved for the determination of these drugs in pharmaceutical formulations were in agreement with label claims and verified by HPLC.

Molecular Diversity, Jan 3, 2020

Cancer is one of the leading causes of death worldwide and requires intense and growing research ... more Cancer is one of the leading causes of death worldwide and requires intense and growing research investments from the public and private sectors. This is expected to lead to the development of new medicines. A determining factor in this process is the structural understanding of molecules with potential anticancer properties. Since the major compounds used in cancer therapies fail to encompass every spectrum of this disease, there is a clear need to research new molecules for this purpose. As it follows, we have studied the class of quinolinones that seem effective for such therapy. This paper describes the structural elucidation of a novel dihydroquinoline by single-crystal X-ray diffraction and spectroscopy characterization. Topology studies were carried through Hirshfeld surfaces analysis and molecular electrostatic potential map; electronic stability was evaluated from the calculated energy of frontier molecular orbitals. Additionally, in silico studies by molecular docking indicated that this dihydroquinoline could act as an anticancer agent due to their higher binding affinity with human aldehyde dehydrogenase 1A1 (ALDH 1A1). Tests in vitro were performed for VERO (normal human skin keratinocytes), B16F10 (mouse melanoma), and MDA-MB-231 (metastatic breast adenocarcinoma), and the results certified that compound as a potential anticancer agent. Graphic abstract A Dihydroquinoline derivative was tested against three cancer cell lines and the results attest that compound as potential anticancer agent.

Journal of Molecular Structure, 2021

In this paper, we performed an in silico-driven design model to synthesize compounds with biologi... more In this paper, we performed an in silico-driven design model to synthesize compounds with biological activity. This rational design has the advantage of decreasing the time and the need for experimental tests and, consequently, the cost related to the search for different candidates. In this way, there is a necessity for more studies that look for new molecules or compounds that may be alternatives to replace the most harmful chemicals for safer options. To contribute to filling this gap, we started an investigation looking for molecules with bioactive potential using a previously developed machine learning model. Leading us to the synthesis, spectroscopic and structural characterization of (E)-2-(4-chlorophenyl)-3-(4-nitrobenzylidene)-1-(phenylsulfonyl)-2,3-dihydroquinolin-4(1 H)-one. Furthermore, considering the predicted biological profile, one of its isomers was incorporated in this study and submitted to experimental validation. The in vitro results indicated that the compounds have antifungal activity against Aspergillus niger in the same range of positive controls. Moreover, both compounds crystallized in the P2 1 / n space group, and their packing is mainly ruled by C-H O interactions. Lastly, we hope that findings can be used as a starting point for new studies where the structural and biological knowledge of dihydroquinolinones leads to the designing of less toxic or nontoxic analogs antifungal agents by changing undesirable fragments by desirable ones in the molecular skeleton.

Journal of Molecular Structure, 2020

Abstract Although the optical properties and applicability of chalcones as potential nonlinear op... more Abstract Although the optical properties and applicability of chalcones as potential nonlinear optical(NLO) materials is well known, hybrids having both chalcone and sulfonamide portions are relatively scarce. In this sense, we are seeking to show if combining both into a double functionalized compound will still have similar or better NLO responses. For this, we have synthetized three sulfonamide-chalcone analogues by changing the substituent bonded to the sulfonamide ring (I = ethoxy; II = Cl and III = Br). These compounds were characterized by spectroscopic methods (NMR, IR and HRMS) and thermal methods (HSM and DSC/TGA). Their crystal structures were determined by Single Crystal X-ray Diffraction (SCXRD) and their molecular structures were compared. Crystallographic results showed that one compound crystallizes in a triclinic system whereas the others crystallize in a monoclinic crystal system. Moreover, their crystal packing is dominated by C–H ⋯ O interactions. In addition to this study and to first characterize these compounds, linear and nonlinear optical (NLO) properties were performed on all three compounds dissolved in dimethyl sulfoxide. One-photon and two-photon absorption (2PA) spectra and incoherent second harmonic generation were obtained by employing different spectroscopic techniques. The interesting results observed in the linear and NLO measurements showed that different groups bounded to the same main backbone did not significantly modify their optical properties, although they strongly affect their crystal structures. σ2PA spectra reveal that the first excited state is allowed by both 1PA and 2PA, which indicates asymmetry in the charge distribution along the π-conjugated molecule structure. NLO properties of compounds I-III agree with other chalcones previously studied, which indicates that adding the benzenesulfonyl group does not influence these properties. Considering the similar experimental values for different substituents, the results further motivate investigation on substituent-based optical properties for other sulfonamide-chalcone hybrids.

Archiv der Pharmazie, Jan 18, 2018

The stereochemistry of non-enzyme catalyzed nucleophilic addition of GSH to 4'-hydroxychalcon... more The stereochemistry of non-enzyme catalyzed nucleophilic addition of GSH to 4'-hydroxychalcone 1 and its bis-Mannich derivative 2 was investigated at different pH values (pH 3.2, 6.1, 7.4, and 8.0). The stereochemical outcome of the reactions was evaluated by HPLC-UV-Vis method. Under strongly acidic conditions (pH 3.2), an unexpected diastereoselective addition of GSH onto the bis-Mannich derivative 2 was observed. Such a selectivity could not be observed in the similar reaction of 2 with N-acetylcysteine. The observed stereoselectivity can be rationalized by ion-pair formation between the protonated Mannich nitrogens and the deprotonated GSH(glutamate)-carboxylate. To the best of our knowledge, this is the first example of reagent-induced asymmetric induction in Michael-type additions of thiols.

Journal of the Brazilian Chemical Society, 2015

Four sulfonamide-chalcone derivatives were prepared and their crystal structure were elucidated b... more Four sulfonamide-chalcone derivatives were prepared and their crystal structure were elucidated by single-crystal X-ray diffraction technique. They were synthesized by Claisen-Schmidt condensation reaction between N-(4-acetylphenyl)benzenesulfonamide or N-(4-acetylphenyl)-2,5-dichlorobenzenesulfonamide with benzaldehyde or p-nitrobenzaldehyde. Values of Z' > 1 are found in three compounds as a consequence of conformerism. The chalcone molecular backbones are featured by different levels of planarity in their conformers. Another conformational variability is in its benzenesulfonamide moiety. In the compound came from N-(4-acetylphenyl) benzenesulfonamide and benzaldehyde, there is a rotation of ca. 180° on the bond axis bridging the sulfonamide and chalcone motifs of one conformer if the two others are taken as references. The cytotoxic activity of all compounds synthesized here and of two other related sulfonamide chalcones was also assessed against three cancer cell lines (SF-295, HCT-8 and MDA-MB-435). The para-nitro compounds were the most active ones among all those tested, regardless of substitution pattern in benzenesulfonamide core.

New Journal of Chemistry, 2023

Physical Chemistry Chemical Physics, 2021

In this contribution, we report the design and theoretical analysis, using the INDO/SCI-SOS quant... more In this contribution, we report the design and theoretical analysis, using the INDO/SCI-SOS quantum chemical formalism, of novel molecular architectures based on planar [N 4 ]-, (2aminobenzylideneiminato)-and tetraazamacrocycle-coordinated nickel(II) complexes, having second-order nonlinear optical (NLO) properties. Calculations indicate that these molecules possess comparable, or even larger, second-order nonlinearity to the bis(salicylaldiminato)Ni II Schiff-base analogues. The nonlinearity of substituted complexes is domin-[a

Journal of Molecular Structure, Mar 1, 2023

Journal of the Brazilian Chemical Society, 2020

Quinolinones are a class of organic compounds known as alkaloids found in several plants and also... more Quinolinones are a class of organic compounds known as alkaloids found in several plants and also can be synthesized. Their large use in therapies regards their wide biological potential like antitumor, psychiatric and neurological agents. Two substances were structurally characterized: (E)-3-(2-nitrobenzylidene)-2-(4-methoxyphenyl)-1-(phenylsulfonyl)-2,3-dihydroquinolin-4(1H)-one (NMQ), and (E)-3-(2-chlorobenzylidene)-2-(2-methoxyphenyl)-1-(phenylsulfonyl)-2,3-dihydroquinolin-4(1H)-one (CMQ). These compounds were synthesized, crystallized, characterized by single crystal X-ray diffraction and theoretical calculations. The NMQ and CMQ crystals are formed by a pair of enantiomers and crystallized in the centrosymmetric group P21/c with similar volume and density. Differences noted on crystal packing and supramolecular arrangement are associated to substituent group chlorine in CMQ and nitro in NMQ. The calculated infrared (IR) spectra show a good agreement with experimental values. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies show CMQ more kinetically stable with a higher resistance to transfer charge than NMQ.

Journal of Molecular Structure, Nov 1, 2020

Compounds with dihydroquinoline-4(1H)-one nuclei have been reported in the literature for being i... more Compounds with dihydroquinoline-4(1H)-one nuclei have been reported in the literature for being important in the development of medicines due to their broad spectrum of activities. In this way, the structural knowledge of this class becomes relevant for obtaining new materials with desired biological properties. This study presents the structural elucidation of five halogenated dihydroquinolines, as well as the discussion about the effect on the molecular conformation of the type and position of halogen atom on aromatic rings. Compounds I and IV differ in halogen substitution on 2-phenyl ring, while compounds III and V differ in halogen substitution on the benzylidene ring. Moreover, compound II has a para-substituted 2-phenyl ring in their molecular structure. The crystal packing of all five molecules is mainly ruled by CeH/O and CeH$$$halogen interactions that form dimers and chains. The shift in position and the kind of the halogen in ring C shows a starring role in the conformation of the studied compounds, and the packaging of these compounds is more susceptible to variations when the halogen position changes.

Journal of Molecular Structure, Sep 1, 2018

Recently, a wide number of bioactivities has been discovered for chalcones. These applications de... more Recently, a wide number of bioactivities has been discovered for chalcones. These applications depend on structural features such as planarity, electronic delocalization paths and substitution pattern on aromatic rings. This work aimed the structural analysis of a novel nitroaminochalcone (C 17 H 12 O 3, NAC) through single crystal X-ray diffraction technique and assessment of its cytotoxicity against tumor cells. NAC is almost completely planar, as evidenced by the low angle formed between its phenyl rings [4.40(12)°], which enables the πelectron delocalization through whole molecule. A resonance-assisted hydrogen bond (RAHB) is another interesting intramolecular feature of NAC, which is assembled between the amino and carbonyl groups into a cyclic S(6) motif. The crystal packing is featured by the formation of dimers stabilized by a ܴ ଶ ଶ (16) motif engaging the carbonyl group and nitrobenzene. These dimers are organized in a 2D layer onto (010) through C-H⋯O interactions involving the nitro e amine groups in a ‫ܥ‬ ଵ ଶ ሺ13ሻ[ܴ ଵ ଶ ሺ4ሻ] motif. Furthermore, Hirshfeld surface analysis showed the crystal packing of NAC is also stabilized by both C-H⋯π and π⋯π interactions. The compound showed high cytotoxicity against human tumor cells.