The Brazilian Cerrado biome is considered one of the 25 hotspots worldwide that contain bioactive compounds due to its great biodiversity; however, the reduction of its native area over time due to the expansion of urbanization and agribusiness may have compromised knowledge of its biological variety. In this context, knowledge about Cerrado species can contribute to its biodiversity preservation. This study aims to describe the isolation, molecular architecture and theoretical calculations of the compound (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5 ethyl -6-methylheptan-2 yl]-10,13 dimethyl 2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H cyclopenta[a]phenanthren-3 ol, extracted from the Brazilian Cerrado Miconia burchellii plant. The supramolecular arrangement was described by Hirshfeld surface analysis, demonstrating the intermolecular interactions in the crystalline packing. The structure-property relationship shows the electrostatic potential map analysis, which reveals that the oxygen region is susceptible to electrophilic attack, and the frontier molecular orbital confirmed the kinetic stability of this compound. This study represents another step forward in the knowledge of compounds with pharmacological and medicinal properties extracted from the Cerrado. 2 however variety context preservation isolation 3S,8S,9S,10R,13R,14S,17R172R,5R5 3S8S9S10R13R14S17R172R5R5 SSSRRSRRR 3S,8S,9S,10R,13R,14S,17R 17 2R,5R 5 3S 8S 9S 10R 13R 14S 17R 2R 5R S R (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)- 6methylheptan2 methylheptan 6 -6-methylheptan- yl10,13 yl1013 yl 10,13 10 13 yl]-10,1 2,3,4,7,8,9,11,12,14,15,16,17dodecahydro1H 234789111214151617dodecahydro1H dodecahydroH 2,3,4,7,8,9,11,12,14,15,16,17 dodecahydro 1H 3 4 7 8 9 11 12 14 15 16 H cyclopentaaphenanthren3 cyclopentaaphenanthren cyclopenta a phenanthren cyclopenta[a]phenanthren- ol plant analysis packing structureproperty structure property attack 17R172R 5R5 3S,8S,9S,10R,13R,14S,17R172R,5R 3S8S9S10R13R14S17R172R5R 3S8S9S10R13R14S17R SSSRRSR 1 2R5R RR (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R) 6methylheptan -6-methylheptan yl10 yl10,1 yl101 1013 10,1 yl]-10, 17dodecahydro1H 234789111214151617 2,3,4,7,8,9,11,12,14,15,16,1 cyclopenta[a]phenanthren (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R yl1 yl10, 101 10, yl]-10 23478911121415161 2,3,4,7,8,9,11,12,14,15,16, yl]-1 2347891112141516 2,3,4,7,8,9,11,12,14,15,16 yl]- 234789111214151 2,3,4,7,8,9,11,12,14,15,1 yl] 23478911121415 2,3,4,7,8,9,11,12,14,15, 2347891112141 2,3,4,7,8,9,11,12,14,15 234789111214 2,3,4,7,8,9,11,12,14,1 23478911121 2,3,4,7,8,9,11,12,14, 2347891112 2,3,4,7,8,9,11,12,14 234789111 2,3,4,7,8,9,11,12,1 23478911 2,3,4,7,8,9,11,12, 2347891 2,3,4,7,8,9,11,12 234789 2,3,4,7,8,9,11,1 23478 2,3,4,7,8,9,11, 2347 2,3,4,7,8,9,11 234 2,3,4,7,8,9,1 23 2,3,4,7,8,9, 2,3,4,7,8,9 2,3,4,7,8, 2,3,4,7,8 2,3,4,7, 2,3,4,7 2,3,4, 2,3,4 2,3, 2,3 2,

Chalcones are compounds with wide interesting biological activities including Alzheimer’s disease. A comparative study was performed between the chalcones (E)-1-(2-aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one and 1-(6-amino-1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one regarding the influence of benzodioxol group on their molecular conformations. The first chalcone was neutralized with dilute hydrochloric acid, while solid of the second was filtered and recrystallized from ethanol, both on centrosymmetric space group P21/c. Their molecular packing were evaluated by Hirshfeld surfaces, and both frontier molecular orbitals and molecular electrostatic potential (MEP) map were carried out by density functional theory (DFT) calculations. The compounds are stabilized by C–H…O and C–H…p interactions, as observed on MEP map, while the HOMO-LUMO gap indicated the conformational stability. The pharmacophore mapping approach was carried out for the identification of potential target candidates and then, further molecular docking analysis targeting the beta-secretase 1 (BACE-1) protein as a tactic to develop potential AD inhibitors, was performed. The AutoDock Vina score in redocking result for 2OHQ is –7.4 and –7.6 kcal moL-1. Additionally, the docking results for compounds inside the active site of the 2OHQ structure showed that both compounds bound to the BACE-1 active site with AutoDock Vina score of –6.0 kcal moL-1.

Heterocyclic chalcones have been prominent in the scientific community due to various biological activities reported for these compounds. The structural knowledge of heterocyclic chalcones can help in the understanding of their mechanism of action. The Hirshfeld surfaces were used to study the supramolecular arrangement of two conformers present into asymmetric unit of the heterocyclic chalcone (2E)-3-(4-methylphenyl)-1-(pyridin-3-yl)-prop-2-en-1-one on crystalline state. In addition, the linear polarizability (α), the first hyperpolarizability (β||z), and the second hyperpolarizability (γ) of the conformers were calculated to get a better insight on the linear and nonlinear optical behaviors of these structures in presence of solvent medium, as well as their band-gap energies. The Hirshfeld surfaces confirmed the presence of C−H···N, C−H···O and C−H···C interactions in packaging stabilization. Finally, the 2D fingeprint plot was used to the quantification of contacts and indicated that there are both π···π and C−H···π interactions present in the compound.

The structures of two methoxylated chalcones, namely (E)-1-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one and (E)-3-(4-ethoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one, reveal the effect of the inclusion of the methoxyl and ethoxyl substituents of the conformation on methoxy-chalcone. Structural comparative study between two chalcones was done in this work and some effects on geometric parameters, such as planarity and dihedral angles, were described. In addition, intermolecular interactions responsible for crystalline packaging were investigated by Hirshfeld surfaces and the values of those interactions were analysed by comparing experimental and theoretical models. The molecular stability was expressed in terms of softness and hardness, both obtained from frontier molecular orbitals. Finally, there is a good agreement between calculated and experimental infrared spectrum, which allowed the assignment of the normal vibrational modes.