Insight into structural description of novel 1,4-Diacetyl-3,6-bis(phenylmethyl)-2,5-piperazinedione: synthesis, NMR, IR, Raman, X-ray, Hirshfeld surface, DFT and docking on breast cancer resistance protein
Etse, Koffi Senam; Zaragoza, Guillermo
2022 • In Journal of Molecular Structure, 1248, p. 131435
crystal structure; DFT calculations, Hirshfeld surface, breast cancer resistance protein; diketopiperazine; puckering parameters; Breast cancer resistance proteins; Crystals structures; DFT calculation; DFT calculation, hirshfeld surface, breast cancer resistance protein; Diacetyl; Diketopiperazines; Hirshfeld surfaces; Puckering parameter; Puckerings; Structural descriptions; Analytical Chemistry; Spectroscopy; Organic Chemistry; Inorganic Chemistry
Abstract :
[en] In this work, novel 1,4-diacetyl-3,6-bis(phenylmethyl)-2,5-piperazinedione (2) is prepared exclusively as the (R,S)-stereoisomer evidenced and confirmed by X-ray diffraction analysis. In addition, spectroscopic (NMR, IR, Raman) analyses were used to characterize the new compound. 2 crystallizes in the Pbca orthorhombic space group, with a symmetry center located at the centroid of the diketopiperazine ring. The structure of 2 is compact with the two phenyl rings folded over and under the diketopiperazine ring, conferring thereby a unique S shape to the molecule. The crystal structure is stabilized by intramolecular interactions, whereas the crystal packing is stabilized by intermolecular H-bond and C−H···π interactions. The different intermolecular interactions were confirmed using Hirshfeld surface analysis and molecular fingerprint. Molecular 2D fingerprint that quantify the different interactions highlights that H···H (58.2%), H···O/O···H (24.8%) and C···H/H···C (14.2%) account for 97.2% of all contacts. The topology of the interaction energy in the crystal structure is obtained and described. The Cremer and Pople puckering parameters indicate that the diketopiperazine ring adopts a flattened chair conformation with Θ = 0.00 ° and Q = 0.2233 (11) Å. Moreover, a computational investigation revealed that the optimized structure of 2 using DFT calculation shows excellent agreement with the experimental data. As potential pharmacological active molecule, the molecular docking on breast cancer resistance protein (BCRP) reveals that 2 could interacts with the binding domain residues Phe728, Tyr949, Ser975 and Val978 and could be consider as promising BCRP inhibitor.
Disciplines :
Chemistry
Author, co-author :
Etse, Koffi Senam ; Université de Liège - ULiège > Département de pharmacie > Chimie analytique
Zaragoza, Guillermo; Unidade de Difracción de Raios X, RIAIDT, Universidade de Santiago de Compostela, Santiago de Compostela, Spain
Language :
English
Title :
Insight into structural description of novel 1,4-Diacetyl-3,6-bis(phenylmethyl)-2,5-piperazinedione: synthesis, NMR, IR, Raman, X-ray, Hirshfeld surface, DFT and docking on breast cancer resistance protein
The authors thank the University of Liège for supporting this research work by letting us to access to most of the platform facilities, C. Malherbe (Laboratoire de Chimie Analytique Inorganique, MolSys, University of Liège) for IR and Raman analyses, and C. Karegeya (Laboratoire de Chimie Inorganique Structurale, GreenMAT, CESAM, University of Liège) for SEM micrographs.
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