Theoretical Prediction of Properties of Cyclopenta[ b ]pyrrol-2-one Derivatives
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TRUCTURE OF MATTER AND QUANTUM CHEMISTRY
Theoretical Prediction of Properties of Cyclopenta[b]pyrrol-2-one Derivatives Li Yan Xua, Yi Zhoub, Bin Wanga, Xiao Rong Wanga,c,d,*, and Qiang Lia a College
of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun, Liaoning, 113001 China b Center for Joint Surgery, Southwest Hospital, Third Military Medical University (Army Medical University), Chongqing, China c State Key Laboratory of Polymer Materials Engineering, Sichuan University, Chengdu, Sichuan, 610065 China d Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, 214122 China * e-mail: [email protected] Received October 9, 2019; revised October 9, 2019; accepted November 12, 2019
Abstract—The geometrical structures of the cyclopenta[b]pyrrol-2-ones were optimized at the DFT/B3LYP/631G* level of theory, and the obtained structures were confirmed to be minima on the potential energy surface by frequency calculations. Based on the optimized configurations, electronic excitation and emission were studied with the TD-DFT method. The energy behavior of A, B, and C have been examined in the THF solvent using the polarizable continuum (PCM) model. Molecular frontier orbital energy levels, UV–Vis spectra, heat maps, and fluorescence properties were investigated in detail. Furthermore, based on an analysis of hydrogen bonding interactions between HIV-1 protease and compound C, it can be concluded that C is expected to form a stable hydrogen bonding with ILE 50. All the work in this paper provides a theoretical basis for the research on pyrrol-2-ones. Keywords: DFT, pyrrol-2-ones, theoretical absorption spectra, fluorescence, electron excitation DOI: 10.1134/S0036024420100313
INTRODUCTION Heterocyclic compounds containing pyrrol-2-ones have a wide range of applications in biology, medicine, chemistry, etc. [1, 2]. The development and application of pyrrol-2-ones medicines (e.g., holomycin, oteromycin, ypaoamide, pyrrocidine A, quinolactacin C, …) have enabled researchers to recognize that this type of derivatives has anti-tumor [3, 4], anti-inflammatory, analgetic [5, 6] properties, and can be used as receptor inhibitors [7, 8]. Therefore, a number of new synthetic methods have been developed by the academia and industry to prepare novel pyrrol-2-ones derivatives [9, 10]. In the previous research papers, our group reported the synthesis of a series of pyrrol-2-one derivatives using the one-pot method [11, 12]. However, the quantum chemistry of these heterocyclic compounds and their kinetics as ligands with acceptors have not been studied yet. Herein, DFT and TDDFT methods were adopted to conduct theoretical studies on these pyrrol-2-ones heterocyclic compounds (A, B, C, and C1–C7). In order to further understand this series of compounds (Scheme 1), molecular frontier orbital energy levels, UV–Vis spectra, heat maps, and fluorescence properties were investigated in detail. Furthermo
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