Synthesis, Structure, Hirshfeld Surface Analysis, Non-Covalent Interaction, and In Silico Studies of 4-Hydroxy-1-[(4-Nitrophenyl)Sulfonyl]Pyrrolidine-2-Carboxyllic Acid

David Izuchukwu Ugwu; Florence Uchenna Eze; Chigozie Julius Ezeorah; Lydia Rhyman; Ponnadurai Ramasami; Groutso Tania; Cosmas Chinweike Eze; Chiamaka Peace Uzoewulu; Blessing Chinweotito Ogboo; Obinna Chibueze Okpareke

doi:10.1007/s10870-023-00978-0

Synthesis, Structure, Hirshfeld Surface Analysis, Non-Covalent Interaction, and In Silico Studies of 4-Hydroxy-1-[(4-Nitrophenyl)Sulfonyl]Pyrrolidine-2-Carboxyllic Acid

J Chem Crystallogr. 2023 Mar 9:1-14. doi: 10.1007/s10870-023-00978-0. Online ahead of print.

Authors

David Izuchukwu Ugwu¹, Florence Uchenna Eze¹, Chigozie Julius Ezeorah^{1

2}, Lydia Rhyman^{3

4}, Ponnadurai Ramasami^{3

4}, Groutso Tania⁵, Cosmas Chinweike Eze^{1

6

7}, Chiamaka Peace Uzoewulu^{1

7}, Blessing Chinweotito Ogboo^{1

8}, Obinna Chibueze Okpareke¹

Affiliations

¹ Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, 410001 Nigeria.
² Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC 29208 USA.
³ Computational Chemistry Group, Department of Chemistry, Faculty of Science, University of Mauritius, Réduit, 808037 Mauritius.
⁴ Centre for Natural Product Research, Department of Chemical Sciences, University of Johannesburg, Doornfontein, Johannesburg, 2028 South Africa.
⁵ School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, 1142 New Zealand.
⁶ Natural Science Unit, School of General Studies, University of Nigeria, Nsukka, 410001 Nigeria.
⁷ Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204 USA.
⁸ Department of Chemistry, State University of NewYork at Buffalo, Buffalo, NY 14260 USA.

Abstract

The new compound 4-hydroxy-1-[(4-nitrophenyl)sulfonyl]pyrrolidine-2-carboxyllic acid was obtained by the reaction of 4-hydroxyproline with 4-nitrobenzenesulfonyl chloride. The compound was characterized using single crystal X-ray diffraction studies. Spectroscopic methods including NMR, FTIR, ES-MS, and UV were employed for further structural analysis of the synthesized compound. The title compound was found to have crystallized in an orthorhombic crystal system with space group P2₁2₁2₁. The S1-N1 bond length of 1.628 (2) Å was a strong indication of the formation of the title compound. The absence of characteristic downfield ¹H NMR peak of pyrrolidine ring and the presence of S-N stretching vibration at 857.82 cm^-1 on the FTIR are strong indications for the formation of the sulfonamide. The experimental study was complemented with computations at the B3LYP/6-311G + + (d,p) level of theory to gain more understanding of interactions in the compound at the molecular level. Noncovalent interaction, Hirsfeld surface analysis and interaction energy calculations were employed in the analysis of the supramolecular architecture of the compound. Predicted ADMET parameters, awarded suitable bioavailability credentials, while the molecular docking study indicated that the compound enchants promising inhibition prospects against dihydropteroate synthase, DNA topoisomerase, and SARS-CoV-2 spike.

Graphical abstract: Herein we present the solid state structure, noncovalent interaction and spectroscopic analysis of a prospective bioactive compound 4-hydroxy-1-[(4-nitrophenyl)sulphonyl]pyrrolidine-2-carboxyllic acid.

Supplementary information: The online version contains supplementary material available at 10.1007/s10870-023-00978-0.

Keywords: Hirshfeld surface; Interaction energy; In silico; Non-covalent interaction; Supramolecular structure; Synthesis.

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