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Structure and Computational Studies of New Sulfonamide Compound: {(4-nitrophenyl)sulfonyl}tryptophan.
Eze, Florence Uchenna; Ezeorah, Chigozie Julius; Ogboo, Blessing Chinweotito; Okpareke, Obinna Chibueze; Rhyman, Lydia; Ramasami, Ponnadurai; Okafor, Sunday Nwankwo; Tania, Groutso; Atiga, Simeon; Ejiyi, Thomas Ugochukwu; Ugwu, Mirabel Chinasa; Uzoewulu, Chiamaka Peace; Ayogu, Jude Ikechukwu; Ekoh, Ogechi Chinelo; Ugwu, David Izuchukwu.
  • Eze FU; Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410001, Nigeria.
  • Ezeorah CJ; Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410001, Nigeria.
  • Ogboo BC; Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC 29208, USA.
  • Okpareke OC; Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410001, Nigeria.
  • Rhyman L; Department of Chemistry, State University of New York at Buffalo, Buffalo, NY 14260, USA.
  • Ramasami P; Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410001, Nigeria.
  • Okafor SN; School of Science, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand.
  • Tania G; Computational Chemistry Group, Department of Chemistry, Faculty of Science, University of Mauritius, Réduit 808037, Mauritius.
  • Atiga S; Centre for Natural Product Research, Department of Chemical Sciences, University of Johannesburg, Doornfontein, Johannesburg 2028, South Africa.
  • Ejiyi TU; Computational Chemistry Group, Department of Chemistry, Faculty of Science, University of Mauritius, Réduit 808037, Mauritius.
  • Ugwu MC; Centre for Natural Product Research, Department of Chemical Sciences, University of Johannesburg, Doornfontein, Johannesburg 2028, South Africa.
  • Uzoewulu CP; Department of Pharmaceutical and Medicinal Chemistry, University of Nigeria, Nsukka 410011, Nigeria.
  • Ayogu JI; School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand.
  • Ekoh OC; School of Science, University of Waikato, Private Bag 3105, Hamilton 3240, New Zealand.
  • Ugwu DI; Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410001, Nigeria.
Molecules ; 27(21)2022 Oct 31.
Article in English | MEDLINE | ID: covidwho-2099665
ABSTRACT
Synthesis of sulfonamide through an indirect method that avoids contamination of the product with no need for purification has been carried out using the indirect process. Here, we report the synthesis of a novel sulfonamide compound, ({4-nitrophenyl}sulfonyl)tryptophan (DNSPA) from 4-nitrobenzenesulphonylchloride and L-tryptophan precursors. The slow evaporation method was used to form single crystals of the named compound from methanolic solution. The compound was characterized by X-ray crystallographic analysis and spectroscopic methods (NMR, IR, mass spectrometry, and UV-vis). The sulfonamide N-H NMR signal at 8.07-8.09 ppm and S-N stretching vibration at 931 cm-1 indicate the formation of the target compound. The compound crystallized in the monoclinic crystal system and P21 space group with four molecules of the compound in the asymmetric unit. Molecular aggregation in the crystal structure revealed a 12-molecule aggregate synthon sustained by O-H⋯O hydrogen bonds and stabilised by N-H⋯O intermolecular contacts. Experimental studies were complemented by DFT calculations at the B3LYP/6-311++G(d,p) level of theory. The computed structural and spectroscopic data are in good agreement with those obtained experimentally. The energies of interactions between the units making up the molecule were calculated. Molecular docking studies showed that DNSPA has a binding energy of -6.37 kcal/mol for E. coli DNA gyrase (5MMN) and -6.35 kcal/mol for COVID-19 main protease (6LU7).
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Full text: Available Collection: International databases Database: MEDLINE Main subject: Tryptophan / COVID-19 Limits: Humans Language: English Journal subject: Biology Year: 2022 Document Type: Article Affiliation country: Molecules27217400

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Full text: Available Collection: International databases Database: MEDLINE Main subject: Tryptophan / COVID-19 Limits: Humans Language: English Journal subject: Biology Year: 2022 Document Type: Article Affiliation country: Molecules27217400