Carbazole derivatives: Synthesis, spectroscopic characterization, antioxidant activity, molecular docking study, and the quantum chemical calculations

SERDAROĞLU G., ULUDAĞ N., Ercag E., Sugumar P., Rajkumar P.

JOURNAL OF MOLECULAR LIQUIDS, cilt.330, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 330
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1016/j.molliq.2021.115651
  • Dergi Adı: JOURNAL OF MOLECULAR LIQUIDS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: Carbazole, Antioxidant activity, Molecular docking, Quantum chemical calculations, CONCISE TOTAL-SYNTHESIS, DESCRIPTORS, PRINCIPLE, ALKALOIDS, HARDNESS, SHIFT, IR
  • Sivas Cumhuriyet Üniversitesi Adresli: Evet

Özet

A various carbazole derivativeswere synthesized for the synthesis 2,3-Dihydro-1H-carbazol-4(9H)-one O-acetyl oxime (3), ethyl 2-(2,3,4,9-tetrahydrospiro[carbazole-1,2'-[1,3]dithiolane]-2-yl)acetate (5), 2- hydroxyethyl {2,3,4,9-tetrahydrospiro[1H-carbazole-1,2'[1,3]dithiolane-4-one]-2-yl}-acetamide (7). These products (3, 5, and 7) were characterized by the spectroscopic techniques (IR, H-1 NMR, C-13 NMR and elemental analysis). Then, the observed FT-IR and NMR peaks of the studied compounds were compared with the calculated values. The FMO analyses disclosed that the (5) would prefer intermolecular interactions more than intramolecular interactions because of its higher energy gap. NBO analyses displayed that the n ->Pi* and Pi ->Pi* interactionswere responsible for the lowering of the stabilization energy. Themolecular docking studies showed that (5) exhibited highest binding affinitywith the human glutathione reductase at binding site (-7.21 kcal/mol). Also, the antioxidant activities were investigated using the CUPRAC method, and TEAC coefficient implied that compound (3) have an antioxidant property. In addition, docking calculations of the compound (3), (5), and(7) were performed on bacterial tyrosinase enzyme and human glutathione reductase protein. (C) 2021 Elsevier B.V. All rights reserved.