Synthesis of novel thiazol-2(3H)-imine derivatives as ergosterol biosynthesis inhibitors, and elucidation of their structures using a 2D NMR technique

OSMANİYE D., LEVENT S., SAĞLIK B. N., Gorgulu S., ÖZKAY Y., KAPLANCIKLI Z. A.

NEW JOURNAL OF CHEMISTRY, vol.47, no.37, pp.17558-17566, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 47 Issue: 37
  • Publication Date: 2023
  • Doi Number: 10.1039/d3nj02883f
  • Journal Name: NEW JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Biotechnology Research Abstracts, Chemical Abstracts Core, Chimica, Compendex, DIALNET
  • Page Numbers: pp.17558-17566
  • Bilecik Şeyh Edebali University Affiliated: No

Abstract

In this study, new imidazole-2,3-dihydrothiazole derivatives were synthesized. It has been noticed that there are few studies on the direction in which the thiazole ring is closed using a thiourea residue. For this purpose, two-dimensional NMR analyses (HMBC, HSQC, and NOESY) were performed for the obtained compounds. The antifungal activities of the compounds were evaluated in vitro using an EUCAST protocol. Compound 2d showed activity against the C. parapsilosis strain with MIC50 = 0.98 mg mL(-1), making it the most potent derivative in the series. In addition, compound 2d inhibited ergosterol biosynthesis by 87.953%. Molecular docking and molecular dynamics simulations performed using compounds 2d and 2e are in harmony with activity studies.