Synthesis, characterization, biological activity and theoretical studies of a 2-amino-6-methoxybenzothiazole-based fluorescent Schiff base


Alpaslan G., Boyacioglu B., DEMİR N., TÜMER Y., Yaper G., YILDIRIM N., ...Daha Fazla

JOURNAL OF MOLECULAR STRUCTURE, cilt.1180, ss.170-178, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1180
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.molstruc.2018.11.065
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.170-178
  • İstanbul Teknik Üniversitesi Adresli: Evet

Özet

A new Schiff base, (E)-3,5-dimethoxy-24(6-methoxybenzold]thiazol-2-yliminolmethyl)- phenol, was prepared from the reaction of 2-amino-6-methoxybenzothiazole and 2-hydroxy-4,6dimethoxybenzaldehyde and characterized with elemental analysis, FTIR, UV-VIS, NMR and single crystal X-ray diffraction techniques. Frontier molecular orbitals, molecular electrostatic potential, and chemical reactivity descriptors of the synthesized compound were studied using molecular modeling methods. The antibacterial and antifungal activities of the Schiff base were studied for its minimum inhibitory concentration. The compound showed a higher effect on yeast than against bacteria. The interactions of the compound with DNA were studied with the ultraviolet visible (UV-VIS) spectra and gel electrophoresis method. The experimental results indicated that the 2-amino-6-methoxybenzothiazole-based Schiff base could bind to DNA via an intercalative mode and showed that it cleaved DNA without the need for external agents. Additionally, the Schiff base showed colorimetric sensor properties for fluoride and cyanide anions in dimethyl sulfoxide. (C) 2018 Elsevier B.V. All rights reserved.