Synthesis and Evaluation of Antioxidant, Antimicrobial and Anticancer Properties of 2-(Prop-2-yn-1-yloxy)benzaldehyde Derivatives

Konuş M., Aydemir S., Yılmaz C., Kıvrak A., Kizildogan A. K., Arpaci P. U.

LETTERS IN ORGANIC CHEMISTRY, cilt.16, sa.5, ss.415-423, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 16 Sayı: 5
  • Basım Tarihi: 2019
  • Doi Numarası: 10.2174/1570178616666181116100232
  • Dergi Adı: LETTERS IN ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.415-423
  • Anahtar Kelimeler: 2-(prop-2-yn-1-yloxy)benzaldehyde, antioxidant, antibacterial, antifungal, anticancer, human breast carcinoma, BENZALDEHYDES, CYTOTOXICITY, CAPACITY, OIL
  • Van Yüzüncü Yıl Üniversitesi Adresli: Evet

Özet

5-bromo-2-(prop-2-yn-1-yloxy)benzaldehyde (compound 3) and 3,5-di-tert-butyl-2-(prop-2-yn-1-yloxy)benzaldehyde (compound 5) were synthesized via nucleophilic substitution reactions. Compound 5 showed higher antioxidant capacity with respect to compound 3 in all the four different antioxidant activity methods used. Moreover, in phosphomolybdenum assay, compound 5, with 1.1 proportion value, showed almost the same total antioxidant capacity compared to universal trolox standard. Furthermore, Broth microdilution method and agar disc diffusion tests demonstrated that the same compound also exhibited good antibacterial activity towards the bacteria Bacillus subtilis. Finally, both of the benzaldehyde compounds showed high antifungal activity against Aspergillus niger. In this study, compound 5 (IC50: 54.3 mu g/ml) showed significant cytotoxic activity against breast adenocarcinoma cell line MCF-7 with respect to compound 3 (IC50: 173.4 mu g/ml).