400
Views
9
CrossRef citations to date
0
Altmetric
Articles

Octa- and tetra-substituted phthalocyanines with methoxyeugenol group: synthesis, characterization and in vitro antimicrobial activity

ORCID Icon, , , &
Pages 1177-1190 | Received 26 Feb 2020, Accepted 16 Apr 2020, Published online: 12 May 2020
 

Abstract

In this study, the novel phthalonitrile derivatives 1 and 2 were synthesized. Tetra-substituted metal-free 1a (H2Pc) and metallophthalocyanines (ZnPc 1b, CoPc 1c and CuPc 1d) bearing four peripheral 4-allyl-2,6-dimethoxyphenol (methoxy-eugenol) groups and octa-substituted metal-free 2a and metallophthalocyanines (ZnPc 2b, CoPc 2c and CuPc 2d) bearing eight peripheral methoxy-eugenol group were synthesized. All new synthesized compounds are characterized by IR, 13C{1H} NMR (for 1 and 2), UV-Vis (for 1a2d) and mass spectroscopy. Antimicrobial activities of the synthesized phthalonitrile derivatives (1 and 2) and phthalocyanine compounds 1a2d were determined by microdilution broth method against nine different bacteria and one yeast species. In this study, CoPc (2c) compound, which has eight peripheral 4-allyl-2,6-dimethoxyphenol, had the highest antibacterial activity (minimum inhibitory concentration [MIC] = 312 μg/mL). In addition, 1b, 1d, 2b and 2d were found to be effective on at least three different bacterial species at different concentrations (MIC = 1250–5000 μg/mL). Shigella flexneri were the most affected bacteria, but none of the compounds were effective against fungal isolate.

Graphical Abstract

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

We are grateful to the research fund of Artvin Çoruh University (P.N: 2019.F90.02.02) and the Scientific & Technological Research Council of Turkey (TUBITAK, project no. 118Z578).

Log in via your institution

Log in to Taylor & Francis Online

PDF download + Online access

  • 48 hours access to article PDF & online version
  • Article PDF can be downloaded
  • Article PDF can be printed
USD 61.00 Add to cart

Issue Purchase

  • 30 days online access to complete issue
  • Article PDFs can be downloaded
  • Article PDFs can be printed
USD 1,057.00 Add to cart

* Local tax will be added as applicable

Related Research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.