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  3. Targeted potent antimicrobial and antitumor oxygen-heterocyclic-based pyran analogues: synthesis and computational studies

Targeted potent antimicrobial and antitumor oxygen-heterocyclic-based pyran analogues: synthesis and computational studies

  • Sci Rep. 2024 Apr 29;14(1):9862. doi: 10.1038/s41598-024-59193-2.
Ashraf H F Abd El-Wahab 1,  Rita M Borik 1,  Al-Anood M Al-Dies 2,  Ahmed M Fouda 3,  Hany M Mohamed 1,  Raafat A El-Eisawy 4 5,  Mohamed H Sharaf 6,  Abdullah Y A Alzahrani 7,  Ahmed A Elhenawy 4 8,  Ahmed M El-Agrody 9
Affiliations

Affiliations

  • 1 Department of Chemistry, College of Science, Jazan University, B.O. Box 114, 45142, Jazan, Kingdom of Saudi Arabia.
  • 2 Chemistry Department, Umm Al-Qura University, Al-Qunfudah University College, 21912, Al-Qunfudah, Saudi Arabia.
  • 3 Chemistry Department, Faculty of Science, King Khalid University, 61413, Abha, Saudi Arabia.
  • 4 Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, 11884, Cairo, Egypt.
  • 5 Department of Chemistry, Faculty of Science, Al-Baha University, 65528, Al-Baha, Saudi Arabia.
  • 6 Department of Botany and Microbiology, Faculty of Science, Al-Azhar University, Cairo, 11884, Egypt.
  • 7 Department of Chemistry, Faculty of Science and Arts, King Khalid University, Mohail Assir, Saudi Arabia.
  • 8 Chemistry Department, Faculty of Science and Art, AlBaha University, 65731, Al Bahah, Saudi Arabia.
  • 9 Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, 11884, Cairo, Egypt. elagrody_am@azhar.edu.eg.
PMID: 38684707 DOI: 10.1038/s41598-024-59193-2
Abstract

The process of creating a series of 3-amino-1-aryl-8-methoxy-1H-benzo[f]chromene-2-carbonitriles (4a-q) involved reacting 6-methoxynaphthalen-2-ol (1), the appropriate aromatic aldehydes (2a-q), and malononitrile (3) in an absolute ethanol/piperidine solution under Ultrasonic irradiation. However, the attempt to create 3-amino-1-aryl-1H-benzo[f]chromene-2,8-dicarbonitrile (6a, d, e) was unsuccessful when 6-cyanonaphthalen-2-ol (5) was stirred at room temperature, reflux, Microwave irradiation, or Ultrasonic irradiation. In addition, the target molecules were screened against Staphylococcus aureus (MRSA), Staphylococcus aureus, Bacillus subtilis, Bacillus cereus, Escherichia coli and Klebsiella pneumonia, as well as a panel of three human Cancer cells lines such as MCF-7, HCT-116, HepG-2 and two normal cell lines HFL-1 and WI-38. The obtained results confirmed that the pyran derivatives (4 m, i, k) which have a double chlorine at 3,4/2,3/2,5-positions, a single halogen atom 3-Cl/4-Br (4c, e) and a double bromine at 3,5-positions with a single methoxy group at 2-position (4n), of phenyl ring, and, to a lesser extent, other pyran derivatives with monoihalogenated (4a, b, d, f), dihalogenated (4 g, h, j, l) or trisubstituent phenyl ring (4o, p, q). Furthermore, compounds 4b-e, g, i, j, m, and n showed negligible activity against the two normal cell lines, HFL-1 and WI-38. Moreover, compound 4 g exhibited the strongest antimicrobial activity among the other pyran derivatives (4a-f, g-q) when compared to Ciprofloxacin. The MIC was assessed and screened for compound 4 g, revealing bactericidal effects. Lastly, SAR and molecular docking were studied.

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