Palladium catalysed cross coupling reactions on 2,3-isoxazol-17α-ethynyltestosterone, their anti-cancer activity, molecular docking studies and ADMET analysis

[Display omitted] •Sonogashira coupling reaction of Danazol with aryl halides was carried out.•The structure of compound was identified by 1H NMR, 13C NMR, FT-IR and mass spectrometry.•Synthetic compounds were examined for anti-cancer potential.•Result showed coupling derivatives 2, 4 and 5 demonstr...

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Veröffentlicht in:Steroids 2024-12, Vol.212, p.109515, Article 109515
Hauptverfasser: Yadav, Astha, Verma, Anmol, Singh, Saurabh Kumar, Prakash, Rohit, Srivastava, Sanjay, Sethi, Arun, Pratap Singh, Ranvijay
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Sprache:eng
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Zusammenfassung:[Display omitted] •Sonogashira coupling reaction of Danazol with aryl halides was carried out.•The structure of compound was identified by 1H NMR, 13C NMR, FT-IR and mass spectrometry.•Synthetic compounds were examined for anti-cancer potential.•Result showed coupling derivatives 2, 4 and 5 demonstrated effective anti-cancer activities.•ADMET analyses of all derivatives have also been carried out. In the current study, the Sonogashira coupling reaction of danazol with aryl halides was carried out, yielding new aryl substituted danazol derivatives. The synthetic compounds were examined for anti-cancer potential on the HeLa human cervical cancer cell line, and they showed promising cytotoxic action. Synthesized compounds 2, 4 and 5 inhibited the growth of HeLa cervical cancer cells, potentially making them effective anti-cancer drugs in the future. Furthermore, molecular docking studies were performed to evaluate the inhibitory impact of danazol derivatives on the Human Papillomavirus (HPV) target protein (1F9F). The docking results showed a significant inhibitory action against the cervical cancer protein (1F9F). The binding energy (ΔG) values of 1, 2, 3, 4 and 5 against the protein 1F9F were −8.01, −8.70, −9.43, −9.58 and −9.75 kcal/mol, indicating a high affinity of the synthesized compounds to bind with the HPV target proteins compared to their parent compound danazol (1). ADMET analyses of all derivatives have also been carried out.
ISSN:0039-128X
1878-5867
1878-5867
DOI:10.1016/j.steroids.2024.109515