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Synthesis, antimicrobial and antiproliferative activities, molecular docking, and computational studies of novel heterocycles

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Abstract

We studied the reaction of enaminone 3 with some nitrogen nucleophiles to afford the corresponding pyrazole 4, isoxazole 5, and pyrimidine 6 derivatives, and the reactivity of enaminone 3 with heterocyclic amines to afford the corresponding fused pyrrolo[1,2-a]pyrimidine 9a, imidazo[1,2-a]pyrimidine 9b, phenylpyrrolo[1,2-a]pyrimidine 9c, and benzo[4,5]imidazo[1,2-a]pyrimidine 11 derivatives. Additionally, the electrophilic azo-coupling reaction of enaminone 3 with aromatic diazonium salts in pyridine afforded the corresponding intermediate hydrazines 13a–d, which cyclized to pyrazolo[5,1-c][1,2,4]triazine derivatives 14a–d. Moreover, addition of (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one (3) with hydrazonoyl chloride derivatives 15a,b gave novel pyrazole derivatives 17a,b. Almost all of the synthesized heterocyclic compounds exhibited antimicrobial and in vitro anticancer activity (HepG2 and MCF-7 cell lines). Furthermore, the molecular docking of the most effective compound, i.e., 7-(4-fluorophenyl)pyrazolo[5,1-c][1,2,4]triazin-3-yl)(2-hydroxyphenyl)methanone (14c), was studied against (PDB ID: 3t88), (PDB ID: 2wje), (PDB ID: 4ynt), and (PDB ID: 1tgh) to investigate its antimicrobial activity when attached to different proteins with short bond length. Compound 14a docked with (PDB ID: 4hdq) and (PDB ID: 3pxe) with energy affinity of −9.946 and −10.55 kcal/mol, with the pyrazolo[5,1-c][1,2,4]triazine derivative involved in the pockets of the proteins. Moreover; the theoretical and investigational studies of compounds 14a,c were compatible with spectral data obtained at HF/6-31G(d) and DFT/B3LYP/6-31G(d) level.

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Authors and Affiliations

  1. Department of Green Chemistry, National Research Center, P.O. Box.12622, Dokki, Cairo, Egypt

    Asmaa M. Fahim

  2. Department of Photochemistry, National Research Centre, P.O. Box.12622, Dokki, Cairo, Egypt

    Hala E. M. Tolan

  3. Tanning Materials Leather Technology Department, National Research Centre, El-Behouth St., Dokki, 12622, Cairo, Egypt

    Hanem Awad

  4. Department of Organometallic and Organometalloid Chemistry, National Research Centre, P.O. Box.12622, Dokki, Cairo, Egypt

    Eman H. I. Ismael

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Fahim, A.M., Tolan, H.E.M., Awad, H. et al. Synthesis, antimicrobial and antiproliferative activities, molecular docking, and computational studies of novel heterocycles. J IRAN CHEM SOC 18, 2965–2981 (2021). https://doi.org/10.1007/s13738-021-02251-7

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