Phthalazine-trione as a blue-green light-emitting moiety: crystal structures, photoluminescence and theoretical calculations

Martins, Felipe Terra; Maia, Lauro J. Q.; Gasparotto, Gisane; Valdo, Ana Karoline Silva Mendanha; Neto, José Antônio Nascimento; Ribeiro, Leandro; Rego, Yuri de Freitas; Silva, Cleiton Moreira da; Fátima, Ângelo de

doi:10.1039/c8nj02976h

Cited by 2 publications

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“…Further, the importance of phthalazine is highlighted by the presence of such pharmacophore as a part of several marketed drugs such as olaparib, azelastine, vatalanib, and zopolrestat ( Figure 1 ; Inskeep et al, 1994 ; Joensuu et al, 2011 ; Gunderson and Moore, 2015 ; Cheng et al, 2019 ). Moreover, phthalazines also exhibit promising prospects as fluorescence probes and luminescence materials ( Saha et al, 2013 ; Martins et al, 2019 ). Similarly, the pyrazole molecule, a five-membered heterocycle with two nitrogen atoms, has emerged as a powerful scaffold due to its therapeutic potential.…”

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confidence: 99%

Novel Pyran-Linked Phthalazinone-Pyrazole Hybrids: Synthesis, Cytotoxicity Evaluation, Molecular Modeling, and Descriptor Studies

et al. 2021

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A series of novel pyran-linked phthalazinone-pyrazole hybrids were designed and synthesized by a facile one-pot three-component reaction employing substituted phthalazinone, 1H-pyrazole-5-carbaldehyde, and active methylene compounds. Optimization studies led to the identification of L-proline and ethanol as efficient catalyst and solvent, respectively. This was followed by evaluation of anticancer activity against solid tumor cell lines of lung and cervical carcinoma that displayed IC50 values in the range of 9.8–41.6 µM. Molecular modeling studies were performed, and crucial interactions with the target protein were identified. The drug likeliness nature of the compounds and molecular descriptors such as molecular flexibility, complexity, and shape index were also calculated to understand the potential of the synthesized molecules to act as lead-like molecule upon further detailed biological investigations as well as 3D-QSAR studies.

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