Recent advances in the synthesis of phthalazin-1(2H)-one core as a relevant pharmacophore in medicinal chemistry

Terán, Carmen; Besada, Pedro; Vila, Noemí; Costas-Lago, Mª Carmen

doi:10.1016/j.ejmech.2018.10.047

Cited by 20 publications

(11 citation statements)

References 123 publications

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“…Some N-substituted phthalazinones have attracted attention as a result of their potential role as anti-asthmatic agents (Ukita et al, 1999), their ability to inhibit thromboxane A2 (TXA2) synthetase and to induce bronchodialation (Yamaguchi et al, 1993). At the present time, a number of phthalazin-1(2H)-onebased drugs are in use (Wu et al, 2012;Teran et al, 2019). A number of reaction pathways to the phthalazinone skeleton are known, notable among which include multi-step reactions involving cyclocondensation reactions of phthalic anhydrides, phthalimides, phthalaldehydic acid or 2-acylbenzoic acids with substituted hydrazines, in the presence of appropriate catalysts (Haider & Holzer, 2004).…”

Section: Chemical Contextmentioning

confidence: 99%

2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study

Izuogu

Asegbeloyin

Jotani³

et al. 2020

Acta Cryst E

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The X-ray crystal structure of the title phthalazin-1-one derivative, C17H16N2O3S {systematic name: 2-[(2,4,6-trimethylbenzene)sulfonyl]-1,2-dihydrophthalazin-1-one}, features a tetrahedral sulfoxide-S atom, connected to phthalazin-1-one and mesityl residues. The dihedral angle [83.26 (4)°] between the organic substituents is consistent with the molecule having the shape of the letter V. In the crystal, phthalazinone-C6-C—H...O(sulfoxide) and π(phthalazinone-N2C4)–π(phthalazinone-C6) stacking [inter-centroid distance = 3.5474 (9) Å] contacts lead to a linear supramolecular tape along the a-axis direction; tapes assemble without directional interactions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of the C—H...O and π-stacking interactions but, also H...H and C—H...C contacts. The calculation of the interaction energies indicate the importance of dispersion terms with the greatest energies calculated for the C—H...O and π-stacking interactions.

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Section: Chemical Contextmentioning

confidence: 99%

2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study

Izuogu

Asegbeloyin

Jotani³

et al. 2020

Acta Cryst E

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“…Magnesium Klorida (101) Magnesium klorida ialah padatan yang umumnya merupakan senyawa garam yang berasal dari asam dan basa kuat, senyawa ini termasuk kedalam senyawa halida ionik yang mudah larut didalam pelarut air, dan biasanya senyawa ini tersedia didalam senyawa hidrat. Senyawa magnesium (102)(103)(104)(105) klorida memiliki sifat fisika dan sifat kimia yaitu diantaranya:…”

Section: Hasil Dan Pembahasan 31 Sifat Senyawa Mgclunclassified

Magnesium Klorida (MgCl2): Karakteristik dan Dinamika Molekuler Pada MgCl2

Wildayati¹,

Zainul²

2019

Preprint

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Magnesium klorida adalah salah satu senyawa kimia dengan rumus MgCl2 dan bentuk hidrat MgCl2.H2O. Magnesium klorida merupakan logam yang kuat, memiliki titik didih 714°C dan titik lebur 1412 °C mampu larut dalam air, serta memiliki sifat thermodinamika seperti∆Hf 298 sebesar-641,3kj/mol dan∆Gf 298 sebesar -591,8 kj/mol. Senyawa ini dapat diperoleh dengan proses kristalisasi dan elektrolisis atau dari reaksi Mg(OH)2 dengan HCl. Magnesium klorida merupakan salah satu garam yang memiliki peranan penting pada industri kimia dan banyak kegunaan dalam kehidupan sehari-hari seperti de-icer, liquid tirest ballast, foam pada instalasi kebakaran. Penelitian ini bertujuan untuk mengetahui karakteristik molekul, dan menganalisis dinamika molekuler serta transport ion pada MgCl2 . Metode yang digunakan adalah metode optimasi dilakukan dengan menggunakan aplikasi Chemoffice3D 15.0 dan ChemDraw Profesional 15.0. Dilihat dari penggambaran chemoffice 15.0 senyawa MgCl2 memiliki karakterisasi transfor ionik yang dapat diukur dari parameter mobilitas ion. Konduktivitas viskositas, dan gerakan hanyut.?Dari?parameter?yang diukur diperoleh?nilai perhitungan kecepatan hanyut Magnesium Klorida (MgCl2) dengan potensial 3,61 V dan jarak antara elektroda adalah 1,5 cm adalah 2, 407 V/ cm.

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“…Phthalazin-1(2H)-one core is a privileged building block for drug development, since phthalazinone derivatives possess a wide spectrum of pharmacological activities, including anticancer, antidiabetic, antiasthmatic, antihistaminic, antihypertensive, antithrombotic, antidepressant, anti-inflammatory and analgesic effects [ 7 , 8 , 9 ]. Several 4-substituted phthalazinones, such as olaparib ( 1 ) and compound 2 ( Figure 1 ), are recognized antitumor agents acting through poly ADP ribose polymerase (PARP) inhibition [ 10 , 11 , 12 ]; pyrazole-phthalazinone hybrids, such as compound 3 , are also promising drug candidates for cancer treatment, acting as aurora kinase inhibitors [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Novel Phthalazin-1(2H)-One Derivatives Displaying a Dithiocarbamate Moiety as Potential Anticancer Agents

et al. 2022

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Nowadays, cancer disease seems to be the second most common cause of death worldwide. Molecular hybridization is a drug design strategy that has provided promising results against multifactorial diseases, including cancer. In this work, two series of phthalazinone-dithiocarbamate hybrids were described, compounds 6–8, which display the dithiocarbamate scaffold at N2, and the compounds 9, in which this moiety was placed at C4. The proposed compounds were successfully synthesized via the corresponding aminoalkyl phthalazinone derivatives and using a one-pot reaction with carbon disulfide, anhydrous H3PO4, and different benzyl or propargyl bromides. The antiproliferative effects of the titled compounds were explored against three human cancer cell lines (A2780, NCI-H460, and MCF-7). The preliminary results revealed significant differences in activity and selectivity depending on the dithiocarbamate moiety location. Thus, in general terms, compounds 6–8 displayed better activity against the A-2780 and MCF-7 cell lines, while most of the analogues of the 9 group were selective toward the NCI-H460 cell line. Compounds 6e, 8e, 6g, 9a–b, 9d, and 9g with IC50 values less than 10 µM were the most promising. The drug-likeness and toxicity properties of the novel phthalazinone-dithiocarbamate hybrids were predicted using Swiss-ADME and ProTox web servers, respectively.

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Recent advances in the synthesis of phthalazin-1(2H)-one core as a relevant pharmacophore in medicinal chemistry

Cited by 20 publications

References 123 publications

2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study

2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study

Magnesium Klorida (MgCl2): Karakteristik dan Dinamika Molekuler Pada MgCl2

Novel Phthalazin-1(2H)-One Derivatives Displaying a Dithiocarbamate Moiety as Potential Anticancer Agents

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