Synthesis and biological activity of structurally diverse phthalazine derivatives: A systematic review

Sangshetti, Jaiprakash N.; Pathan, Shahebaaz K.; Patil, Rajesh B.; Ansari, Siddique Akber; Chhajed, Santosh S.; Arote, Rohidas; Shinde, Devanand B.

doi:10.1016/j.bmc.2019.07.050

Cited by 43 publications

(19 citation statements)

References 176 publications

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“…Compounds containing pyridine, pyridazine, pyrimidine, pyrazine, -and their fused derivatives-, are described to possess a wide range of biological activities, with these including antiviral, anti-HIV, antituberculosis, antimalarial, antileishmanial, antibacterial, antifungal, anti-inflammatory, anticancer, antihypertensive, diuretics, antiaggregative, antiplatelet, cardiotonics, antineurodegenerative, antidepressant, anxiolytics, anticonvulsivant, analgesic, sedatives, antiallergic, etc. [16,21,[40][41][42][43][44][45][46][47][48][49][50][51][52][53]. A large variety of syntheses are described for these compounds, with some of them using MW technology.…”

Section: Six Membered Ring Azaheterocyclesmentioning

confidence: 99%

Microwave Assisted Reactions of Azaheterocycles Formedicinal Chemistry Applications

et al. 2020

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Microwave (MW) assisted reactions have became a powerful tool in azaheterocycles chemistry during the last decades. Five and six membered ring azaheterocycles are privileged scaffolds in modern medicinal chemistry possessing a large variety of biological activity. This review is focused on the recent relevant advances in the MW assisted reactions applied to azaheterocyclic derivatives and their medicinal chemistry applications from the last five years. The review is divided according to the main series of azaheterocycles, more precisely 5- and 6-membered ring azaheterocycles (with one, two, and more heteroatoms) and their fused analogues. In each case, the reaction pathways, the advantages of using MW, and considerations concerning biological activity of the obtained products were briefly presented.

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Section: Six Membered Ring Azaheterocyclesmentioning

confidence: 99%

Microwave Assisted Reactions of Azaheterocycles Formedicinal Chemistry Applications

et al. 2020

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“…Among diverse N-heterocycles, phthalazines represent a valuable class of compounds and are important subunits of a broad variety of natural products with remarkable biological activities [1][2][3] and are ubiquitous in pharmaceuticals. [4][5][6] An impressive number of known drugs contain a phthalazine core, e.g., hydralazine (used to treat high blood pressure and heart failure), 7 carbazeran (potent cardiac stimulant) 8 and vatalanib (anti-cancer drug) 9,10 and recently reported drug candidate A-196 (potent and selective inhibitor of protein lysine methyltransferases (PKMTs) (Figure 1a).…”

Section: Introductionmentioning

confidence: 99%

Light-driven catalyst-free access to phthalazines: Merging two metal-free domino reactions in one-pot

Guryev

Schuster

Tsogoeva

2022

Preprint

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We report the development of an unprecedented metal-free four-step one-pot synthetic strategy to access high-value functionalized phthalazines using o-methyl benzophenones as starting compounds. Combination of a light-mediated enolization of o-methyl benzophenones/Diels-Alder reaction domino process with a subsequent deprotection/aromatization domino reaction in one-pot leads to sustainable and efficient organic synthesis. The tangible advantages, i.e. absence of catalysts or additives, utilization of commercially available and/or easily accessible substrates, mild reaction conditions, simplicity, and single work-up procedure, make this combined process highly appealing for the direct construction of various 1-aryl-phthalazines.

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“…Phthalazine and its derivative phthalazinone are heterocyclic scaffolds that are extensively explored for potential application in the treatment of a wide range of medical conditions (Vila et al, 2015). Given its significance as a pharmacophore, phthalazine is a key moiety in various new chemical entities that exhibit antidiabetic, anticonvulsant, anti-inflammatory, antihypertensive, and analgesic activities (Young Taek et al, 2017;Sangshetti et al, 2019;Mohd and Mohammad, 2020). Particularly, a wide array of phthalazine-derived compounds have been reported as anticancer agents for various molecular targets (Sung Kim et al, 2004;Loh et al, 2005;Wang et al, 2014).…”

Section: Introductionmentioning

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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Synthesis and biological activity of structurally diverse phthalazine derivatives: A systematic review

Cited by 43 publications

References 176 publications

Microwave Assisted Reactions of Azaheterocycles Formedicinal Chemistry Applications

Microwave Assisted Reactions of Azaheterocycles Formedicinal Chemistry Applications

Light-driven catalyst-free access to phthalazines: Merging two metal-free domino reactions in one-pot

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

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