Advances in synthesis and biological activities of quinazoline scaffold analogues: A review

Murthy Boddapati, S.N.; Babu Bollikolla, Hari; Geetha Bhavani, K; Singh Saini, Harshdeep; Ramesh, Navudu; Babu Jonnalagadda, Sreekantha

doi:10.1016/j.arabjc.2023.105190

Cited by 9 publications

(4 citation statements)

References 98 publications

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“…Meanwhile, quinazoline alkaloids (QAs) as a series of heterocyclic compounds with nitrogen are one of the most significant heterocyclic motifs with diverse chemical reactivities and biological applications [53,54]. Especially, their derivatives play a crucial role in medicinal chemistry, evident in the chemical makeup of a wide range of FDA approved medications, clinical candidates, and bioactive compounds [55]. Unfortunately, none of the isolated alkaloids did not show any obvious antibacterial or cytotoxic activity in our preliminary pharmacological activity experiments.…”

Section: Discussionmentioning

confidence: 92%

Chemical Constituents and Bioactivities of the Plant-Derived Fungus Aspergillus fumigatus

Sang,

Zhang,

Qiu

et al. 2024

Molecules

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A new bergamotane sesquiterpenoid, named xylariterpenoid H (1), along with fourteen known compounds (2–15), were isolated from the crude extract of Aspergillus fumigatus, an endophytic fungus isolated from Delphinium grandiflorum L. Their structures were elucidated mainly by extensive analyses of NMR and MS spectroscopic data. In addition, the screening results of antibacterial and cytotoxic activities of compounds 1–15 showed that compound 4 displayed antibacterial activities against Staphylococcus aureus and MRSA (methicillin-resistant S. aureus) with an MIC value of 3.12 µg/mL.

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Section: Discussionmentioning

confidence: 92%

Chemical Constituents and Bioactivities of the Plant-Derived Fungus Aspergillus fumigatus

Sang,

Zhang,

Qiu

et al. 2024

Molecules

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“…3,4-Dihydroquinazolines and quinazolinones are the privileged N -heterocyclic scaffolds found in many natural products, pharmaceuticals, and bioactive molecules (Figure ). In addition, they are used as functional materials with excellent photophysical properties and potential ligands in asymmetric reactions . Consequently, a diverse range of synthetic routes for their formation have been developed …”

Section: Introductionmentioning

confidence: 99%

One-Pot Three-Component Reaction for the Synthesis of 3,4-Dihydroquinazolines and Quinazolin-4(3H)-ones

Chen,

Ji,

Choi

et al. 2024

J. Org. Chem.

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A highly efficient and straightforward one-pot synthesis of diversely substituted 3,4-dihydroquinazolines and quinazolin-4(3H)-ones has been achieved through a domino three-component assembly reaction of arenediazonium salts, nitriles, and bifunctional aniline derivatives. This new protocol involves three C−N bond formations through the initial formation of N-arylnitrilium intermediates from arenediazonium salts and nitriles, followed by the sequential nucleophilic addition and cyclization reactions with bifunctional anilines, leading to such Nheterocyclic compounds of biological and pharmacological importance. This method offers a simple, expedient, and robust approach with the use of amenable and easily accessible reactants/ reagents under metal-free mild conditions, good functional group tolerance, and high efficiency. The synthetic applications were also demonstrated by derivatization of the products obtained from these processes and syntheses of a diverse range of valuable polycyclic N-heterocycles.

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“…Additionally, further structural modification at the 4-position of the quinazoline ring to further occupy the catalytic machinery in the pocket seems to have a significant impact on the activity and even selectivity for DYRK1A. Meanwhile, the 4-position of the quinazoline ring exhibiting high reactivity has been widely studied and reported. − Based on such a binding mode, with respect to synthetic tractability and freedom to operate, we have mainly focused our research on the catalytic machinery that has not been fully bound by the scaffold, resulting in the generation of 4-position substituted derivatives with completely different structures on the quinazoline moiety. Through fragment fusion and target-based drug design (TBDD) strategies, we reported the structure-guided development of the 6-(1 H -pyrrolo[2,3- b ]pyridin-3-yl)quinazoline-4-substituted series as DYRK1A inhibitors, which showed highly potent inhibitory activity against DYRK1A.…”

Section: Introductionmentioning

confidence: 99%

Discovery of ZJCK-6-46: A Potent, Selective, and Orally Available Dual-Specificity Tyrosine Phosphorylation-Regulated Kinase 1A Inhibitor for the Treatment of Alzheimer’s Disease

Chen,

Gao,

et al. 2024

J. Med. Chem.

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Targeting dual-specificity tyrosine phosphorylationregulated kinase 1A (DYRK1A) has been verified to regulate the progression of tau pathology as a promising treatment for Alzheimer's disease (AD), while the research progress on DYRK1A inhibitors seemed to be in a bottleneck period. In this work, we identified 32 (ZJCK-6-46) as the most potential DYRK1A inhibitor (IC 50 = 0.68 nM) through rational design, systematic structural optimization, and comprehensive evaluation. Compound 32 exhibited acceptable in vitro absorption, distribution, metabolism, and excretion (ADME) properties and significantly reduced the expression of p-Tau Thr212 in Tau (P301L) 293T cells and SH-SY5Y cells. Moreover, compound 32 showed favorable bioavailability, blood−brain barrier (BBB) permeability, and the potential of ameliorating cognitive dysfunction by obviously reducing the expression of phosphorylated tau and neuronal loss in vivo, which was deserved as a valuable molecular tool to reveal the role of DYRK1A in the pathogenesis of AD and to further promote the development of anti-AD drugs.

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Advances in synthesis and biological activities of quinazoline scaffold analogues: A review

Cited by 9 publications

References 98 publications

Chemical Constituents and Bioactivities of the Plant-Derived Fungus Aspergillus fumigatus

Chemical Constituents and Bioactivities of the Plant-Derived Fungus Aspergillus fumigatus

One-Pot Three-Component Reaction for the Synthesis of 3,4-Dihydroquinazolines and Quinazolin-4(3H)-ones

Discovery of ZJCK-6-46: A Potent, Selective, and Orally Available Dual-Specificity Tyrosine Phosphorylation-Regulated Kinase 1A Inhibitor for the Treatment of Alzheimer’s Disease

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