Natural quinazolinones: From a treasure house to promising anticancer leads

Li, Hanbing; Fu, Gaohang; Zhong, Weihui

doi:10.1016/j.ejmech.2022.114915

Cited by 20 publications

(16 citation statements)

References 188 publications

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“…3). [89][90][91][92] For example, the sulfonamide 3m could be transformed into antidiabetic sulfonylurea derivative 3m-urea in 98% yield and 98% ee, which demonstrated the scalability of this powerful protocol for the synthesis of bioactive compounds.…”

Section: Synthetic Applicationsmentioning

confidence: 96%

Electrochemically driven Nickel-Catalyzed Enantioselective Reductive Conjugate (Hetero)Arylation of Enones

Ye,

Ma,

Zhang

et al. 2024

Preprint

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Herein, we report an electrochemical nickel-catalyzed enantioselective reductive conjugate (hetero)arylation of enones in an undivided cell with low-cost electrodes in the absence of external reductants. Aryl bromides/iodides/triflates or vinyl bromides were employed as electrophilic reagents for the efficient preparation of more than 50 valuable β-arylated ketones in a simple manner (up to 97% yield, 97% ee). With the advantages of electrochemistry, excellent functional group tolerance and late-stage modification of complex natural products and pharmaceuticals made the established protocol greener and more economic. Mechanism investigation suggest that a NiI/NiIII cycle is involved in this electro-reductive reaction rather than metal reductant driven Ni0/NiII cycle. Overall, the efficient electrochemical activation and turnover of the nickel catalyst avoid the drawbacks posed by the employment of stoichiometric amount of sensitive metal powder reductants.

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Section: Synthetic Applicationsmentioning

confidence: 96%

Electrochemically driven Nickel-Catalyzed Enantioselective Reductive Conjugate (Hetero)Arylation of Enones

Ye,

Ma,

Zhang

et al. 2024

Preprint

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“…Alkaloids are a diverse group of naturally occurring compounds that contain ring structures and mostly basic nitrogen atoms. [1] Due to their wide pharmacological activity, alkaloids are compelling compounds for the development of drugs and have great potential for the treatment of a wide array of pathologies. These promising alkaloids include luotonin, camptothecin, tryptanthrin, and rutaecarpine.…”

Section: Introductionmentioning

confidence: 99%

FeCl₃/KI‐Catalyzed Tandem Oxidative Cyclization for Switchable Total Synthesis of Luotonin A, B and Derivatives

Song,

Wang,

et al. 2024

Adv Synth Catal

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A total synthesis strategy was developed for the synthesis of luotonin A, B and their analogues using synergistic FeCl<sub>3</sub>/KI‐catalyzed oxidative cyclization. This protocol utilizes cheap and widely available N‐propargyl 2‐methyl‐quinazolinones and arylamines under mild conditions, and it has a wide substrate scope and high atom economy. Different natural products (luotonin A, B and derivatives) can be synthesized via a unique switchable approach. Further transformations from luotonin B to luotonin E and structural modification of natural products demonstrate the potential applications of this method. Moreover, camptothecin can also be modified with the reported protocol to afford the hydroxyl‐substituted product.

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“…Quinazolinones have a wide range of biological activities and pharmacological properties [11], including anti-inflammatory [10], bactericidal [12], anti-tuberculosis [13], anti-diabetic [14], anti-HIV [15], and anti-cancer [16] effects. In particular, natural quinazolinones and quinazolinone derivatives have shown great potential in anticancer research, and several quinazolinone derivatives have been used in clinical cancer treatments, such as idelalisib, nolatrexed, and raltitrexed dihydrochloride [17]; however, no studies on the anti-cancer properties of MITC quinazolinone derivatives have been reported.…”

Section: Introductionmentioning

confidence: 99%

Moringa oleifera Lam. Isothiocyanate Quinazolinone Derivatives Inhibit U251 Glioma Cell Proliferation through Cell Cycle Regulation and Apoptosis Induction

Xie

Yang

Xia

et al. 2023

IJMS

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A major active constituent of Moringa oleifera Lam. is 4-[(α-L-rhamnose oxy) benzyl] isothiocyanate (MITC). To broaden MITC’s application and improve its biological activity, we synthesized a series of MITC quinazolinone derivatives and evaluated their anticancer activity. The anticancer effects and mechanisms of the compound with the most potent anticancer activity were investigated further. Among 16 MITC quinazolinone derivatives which were analyzed, MITC-12 significantly inhibited the growth of U251, A375, A431, HCT-116, HeLa, and MDA-MB-231 cells. MITC-12 significantly inhibited U251 cell proliferation in a time- and dose-dependent manner and decreased the number of EdU-positive cells, but was not toxic to normal human gastric mucosal cells (GES-1). Further, MITC-12 induced apoptosis of U251 cells, and increased caspase-3 expression levels and the Bax:Bcl-2 ratio. In addition, MITC-12 significantly decreased the proportion of U251 cells in the G1 phase and increased it in S and G2 phases. Transcriptome sequencing showed that MITC-12 had a significant regulatory effect on pathways regulating the cell cycle. Further, MITC-12 significantly decreased the expression levels of the cell cycle-related proteins CDK2, cyclinD1, and cyclinE, and increased those of cyclinA2, as well as the p-JNK:JNK ratio. These results indicate that MITC-12 inhibits U251 cell proliferation by inducing apoptosis and cell cycle arrest, activating JNK, and regulating cell cycle-associated proteins. MITC-12 has potential for use in the prevention and treatment of glioma.

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Natural quinazolinones: From a treasure house to promising anticancer leads

Cited by 20 publications

References 188 publications

Electrochemically driven Nickel-Catalyzed Enantioselective Reductive Conjugate (Hetero)Arylation of Enones

Electrochemically driven Nickel-Catalyzed Enantioselective Reductive Conjugate (Hetero)Arylation of Enones

FeCl₃/KI‐Catalyzed Tandem Oxidative Cyclization for Switchable Total Synthesis of Luotonin A, B and Derivatives

Moringa oleifera Lam. Isothiocyanate Quinazolinone Derivatives Inhibit U251 Glioma Cell Proliferation through Cell Cycle Regulation and Apoptosis Induction

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Natural quinazolinones: From a treasure house to promising anticancer leads

Cited by 20 publications

References 188 publications

Electrochemically driven Nickel-Catalyzed Enantioselective Reductive Conjugate (Hetero)Arylation of Enones

Electrochemically driven Nickel-Catalyzed Enantioselective Reductive Conjugate (Hetero)Arylation of Enones

FeCl3/KI‐Catalyzed Tandem Oxidative Cyclization for Switchable Total Synthesis of Luotonin A, B and Derivatives

Moringa oleifera Lam. Isothiocyanate Quinazolinone Derivatives Inhibit U251 Glioma Cell Proliferation through Cell Cycle Regulation and Apoptosis Induction

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FeCl₃/KI‐Catalyzed Tandem Oxidative Cyclization for Switchable Total Synthesis of Luotonin A, B and Derivatives