Synthesis and Cytotoxic Evaluation of New Fluoro and Trifluoromethyl Substituents Containing Chromeno[2,3‐<i>d</i>]pyrimidines

Thành, Nguyễn Hà; Van, Ha Nguyen; Thi, Phuong Nguyen; Thi, Tuyet Anh Dang; Le‐Nhat‐Thuy, Giang; Thi, Quynh Giang Nguyen; Tuan, Anh Nguyen; Thi, Cham Ba; Quang, Hung Tran; Nguyen, Tuyen Van

doi:10.1002/slct.202300227

Cited by 5 publications

(2 citation statements)

References 60 publications

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“…69,70 In our previous study, utilizing DABCO as a base catalyst and acetonitrile as a solvent, we successfully synthesized 2-amino-5,10-dioxo-4-aryl-5,10-dihydro-4 H -benzo[ g ]chromene-3-carbonitrile compounds in good yields via the microwave-assisted three-component reaction of 1,4-naphthoquinone, malononitrile, and various arylaldehydes. 49 Therefore, in this study, 0.2 mmol of DABCO as a base catalyst was added to the mixture of cyclohexane-1,3-dione (1 mmol), malononitrile (1 mmol), and 4-methoxyaldehyde (1 mmol) in acetonitrile. The reaction mixture was stirred at 82 °C in 15 min under microwave irradiation to furnish 2-amino-4-(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4 H -chromene-3-carbonitrile ( 6a ).…”

Section: Resultsmentioning

confidence: 99%

“…A number of reports have appeared in the literature regarding the multicomponent synthesis of pyrano[2,3- d ]pyrimidines, which are unsaturated six-membered heterocycles formed by fusion of pyran and pyrimidine rings. 48–52 Nevertheless, less works have employed the 2-amino-4 H -pyran-3-carbonitrile derivatives to construct pyrano[2,3- d ]pyrimidines skeleton directly. Furthermore, numerous effective synthetic methods have been recorded for generating 2-amino-4 H -pyran-3-carbonitrile intermediates.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Evaluation of Acetylcholinesterase Inhibitory and Cytotoxic Activities of Pyrano[2,3-d]pyrimidines

Thanh,

Giang,

et al. 2023

Natural Product Communications

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Objective: The study was conducted to evaluate the in vitro acetylcholinesterase (AchE) inhibition activity of novel pyrano[2,3- d]pyrimidine derivatives. Methods: A series of new pyrano[2,3- d]pyrimidine derivatives were synthesized in moderate to good yields (63%-81%) by using microwave-prompted “one-pot” two-step multicomponent reactions of cyclohexane-1,3-dione, malononitrile, aldehydes, and acetic anhydride. Noticeably, Diazabicyclo[2.2.2]octane was successfully employed as a basic catalyst for the formation of 2-amino-4H-pyran-3-carbonitrile intermediates. These products were identified using spectral data, and assessed in terms of their AChE inhibition activity and cytotoxicity against three types of human cancer cell lines including epidermoid carcinoma (KB), hepatoma carcinoma (HepG2), and non-small lung cancer (A549) cell lines. Results: Most of the products depicted moderate to good AChE inhibitory activity, among them, one product with methoxy moiety at meta-position on phenyl group showed the best AchE inhibition activity with IC50 values of 2.20 ± 0.17 µg/mL. Moreover, products exhibited no cytotoxicity against cancer cell lines. Conclusion: This study highlighted that pyrano[2,3- d]pyrimidine derivatives as promising candidates for further investigations directed to the discovery of new AChE inhibitors which could be used in Alzheimer's disease therapy.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Acetylcholinesterase Inhibitory and Cytotoxic Activities of Pyrano[2,3-d]pyrimidines

Thanh,

Giang,

et al. 2023

Natural Product Communications

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Synthesis and Biological Evaluation of New Benzochromenopyrimidines for the Therapy of Colon and Lung Cancer

Choura,

El Ghali,

Bernard

et al. 2024

ChemistrySelect

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Herein we report the synthesis of ten newly substituted 3‐phenyl‐5‐aryl‐3,5‐dihydro‐4H‐benzo[6,7]chromeno[2,3‐d]pyrimidin‐4,6,11‐triones (“benzochromenopyrimidines”) in a one‐step reaction, by reacting ethyl 2‐amino‐4‐aryl‐5,10‐dioxo‐5,10‐dihydro‐4H‐benzo[g]chromene‐3‐carboxylates with aniline, and triethyl orthoformate, under acidic catalyst and solvent‐free conditions. These benzochromenopyrimidines were submitted to biological evaluation for in vitro anti‐cancer activity, several derivatives showing higher activity than commonly used chemotherapeutic agents such as oxaliplatin, 5‐fluorouracil, and paclitaxel. In particular, the 5‐(2‐Methoxyphenyl)‐3‐phenyl‐3,5‐dihydro‐4H‐benzo[6,7]chromeno[2,3‐d]pyrimidine‐4,6,11‐trione was identified as the most potent inhibitor among all the new ligands, showing significant cytotoxic activity against all the cancer cell lines tested [human colon cancer cell lines, LoVo and HCT‐116; human lung cancer cells (A549 line)], as evidenced by the significant decrease in IC50 values, while maintaining low cytotoxicity against normal cells. These promising results suggest that this compound deserves further investigation as a potential hit compound for the development of a selective anticancer drug in cancer therapy.

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Synthesis, in vitro Α-Glucosidase, and acetylcholinesterase inhibitory activities of novel Indol-Fused Pyrano[2,3-D]Pyrimidine compounds

Nguyen,

Tuan,

Thi

et al. 2024

Bioorganic & Medicinal Chemistry Letters

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Synthesis and Cytotoxic Evaluation of New Fluoro and Trifluoromethyl Substituents Containing Chromeno[2,3‐d]pyrimidines

Cited by 5 publications

References 60 publications

Synthesis and Evaluation of Acetylcholinesterase Inhibitory and Cytotoxic Activities of Pyrano[2,3-d]pyrimidines

Synthesis and Evaluation of Acetylcholinesterase Inhibitory and Cytotoxic Activities of Pyrano[2,3-d]pyrimidines

Synthesis and Biological Evaluation of New Benzochromenopyrimidines for the Therapy of Colon and Lung Cancer

Synthesis, in vitro Α-Glucosidase, and acetylcholinesterase inhibitory activities of novel Indol-Fused Pyrano[2,3-D]Pyrimidine compounds

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