4-(Dimethylamino)pyridine as an Efficient Catalyst for One-Pot Synthesis of 1,4-Pyranonaphthoquinone Derivatives viaMicrowave-Assisted Sequential Three Component Reaction in Green Solvent

Thành, Nguyễn Hà; Phương, Hoàng Thị; Giang, Le Nhat Thuy; Giang, Nguyen Thi Quynh; Hà, Nguyễn Thị Thu; Anh, Đang Thi Tuyet; Cuong, Vu Duc; Tuyen, Nguyen Van; Kiệm, Phan Văn

doi:10.1177/1934578x211053951

Cited by 9 publications

(5 citation statements)

References 42 publications

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“…20 Owing to the significant role of heterocyclic ring systems in drug discovery and development, many studies have been undertaken to develop biologically active heterocyclic compounds. 21–29…”

Section: Introductionmentioning

confidence: 99%

“…20 Owing to the signicant role of heterocyclic ring systems in drug discovery and development, many studies have been undertaken to develop biologically active heterocyclic compounds. [21][22][23][24][25][26][27][28][29] Podophyllotoxin, an important plant-derived natural product, has several semisynthetic derivatives such as etoposide, teniposide and etophos, which have been employed in chemotherapy for various cancer types. 30 Although podophyllotoxin and its derivatives have been known as tubulin polymerization or DNA topoisomerase II inhibitors, they are too toxic for therapeutic use and causes some side effects.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, molecular docking analysis and in vitro evaluation of new heterocyclic hybrids of 4-aza-podophyllotoxin as potent cytotoxic agents

Nguyen,

Van,

Pham-The

et al. 2024

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular docking analysis and in vitro evaluation of new heterocyclic hybrids of 4-aza-podophyllotoxin as potent cytotoxic agents

Nguyen,

Van,

Pham-The

et al. 2024

RSC Adv.

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“…[9][10][11]27 4-Azapodophyllotoxin analogs (4) displayed outstanding cytotoxic activity against HepG2 and SK-Lu-1 cell lines with an IC 50 < 44 nM (Figure 1). Inspired by the profound biological activities of 4-azapodophyllotoxin, especially 4-aza-podophyllotoxin containing either a difluoromethyl ether group (2) or one fluorine atom (3), as well as a continuation of our research on the discovery of bioactive compounds [28][29][30][31][32][33][34] ; herein, we introduce the synthesis of 2 new potent fluorinated podophyllotoxin-naphthoquinones via multicomponent reactions, and their cytotoxic evaluation against 4 human cancer cell lines (KB, HepG2, MCF7, and A459). Moreover, molecular docking studies were conducted to investigate more deeply and objectively the approximate binding modes of the 2 synthesized compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking, and Cytotoxic Evaluation of Fluorinated Podophyllotoxin Derivatives

Thành

Bao

Pham-The

et al. 2023

Natural Product Communications

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Objective: The study was conducted to evaluate the in vitro and in silico anticancer activity of fluorinated podophyllotoxin derivatives. Methods: Microwave-assisted multicomponent reactions were carried out in an Anton Paar Microwave Synthetic Reactor Monowave 400 in order to synthesize fluorinated podophyllotoxin derivatives. These products were identified by spectral analysis and evaluated for their cytotoxicity against 4 types of human cancer cell lines (KB, HepG2, A549, and MCF7), as well as human embryonic kidney (Hek) 293 cells using MTT protocol. Molecular docking was conducted using 2 crystal structures of tubulin—colchicine (PDB ID: 4O2B) and topoisomerase II—etoposide (PDB ID: 3QX3) complexes. Results: Two potent cytotoxic fluorinated podophyllotoxin–naphthoquinone compounds were synthesized in good yields. They displayed high cytotoxic activity against all the tested cell lines, with IC50 values ranging from 0.58 to 3.17 µM. Notably, product 8a showed low toxicity against the Hek-293 cell line. Molecular docking results showed that products 8a and 8b participated in the same key interactions provided by etoposide with both topoisomerase and DNA chain domains. The binding energy values calculated for 8a and 8b are acceptable. Conclusion: This study revealed that products 8a and 8b exhibited promising in vitro and in silico anticancer activity and could be recognized as promising anticancer agents.

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“…Furthermore, numerous effective synthetic methods have been recorded for generating 2-amino-4H-pyran-3-carbonitrile intermediates. [53][54][55][56][57][58][59][60][61][62] Therefore, as part of our ongoing research focused on the discovery of novel bioactive compounds, [63][64][65][66][67] in this study, we focused on the synthesis and biological evaluation of novel pyrano[2,3-d ]pyrimidine compounds 8a-k. The newly synthesized molecules were evaluated for their AChE inhibitory activity, along with an evaluation of their cytotoxicity, to investigate their potential for use in treating AD.…”

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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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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4-(Dimethylamino)pyridine as an Efficient Catalyst for One-Pot Synthesis of 1,4-Pyranonaphthoquinone Derivatives ***via*Microwave-Assisted Sequential Three Component Reaction in Green Solvent**

Cited by 9 publications

References 42 publications

Synthesis, molecular docking analysis and in vitro evaluation of new heterocyclic hybrids of 4-aza-podophyllotoxin as potent cytotoxic agents

Synthesis, molecular docking analysis and in vitro evaluation of new heterocyclic hybrids of 4-aza-podophyllotoxin as potent cytotoxic agents

Synthesis, Molecular Docking, and Cytotoxic Evaluation of Fluorinated Podophyllotoxin Derivatives

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

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