Synthesis and antiviral activity of 4-(7,7-dimethyl-4-[4-{N-aroyl/benzyl}1-piperazinyl]-5,6,7,8-tetrahydroquinazolin-2-yl)morpholine derivatives

Selvakumar, Balaraman; Vaidyanathan, Saraswathy; Subbiah, Madhuri; Elango, Kuppanagounder P.

doi:10.24820/ark.5550190.p010.037

Cited by 7 publications

(2 citation statements)

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“…Morpholine derivatives exhibit a diverse array of biological activities, making them a subject of extensive interest and investigation. These compounds have demonstrated their potential such as anticancer (Zhu et al., 2014), anti‐inflammatory (Rathore et al., 2017) anti‐viral (Selvakumar et al., 2017), anti‐oxidant (Gürsoy Kol et al., 2016), anti‐microbial (Salem et al., 2021), analgesic (Ahmadi et al., 2011), and anti‐leishmanial (Süleymanoğlu et al., 2018). On the other hand, quinazolines and/or quinazolinone derivatives are also privileged compound class with a broad spectrum of biological activities such as anti‐cancer (Tokalı, Şenol, et al., 2023) anti‐microbial and anti‐fungal (Mostafavi et al., 2019), anti‐convulsant (Patel et al., 2016), anti‐histaminic (Alagarsamy et al., 2013), anti‐inflammatory (Farag et al., 2015), anti‐leishmanial (Romero et al., 2019), anti‐oxidant and DNA protective (Kuntikana et al., 2016), anti‐tumor (Rahmannejadi et al., 2020), anti‐viral (Wang et al., 2020), anti‐cholinergic (Tokalı et al., 2021), and anti‐diabetic (Tokalı, Demir, et al., 2022).…”

Section: Introductionmentioning

confidence: 99%

A series of quinazolin‐4(3H)‐one‐morpholine hybrids as anti‐lung‐cancer agents: Synthesis, molecular docking, molecular dynamics, ADME prediction and biological activity studies

Tokalı,

Şenol,

Ateşoğlu

et al. 2024

Chem Biol Drug Des

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In this study, we synthesized 15 novel quinazoline‐morpholinobenzylideneamino hybrid compounds from methyl anthranilate and we assessed their cytotoxicity via in vitro assays against A549 and BEAS‐2B cell lines. Molecular docking studies were conducted to evaluate the protein‐ligand interactions and inhibition mechanisms on nine different molecular targets, while molecular dynamics (MD) simulations were carried out to assess the stability of the best docked ligand–protein complexes. Additionally, ADME prediction was carried out to determine physicochemical parameters and drug likeness. According to the cytotoxicity assays, compound 1 (IC50 = 2.83 μM) was found to be the most active inhibitor against A549 cells. While the selectivity index (SI) of compound 1 is 29, the SI of the reference drugs paclitaxel and sorafenib, used in this study, are 2.40 and 4.92, respectively. Among the hybrid compounds, 1 has the best docking scores against VEGFR1 (−11.744 kcal/mol), VEGFR2 (−12.407 kcal/mol) and EGFR (−10.359 kcal/mol). During MD simulations, compound 1 consistently exhibited strong hydrogen bond interactions with the active sites of VEGFR1 and 2, and these interactions were maintained for more than 90% of the simulation time. Additionally, the RMSD and RMSF values of the ligand–protein complexes exhibited high stability at their minimum levels around 1–2 Å. In conclusion, these findings suggest that compound 1 may be a potent and selective inhibitor candidate for lung cancer treatment and inhibition of VEGFR2, especially.

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Section: Introductionmentioning

confidence: 99%

A series of quinazolin‐4(3H)‐one‐morpholine hybrids as anti‐lung‐cancer agents: Synthesis, molecular docking, molecular dynamics, ADME prediction and biological activity studies

Tokalı,

Şenol,

Ateşoğlu

et al. 2024

Chem Biol Drug Des

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“…It is known that disubstituted piperazines can exhibit a wide range of pharmacological activity; they can act as anticonvulsant, 17 antifungal, 18 antiviral, 19 radioprotective, 20 antibacterial and antimalarial 21,22 agents. Accordingly, our studies in this field have shown that piperazine derivatives of pyrano [3,4-c]pyridines display high antibacterial 23 and neurotropic activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 1,2,3-triazole-based hybrids via click reactions

Sirakanyan¹,

Ghochikyan²,

Spinelli³

et al. 2021

Arkivoc

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1,2,3-Triazoles have attracted the interest of researchers due to their wide range of biological activities which include antitumor, anti-leishmanial, bioluminescent and fungicidal activities This paper describes the synthesis of novel triazole hybrids containing biologically active fragments through cycloaddition (click) reactions, with the aim of increasing the diversity of known and active 1,2,3-triazole derivatives. All new compounds have been characterized by physicochemical methods.

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Synthesis and antiviral study of 4-(7,7-dimethyl-4-(piperazin-1-yl)-5,6,7,8-tetrahydroquinazolin-2-yl) morpholine derivatives

et al. 2017

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Synthesis and antiviral activity of 4-(7,7-dimethyl-4-[4-{N-aroyl/benzyl}1-piperazinyl]-5,6,7,8-tetrahydroquinazolin-2-yl)morpholine derivatives

Cited by 7 publications

References 10 publications

A series of quinazolin‐4(3H)‐one‐morpholine hybrids as anti‐lung‐cancer agents: Synthesis, molecular docking, molecular dynamics, ADME prediction and biological activity studies

A series of quinazolin‐4(3H)‐one‐morpholine hybrids as anti‐lung‐cancer agents: Synthesis, molecular docking, molecular dynamics, ADME prediction and biological activity studies

Synthesis of novel 1,2,3-triazole-based hybrids via click reactions

Synthesis and antiviral study of 4-(7,7-dimethyl-4-(piperazin-1-yl)-5,6,7,8-tetrahydroquinazolin-2-yl) morpholine derivatives

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