1,2,4-triazole derivatives with morpholine; DFT study and antileishmanial activity

Süleymanoğlu, Nevin; Ustabaş, Reşat; Direkel, Şahin; Alpaslan, Yelda Bingöl; Ünver, Yasemin

doi:10.1139/cjp-2017-0710

Cited by 8 publications

(3 citation statements)

References 24 publications

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“…Thiol forms can adopt different configurations depending on the hydrogen position and which nitrogen donates it. 125 Thiol tautomers with an amine group (−NH 2 ) have been labeled with a single superscript (2a′, 3a′) and thiol forms with an unsaturated −NH group with a double superscript (2a″, 3a″). Different letters have been used to distinguish when the tautomeric forms attain a structural change caused by isomerization (e.g., 2a″, 2c″).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synergy Effects in Heavy Metal Ion Chelation with Aryl- and Aroyl-Substituted Thiourea Derivatives

et al. 2021

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Detection and removal of metal ion contaminants have attracted great interest due to the health risks that they represent for humans and wildlife. Among the proposed compounds developed for these purposes, thiourea derivatives have been shown as quite efficient chelating agents of metal cations and have been proposed for heavy metal ion removal and for components of high-selectivity sensors. Understanding the nature of metal−ionophore activity for these compounds is thus of high relevance.We present a theoretical study on the interaction between substituted thioureas and metal cations, namely, Cd 2+ , Hg 2+ , and Pb 2+ . Two substituent groups have been chosen: 2-furoyl and mtrifluoromethylphenyl. Combining density functional theory simulations with wave function analysis techniques, we study the nature of the metal−thiourea interaction and characterize the bonding properties. Here, it is shown how the N,N′-disubstituted derivative has a strong affinity for Hg 2+ , through cation−hydrogen interactions, due to its greater oxidizing capacity.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Synergy Effects in Heavy Metal Ion Chelation with Aryl- and Aroyl-Substituted Thiourea Derivatives

et al. 2021

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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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“…Leishmaniasis is a disease caused by Leishmania parasites and transmitted by the bites of some sandflies, which differs clinically and epidemiologically, and is an important health problem worldwide [9,10]. Visceral leishmaniasis (VL, Kala-Azar), cutaneous leishmaniasis (CL, Oriental Boil), and mucocutaneous leishmaniasis (MCL) are three different clinical forms of leishmaniasis [11].…”

Section: Introductionmentioning

confidence: 99%

DFT Study and Antiparasitic Activity of Some Azo Dyes Containing Uracil

Süleymanoğlu

Kubaşık

Direkel

2021

Journal of Chemistry

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In this study, for the first time, molecular modeling and antiparasitic activity studies were carried out on some azo dyes containing uracil, 6-amino-5-[(4-nitrophenyl) diazenyl] pyrimidine-2,4 (1H, 3H)-dione (dye I) and 6-amino-5-[(4-bromophenyl) diazenyl] pyrimidin-2,4 (1H, 3H)-dione (dye II), which were resynthesized using the same method in the literature and whose molecular structures were confirmed using FTIR and 1H-NMR methods. In molecular modeling study, all calculations were performed using DFT/B3LYP/6-311++G(d,p) method. The molecular structures of the possible tautomeric forms of dyes I and II were optimized, and their molecular total energies were calculated in the gas phase and DMSO solvent. IR and 1H-NMR spectral data of the possible tautomeric forms of dyes were obtained, and theoretical spectral data were compared with experimental ones. The evaluations show that, for both dyes, the spectral data of the imine-diketo-hydrazone form, which has the lowest energy and is hence determined to be the most stable form, are in agreement with the experimental ones. In antiparasitic activity study, dyes I and II were tested for the first time against parasites Leishmania infantum, Leishmania major, Leishmania tropica promastigotes, and Trichomonas vaginalis trophozoites. In vitro antileishmanial activities against Leishmania promastigotes were tested by microdilution broth assay with Alamar Blue in RPMI 1640 medium, and in vitro trichomonacidal activities against Trichomonas vaginalis parasite were tested using TYM medium. In tests, antileishmanial and trichomonacidal effects were determined by comparing the obtained minimum inhibitory concentration (MIC) and minimum lethal concentration (MLC) values with those obtained for standard drugs (amphotericin B and metronidazole, respectively).

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1,2,4-triazole derivatives with morpholine; DFT study and antileishmanial activity

Cited by 8 publications

References 24 publications

Synergy Effects in Heavy Metal Ion Chelation with Aryl- and Aroyl-Substituted Thiourea Derivatives

Synergy Effects in Heavy Metal Ion Chelation with Aryl- and Aroyl-Substituted Thiourea Derivatives

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

DFT Study and Antiparasitic Activity of Some Azo Dyes Containing Uracil

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