9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-10-<i>p</i>-tolyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

Odabaşoğlu, Mustafa; Kaya, Muharrem; Büyükgüngör, Orhan; Yıldırır, Yılmaz; Türker, Lemi

doi:10.1107/s1600536807010926

Cited by 4 publications

(3 citation statements)

References 18 publications

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“…Bond distances and angles in (I) are in good agreement with the corresponding values obtained for related 3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione derivatives (Odabaşog lu et al, 2007;Sivaraman et al, 1996). The molecular structure of (I), with the atom-labelling scheme, is shown in Fig.…”

Section: Commentsupporting

confidence: 84%

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10-(4-Bromophenyl)-9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione

et al. 2007

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The crystal structure of the title compound, C30H32BrNO3, is stabilized by two C—H...O intermolecular hydrogen bonds and one weak C—H...π interaction. C—H...O hydrogen bonds generate C(10) chains and an R22(16) ring motif. In the title compound, the central pyridine ring in the acridinedione system is approximately planar while the outer two rings adopt half‐chair conformations. The buckling angle between the two halves [at the N...C(PhOMe) line] of 6.94 (2)° shows the degree of planarity of the acridinedione system. The dihedral angle between the planes of the two aromatic rings is 9.66 (2)°.

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Section: Commentsupporting

confidence: 84%

“…The present work is part of a structural study of tetrahydroacridine-1,8(2H,5H,9H,10H)-dione compounds (Odabaşog lu et al, 2007) and we report here the structure of the title compound, (I).…”

Section: Commentmentioning

confidence: 99%

10-(4-Bromophenyl)-9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione

et al. 2007

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“…Their compounds have been utilized in therapy to treat cardiovascular disorders 21 and cancer 17 . Acridine-1,8-diones are also useful as promoters 22 , 23 , photo sensitizers, and laser dyes 22 , 24 , 25 . Due to the fact that even small modifications to the 1,4-dihydropyridine (DHP) moiety can have significant effects on pharmacology 26 , 27 , the synthetic community has shown renewed interest in this core structure 28 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxicity evaluation of novel 1,8-acridinedione derivatives bearing phthalimide moiety as potential antitumor agents

Khatab,

Hammad,

El‐Fakharany

et al. 2023

Sci Rep

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In this study, we aimed to develop hybrid antitumor compounds by synthesizing and characterizing novel N-substituted acrididine-1,8-dione derivatives, designed as hybrids of phthalimide and acridine-1,8-diones. We employed a three-step synthetic strategy and characterized all compounds using IR, 1H NMR, 13C NMR, and LC–MS. The cytotoxicity and antitumor activity of five compounds (8c, 8f, 8h, 8i, and 8L) against four cancer cell lines (H460, A431, A549, and MDA-MB-231) compared to human skin fibroblast cells were evaluated. Among the synthesized compounds, compound 8f showed promising activity against skin and lung cancers, with favorable IC50 values and selectivity index. The relative changes in mRNA expression levels of four key genes (p53, TOP2B, p38, and EGFR) in A431 cells treated with the five synthesized compounds (8c, 8f, 8h, 8i, and 8L) were also investigated. Additionally, molecular docking studies revealed that compound 8f exhibited high binding affinity with TOP2B, p38, p53, and EGFR, suggesting its potential as a targeted anticancer therapy. The results obtained indicate that N-substituted acrididine-1,8-dione derivatives have the potential to be developed as novel antitumor agents with a dual mechanism of action, and compound 8f is a promising candidate for further investigation.

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Acridinedione-phthalimide conjugates: Intramolecular electron transfer and singlet oxygen generation studies for optical and photodynamic therapy applications

El-Khouly,

Khatab,

Abdel-Shafi

et al. 2024

Photochem Photobiol Sci

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We reported herein the synthesis, characterization of hybrid conjugates composed of phthalimide (Phth) and acridine-1,8-diones (Acr) for optical and medical applications. For the synthetic procedure, a three-step synthetic strategy has been utilized. The optical properties of the examined 1,8-acridinedione–phthalimide connected molecules (AcrPhth 1–5) have been examined utilizing various spectroscopic techniques, e.g., steady-state absorption and fluorescence, and time-correlated single photon counting. The steady-state absorption studies showed that AcrPhth 1–5 absorbs the light in the UV and visible region. The fluorescence studies of AcrPhth 1–5 exhibited significant fluorescence quenching compared to the acridinedione control compounds (Acr 1–5) suggesting the occurrence of electron-transfer reactions from the electron donating acridinedione moiety (Acr) to the electron accepting phthalimide moiety (Phth). The rate and efficiency of the electron-transfer reactions were determined from the fluorescence lifetime measurements indicating the fast electron-transfer processes of the covalently connected AcrPhth 1–5 conjugates. Computational studies supported the intramolecular electron-transfer reaction of AcrPhth conjugates using ab initio B3LYP/6-311G methods. In the optimized structures, the HOMO was found to be entirely located on the Acr entity, while the LUMO was found to be entirely on the Phth entity. Further, the synthesized compounds were tested as photosensitizers for generating the singlet oxygen species, which is a key factor in the photodynamic therapy (PDT) applications. The nanosecond laser flash measurements enable us to detect the triplet-excited states of examined Acr and AcrPhth conjugates, determining the triplet quantum yields, and direct detecting the singlet oxygen in an accurate way. From this observation, the singlet quantum yields were found to be in the range of 0.12–0.27 (for Acr 1–5) and 0.07–0.19 (for AcrPhth 1–5 conjugates). The molecular docking studies revealed that compound AcrPhth 2 exhibited high binding affinity with for key genes (p53, TOP2B, p38, and EGFR) suggesting its potential as a targeted anticancer therapy. Graphical abstract

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9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-10-p-tolyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

Cited by 4 publications

References 18 publications

10-(4-Bromophenyl)-9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione

10-(4-Bromophenyl)-9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione

Synthesis and cytotoxicity evaluation of novel 1,8-acridinedione derivatives bearing phthalimide moiety as potential antitumor agents

Acridinedione-phthalimide conjugates: Intramolecular electron transfer and singlet oxygen generation studies for optical and photodynamic therapy applications

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