Synthesis of carbocyclic derivatives of 9 (10 H)‐acridinone, 9H‐carbazole and 10 H‐phenothiazine 5,5‐dioxide as potential immunomodulating agents

Szulc, Zdzisław M.; Młochowski, J.; Palus, Jerzy

doi:10.1002/prac.19883300625

Cited by 20 publications

(3 citation statements)

References 9 publications

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“…An Ullmann-type coupling of 2-chlorobenzoic acid 2 with p -toluidine provided 2-aminoarylbenzoic acid 3 , which was successively treated with H 2 SO 4 to give 2-methylacridin-9(10 H )-one 4 (Fig. 1B) in 65% yield 32,33 . Subsequently, N -alkylation of acridone 4 with methyl chloroacetate and K 2 CO 3 as base under microwave irradiation at 100 °C furnished methyl 9-oxo-10(9 H )-acridineacetate 5 , that was converted to the corresponding carboxylic acid 6 using NaOH in refluxing ethanol followed by acidification.…”

Section: Resultsmentioning

confidence: 99%

Probing the Inhibition of Microtubule Affinity Regulating Kinase 4 by N-Substituted Acridones

Voura

Khan

Thysiadis

et al. 2019

Sci Rep

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Microtubule affinity regulating kinase 4 (MARK4) becomes a unique anti-cancer drug target as its overexpression is responsible for different types of cancers. In quest of novel, effective MARK4 inhibitors, some acridone derivatives were synthesized, characterized and evaluated for inhibitory activity against human MARK4. Among all the synthesized compounds, three (7b, 7d and 7f) were found to have better binding affinity and enzyme inhibition activity in µM range as shown by fluorescence binding, ITC and kinase assays. Here we used functional assays of selected potential lead molecules with commercially available panel of 26 kinases of same family. A distinctive kinase selectivity profile was observed for each compound. The selective compounds were identified with submicromolar cellular activity against MARK4. Furthermore, in vitro antitumor evaluation against cancerous cells (MCF-7 and HepG2) revealed that compounds 7b, 7d and 7f inhibit cell proliferation and predominantly induce apoptosis in MCF-7 cells, with IC50 values of 5.2 ± 1.2 μM, 6.3 ± 1.2 μM, and 5.8 ± 1.4 μM respectively. In addition, these compounds significantly upsurge the oxidative stress in cancerous cells. Our observations support our approach for the synthesis of effective inhibitors against MARK4 that can be taken forward for the development of novel anticancer molecules targeting MARK4.

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Section: Resultsmentioning

confidence: 99%

Probing the Inhibition of Microtubule Affinity Regulating Kinase 4 by N-Substituted Acridones

Voura

Khan

Thysiadis

et al. 2019

Sci Rep

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“…[18,19] The small energy gap (ΔE ST ) between the singlet, S 1 and triplet, T 1 states, typically around 0.2 eV, is instrumental in facilitating efficient reverse intersystem crossing (rISC). [20][21][22][23][24][25] PTZ's sulfur (S) and nitrogen (N) atoms are crucial in this mechanism, enhancing intramolecular charge transfer and impacting its luminescent properties. [26][27][28] The transition in oxidation states, progressing from sulfide (+ 2) to sulfoxide (+ 4) and sulfone (+ 6) within the phenothiazine unit, induces a profound alteration in the electronic characteristics of phenothiazine 5-oxide and phenothiazine 5,5dioxide units.…”

Section: Introductionmentioning

confidence: 99%

“…In OLED systems, PTZ‐based chromophores demonstrate thermally activated delayed fluorescence (TADF) with 100 % internal quantum efficiency [18,19] . The small energy gap (Δ E ST ) between the singlet, S 1 and triplet, T 1 states, typically around 0.2 eV, is instrumental in facilitating efficient reverse intersystem crossing (rISC) [20–25] . PTZ's sulfur (S) and nitrogen (N) atoms are crucial in this mechanism, enhancing intramolecular charge transfer and impacting its luminescent properties [26–28] …”

Section: Introductionmentioning

confidence: 99%

Exploring the Theoretical Foundations of Thermally Activated Delayed Fluorescence (TADF) Emission: A Comprehensive TD‐DFT Study on Phenothiazine Systems

Banerjee,

Anoop

2024

Chemistry A European J

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This study conducts a thorough theoretical investigation of Thermally Activated Delayed Fluorescence (TADF) in phenothiazine‐based systems, examining ten molecular configurations recognized experimentally as TADF‐active. Employing Time‐Dependent Density Functional Theory (TD‐DFT), our analysis spans the investigation of singlet‐triplet energy gaps ($\Delta E_{ST}$), spin‐orbit coupling, and excitation characteristics using Multiwfn. This approach validates the adherence to El Sayed's rule across these systems but also provides a detailed understanding of charge transfer dynamics, as visualized through heat maps. A significant aspect of our study is the exploration of different oxidation states of sulfur and site substitutions on phenothiazine. This systematic variation aims to identify additional TADF‐active compounds, drawing parallels with properties characterizing other known TADF emitters. Our investigation into Reverse Intersystem Crossing (rISC) rates and the analysis of dihedral angles in relation to $\Delta E_{ST}$ values offer nuanced insights into the TADF behaviours of these molecules. By integrating rigorous computational analysis, we provide a foundational understanding that enhances the design and optimization of phenothiazine‐based materials for optoelectronic applications. This work not only advances our theoretical understanding of TADF in phenothiazine derivatives but also serves as a guide for experimentalists and industry professionals in the strategic design of new TADF materials.

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Kinetics and mechanism of thermal gas-phase elimination of ?-substituted carboxylic acids: role of relative basicity of ?-substituents and acidity of incipient proton

Al‐Awadi

Kaul

El‐Dusouqui

2000

J. Phys. Org. Chem.

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Synthesis of carbocyclic derivatives of 9 (10 H)‐acridinone, 9H‐carbazole and 10 H‐phenothiazine 5,5‐dioxide as potential immunomodulating agents

Cited by 20 publications

References 9 publications

Probing the Inhibition of Microtubule Affinity Regulating Kinase 4 by N-Substituted Acridones

Probing the Inhibition of Microtubule Affinity Regulating Kinase 4 by N-Substituted Acridones

Exploring the Theoretical Foundations of Thermally Activated Delayed Fluorescence (TADF) Emission: A Comprehensive TD‐DFT Study on Phenothiazine Systems

Kinetics and mechanism of thermal gas-phase elimination of ?-substituted carboxylic acids: role of relative basicity of ?-substituents and acidity of incipient proton

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