Practical approach to N-benzyl derivatives of 2-amino-8-methoxy-4H-chromene-3-carbonitrile by reductive amination: Exploration of their effects against protein kinases and in silico ADME profiling

Dhiabi, Marwa; Bouattour, Ali; Fakhfakh, Mehdi; Abid, Souhir; Paquin, Ludovic; Thomas, Robert; Bach, Stéphane; Bazureau, Jean Pierre; Ammar, Houcine

doi:10.1016/j.molstruc.2022.134319

Cited by 5 publications

(3 citation statements)

References 26 publications

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“…Pharmaceuticals 2024, 17, x FOR PEER REVIEW in order to identify novel potential anticancer compounds. In continuation of p work [16], it seemed interesting to synthesize some new N-benzylidene derivati amino-4-imino-3,5-dihydro-4H-chromene [2,3-d]pyrimidines and to appraise the toxic activities on a panel of tumoral cell lines. To better understand the pharmac interest of these novel compounds, ADME predictions will be investigated.…”

Section: Synthesis Chemistrymentioning

confidence: 99%

“…In this context and due to the synthetic potential around the 2-amino-4 H -chromene platform and their chromeno[2,3- d ]pyrimidine derivatives, the herein study was designed in order to identify novel potential anticancer compounds. In continuation of previous work [ 16 ], it seemed interesting to synthesize some new N -benzylidene derivatives of 3-amino-4-imino-3,5-dihydro-4 H -chromene[2,3- d ]pyrimidines and to appraise their cytotoxic activities on a panel of tumoral cell lines. To better understand the pharmacological interest of these novel compounds, ADME predictions will be investigated.…”

Section: Introductionmentioning

confidence: 99%

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Design and Synthesis of Novel N-Benzylidene Derivatives of 3-Amino-4-imino-3,5-dihydro-4H-chromeno[2,3-d]pyrimidine under Microwave, In Silico ADME Predictions, In Vitro Antitumoral Activities and In Vivo Toxicity

Karoui,

Dhiabi,

Fakhfakh

et al. 2024

Pharmaceuticals

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The synthesis of a series of new N-benzylidene derivatives of 3-amino-4-imino-3,5-dihydro-4H-chromeno[2,3-d]pyrimidine 10(a-l) bearing two points of molecular diversity is reported. These new compounds were synthesized in five steps including two steps under microwave dielectric heating. They were fully characterized using 1H and 13C NMR, FTIR and HRMS. The in silico physicochemical properties of compounds 10(a-l) were determined according to Lipinski’s rules of five (RO5) associated with the prediction of their bioavailability. These new compounds 10(a-l) were tested for their antiproliferative activities in fibroblasts and eight representative human tumoral cell lines (Huh7 D12, Caco2, MDA-MB231, MDA-MB468, HCT116, PC3, MCF7 and PANC1). Among them, the compounds 10h and 10i showed sub-micromolar cytotoxic activity on tumor cell lines (0.23 < IC50 < 0.3 μM) and no toxicity on fibroblasts (IC50 > 25 μM). A dose-dependent inhibition of Store-Operated Ca+2 Entry (SOCE) was observed in the HEK293 cell line with 10h. In vitro embryotoxicity and angiogenesis on the mCherry transgenic zebrafish line showed that 10h presented no toxic effect and no angiogenic effect on embryos with a dose of 5 μM at 72 hpf.

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Section: Synthesis Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Novel N-Benzylidene Derivatives of 3-Amino-4-imino-3,5-dihydro-4H-chromeno[2,3-d]pyrimidine under Microwave, In Silico ADME Predictions, In Vitro Antitumoral Activities and In Vivo Toxicity

Karoui,

Dhiabi,

Fakhfakh

et al. 2024

Pharmaceuticals

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“…In Figure 4, bioavailability radar diagrams related to the physicochemical properties of ( 1) and ( 2) with BOILED-Egg presentations were given. The pink colored region in the radar diagram symbolizes the appropriate physicochemical area for oral bioavailability (Dhiabi et al, 2023). According to the radar diagram, ( 1) and ( 2) are in the pink area except for the saturation value.…”

Section: Lipophilic Character Analysismentioning

confidence: 99%

Flutriafol ve Triflorlanmış Analoğunun HOMO-LUMO, ESP, NBO ve Lipofilik Karakter Analizleri

SERİN

2023

Ordu Üniversitesi Bilim Ve Teknoloji Dergisi

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This current study focuses on the exploration of the impacts of OH/F isosteric replacement using computational chemistry methods. To this end, Density Functional Theory (DFT) calculations at B3LYP/6-311++G (d, p) level of theory were carried out on flutriafol, a broad-spectrum fungicide, and its trifluorinated analogue. The reflections of OH/F isosteric replacement on frontier molecular orbital energies, reactivity behaviors, electrostatic surface properties and intramolecular interactions were investigated. Also, one of the important consequences of isosteric and bioisosteric replacements is the modification in lipophilic character, which is a remarkable parameter in many respects. Therefore, lipophilic character evaluations were performed for mentioned molecules using SwissADME and Molinspiration software.

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Synthesis, In Vitro α-Amylase Inhibition Activity and Molecular Docking of some Coumarin Derivatives

Chaabouni,

Dhouib,

Khdhiri

et al. 2024

Chemistry Africa

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Practical approach to N-benzyl derivatives of 2-amino-8-methoxy-4H-chromene-3-carbonitrile by reductive amination: Exploration of their effects against protein kinases and in silico ADME profiling

Cited by 5 publications

References 26 publications

Design and Synthesis of Novel N-Benzylidene Derivatives of 3-Amino-4-imino-3,5-dihydro-4H-chromeno[2,3-d]pyrimidine under Microwave, In Silico ADME Predictions, In Vitro Antitumoral Activities and In Vivo Toxicity

Design and Synthesis of Novel N-Benzylidene Derivatives of 3-Amino-4-imino-3,5-dihydro-4H-chromeno[2,3-d]pyrimidine under Microwave, In Silico ADME Predictions, In Vitro Antitumoral Activities and In Vivo Toxicity

Flutriafol ve Triflorlanmış Analoğunun HOMO-LUMO, ESP, NBO ve Lipofilik Karakter Analizleri

Synthesis, In Vitro α-Amylase Inhibition Activity and Molecular Docking of some Coumarin Derivatives

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