Benzochromenopyrimidines: Synthesis, Antiproliferative Activity against Colorectal Cancer and Physicochemical Properties

Choura, Emna; Elghali, Fares; Bernard, Paul J.; Msalbi, Dhouha; Marco‐Contelles, José; Aifa, Sami; Ismaïli, Lhassane; Chabchoub, Fakher

doi:10.3390/molecules27227878

Cited by 5 publications

(13 citation statements)

References 38 publications

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“…This is particularly important to facilitate the attack of aniline, considering the less reactive nitrogen atom of an aniline compared to the good nucleophilicity possessed by benzylamine (aliphatic amine) used in our previously reported work. [26] The spectroscopic and analytical data of all the newly synthesized compounds 3 a-j were in good agreement with the desired structures (Supporting Information).…”

Section: Chemistrysupporting

confidence: 63%

“…In a previous study, we contributed to this field by developing novel benzochromenopyrimidine derivatives. [26] Specifically, we synthesized two compounds, namely, 3-benzyl-5-(3-hydroxyphenyl)-3,5-dihydro-4H-benzo [6,7]chromeno [2,3d]pyrimidine-4,6,11-trione (VII-a) and 3-benzyl-5-phenyl-3,5-dihydro-4H-benzo [6,7]chromeno [2,3-d]pyrimidine-4,6,11-trione (VII-b). These compounds exhibited potent activity against the LoVo and HCT-116 cell lines as shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Biological Evaluation of New Benzochromenopyrimidines for the Therapy of Colon and Lung Cancer

Choura,

El Ghali,

Bernard

et al. 2024

ChemistrySelect

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Herein we report the synthesis of ten newly substituted 3‐phenyl‐5‐aryl‐3,5‐dihydro‐4H‐benzo[6,7]chromeno[2,3‐d]pyrimidin‐4,6,11‐triones (“benzochromenopyrimidines”) in a one‐step reaction, by reacting ethyl 2‐amino‐4‐aryl‐5,10‐dioxo‐5,10‐dihydro‐4H‐benzo[g]chromene‐3‐carboxylates with aniline, and triethyl orthoformate, under acidic catalyst and solvent‐free conditions. These benzochromenopyrimidines were submitted to biological evaluation for in vitro anti‐cancer activity, several derivatives showing higher activity than commonly used chemotherapeutic agents such as oxaliplatin, 5‐fluorouracil, and paclitaxel. In particular, the 5‐(2‐Methoxyphenyl)‐3‐phenyl‐3,5‐dihydro‐4H‐benzo[6,7]chromeno[2,3‐d]pyrimidine‐4,6,11‐trione was identified as the most potent inhibitor among all the new ligands, showing significant cytotoxic activity against all the cancer cell lines tested [human colon cancer cell lines, LoVo and HCT‐116; human lung cancer cells (A549 line)], as evidenced by the significant decrease in IC50 values, while maintaining low cytotoxicity against normal cells. These promising results suggest that this compound deserves further investigation as a potential hit compound for the development of a selective anticancer drug in cancer therapy.

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Section: Chemistrysupporting

confidence: 63%

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New Benzochromenopyrimidines for the Therapy of Colon and Lung Cancer

Choura,

El Ghali,

Bernard

et al. 2024

ChemistrySelect

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“…Furthermore, the researchers tested the antiproliferative activity of all synthesized compounds against two colorectalcancer-cell lines human LoVo and HCT-116. 115 Scheme 88 Benzo[g]chromeno pyrimidine derivatives 283a-j.…”

Section: Benzochromenopyrimidine Derivativesmentioning

confidence: 99%

“…Using a straightforward and cost-effective method, Choura et al 115 produced 3-benzyl-5-aryl-3,5-dihydro-4Hbenzo [6,7]chromeno [2,3-d]pyrimidin-4,6,11-triones 283aj through a one-pot, three-component reaction. The reaction involved readily available 2-hydroxy-1,4-naphthoquinone (1) heated at reflux with aryl 2-cyano-3-arylacrylates 280a-j in the presence of a catalytic amount of triethylamine to form intermediate 2-amino-4-aryl-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carboxylates 281aj.…”

Section: Benzochromenopyrimidine Derivativesmentioning

confidence: 99%

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Recent Advances in the Synthesis of 2-Hydroxy-1,4-naphthoquinone (Lawsone) Derivatives

Sagar,

Shankar,

Khanna

et al. 2023

SynOpen

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Lawsone, also known as 2-hydroxy-1,4-naphthoquinone, has been extensively studied and found to be a crucial precursor in the production of a diverse range of natural products like molecular scaffolds, which are highly sought after for biological research purposes. Due to its unique chemical composition, Lawsone has been utilized for over a century as a starting material for the synthesis of numerous biologically active molecules and materials, showcasing intriguing properties across a wide range of scientific and technological applications. Additionally, Lawsone has been widely used in organic synthesis processes, with its various applications. The recent advances in the synthesis of different scaffolds starting from Lawsone and their applications are being discussed in details in the current review covering the literature during the period of 2017-2023.

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New copper (II) complexes bearing tryptophan‐based Schiff bases and 2,2′‐bipyridine: Crystal structures, DNA/BSA interactions and antiproliferative activities

Özbağcı,

Gültekin,

Aydın

et al. 2024

Applied Organom Chemis

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Abstract[Cu(5‐ClSal‐Trp)(bpy)]·CH3OH (1) and [Cu(3,5‐ClSal‐Trp)(bpy)]·H2O (2) (5‐ClSal‐Trp: Schiff base derived from 5‐chlorosalicylaldehyde and tryptophan, 3,5‐ClSal‐Trp: Schiff base derived from 3,5‐dichlorosalicylaldehyde and tryptophan, bpy: 2,2′‐bipyridine) have been synthesized and analyzed by CHN analysis, FTIR, electronic absorption spectroscopy, ESI‐MS and XRD techniques. Interaction of the complexes with biomolecules {calf thymus DNA (CT‐DNA) and bovine serum albumin (BSA)} has been researched by fluorescence and electronic absorption spectroscopy. The results show that the complexes can bind via a moderate intercalation binding mode. According to the results obtained with both methods, the logKb and logKSV values of the complexes were found to be very close to each other. BSA quenching mechanism was found to be static. The results showed that the interaction between the complexes and BSA is driven by the hydrogen bond and van der Waals interaction. Additionally, the r values of the complexes (the complex 1 = 0.59 nm and the complex 2 = 0.53 nm) calculated from FRET theory suggested that the distance between the complexes (acceptor) and BSA (donor) is quite close. The complexes exhibited free radical scavenging activity compared to the standard antioxidant β‐carotene and catechin. Antiproliferative efficiency of the complexes on both breast cancer cells (MCF‐7 and MDA‐MB‐231) were also researched using the Sulforhodamine B (SRB) viability assay. It was found that the complex 1 (IC50 = 10.99 μM) exhibited higher cytotoxicity than cisplatin (IC50 = 15.6 μM) against MDA‐MB‐231 cell line. Additionally, intracellular reactive oxygen species (ROS) formation was determined by dihydroethidium (DHE) fluorescent staining. N‐acetylcysteine (NAC) was used as an efficient reactive oxygen species (ROS) scavenger. It was observed that newly synthesized Cu (II) complexes exhibited anti‐growth potential in human breast cancer cells. Additionally, it was determined that the complexes induced reactive oxygen species (ROS) formation in cells in a dose‐dependent manner.

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Benzochromenopyrimidines: Synthesis, Antiproliferative Activity against Colorectal Cancer and Physicochemical Properties

Cited by 5 publications

References 38 publications

Synthesis and Biological Evaluation of New Benzochromenopyrimidines for the Therapy of Colon and Lung Cancer

Synthesis and Biological Evaluation of New Benzochromenopyrimidines for the Therapy of Colon and Lung Cancer

Recent Advances in the Synthesis of 2-Hydroxy-1,4-naphthoquinone (Lawsone) Derivatives

New copper (II) complexes bearing tryptophan‐based Schiff bases and 2,2′‐bipyridine: Crystal structures, DNA/BSA interactions and antiproliferative activities

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