Characterization of novel heterocyclic compounds based on 4-aryl-4H-chromene scaffold as anticancer agents: Design, synthesis, antiprofilerative activity against resistant cancer cells, dual β-tubulin/c-Src inhibition, cell cycle arrest and apoptosis induction

Abdelall, Eman K. A.; Elshemy, Heba A.H.; Labib, Madlen B.; Mohamed, F.

doi:10.1016/j.bioorg.2021.105591

Cited by 14 publications

(13 citation statements)

References 60 publications

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“…Fig. 11 presents a summary of previously reported IC 50 values of related compounds which include 2-amino-7-(dimethylamino)-4-(5- m -tolylisoxazol-3-yl)-4 H -chromene-3-carbonitrile ( A ); 68 2-amino-7-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yloxy)-4- p -tolyl-4 H -chromene-3-carbonitrile ( B ); 69 2-(2-(2-amino-3-cyano-4-(3,4-dimethoxyphenyl)-4 H -chromen-7-yloxy)acetyl)- N -(4-methoxyphenyl)hydrazinecarbothioamide ( C ); 67 N -(2,4-dimethoxyphenyl)-12-phenyl-12 H -naphtho[1′,2′:5,6]pyrano[2,3- d ]pyrimidin-11-amine ( D ); 70 1,1′-4-(1 H -pyrrol-1-yl)phenyl ferrocenedicarboxylate ( E ) 71 and 4-bromophenyl ferrocenecarboxylate ( F ). 72 Compounds A to F exhibited the highest cytotoxicity towards MCF-7 cell lines in their respective studies and this provides a comparative perspective on the cytotoxic activities of 1a , 1b , 3a , and 3j .…”

Section: Resultsmentioning

confidence: 99%

The link between relative stability constant of DNA- and BSA-chromenopyrimidine complexes and cytotoxicity towards human breast cancer cells (MCF-7)

et al. 2023

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Section: Resultsmentioning

confidence: 99%

The link between relative stability constant of DNA- and BSA-chromenopyrimidine complexes and cytotoxicity towards human breast cancer cells (MCF-7)

et al. 2023

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“…Different biological (serum or amino acid deprivation), physical (elutriation, mitosis), or chemical (colchicine, nocodazole, thymidine) treatments are widely used for cell synchronization. There are many chemical drugs, such as paclitaxel, bisindole alkaloids, combretastatin hybrids, tyrosine kinase inhibitors, acrylamide derivatives, and the CDK4/6 inhibitor ly2835219, and 4-aryl-4 h-chromene derivatives 6a-d, can arrest cells in the G0-G1 phase [11,[27][28][29][30][31] . However, the toxic effects of drugs cannot be ignored.…”

Section: Discussionmentioning

confidence: 99%

Tubulin beta 4B chain is involved in the cell cycle process of mouse spermatogonia through CDK2

Mao

Zeng

Kuang

et al. 2022

Preprint

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Tubb4b (tubulin beta-4b chain) is essential for spermatogonia cell growth and development as a microtubule network protein, and its regulatory mechanism remains to be studied. To deeply understand the role of Tubb4b in spermatogonia cell proliferation and the cell cycle, we studied the role of spermatogonia in the control and TUBB4B-KO groups in different cell cycle phases by flow cytometry. We detected the crucial protein CDK2 in each stage by qRT–PCR and Western blotting. The results showed that under the induction of serum starvation, thymidine, and nocodazole under different conditions, mouse spermatogonia remained in the G0-G1 phase, S phase, and G2-M phase, respectively, and the change in the spermatogonia cycle in the Tubb4b-KO group was slower than that in the control group. In the study of cycle synchronization, it was found that the mRNA level of Cdk2 in the G2-M phase increased significantly (P < 0.001), accompanied by the accumulation of CDK2 protein. In the Tubb4b-KO group, the mRNA level of Cdk2 increased significantly in the G0-G1 phase (P < 0.05), decreased significantly in the S phase (P < 0.05) and was accompanied by the fluctuation of CDK2 protein. These data suggest that Tubb4b has the potential to play an important role during the spermatogonial cell cycle by affecting the fluctuating expression of CDK2.

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“…The docking studies demonstrated that 11 interacted with various amino acids like Met344, Thr341, Gln27and 8, and Ala393 by forming hydrogen bonding. [30] Zhang and group designed and synthesized imidazo[4,5c]pyridine-2-one hybrids for glioblastoma treatment. These molecules are explored as Src family kinase inhibitors.…”

Section: Recent Development Of Src Kinase Inhibitorsmentioning

confidence: 99%

“…In addition, in the early and late phases of apoptosis, 11 generated a 7‐ and 63‐fold increase in an apoptotic cell population. The docking studies demonstrated that 11 interacted with various amino acids like Met344, Thr341, Gln27and 8, and Ala393 by forming hydrogen bonding [30] …”

Section: Recent Development Of Src Kinase Inhibitorsmentioning

confidence: 99%

Medicinal Chemistry Perspectives on Recent Advances in Src Kinase Inhibitors as a Potential Target for the Development of Anticancer Agents: Biological Profile, Selectivity, Structure‐Activity Relationship

Teli¹,

Pal²,

Maji³

et al. 2023

Chemistry & Biodiversity

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The physiological Src proto‐oncogene is a protein tyrosine kinase receptor that served as the essential signalling pathway in different types of cancer. The etiology of cancer involved various signalling pathways and Src signalling pathways are also involved in those clusters. Although the dysregulation of Src kinase resulted in cancer being discovered in the late 19th century it is still considered a cult pathway because it is not much explored by different medicinal chemists and oncologists. In this review, we have elaborated about the structure and activation of Src kinase, as well as the development of Src kinase inhibitors. Our group also provided a comprehensive overview of Src inhibitors throughout the last two decades, including their biological activity, structure‐activity relationship, and Src kinase selectivity. The Src binding pocket has been investigated in detail to better comprehend the interaction of Src inhibitors with amino acid residues. We have strengthened the literature with our contribution in terms of molecular docking and ADMET studies of top compounds. We hope that the current analysis will be a useful resource for researchers and provide glimpse of direction toward the design and development of more specific, selective, and potent Src kinase inhibitors.

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Characterization of novel heterocyclic compounds based on 4-aryl-4H-chromene scaffold as anticancer agents: Design, synthesis, antiprofilerative activity against resistant cancer cells, dual β-tubulin/c-Src inhibition, cell cycle arrest and apoptosis induction

Cited by 14 publications

References 60 publications

The link between relative stability constant of DNA- and BSA-chromenopyrimidine complexes and cytotoxicity towards human breast cancer cells (MCF-7)

The link between relative stability constant of DNA- and BSA-chromenopyrimidine complexes and cytotoxicity towards human breast cancer cells (MCF-7)

Tubulin beta 4B chain is involved in the cell cycle process of mouse spermatogonia through CDK2

Medicinal Chemistry Perspectives on Recent Advances in Src Kinase Inhibitors as a Potential Target for the Development of Anticancer Agents: Biological Profile, Selectivity, Structure‐Activity Relationship

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