Induction of intrinsic apoptosis pathway in colon cancer HCT-116 cells by novel 2-substituted-5,6,7,8-tetrahydronaphthalene derivatives

Gamal-Eldeen, Amira M.; Hamdy, Nehal A.; Abdel-Aziz, Hatem A.; El-Hussieny, Enas A.; Fakhr, Issa M.I.

doi:10.1016/j.ejmech.2014.03.021

Cited by 48Synthesis and biological activityBioactive Compounds and Antitumor AgentsSynthesis and Characterization of Heterocyclic Compounds

Induction of intrinsic apoptosis pathway in colon cancer HCT-116 cells by novel 2-substituted-5,6,7,8-tetrahydronaphthalene derivatives

Gamal-Eldeen, Amira M., Hamdy, Nehal A., Abdel-Aziz, Hatem A., El-Hussieny, Enas A., Fakhr, Issa M.I.·2014·European Journal of Medicinal Chemistry

DOI 10.1016/j.ejmech.2014.03.021

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Abstract

2-Acetyl tetralin (1) reacted with N,N-dimethylformamide dimethylacetal (DMF-DMA) to afford the enaminone 3. The reaction of 3 with piperidine and morpholine afforded the trans enaminone 5a,b, respectively. Compound 3 was treated with primary aromatic amines to give secondary enaminones 6a-e. The enaminone 3 reacted with acetylglycine and hippuric acid to yield pyranones 10a, b, respectively. The reaction of enaminone 3 with 1,4-benzoquinone and 1,4-naphthoquinone gave benzofuranyl tetralin derivatives 14a,b, respectively. Also, when 3 reacted with 5-amino-3-phenyl-1H-pyrazole 15a and 5-amino-1,2,3-triazole 15b, it afforded the new pyrazolo[1,5-a]pyrimidine 17a and 1,2,3-triazolo[1,5-a]pyrimidine 17b, respectively. While the reaction of 3 with pyrimidines 18a, b resulted in the formation of pyrido[2,3-d]pyrimidine derivatives 20a, b, respectively. Investigations of the cytotoxic effect of those compounds against different human cell lines indicated that some compounds showed high selective cytotoxicity against colon cancer HCT-116 cells. Some of these compounds led to DNA damaging and fragmentation that was associated with the induction of apoptosis via mitochondrial pathway. This pathway is initiated by the impairment of mitochondrial transmembrane potential (Δψm) and in response to that the mitochondria released cytochrome c increased, that in turn activated caspase-9 and caspase-3 and induced apoptosis. Compounds 17b and 20b were promising anti-cancer agents that induced intrinsic apoptosis pathway in colon cancer cells.

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THN-fused C3-spirooxindoles should possess good druglikeness because THN and spirooxindole derivatives are privileged drug-like architectures.
“We started with THN54, 55, 56, 57, 58, 59, 60, 61 and spirooxindole derivatives62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72 because they are privileged drug-like architectures, so the resulting THN-fused C3-spirooxindoles should possess good druglikeness (Fig. 2C).”
From Rational drug design, synthesis, and biological evaluation of novel chiral tetrahydronaphthalene-fused spirooxindole as MDM2-CDK4 dual inhibitor against glioblastoma (2020) · cites this paper as [59]

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Authors: Gamal-Eldeen, A. M., Hamdy, N. A., Abdel-Aziz, H. A., El-Hussieny, E. A., & Fakhr, I. M. I.
Affiliations: National Research Centre (EG)
Corresponding author: Hamdy, Nehal A.
ORCID: Hamdy, Nehal A.
Fakhr, Issa M.I.
Venue: European Journal of Medicinal Chemistry
Publisher: Elsevier BV
Published: 2014-04
Volume: 77
Pages: 323-333
ISSN: 0223-5234 (ISSN-L)
DOI: 10.1016/j.ejmech.2014.03.021
OpenAlex: W1993716579
Cited by: 48
References: 82
Citations by year: 2026: 1 · 2025: 4 · 2024: 2 · 2023: 5 · 2022: 5 · 2021: 3 · 2020: 5 · 2019: 5 · 2018: 4 · 2017: 5 · 2016: 5 · 2015: 3 · 2014: 1
FWCI: 2.06
Type: journal article
Language: en
Open access: closed
Locations: European Journal of Medicinal Chemistry (publishedVersion)
PubMed (publishedVersion)
Topics: Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Bioactive Compounds and Antitumor Agents
Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Characterization of Heterocyclic Compounds
Keywords: mitochondrial apoptosis, colon cancer, HCT116 cells, tetralin derivatives, enaminones, pyranones, pyrazolo[1,5-a]pyrimidines, pyrido[2,3-d]pyrimidines, cytochrome c release, caspase-9, caspase-3, mitochondrial membrane potential, DNA fragmentation, selective cytotoxicity, anticancer agents
MeSH terms: Antineoplastic Agents, Colonic Neoplasms, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Humans, Models, Molecular, Pyrazoles, Pyridines, Pyrimidines, Pyrimidinones, Structure-Activity Relationship, Tumor Cells, Cultured, Molecular Structure, Apoptosis, HCT116 Cells, Cell Proliferation, MCF-7 Cells

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Induction of intrinsic apoptosis pathway in colon cancer HCT-116 cells by novel 2-substituted-5,6,7,8-tetrahydronaphthalene derivatives

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