Synthesis of (3-(naphthalen-1-yl)oxiran-2-yl)(5,6,7,8-tetrahydronaphthalen-2-yl)methanone and reaction with some nucleophiles for anticancer evaluation

Gouhar, Rasha S.; Raafat, Eman

doi:10.1007/s11164-014-1679-5

Cited by 7 publications

(4 citation statements)

References 7 publications

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“…For example, the plant‐derived podophyllotoxin and its semisynthetic derivatives including etoposide, teniposide, doxorubicin, daunorubicin, epirubicin, and idarubicin, were clinically used as chemotherapy agents [3,4] . Furthermore, many studies have been performed on this type of compound for use as an efficient antitumor agent [5–15] . Noting that two compounds YM155 and NSC80467 of tetraline fused with imidazole were identified as the inhibitors of survivin protein for promising selectivity anticancer drugs [16,17] .…”

Section: Introductionmentioning

confidence: 99%

“…[3,4] Furthermore, many studies have been performed on this type of compound for use as an efficient antitumor agent. [5][6][7][8][9][10][11][12][13][14][15] Noting that two compounds YM155 and NSC80467 of tetraline fused with imidazole were identified as the inhibitors of survivin protein for promising selectivity anticancer drugs. [16,17] Because survivin is known to be expressed across most tumor cell types but is rarely present in normal and non-malignant adult cells.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Antiproliferative Evaluation, and Molecular Docking Study of Novel Longifolene‐Derived Tetraline Fused Thiazole‐Amide Derivatives

Lan

Zhu

Lin

et al. 2023

Chemistry & Biodiversity

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Twenty novel longifolene-derived tetraline fused thiazole-amide compounds were synthesized from longifolene, a renewable natural resource. Their structures were characterized by FT-IR, NMR, ESI-MS, and elemental analysis. The in vitro antiproliferative activity of these compounds against SK-OV-3 ovarian cancer cell lines, MCF-7 human breast cancer cell lines, HepG2 human liver cancer cell lines, A549 human lung adenocarcinoma cell lines, and T-24 human bladder cancer cell lines was tested by MTT assay. Compounds 6a-6c displayed significant and broad-spectrum antiproliferative activity against almost the tested cancer cell lines with IC 50 in the range of 7.84 to 55.88 μM, of which compound 6c exhibited excellent antiproliferative activities with 7.84 μM IC 50 against SKOV-3, 13.68 μM IC 50 against HepG2, 15.69 μM IC 50 against A549, 19.13 μM IC 50 against MCF-7, and 22.05 μM IC 50 against T-24, showing better and broad-spectrum antiproliferative effect than that of the positive control 5-FU. Furthermore, the action model was analyzed by the molecular docking study. Some intriguing structure-activity relationships were found and discussed herein by DFT theoretical calculation.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Antiproliferative Evaluation, and Molecular Docking Study of Novel Longifolene‐Derived Tetraline Fused Thiazole‐Amide Derivatives

Lan

Zhu

Lin

et al. 2023

Chemistry & Biodiversity

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“…The tetralin ring also exists in the structures of some clinically used anticancer drugs, for example, the anthracycline antibiotics doxorubicin, daunorubicin, epirubicin, and idarubicin [3], and so on. Many studies have been performed on tetralin derivatives for use as efficient antitumor agents [4][5][6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety

et al. 2020

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Seventeen novel 2-(5-amino-1-(substituted sulfonyl)-1H-1,2,4-triazol-3-ylthio)-6- isopropyl-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one compounds were synthesized from the abundant and naturally renewable longifolene and their structures were confirmed by FT-IR, NMR, and ESI-MS. The in vitro cytotoxicity of the synthesized compounds was evaluated by standard MTT assay against five human cancer cell lines, i.e., T-24, MCF-7, HepG2, A549, and HT-29. As a result, compounds 6d, 6g, and 6h exhibited better and more broad-spectrum anticancer activity against almost all the tested cancer cell lines than that of the positive control, 5-FU. Some intriguing structure–activity relationships were found and are discussed herein by theoretical calculation.

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“…Due to high toxicity, low water solubility, acquired drug resistance and gastrointestinal discomfort, numerous structural modifications were performed, consequently NK611, NPF, GL-311 and TOP53 molecules have been discovered which are being tested in clinical trials, presently [ 27 , 28 , 29 ]. Besides, many studies have been carried out to achieve appropriate tetralin derivatives in terms of all aspects to be an efficacious anticancer drug [ 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ].…”

Section: Introductionmentioning

confidence: 99%

New Thiazoline-Tetralin Derivatives and Biological Activity Evaluation

et al. 2018

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In this study, novel N′-(3-cyclohexyl/phenyl-4-(substituted phenyl)thiazole-2(3H)-ylidene)-2-[(5,6,7,8-tetrahydronaphthalen-2-yl)oxy]acetohydrazide (4a–4k) derivatives were synthesized and their anticancer potency were evaluated on human breast adenocarcinoma cell line (MCF-7), human lung carcinoma cell line (A549) and mouse embryoblast cell line (NIH/3T3) using the MTT method, DNA synthesis inhibition and flow cytometric analysis. Compound 4e bearing 4-methoxyphenyl moiety exhibited the highest antitumor efficiency against MCF-7 cell line with higher DNA synthesis inhibition and apoptotic cell percentages (ealy+late apoptotic cell). On the other hand, compounds 4f, 4g, and 4h bearing 4-bromo, 4-chloro and 4-florophenyl moieties, respectively caused excellent apoptosis levels against A549 cell line when treated with lower concentration even than cisplatin. Anticholinesterase activity of the compounds were also tested, compound 4h showed 49.92% inhibition of acetylcholinesterase (AChE).

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Synthesis of (3-(naphthalen-1-yl)oxiran-2-yl)(5,6,7,8-tetrahydronaphthalen-2-yl)methanone and reaction with some nucleophiles for anticancer evaluation

Cited by 7 publications

References 7 publications

Synthesis, Antiproliferative Evaluation, and Molecular Docking Study of Novel Longifolene‐Derived Tetraline Fused Thiazole‐Amide Derivatives

Synthesis, Antiproliferative Evaluation, and Molecular Docking Study of Novel Longifolene‐Derived Tetraline Fused Thiazole‐Amide Derivatives

Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety

New Thiazoline-Tetralin Derivatives and Biological Activity Evaluation

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