Synthesis and biological evaluation of new chloro/acetoxy substituted isoindole analogues as new tyrosine kinase inhibitors

Köse, Aytekin; Kaya, Meltem; Kishalı, Nurhan; Akdemir, Atilla; Şahin, Ertan; Kara, Yunus; Şanlı‐Mohamed, Gülşah

doi:10.1016/j.bioorg.2019.103421

Cited by 13 publications

(28 citation statements)

References 26 publications

(34 reference statements)

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“…In light of this information, we decided to examine the effects of cytotoxicities of N -benzylisoindole-1,3-dione derivatives against adenocarcinoma (A549-Luc) cells to expand these studies. Benzyl derivatives of isoindole-1,3-dione 3 and 4 were synthesized according to the method used in our previous work . First, the cytotoxic effects of both compounds against A549-Luc cells were examined.…”

Section: Resultsmentioning

confidence: 99%

“…The substances were obtained from Dr. Kara’s lab and purified by crystallization. The structure and individuality of the obtained substances were proved by nuclear magnetic resonance (NMR) analysis and elemental analysis …”

Section: Methodsmentioning

confidence: 99%

“…They have thoroughly explored the electronic properties of the functional group on the cytotoxicity of some cantharimide derivatives. The tumor inhibitory influence of N -methylcantharimide has been explored in animals. , Recently, we have studied a versatile synthetic approach to the synthesis of new norcantharimide derivatives. − We reported the antiproliferative properties of some of the isoindole-1,3-dione derivatives against different cell lines like MCF-7, A549, HeLa, and HT-29 cell lines. More recently, in particular, we reported the synthesis of diacetoxy and chloroacetoxy substituted isoindole derivatives and their inhibitory effects on the viability of HeLa cells .…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of In Vivo Biological Activity Profiles of Isoindole-1,3-dione Derivatives: Cytotoxicity, Toxicology, and Histopathology Studies

et al. 2023

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The anticancer activity of N-benzylisoindole-1,3-dione derivatives was evaluated against adenocarcinoma (A549-Luc). First, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide activity assay studies of two isoindole-1,3-dione derivatives were performed against A549 cell lines. Both compounds showed inhibitory effects on the viability of A549 cells. Then, we explored the potential of these compounds as active ingredients by in vivo studies. Nude mice were given A549-luc lung cancer cells, and tumor growth was induced with a xenograft model. Then, nude mice were divided into three groups: the control group, compound 3 group, and compound 4 group. After application of each compound to the mice, tumor sizes, their survival, and weight were determined for 60 days. Furthermore, toxicological studies were performed to examine the effects of the drugs in mice. In addition to toxicological studies, histopathological analyses of organs taken from mice were performed, and the results were evaluated. The obtained results showed that both N-benzylisoindole derivatives are potential anticancer agents.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Evaluation of In Vivo Biological Activity Profiles of Isoindole-1,3-dione Derivatives: Cytotoxicity, Toxicology, and Histopathology Studies

et al. 2023

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“…Isoindoles are compounds revealing their own activity. It was reported that the IC 50 values of some isoindole derivatives against HeLa cells are placed between 140.60 and 383.82 µM [ 61 ]. Therefore, developed Pcs should present an optimal photostability.…”

Section: Resultsmentioning

confidence: 99%

New Metallophthalocyanines Bearing 2-Methylimidazole Moieties—Potential Photosensitizers against Staphylococcus aureus

Wierzchowski

Ziental

Łażewski

et al. 2022

IJMS

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Newly developed tetra- and octasubstituted methimazole-phthalocyanine conjugates as potential photosensitizers have been obtained. Synthesized intermediates and final products were characterized by the MALD-TOF technique and various NMR techniques, including 2D methods. Single-crystal X-ray diffraction was used to determine the crystal structures of dinitriles. The studied phthalocyanines revealed two typical absorption bands—the Soret band and the Q band. The most intense fluorescence was observed for octasubstituted magnesium(II) phthalocyanine in DMF (ΦFL = 0.022). The best singlet oxygen generators were octasubstituted magnesium(II) and zinc(II) phthalocyanines (Φ∆ 0.56 and 0.81, respectively). The studied compounds presented quantum yields of photodegradation at the level between 10−5 and 10−6. Due to their low solubility in a water environment, the liposomal formulations were prepared. Within the studied group, octasubstituted zinc(II) phthalocyanine at the concentration of 100 µM activated with red light showed the highest antibacterial activity against S. aureus equal to a 5.68 log reduction of bacterial growth.

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“…synthesized new norcantharimide derivatives and investigated the cytotoxic activities of these compounds. They reported that the new norcantharimide derivatives show high anticancer activity in lung and breast cancer …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic Characterizations of Novel Norcantharimides, Their ADME Properties and Docking Studies Against COVID‐19 M^pr°

Özkan

Adem

2020

ChemistrySelect

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A series of novel Norcantharimide derivatives were synthesized and their structures were characterized by FTIR, 1 H and 13 C NMR spectroscopy as well as elemental analyses. The absorption, distribution, metabolism and excretion (ADME) properties of the synthesized molecules were investigated. The results obtained in silico demonstrated that these molecules can be considered as orally active drug candidates due to their physicochemical properties. Also, docking studies demon-strated that all derivatives exhibit a good theoretical affinity with MolDock Score in between 124-138 against the main protease of Coronavirus Disease 2019 (COVID-19 M pr°) that caused worldwide epidemics. We believe that newly synthesized norcantharimide derivatives can guide many future studies in organic synthesis, medicine and pharmaceutical applications.[a] Dr.

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Synthesis and biological evaluation of new chloro/acetoxy substituted isoindole analogues as new tyrosine kinase inhibitors

Cited by 13 publications

References 26 publications

Evaluation of In Vivo Biological Activity Profiles of Isoindole-1,3-dione Derivatives: Cytotoxicity, Toxicology, and Histopathology Studies

Evaluation of In Vivo Biological Activity Profiles of Isoindole-1,3-dione Derivatives: Cytotoxicity, Toxicology, and Histopathology Studies

New Metallophthalocyanines Bearing 2-Methylimidazole Moieties—Potential Photosensitizers against Staphylococcus aureus

Synthesis, Spectroscopic Characterizations of Novel Norcantharimides, Their ADME Properties and Docking Studies Against COVID‐19 M^pr°

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Synthesis and biological evaluation of new chloro/acetoxy substituted isoindole analogues as new tyrosine kinase inhibitors

Cited by 13 publications

References 26 publications

Evaluation of In Vivo Biological Activity Profiles of Isoindole-1,3-dione Derivatives: Cytotoxicity, Toxicology, and Histopathology Studies

Evaluation of In Vivo Biological Activity Profiles of Isoindole-1,3-dione Derivatives: Cytotoxicity, Toxicology, and Histopathology Studies

New Metallophthalocyanines Bearing 2-Methylimidazole Moieties—Potential Photosensitizers against Staphylococcus aureus

Synthesis, Spectroscopic Characterizations of Novel Norcantharimides, Their ADME Properties and Docking Studies Against COVID‐19 Mpr°

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Synthesis, Spectroscopic Characterizations of Novel Norcantharimides, Their ADME Properties and Docking Studies Against COVID‐19 M^pr°