Substituted thiazoles VII. Synthesis and antitumor activity of certain 2-(substituted amino)-4-phenyl-1,3-thiazole analogs

Hassan, Ghada S.; El‐Messery, Shahenda M.; Al-Omary, Fatmah A. M.; El‐Subbagh, Hussein I.

doi:10.1016/j.bmcl.2012.08.095

Cited by 64 publications

(26 citation statements)

References 33 publications

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“…Thiazole derivatives have attracted the interest of medicinal chemists due to a variety of their biological activities including antibacterial, anti-fungal, anti-HIV, anti-hypertension, anti-inflammatory, anti-cancer, anti-convulsive and anti-depressant [5][6][7][8][9][10]. The mechanisms of 1,3-thiazole derivatives antitumor activity may be associated with DNA intercalation [11,12], PRL-3, SHP-2 and JSP-1 inhibition [13][14][15][16], tumor necrosis factor (TNFα) [17], anti-apoptotic bio-complex Bcl-XL-BH3 [18], integrin avb3 [19], others. Thiazole ring belongs to the privileged scaffolds in modern medicinal chemistry [11,20,21], particularly at discovering new anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

“…The mechanisms of 1,3-thiazole derivatives antitumor activity may be associated with DNA intercalation [11,12], PRL-3, SHP-2 and JSP-1 inhibition [13][14][15][16], tumor necrosis factor (TNFα) [17], anti-apoptotic bio-complex Bcl-XL-BH3 [18], integrin avb3 [19], others. Thiazole ring belongs to the privileged scaffolds in modern medicinal chemistry [11,20,21], particularly at discovering new anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

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Antineoplastic activity of novel thiazole derivatives

Finiuk¹,

Hreniuh²,

Ostapiuk³

et al. 2017

Biopolym. Cell

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The development of novel efficient substances for anticancer chemotherapy is an important problem of medicinal chemistry. Aim. To evaluate the level of cytotoxic action of novel thiazole derivatives towards tumor cell lines of different origin. Methods. Four N acylated 2-amino-5-benzyl-1,3-thiazoles (5a-d) were synthesized by reaction of 2-amino-5-R-benzyl-1,3-thiazoles with acid chlorides in the presence of triethylamine in the dioxane medium. Anticancer screening of the synthesized thiazoles was performed by the MTT assay. Results. Thiazole derivatives were shown to exert antineoplastic activity towards different types of tumor cells. The anti-glioma and anti-melanoma selectivity of these derivatives action was demonstrated. The compound 5a was found to be the most toxic for human glioblastoma U251 cells and human melanoma WM793 cells. At the same time, the created compounds possessed low toxicity towards pseudo-normal cells. Conclusion. The novel thiazole derivative 5a was the most toxic against human glioblastoma and melanoma cells. K e y w o r d s: thiazole derivatives, 2-amino-5-benzyl-1,3-thiazoles, anticancer activity, leukemia, glioblastoma, melanoma.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antineoplastic activity of novel thiazole derivatives

Finiuk¹,

Hreniuh²,

Ostapiuk³

et al. 2017

Biopolym. Cell

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“…Urea function not only does provide pharmacodynamic benefits, but it is also less metabolically labile than ester. Thiazole (Hassan et al, 2012;Licciulli et al, 2013;Wang et al, 2013) and 4-fluorophenyl (Zhang et al, 2013b) were the selected motif to append the caffeic scaffold via urea linker because these moieties appeared to be binding motif in potent EGFR tyrosine kinase inhibitors such as lapatinib, sorafenib and FRAX597 (Licciulli et al, 2013). Thus, these motifs were included in the molecular expansion to increase interaction and binding capability of the designed compound.…”

Section: Chemistrymentioning

confidence: 99%

Lead compound bearing caffeic scaffold induces EGFR suppression in solid tumor cancer cells

Mudjupa

Abdelhamed

Refaat

et al. 2015

JAB

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Available online xxxKeywords: Caffeic acid derivatives EGFR inhibitor Triple-negative breast cancer Non-small cell lung cancer Molecular modeling Abbreviations: CA, caffeic acid CAPE, caffeic acid phenethyl ester EGFR, epidermal growth factor receptor RTK, receptor tyrosine kinase TNBC, triple-negative breast cancer a b s t r a c t A small molecule EGFR inhibitor, 4-(2-(3-(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)ureido) vinyl)-1,2-phenylene diacetate (CIU1) was designed in silico by using caffeic scaffold as core structure. The designed compound showed anti-proliferative action against different solid tumor cell lines, particularly metastatic breast cancer cells. CIU1 inhibited the growth of EGFR-overexpressing MDA-MB-468 triple-negative breast cancer cells and wild-type nonsmall-cell lung cancer H460 cells with IC 50 values of 8.96 mM and 12.98 mM, respectively, these anti-proliferative effects of CIU1 were comparable to gefitinib (a specific EGFR inhibitor) or lapatinib (a dual EGFR and HER2 tyrosine kinase inhibitor). Interestingly CIU1 effectively inhibited the invasive hormone-dependent MCF-7 cancer cells with an IC 50 2.34 mM. The immunoblot analyses revealed that CIU1 induced programmed cell death and suppressed EGFR expression in EGFR-overexpressing breast cancer (MDA-MB468) and lung cancer (PC-9) cells. The findings substantiated our design strategy and demonstrated the potential of CIU1 as new lead for further optimization in the development of anticancer drugs against advanced solid tumors.

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“…On the other hand, azoles derivatives are well known for their great biological (Kaur et al, 2014;Lu et al, 2012;Bondock et al, 2013) and medicinal significance (Kumar et al, 2013a;Hassan et al, 2012). Among azoles, substituted pyrazoles have possessed a broad spectrum of biological properties such as anti-tumor (Mohareb et al, 2012), antitubercular (Ravala et al, 2011), antioxidant (Al-Ayed, 2011, anti-inflammatory (Kumar et al, 2013b;Bekhit et al, 2009), anti-bacterial (Kumar et al, 2005), anti-obesity (Gupta et al, 2011), and antidepressant (Aziz et al, 2009) activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some pyrazolylaldehyde N-isonicotinoyl hydrazones and 2,5-disubstituted 1,3,4-oxadiazoles as DNA photocleaving agents

Kumar

Beniwal

2015

Med Chem Res

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In search of potential biologically active compounds, some novel 2,5-disubstituted 1,3,4-oxadiazole derivatives have been prepared conveniently via oxidation of newly synthesized pyrazolylaldehyde N-isonicotinoyl hydrazones by (diacetoxyiodo)benzene in dichloromethane under mild reaction conditions. Compounds were obtained in excellent yields, and their structures have been established on the basis of their FT-IR, 1 H, 13 C NMR, and mass spectral data. The DNA photocleavage potential for all the synthesized compounds was evaluated using agarose gel electrophoresis. It has been observed that oxadiazole derivatives showed a significant level of DNA photocleavage activity when compared with their corresponding hydrazones, and some modifications in the basic structure may lead to construct some potential chemotherapeutic agents in future.

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Substituted thiazoles VII. Synthesis and antitumor activity of certain 2-(substituted amino)-4-phenyl-1,3-thiazole analogs

Cited by 64 publications

References 33 publications

Antineoplastic activity of novel thiazole derivatives

Antineoplastic activity of novel thiazole derivatives

Lead compound bearing caffeic scaffold induces EGFR suppression in solid tumor cancer cells

Synthesis of some pyrazolylaldehyde N-isonicotinoyl hydrazones and 2,5-disubstituted 1,3,4-oxadiazoles as DNA photocleaving agents

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