Synthesis and antitumor-evaluation of 1,3-selenazole-containing 1,3,4-thiadiazole derivatives

Zhao, Haichuan; Shi, Yan‐Ping; Liu, Yu‐Ming; Li, Caiwen; Xuan, Lina; Wang, Peng; Zhang, Kai; Chen, Baoquan

doi:10.1016/j.bmcl.2013.10.062

Cited by 43 publications

(17 citation statements)

References 16 publications

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“…A modification of the carbon disulphide-thiosemicarbazide procedure which results in higher yield of 2-amino-5-marcapto-1,3,4-thiadiazole is carried out in dimethylformamide at 80°, the yield is over 90% 25 .…”

Section: Methodsmentioning

confidence: 99%

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Chemistry, synthesis and progress report on biological activities of thiadiazole compounds - a review

Asif¹

2016

Mediterr.J.Chem.,

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Thiadiazoles are an important class of heterocyclic compounds that exhibit diverse applications in organic synthesis, pharmaceutical and biological applications. They are also useful as oxidation inhibitors, cyanine dyes, metal chelating agents, anti-corrosion agents. Researchers across the globe are working on this moiety due to their broad spectrum of applications of thiadiazole chemistry. This article provides information about developments, exploration, synthetic strategies, techniques for the synthesis of thiadiazoles and their diverse biological activities, structure-activity relationship of the compounds and physical properties. This article is an important tool for organic and medicinal chemists to develop newer thiadiazole compounds that could be better agents in terms of efficacy and safety.

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Section: Methodsmentioning

confidence: 99%

“…The benzalthiosemicarbazones could be oxidatively cyclize to form 2-amino-5-phenyl-1,3,4-thiadiazole by ferric chloride 25 . A large number of 5-substituted 2-amino-1,3,4-thiadiazole have been prepared by this procedure 26 .…”

Section: Methodsmentioning

confidence: 99%

Chemistry, synthesis and progress report on biological activities of thiadiazole compounds - a review

Asif¹

2016

Mediterr.J.Chem.,

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“…Based on the advantages related to the presence of selenium and the importance of heterocycles in the field of medicinal chemistry, synthesis of organoselenium compounds containing 1,3-selenazole ring, as well as study of their biological application, is in focus of current research. Many functionalized 1,3-selenazole rings are important constituent of pharmacologically active compounds (Zhao et al, 2013 ). 1,3-Selenazole derivatives are known to inhibit the synthesis of nitric acid (Ueda et al, 2005 ) and they act as antagonists for histamine H2 receptors (van der Goot et al, 1994 ).…”

Section: Introductionmentioning

confidence: 99%

Selenazolyl-hydrazones as Novel Selective MAO Inhibitors With Antiproliferative and Antioxidant Activities: Experimental and In-silico Studies

et al. 2018

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The novel approach in the treatment of complex multifactorial diseases, such as neurodegenerative disorders and cancer, requires a development of efficient multi-targeting oriented drugs. Since oxidative stress significantly contributes to the pathogenesis of cancer and neurodegenerative disorders, potential drug candidates should possess good antioxidant properties. Due to promising biological activities shown for structurally related (1,3-thiazol-2-yl)hydrazones, a focused library of 12 structurally related benzylidene-based (1,3-selenazol-2-yl)hydrazones was designed as potential multi-targeting compounds. Monoamine oxidases (MAO) A/B inhibition properties of this class of compounds have been investigated. Surprisingly, the p-nitrophenyl-substituted (1,3-selenazol-2-yl)hydrazone 4 showed MAO B inhibition in a nanomolar concentration range (IC50 = 73 nM). Excellent antioxidant properties were confirmed in a number of different in vitro assays. Antiproliferative activity screening on a panel of six human solid tumor cell lines showed that potencies of some of the investigated compounds was comparable or even better than that of the positive control 5-fluorouracil. In-silico calculations of ADME properties pointed to promising good pharmacokinetic profiles of investigated compounds. Docking studies suggest that some compounds, compared to positive controls, have the ability to strongly interact with targets relevant to cancer such as 5′-nucleotidase, and to neurodegenerative diseases such as the small conductance calcium-activated potassium channel protein 1, in addition to confirmation of inhibitory binding at MAO B.

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“…2010; Cressier et al, 2009), antibacterial (Foroumadi et al, 2007;Dubey et al, 2012), antidepressant (Yusuf et al, 2008;Clerici and Pocar, 2001), antidiabetic (Pattn et al, 2011;Lee et al, 2010), antifungal (Liu et al, 2008;Xu et al, 2013), anticonvulsant (Siddiqui et al, 2013;Sharma et al, 2014), and antiinflammatory effects (Dekhane et al, 2011;Amir et al, 2007). In particular, a few of differently substituted 1,3,4-thiadiazoles have been found to exhibited anticancer activities (Hamama et al, 2013;Hosseinzadeh et al, 2013;Zhao et al, 2013;Kumar et al, 2010Kumar et al, , 2011. Moreover, the sulfur atom of 1,3,4-thiadiazole imparts improved liposolubility, and the mesoionic nature of 1,3,4-thiadiazole makes this class of compounds to show good tissue permeability.…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, the sulfur atom of 1,3,4-thiadiazole imparts improved liposolubility, and the mesoionic nature of 1,3,4-thiadiazole makes this class of compounds to show good tissue permeability. Importantly, the combination of different heterocyclic backbone with thiadiazole nucleus carrying the methylthio group which is considered a key structural component for pharmacological activity, may show synergistic effect, and thus has drawn widespread attention in recent years (Foroumadi et al, 2007;Xu et al, 2013;Zhao et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in vitro antiproliferative activity of novel benzisoselenazolone derivatives

et al. 2014

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A series of novel benzisoselenazolone derivatives bearing 1,3,4-thiadiazole moiety were designed, synthesized and evaluated for their in vitro antiproliferative activities against human cancer cell lines SMMC-7721, MCF-7, A549, and normal cell lines L929 by CCK-8 assay.The bioassay results demonstrated that most of the tested compounds showed potent antitumor activities, and some compounds exhibited better effects than positive control ebselen and ethaselen against various cancer cell lines. Among these compounds, compound 7l showed significant antiproliferative activity against SMMC-7721 cells, with IC 50 values of 2.18 lM. Compound 7j exhibited the best inhibitory effect against MCF-7 cells, with IC 50 values of 2.89 lM. Compounds 7e and 7i displayed highly effective antitumor activities against A549 cells, with IC 50 values of 2.33 and 2.33 lM, respectively. Furthermore, most of the tested compounds showed weak cytotoxic effect against the normal cell lines L929. The pharmacological results suggest that the substituents of benzoylmethylthio-moiety at position-2 on 1,3,4-thiadiazole are vital for modulating antiproliferative activities against various tumor cell lines.

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Synthesis and antitumor-evaluation of 1,3-selenazole-containing 1,3,4-thiadiazole derivatives

Cited by 43 publications

References 16 publications

Chemistry, synthesis and progress report on biological activities of thiadiazole compounds - a review

Chemistry, synthesis and progress report on biological activities of thiadiazole compounds - a review

Selenazolyl-hydrazones as Novel Selective MAO Inhibitors With Antiproliferative and Antioxidant Activities: Experimental and In-silico Studies

Synthesis and in vitro antiproliferative activity of novel benzisoselenazolone derivatives

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