Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation

Mesenzani, Ornella; Massarotti, Alberto; Giustiniano, Mariateresa; Pirali, Tracey; Bevilacqua, Valentina; Caldarelli, Antonio; Canonico, P.L.; Sorba, Giovanni; Novellino, Ettore; Genazzani, Armando A.; Tron, Gian Cesare

doi:10.1016/j.bmcl.2010.11.113

Cited by 47 publications

(27 citation statements)

References 24 publications

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“…The activity of the lead compounds, as well as of curcumin, was then investigated, building a full concentration-response curve, in a neuroblastoma cell line (SH-SY5Y) exquisitely sensitive to antitubulin agents. 19 The cytotoxic activity was confirmed, but the rank of potency was slightly modified, with only 4k significantly more cytotoxic than curcumin. Results relative to the vehicle (DMSO) and representative of 8-12 different data points AV ± S.D.…”

Section: Biological Resultsmentioning

confidence: 83%

Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids

Caldarelli

Penucchini

Caprioglio

et al. 2013

Bioorganic & Medicinal Chemistry

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Section: Biological Resultsmentioning

confidence: 83%

Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids

Caldarelli

Penucchini

Caprioglio

et al. 2013

Bioorganic & Medicinal Chemistry

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“…Similarly, Mesenzani O et al [37] replaced the double bond of antitubulin chalcones with triazoles and tetrazoles. His study suggested that the double bond in the chalcone scaffold may not be essential for the interaction with tubulin, and that these new analogues may have the advantage of being metabolically stable due to the introduction of a chemically inert heterocyclic ring (i.e.…”

Section: Chalcones Target Tubulin Polymerizationmentioning

confidence: 99%

Molecular Targeted Approaches to Cancer Therapy and Prevention Using Chalcones

Jandial¹,

Blair²,

Zhang³

et al. 2014

CCDT

112

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There is an emerging paradigm shift in oncology that seeks to emphasize molecularly targeted approaches for cancer prevention and therapy. Chalcones (1,3-diphenyl-2-propen-1-ones), naturally-occurring compounds with widespread distribution in spices, tea, beer, fruits and vegetables, consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α, β-unsaturated carbonyl system. Due to their structural diversity, relative ease of chemical manipulation and reaction of α, β-unsaturated carbonyl moiety with cysteine residues in proteins, some lead chalcones from both natural products and synthesis have been identified in a variety of screening assays for modulating important pathways or molecular targets in cancers. These pathways and targets that are affected by chalcones include MDM2/p53, tubulin, proteasome, NF-kappa B, TRIAL/death receptors and mitochondria mediated apoptotic pathways, cell cycle, STAT3, AP-1, NRF2, AR, ER, PPAR-γ and β-catenin/Wnt. Compared to current cancer targeted therapeutic drugs, chalcones have the advantages of being inexpensive, easily available and less toxic; the ease of synthesis of chalcones from substituted benzaldehydes and acetophenones also makes them an attractive drug scaffold. Therefore, this review is focused on molecular targets of chalcones and their potential implications in cancer prevention and therapy.

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“…General procedure for synthesis of phenyl(2H -tetrazol-5-yl) methanamine derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) To a mixture of α-amino nitrile (1.00 mol), sodium azide (1.05 mol), and zinc chloride (0.50 mol), isopropyl alcohol was refluxed for 16 h. The progress of the reaction was Compd.…”

Section: Chemistrymentioning

confidence: 99%

“…The in vitro minimal inhibitory concentrations (MICs) of the target compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) were determined by the disk diffusion method according to the methods defined by the National Committee for Clinical Laboratory Standards [21]. The MIC was defined as the lowest concentration that showed no growth.…”

Section: Antifungal Studiesmentioning

confidence: 99%

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Design, synthesis, and evaluations of antifungal activity of novel phenyl(2H-tetrazol-5-yl)methanamine derivatives

Salake¹,

Chothe²,

Nilewar

et al. 2013

J Chem Biol

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Fungal infections pose a continuous and serious threat to human health and life. The intrinsic resistance has been observed in many genera of fungi. Many fungal infections are caused by opportunistic pathogens that may be endogenous (Candida infections) or acquired from the environment (Cryptococcus and Aspergillus infections). So, new therapeutic strategies are needed to combat various fungal infections. Fluconazole shows good antifungal activity with relatively low toxicity and is preferred as first line antifungal therapy, but it has suffered from severe drug resistance. So, there is a need to design novel analogues by modification of fluconazole-like structure. A novel series of phenyl(2H -tetrazol-5-yl)methanamine derivatives were synthesized by reaction of α-amino nitrile with sodium azide and ZnCl 2 in presence of isopropyl alcohol. They were evaluated for antifungal activity against Candida albicans and Aspergillus niger and subjected to docking study against 1EA1.

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Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation

Cited by 47 publications

References 24 publications

Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids

Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids

Molecular Targeted Approaches to Cancer Therapy and Prevention Using Chalcones

Design, synthesis, and evaluations of antifungal activity of novel phenyl(2H-tetrazol-5-yl)methanamine derivatives

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