Synthesis and biological evaluation of triazole-vanillin molecular hybrids as anti-cancer agents

Sharma, G, Kandikonda, S, Reddy, S, Nagalingam, A, Cunningham, K, Ummanni, R, Hugel, H, Sharma, D and Malhotra, S 2017, 'Synthesis and biological evaluation of triazole-vanillin molecular hybrids as anti-cancer agents', Current Bioactive Compounds, vol. 13, no. 3, pp. 223-235.


Document type: Journal Article
Collection: Journal Articles

Title Synthesis and biological evaluation of triazole-vanillin molecular hybrids as anti-cancer agents
Author(s) Sharma, G
Kandikonda, S
Reddy, S
Nagalingam, A
Cunningham, K
Ummanni, R
Hugel, H
Sharma, D
Malhotra, S
Year 2017
Journal name Current Bioactive Compounds
Volume number 13
Issue number 3
Start page 223
End page 235
Total pages 13
Publisher Bentham Science Publishers
Abstract Background: Triazole based drugs are widely used in cancer patients for the treatment of life-threatening invasive fungal infections. A recent report on the usefulness of 1,2, 3- triazole scaffold for the inhibition of tyrosine kinases stimulated our curiosity to design new molecules based on this moiety. Methods: A series of new heterocyclic compounds containing 1,2,3 triazole moiety tethered to substituted vanillin or isovanillin were synthesized and analysed for their anticancer activity. The cyclopen-tyl/cyclohexyl ethers derived from vanillin and isovanillin were subsequently treated with MeMgI to give the carbinols. Reaction of these carbinols with TMSN 3 and ZrCl 4 as Lewis acid gave the desired azides. Click chemistry on azides with diverse acetylenes furnished the triazoles. The new triazole hybribs were screened o against 60 human cancer cell lines at a 10μM dose for their potential anticancer activity. Results: The two active compounds (8a, 10a) showed strong inhibitory effect against different cell lines, with highest inhibition against breast cancer panel. To elucidate the underlying molecular mechanisms, these compounds were examined for their clonogenic potential and anchorage-independent growth of estrogen receptor positive (MCF7 and T47D) and estrogen receptor negative (MDA-MB-231 and MDA-MB-468) breast cancer cells and investigated for induction apoptotic pathways. Conclusion: The outcomes from the current study will add much to the existing knowledge of the breast cancer research. This provides a rewarding conclusion and opens the way for future researchers to design and synthesize the novel active compounds against breast cancer.
Subject Organic Chemical Synthesis
Medicinal and Biomolecular Chemistry not elsewhere classified
Keyword(s) Anticancer
Apoptosis
Breast cancer
Cancer therapy
Molecular hybrids
Triazole-vanillin
DOI - identifier 10.2174/1573407213666161128122552
Copyright notice © 2017 Bentham Science Publishers
ISSN 1573-4072
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