Synthesis and biological evaluation of naphthalene, furan and pyrrole based chalcones as cytotoxic and antimicrobial agents

Abhishek Budhiraja, Kanika Kadian, Mandeep Kaur, Vikas Aggarwal, Atul Garg, Sameer Sapra, Kunal Nepali, O. P. Suri, K. L. Dhar

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. These show antibacterial, antifungal, antitumour and antiinflammatory properties, and also are intermediates in the biosynthesis of flavonoids, substances widespread in plants with an array of biological activities. These biaryl propenones show potent toxicity to several cancer cell lines and interact with tubulin at its colchicine-binding site. Tubulin binding molecules interfere with the dynamic instability of microtubules and thereby disrupt microtubule inducing cell cycle arrest in the M phase, forming abnormal spindles and finally leading to apoptotic cell death. Basically Chalcones consists of C 6-C 3-C 6 units but in the present study we report the reactions of 1-acetylnaphthalene, 2-acetylfuran and 2-acetylpyrrole with aldehydes, thus getting compounds akin to chalcones. 31 analogues have been synthesised and evaluated for cytotoxic potential against PC-3, OVCAR, IMR-32 and HEP-2. Compound 9 was found to be the most cytotoxic with inhibition ranging from 72 to 88% against the cell lines employed. The synthetics were also evaluated for antimicrobial activity and compound 25 was found to be the most potent.

Original languageEnglish
Pages (from-to)2133-2140
Number of pages8
JournalMedicinal Chemistry Research
Volume21
Issue number9
DOIs
Publication statusPublished - Sep 1 2012
Externally publishedYes

Fingerprint

Chalcones
Pyrroles
Cytotoxins
Anti-Infective Agents
Cells
Tubulin
Microtubules
M Phase Cell Cycle Checkpoints
Chalcone
Cell Line
Biosynthesis
Colchicine
Cell death
Bioactivity
Ketones
Flavonoids
Aldehydes
Toxicity
Cell Death
Anti-Inflammatory Agents

Keywords

  • Cancer
  • Cell lines
  • Chalcones
  • Cytotoxic

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

Cite this

Synthesis and biological evaluation of naphthalene, furan and pyrrole based chalcones as cytotoxic and antimicrobial agents. / Budhiraja, Abhishek; Kadian, Kanika; Kaur, Mandeep; Aggarwal, Vikas; Garg, Atul; Sapra, Sameer; Nepali, Kunal; Suri, O. P.; Dhar, K. L.

In: Medicinal Chemistry Research, Vol. 21, No. 9, 01.09.2012, p. 2133-2140.

Research output: Contribution to journalArticle

Budhiraja, Abhishek ; Kadian, Kanika ; Kaur, Mandeep ; Aggarwal, Vikas ; Garg, Atul ; Sapra, Sameer ; Nepali, Kunal ; Suri, O. P. ; Dhar, K. L. / Synthesis and biological evaluation of naphthalene, furan and pyrrole based chalcones as cytotoxic and antimicrobial agents. In: Medicinal Chemistry Research. 2012 ; Vol. 21, No. 9. pp. 2133-2140.
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