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One pot synthesis and anticancer activity of dimeric phloroglucinols.

Bioorganic & medicinal chemistry letters (2012-02-22)
Siddheshwar K Chauthe, Sandip B Bharate, Giridharan Periyasamy, Amit Khanna, Kamlesh K Bhutani, Prabhu D Mishra, Inder P Singh
ABSTRACT

A series of dimeric phloroglucinol compounds were synthesized in a single step using commercially available phloroglucinol and methanesulfonic acid. Based on the reported anticancer activity of plant derived dimeric phloroglucinols, these synthesized compounds were evaluated for their in vitro anti-proliferative activities against various cancer cell lines. Several compounds demonstrated in vitro cytotoxic effects across a wide array of tumor cell types. The compound 29 with pyridin-3-yl group on linker methylene and two diisovaleryl phloroglucinol moieties was found to be the most active in all the five cancer cell lines having a low IC(50) of 5.5 μM in colon cancer cell lines (HCT116).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sodium methanesulfonate, 98%
Sigma-Aldrich
Potassium methanesulfonate, ≥98.0% (dry substance, T)
Sigma-Aldrich
Silver methanesulfonate
Sigma-Aldrich
Methanesulfonic acid solution, 70 wt. % in H2O
Sigma-Aldrich
Methanesulfonic acid, ≥99.0%
Sigma-Aldrich
Methanesulfonic acid solution, 4 M (with 0.2% (w/v) tryptamine)
Supelco
Methanesulfonic acid concentrate, 0.1 M CH3SO3H in water (0.1N), eluent concentrate for IC