Background: Compounds containing furo[3,2-b]pyridine framework have shown interesting pharmacological properties, including anticancer activities. Though these compounds are generally synthesized via the heteroannulation processes involving acetylenic derivatives, some of them are complex.
Objective: The study aimed to explore a series of 2-substituted furo[3,2-b]pyridines for their cytotoxic properties against cancer cell lines in vitro.
Methods: We developed a convenient synthesis of 2-substituted furo[3,2-b]pyridines via sequential (i) C-C coupling followed by (ii) C-O bond-forming reactions in a single pot. The reactions were performed under ultrasound irradiation in the presence of Pd/C as an inexpensive, stable and widely used catalyst. A range of 2- substituted furo[3,2-b]pyridines were synthesized via coupling of 3-chloro-2-hydroxy pyridine with terminal alkynes in the presence of 10% Pd/C-CuI-PPh3-Et3N in EtOH. The in vitro evaluation of all these compounds was carried out against MDA-MB-231 and MCF-7 cell lines and subsequently against SIRT1.
Results: The furo[3,2-b]pyridine derivative 3b showed encouraging growth inhibition of both MDAMB-231 and MCF-7 cell lines and inhibition of SIRT1. The compound 3b also showed apoptosis-inducing potential when tested against MCF-7 cells.
Conclusion: The Pd/C-Cu catalysis under ultrasound accomplished a one-pot and direct access to 2-substituted furo[3,2-b]pyridine derivatives, some of which showed anticancer properties.
[http://dx.doi.org/10.1039/c3ob41069b] [PMID: 23824158]
[http://dx.doi.org/10.1038/nature06261] [PMID: 18046409]
[http://dx.doi.org/10.1002/1521-3765(20020201)8:3<622:AID-CHEM622>3.0.CO;2-0] [PMID: 11859857]
[http://dx.doi.org/10.1016/j.ejmech.2015.08.032] [PMID: 26312433]
[http://dx.doi.org/10.1038/srep32213] [PMID: 27573798]
[http://dx.doi.org/10.2174/1568026617666170104145640] [PMID: 28056738]