Synthesis of 2-substituted Furo[3,2-b]pyridines Under Pd/C-Cu Catalysis Assisted by Ultrasound: Their Evaluation as Potential Cytotoxic Agents

Author(s):

Dandamudi Sri Laxmi, Suryadevara V. Vardhini, Venkata R. Guttikonda, Mandava V.B. Rao* and Manojit Pal*   Pages 932 - 940 ( 9 )

Abstract:

<P>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. </P><P> 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. </P><P> 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. </P><P> 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. </P><P> 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.</P>

Keywords:

Furo[3,2-b]pyridine, ultrasound, Pd/C, cancer, catalysis, cytotoxic agents.

Affiliation:

Department of Chemistry, Krishna University, Machilipatnam-521 001, Andhra Pradesh, Department of Chemistry, Amritasai Institute of Science and Technology, Paritala, Krishna Dist., -521 180, Andhra Pradesh, Department of Chemistry, SRR & CVR Govt. Degree College, Vijayawada, Andhra Pradesh, Department of Chemistry, Krishna University, Machilipatnam-521 001, Andhra Pradesh, Dr. Reddy's Institute of Life Sciences, University of Hyderabad Campus, Hyderabad-500046

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