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Molecules 2015, 20(9), 17152-17165; doi:10.3390/molecules200917152

Design, Synthesis and Biological Evaluation of Novel 5H-Chromenopyridines as Potential Anti-Cancer Agents

1
Department of Pharmaceutical Sciences, College of Pharmacy, University of Tennessee Health Science Center, 847 Monroe Avenue, Memphis, TN 38163, USA
2
Department of Pathology and Laboratory Medicine, College of Medicine and the Center for Cancer Research, University of Tennessee Health Science Center, 19 S Manassas, Memphis, TN 38163, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 20 July 2015 / Revised: 10 September 2015 / Accepted: 11 September 2015 / Published: 17 September 2015
View Full-Text   |   Download PDF [889 KB, uploaded 17 September 2015]   |  

Abstract

A novel series of 5H-chromenopyridines was identified as anticancer agents in our continuing effort to discover and develop new small molecule anti-proliferative agents. Based on our initial lead SP-6-27 compound, we designed and synthesized novel tricyclic 5H-thiochromenopyridine and 5H-chromenopyridine analogs to evaluate the impact of an additional ring, as well as conformational flexibility on cytotoxic activity against human melanoma and glioma cell lines. All of the 5H-thiochromenopyridines have been achieved in good yields (89%–93%) using a single-step, three-component cyclization without the need for purification. The 5H-chromenopyridine analog of the potent 5H-thiochromenopyride was obtained in a good yield upon purification. All newly-prepared 5H-thiochromenopyridines showed good to moderate cytotoxicity against three melanoma and two glioma cell lines (3–15 μM). However, the 5H-chromenopyridine analogue that we prepared in our laboratory lost cytotoxic activity. The moderate cytotoxic activity of 5H-thiochromenopyridines shows the promise of developing chromenopyridines as potential anticancer agents. View Full-Text
Keywords: glioma; melanoma; chromene; chromenopyridine; anti-proliferative activity glioma; melanoma; chromene; chromenopyridine; anti-proliferative activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Banerjee, S.; Wang, J.; Pfeffer, S.; Ma, D.; Pfeffer, L.M.; Patil, S.A.; Li, W.; Miller, D.D. Design, Synthesis and Biological Evaluation of Novel 5H-Chromenopyridines as Potential Anti-Cancer Agents. Molecules 2015, 20, 17152-17165.

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