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Novel Pyrazolo[3,4-d]pyrimidine Derivatives as Potential Antitumor Agents: Exploratory Synthesis, Preliminary Structure-Activity Relationships, and in Vitro Biological Evaluation

1
State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medicinal School, Sichuan University, Chengdu 610041, Sichuan, China
2
College of Chemistry and Chemical Engineering, Chongqing University of Science and Technology, Chongqing 401331, China
*
Author to whom correspondence should be addressed.
These authors equally contributed to this work.
Molecules 2011, 16(12), 10685-10694; https://doi.org/10.3390/molecules161210685
Received: 20 November 2011 / Revised: 2 December 2011 / Accepted: 13 December 2011 / Published: 20 December 2011
(This article belongs to the Section Medicinal Chemistry)
In a cell-based screen of novel anticancer agents, the hit compound 1a which bears a pyrazolo[3,4-d]pyrimidine scaffold exhibited high inhibitory activity against a panel of four different types of tumor cell lines. In particular, the IC50 for A549 cells was 2.24 µM, compared with an IC50 of 9.20 µM for doxorubicin, the positive control. Four synthetic routes of the key intermediate 3 of 1a were explored and 1a was prepared via route D on the gram scale for further research. Two analogs of 1a were synthesized and their preliminary structure-activity relationships were studied. Flow cytometric analysis revealed that compound 1a could significantly induce apoptosis in A549 cells in vitro at low micromolar concentrations. These results suggest that the target compound 1a and its analogs with the pyrazolo[3,4-d]pyrimidine scaffold might potentially constitute a novel class of anticancer agents, which requires further studies. View Full-Text
Keywords: pyrazolo[3,4-d]pyrimidine; exploratory synthesis; anticancer activity; apoptosis pyrazolo[3,4-d]pyrimidine; exploratory synthesis; anticancer activity; apoptosis
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He, H.-Y.; Zhao, J.-N.; Jia, R.; Zhao, Y.-L.; Yang, S.-Y.; Yu, L.-T.; Yang, L. Novel Pyrazolo[3,4-d]pyrimidine Derivatives as Potential Antitumor Agents: Exploratory Synthesis, Preliminary Structure-Activity Relationships, and in Vitro Biological Evaluation. Molecules 2011, 16, 10685-10694.

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