Diversity-oriented TsOH catalysis-enabled construction of tanshinone-substituted bis(indolyl/pyrrolyl)methanes and their biological evaluation for anticancer activities |
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Authors: | Xiong-Wei Liu Zhi-Yong Chen Guan-Lian Wang Xi-Tao Ma Yi Gong |
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Institution: | 1. Guizhou Medicine Edicine Edible Plant Resources Research and Development Center, Guizhou University, Guiyang, China;2. Department of Adverse Drug Reaction, Affiliated Hospital of Chengdu University of Traditional Chinese Medicine, Chengdu, China |
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Abstract: | We have developed an efficient and straightforward methodology for the synthesis of novel tanshinone-substituted bis(indolyl/pyrrolyl)methane scaffolds 3 through TsOH catalysis-enabled addition of indoles or pyrroles 1 with tanshinones 2 based on molecular hybridization strategy. Products were smoothly obtained in good yields (up to 81% yield). This protocol also represents the first construction of tanshinone skeleton-fused bis(indolyl/pyrrolyl)methane scaffolds, thus leading to new knowledge in the fields of both molecular complexity and diversity-oriented synthesis and the lead compound discovery. Furthermore, their biological activities against human leukemia cells K562, human prostate cancer cells PC-3, and human lung cancer cells A549 have been preliminarily demonstrated by in vitro assays. The results demonstrated that most of these compounds 3 obtained by this protocol showed comparable activity to the positive control of cisplatin. |
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Keywords: | Antitumor activity bis(indolyl/pyrrolyl)methanes molecular hybridization tanshinone TsOH |
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