Lewis acid-mediated cross-coupling reaction of 7-azaindoles and aldehydes: Cytotoxic evaluation of C3-linked bis-7-azaindoles |
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Authors: | Suk Hun Lee Kunyoung Kim Yeong Uk Jeon Amit Kundu Prasanta Dey Jong Yeon Hwang Neeraj Kumar Mishra Hyung Sik Kim In Su Kim |
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Affiliation: | 1. School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea;2. Division of Bio & Drug Discovery, Korea Research Institute of Chemical Technology, Daejeon 34114, Republic of Korea |
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Abstract: | The synthesis of 3,3′-bis-7-indolylmethane derivatives is important for their further development as pharmaceutical compounds and other synthetic purposes. Herein, we describe the zinc- or acid-mediated cross-coupling reaction of 7-azaindoles with aldehydes, such as paraformaldehyde, alkyl aldehydes, aryl aldehydes, enal, and α-ketoaldehyde, providing the corresponding C3-linked bis-7-azaindole derivatives, which are a crucial class towards the development of novel bioactive compounds. High levels of site selectivity and functional group tolerance were observed. Synthesized 3,3′-bis-7-azaindole derivatives were evaluated against human breast adenocarcinoma cells (MCF-7) and human ovarian carcinoma cells (SKOV-3), respectively. Notably, compounds 3s and 4e displayed promising anticancer properties competitive with anticancer doxorubicin as a positive control. |
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Keywords: | Corresponding authors. Aldehydes Azaindoles Bisazaindoles Cytotoxicity Structure-activity relationship |
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