Synthesis and cytotoxic activity of some novel 2’-hydroxychalcones containing murrayafoline A

Le Duc Anh; Luu Van Chinh; Truong Ngoc Hung; Nguyen Manh Cuong; Pham Hong Ngoc

doi:10.15625/2525-2518/16785

Author affiliations

Authors

Le Duc Anh Institute of Chemistry - Material, Institute of Military Science and Technology, 17 Hoang Sam, Cau Giay, Ha Noi, Viet Nam
Luu Van Chinh 2Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Ha Noi, Viet Nam
Truong Ngoc Hung 2Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Ha Noi, Viet Nam
Nguyen Manh Cuong 2Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Ha Noi, Viet Nam
Pham Hong Ngoc Thuy Loi University, 175 Tay Son, Dong Da, Ha Noi, Viet Nam

DOI:

https://doi.org/10.15625/2525-2518/16785

Keywords:

murrayafoline A, 2'-hydroxychalcone, cytotoxicity, chloromethyl, N-alkyl, Claisen-Schmidt

Abstract

2’-Hydroxychalcones and murrayafoline A, a natural compounds isolated from Glycomis stenocarpa, have been reported to have the promising anti-cancer activity. In this study, a series of 2'-hydroxychalcones containing murrayafoline A (MuA) 6a-f were achieved by Claisen-Schmidt condensation of the key intermediate 5'-(1-methoxy-3-methyl-carbazolyl)methyl-2'-hydroxyacetophenone 4 with various aldehydes 5a-f with purpose of combining activity of two precusors. Their structures were determined by NMR and MS spectral data. Screening for cytotoxicity of compounds showed that compounds 6a-6d expressed cytotoxic activity, notably compound 6a displayed activity against all tested cell lines LU-1, Hep-G2, MCF-7, P338, and SW480 with the IC₅₀values ranging from 23.97 to 80.19 μg/mL. Clearly, the substitution at position of N-H group of murrayafoline a led to a decline in the cytotoxicity of the obtained derivatives. This finding suggests the presence of the N-H group might be play a crucial role for the cytotoxicity of the murrayafoline A derivatives.

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