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Design and synthesis of novel sugar‐based nitrogen‐containing heterocycles as potential anticancer agents under microwave in water
Author(s) -
Liu Jian,
Wu Chunlei,
Jin Huimin,
Du Kui,
Zheng Hui
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3707
Subject(s) - chemistry , glycosyl , combinatorial chemistry , rational design , a549 cell , sugar , organic chemistry , stereochemistry , biochemistry , nanotechnology , cell , materials science
A series of novel glycosyl nitrogen‐containing heterocycles derivatives were designed and synthesized. With the help of microwave, the reaction was carried out in water rapidly and afforded the target compounds in good yields. The acid catalysts that were essential for this kind of reaction under traditional heating method were avoided through this strategy. Preliminary biological evaluation showed that most of the compounds could inhibit the growth of A549 cells, but the inhibition of HepG‐2 cells was relatively poor. Notably, compound 2i displayed the best potency with an IC 50 value of 3.42 μM against A549 cell lines, which is comparable with the common anticarcinogen paclitaxel (5.12 μM). Molecular modeling studies suggested that 2i may bind to the ATP‐binding site of epidermal growth factor receptor (EGFR), indicating a rational design strategy. These results provide a starting point for designing glycosyl nitrogen‐containing heterocycles as the potential drugs in lung cancer therapy.