Abstract
Twelve (+)-nopinone-based 2-amino-3-cya- nopyridines 4a-l were synthesized from (-)-β-pinene. The structures of these compounds were characterized by FT-IR, 1 H NMR, and ESI-MS. All the compounds were tested for their anticancer activity against lung cancer cell line A549, gastric cancer cell line MKN45 and breast cancer cell line MCF7 by MTT method, respectively. The results showed that compounds 4f, 4j and 4k had promising anticancer activity against these cancer cell lines, in particular, compound 4f exhibited broad-spectrum and highly efficient anticancer activity against cell lines A549, MKN45 and MCF7 with IC50 of 23.78, 67.61 and 53.87 µmol$L -1 , respectively. The preliminary analysis of the structure activity relationship implied that the Br or Cl substituted group of the benzene ring in these derivatives significantly contributed to the anticancer activity.
Highlights
Natural products are important source for drug development in all major disease areas due to their structure diversity and low side effects[1]. β-Pinene is a naturally occurring monoterpene and commonly occurs in many natural essential oils, including turpentine, tarragon and tea tree oils[2,3,4]
The structure of (+)-nopinone was confirmed by FT-IR, 1H NMR and ESI-MS, and values were in good agreement with those reported in the literature[18]
A series of 2-amino-3-cyanopyridine compounds 4a–l derived from (–)-nopinone were synthesized through the Shengliang LIAO et al Anticancer activity of pyridine derivatives of β-pinene one-pot multicomponent reaction
Summary
Natural products are important source for drug development in all major disease areas due to their structure diversity and low side effects[1]. β-Pinene is a naturally occurring monoterpene and commonly occurs in many natural essential oils, including turpentine, tarragon and tea tree oils[2,3,4]. Research has shown that β-pinene and its derivatives displayed broad-spectrum biological activity, such as anticancer, antibacterial, antifungal, antidiabetic. 2-amino-3-cyanopyridines are known to have a range of biological activity[11,12,13,14]. The anticancer activity of these compounds has especially attracted great interest because of their different modes of action[15]. With both β-pinene and 2-amino-3-cyanopyridine having potential anticancer activity, there is a possibility that synthesis of the β-pinene derivatives with a 2-amino-3-cyanopyridine core may lead to more active anticancer agents. A series of (+)-nopinone-based 2-amino-3cyanopyridines were prepared (Fig. 1), and their anticancer activity against human cancer cell lines A549, MKN45 and MCF7 were evaluated
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