Abstract

A pair of C9-C10-trans-C10-artemisinin-purine hybrids (A and B) were stereoselectively synthesized under a protonic acid condition, which were structurally characterized by 1H NMR, 13C NMR, IR, HRMS and single crystal X-ray diffraction. Further structural analyses were conducted by Density Functional Theory (DFT) Calculation. DFT-optimized structures of A and B were consistent with X-ray data, so were DFT-based molecular vibrations with IR data. Intramolecular hydrogen bonds played significant role in stabilization of crystal structures both A and B which were chemical stable. Finally, antiproliferative effects of A and B were evalua­ted in human breast cancer cell lines T47D and MDA-MB-436. The anticancer activities of two novel compounds were equivalent to the positive control (mercaptopurine) towards the ER+ cell line T47D, while A was more potent than the positive control in triple-negative-type MDA-MB-436 cells.

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