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Molecules 2016, 21(2), 212; doi:10.3390/molecules21020212

Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline

1
College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
2
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 10 January 2016 / Revised: 3 February 2016 / Accepted: 4 February 2016 / Published: 15 February 2016
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [2036 KB, uploaded 15 February 2016]   |  

Abstract

A series of novel 13- to 15-member hydroxyproline-based macrocycles, which contain alkyl-alkyl ether and alkyl-aryl ether moieties, have been synthesized by the strategy of macrocyclization utilising azide-alkyne cycloaddition, Mitsunobu protocol and amide formation. Their anti-tumor activities towards A549, MDA-MB-231 and Hep G2 cells were screened in vitro by an MTT assay. The results indicated that 13-member macrocycle 33 containing alkene chain showed the best results, exhibiting the highest inhibitory effects towards lung cancer cell line A549, which was higher than that of the reference cisplatin (IC50 value = 2.55 µmol/L). View Full-Text
Keywords: macrocycle; 4-hydroxyproline; azide-alkyne cycloaddition; Mitsunobu reaction; amide formation; anti-tumor activity macrocycle; 4-hydroxyproline; azide-alkyne cycloaddition; Mitsunobu reaction; amide formation; anti-tumor activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Cao, G.; Yang, K.; Li, Y.; Huang, L.; Teng, D. Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline. Molecules 2016, 21, 212.

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