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Bioorg Med Chem Lett. 2014 Jul 15;24(14):3131-6. doi: 10.1016/j.bmcl.2014.05.005. Epub 2014 May 15.

Synthesis and antiangiogenic activity of 6-amido-2,4,5-trimethylpyridin-3-ols.

Author information

1
College of Pharmacy and Institute for Drug Research, Yeungnam University, Gyeongsan 712-749, Republic of Korea.
2
Department of Pharmacy and Institute of Pharmaceutical Science and Technology, Hanyang University, Ansan 426-791, Republic of Korea.
3
Department of Pharmacy and Institute of Pharmaceutical Science and Technology, Hanyang University, Ansan 426-791, Republic of Korea. Electronic address: tnam@hanyang.ac.kr.
4
College of Pharmacy and Institute for Drug Research, Yeungnam University, Gyeongsan 712-749, Republic of Korea. Electronic address: jakim@yu.ac.kr.
5
College of Pharmacy and Institute for Drug Research, Yeungnam University, Gyeongsan 712-749, Republic of Korea. Electronic address: jeongb@ynu.ac.kr.

Abstract

We recently reported that 6-aminoalkyl-2,4,5-trimethylpyridin-3-ols, novel series of 6-aminopyridin-3-ol-based antioxidants, have high antiangiogenic activities. In pursuit of wider variety in the analogues, we here report the synthesis and antiangiogenic activities of 6-amidoalkyl-2,4,5-trimethylpyridin-3-ols, which would not be considered excellent antioxidants because of the poorer electron-donating effect of the C(6)-amido group than the corresponding C(6)-amino group. The selected 6-amido compounds showed up to several fold-higher antiangiogenic activities and up to an order of magnitude better antitumor activities in the chick embryo chorioallantoic membrane (CAM) assay than SU4312, a positive control. We also found that paracetamol, as a direct phenolic analogue of our simplest 6-amidopyridin-3-ol, showed a moderate level of antiangiogenic activity. We propose this study will offer a basis for a scaffold of novel angiogenesis inhibitors that can perturb angiogenesis-related pathologies.

KEYWORDS:

Amidopyridinol; Angiogenesis; Antiangiogenic; Antitumor; Chick chorioallantoic membrane assay

PMID:
24894557
DOI:
10.1016/j.bmcl.2014.05.005
[Indexed for MEDLINE]

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