Inhibition of LPS-stimulated ROS production by fluorinated and hydroxylated chalcones in RAW 264.7 macrophages with structure-activity relationship study

  • Bioorg Med Chem Lett. 2017 Mar 1;27(5):1205-1209. doi: 10.1016/j.bmcl.2017.01.061.
Ganesh Bist  1 ,  Nirmala Tilija Pun  1 ,  Til Bahadur Thapa Magar  1 ,  Aarajana Shrestha  1 ,  Hye Jin Oh  1 ,  Amrita Khakurel  1 ,  Pil-Hoon Park  2 ,  Eung-Seok Lee  3
Affiliations
  • 1. College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Republic of Korea.
  • 2. College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Republic of Korea. Electronic address: [email protected].
  • 3. College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Republic of Korea. Electronic address: [email protected].
PMID: 28159411 DOI: 10.1016/j.bmcl.2017.01.061
Abstract

Based on the importance of the previous fluorinated and/or hydroxylated Chalcones studies, thirty-six compounds were designed as phenyl or hydroxyphenyl bearing fluoro, trifluoromethyl or trifluoromethoxy phenyl propenones and synthesized by applying modified Claisen-Schmidt condensation reaction as a single step. Inhibitory effects of the synthesized compounds on ROS production stimulated by LPS in RAW 264.7 macrophage were evaluated. Structure-activity relationship (SAR) study revealed that the compounds possessing para-hydroxyphenyl group combined with meta-fluoro or meta-trifluoromethyl phenyl group, and meta/para-hydroxyphenyl group combined with ortho-trifluoromethoxyphenyl group have an essential role in inhibiting the LPS-stimulated ROS production in RAW 264.7 macrophages. The most significant inhibitory effect on LPS-stimulated ROS production in RAW 264.7 macrophages was observed in compound 30 that possessed para-hydroxyphenyl group along with ortho-trifluoromethoxyphenyl group.

Keywords
Fluorinated and hydroxylated chalcones; Inhibition of LPS-stimulated ROS production; SAR study.