Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents

Mopur Vijaya Bhaskar Reddy, Hsin Yi Hung, Ping Chung Kuo, Guan Jhong Huang, Yu Yi Chan, Shiow Chyn Huang, Shwu Jen Wu, Susan L. Morris-Natschke, Kuo Hsiung Lee, Tian Shung Wu

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Twenty-one chalcones were prepared via aldol condensation and subsequent reduction of these compound led to the corresponding dihydrochalcone and 1,3-diphenylpropane derivatives. The synthetic products were examined for their effects on NO inhibition in LPS-activated mouse peritoneal macrophages. Among the tested compounds, a 1,3-diarylpropane analog, 2-(3-(3,4-dimethoxyphenyl)propyl)-5-methoxyphenol (3p), displayed the most significant inhibitory effects against NO production. To investigate the mechanism of action, the effects of 3p on iNOS and COX-2 protein expression were studied by immunoblot. The results concluded that 3p is capable of inhibiting iNOS expression in LPS-induced RAW264.7 cells via attenuation of NF-κB signaling by ERK, p38, and JNK.

Original languageEnglish
Pages (from-to)1547-1550
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume27
Issue number7
DOIs
Publication statusPublished - 2017 Jan 1

Fingerprint

Chalcones
Lead compounds
Chalcone
Macrophages
Peritoneal Macrophages
Condensation
Anti-Inflammatory Agents
Derivatives
Proteins
3-hydroxybutanal
1,3-diphenylpropane
dihydrochalcone

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Vijaya Bhaskar Reddy, Mopur ; Hung, Hsin Yi ; Kuo, Ping Chung ; Huang, Guan Jhong ; Chan, Yu Yi ; Huang, Shiow Chyn ; Wu, Shwu Jen ; Morris-Natschke, Susan L. ; Lee, Kuo Hsiung ; Wu, Tian Shung. / Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents. In: Bioorganic and Medicinal Chemistry Letters. 2017 ; Vol. 27, No. 7. pp. 1547-1550.
@article{f88ab19680134aee8418895884553f14,
title = "Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents",
abstract = "Twenty-one chalcones were prepared via aldol condensation and subsequent reduction of these compound led to the corresponding dihydrochalcone and 1,3-diphenylpropane derivatives. The synthetic products were examined for their effects on NO inhibition in LPS-activated mouse peritoneal macrophages. Among the tested compounds, a 1,3-diarylpropane analog, 2-(3-(3,4-dimethoxyphenyl)propyl)-5-methoxyphenol (3p), displayed the most significant inhibitory effects against NO production. To investigate the mechanism of action, the effects of 3p on iNOS and COX-2 protein expression were studied by immunoblot. The results concluded that 3p is capable of inhibiting iNOS expression in LPS-induced RAW264.7 cells via attenuation of NF-κB signaling by ERK, p38, and JNK.",
author = "{Vijaya Bhaskar Reddy}, Mopur and Hung, {Hsin Yi} and Kuo, {Ping Chung} and Huang, {Guan Jhong} and Chan, {Yu Yi} and Huang, {Shiow Chyn} and Wu, {Shwu Jen} and Morris-Natschke, {Susan L.} and Lee, {Kuo Hsiung} and Wu, {Tian Shung}",
year = "2017",
month = "1",
day = "1",
doi = "10.1016/j.bmcl.2017.02.038",
language = "English",
volume = "27",
pages = "1547--1550",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Limited",
number = "7",

}

Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents. / Vijaya Bhaskar Reddy, Mopur; Hung, Hsin Yi; Kuo, Ping Chung; Huang, Guan Jhong; Chan, Yu Yi; Huang, Shiow Chyn; Wu, Shwu Jen; Morris-Natschke, Susan L.; Lee, Kuo Hsiung; Wu, Tian Shung.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 27, No. 7, 01.01.2017, p. 1547-1550.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents

AU - Vijaya Bhaskar Reddy, Mopur

AU - Hung, Hsin Yi

AU - Kuo, Ping Chung

AU - Huang, Guan Jhong

AU - Chan, Yu Yi

AU - Huang, Shiow Chyn

AU - Wu, Shwu Jen

AU - Morris-Natschke, Susan L.

AU - Lee, Kuo Hsiung

AU - Wu, Tian Shung

PY - 2017/1/1

Y1 - 2017/1/1

N2 - Twenty-one chalcones were prepared via aldol condensation and subsequent reduction of these compound led to the corresponding dihydrochalcone and 1,3-diphenylpropane derivatives. The synthetic products were examined for their effects on NO inhibition in LPS-activated mouse peritoneal macrophages. Among the tested compounds, a 1,3-diarylpropane analog, 2-(3-(3,4-dimethoxyphenyl)propyl)-5-methoxyphenol (3p), displayed the most significant inhibitory effects against NO production. To investigate the mechanism of action, the effects of 3p on iNOS and COX-2 protein expression were studied by immunoblot. The results concluded that 3p is capable of inhibiting iNOS expression in LPS-induced RAW264.7 cells via attenuation of NF-κB signaling by ERK, p38, and JNK.

AB - Twenty-one chalcones were prepared via aldol condensation and subsequent reduction of these compound led to the corresponding dihydrochalcone and 1,3-diphenylpropane derivatives. The synthetic products were examined for their effects on NO inhibition in LPS-activated mouse peritoneal macrophages. Among the tested compounds, a 1,3-diarylpropane analog, 2-(3-(3,4-dimethoxyphenyl)propyl)-5-methoxyphenol (3p), displayed the most significant inhibitory effects against NO production. To investigate the mechanism of action, the effects of 3p on iNOS and COX-2 protein expression were studied by immunoblot. The results concluded that 3p is capable of inhibiting iNOS expression in LPS-induced RAW264.7 cells via attenuation of NF-κB signaling by ERK, p38, and JNK.

UR - http://www.scopus.com/inward/record.url?scp=85013911860&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85013911860&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2017.02.038

DO - 10.1016/j.bmcl.2017.02.038

M3 - Article

C2 - 28256373

AN - SCOPUS:85013911860

VL - 27

SP - 1547

EP - 1550

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 7

ER -