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Molecules 2017, 22(6), 898; doi:10.3390/molecules22060898

Synthesis of Gallic Acid Analogs as Histamine and Pro-Inflammatory Cytokine Inhibitors for Treatment of Mast Cell-Mediated Allergic Inflammation

1
College of Pharmacy and Gachon Institute of Pharmaceutical Sciences, Gachon University, Incheon 21936, Korea
2
Department of Pharmacology, School of Medicine, Kyungpook National University, Daegu 41944, Korea
3
College of Pharmacy, Woosuk University, Jeonbuk 565-701, Korea
*
Authors to whom correspondence should be addressed.
Academic Editor: Muraleedharan G. Nair
Received: 18 April 2017 / Revised: 25 May 2017 / Accepted: 26 May 2017 / Published: 29 May 2017
(This article belongs to the Special Issue Anti-inflammatory Agents)
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Abstract

Gallic acid (3,4,5-trihydroxybenzoic acid), is a natural product found in various foods and herbs that are well known as powerful antioxidants. Our previous report demonstrated that it inhibits mast cell-derived inflammatory allergic reactions by blocking histamine release and pro-inflammatory cytokine expression. In this report, various amide analogs of gallic acid have been synthesized by introducing different amines through carbodiimide-mediated amide coupling and Pd/C-catalyzed hydrogenation. These compounds showed a modest to high inhibitory effect on histamine release and pro-inflammatory cytokine expression. Among them, the amide bearing (S)-phenylglycine methyl ester 3d was found to be more active than natural gallic acid. Further optimization yielded several (S)- and (R)-phenylglycine analogs that inhibited histamine release in vitro. Our findings suggest that some gallamides could be used as a treatment for allergic inflammatory diseases. View Full-Text
Keywords: gallic acid; allergic inflammation; histamine; pro-inflammatory cytokine gallic acid; allergic inflammation; histamine; pro-inflammatory cytokine
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Fei, X.; Je, I.-G.; Shin, T.-Y.; Kim, S.-H.; Seo, S.-Y. Synthesis of Gallic Acid Analogs as Histamine and Pro-Inflammatory Cytokine Inhibitors for Treatment of Mast Cell-Mediated Allergic Inflammation. Molecules 2017, 22, 898.

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