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Literature DB >> 25807261

Discovery of benzo[f]indole-4,9-dione derivatives as new types of anti-inflammatory agents.

You-Ren Chen¹, Chih-Hua Tseng², Yeh-Long Chen³, Tsong-Long Hwang^4,5, Cherng-Chyi Tzeng⁶.

Abstract

Certain benzo[f]indole-4,9-dione derivatives were synthesized and evaluated for their inhibitory effects on superoxide anion generation and neutrophil elastase (NE) release in formyl-l-methionyl-l-leucyl-l-phenylalanine (fMLF)-activated human neutrophils. Results indicated that (Z)-1-benzyl-4-(hydroxyimino)-1H-benzo[f]indol-9(4H)-one (10) showed a potent dual inhibitory effect on NE release and superoxide anion generation with IC50 value of 2.78 and 2.74 μM respectively. The action mechanisms of 10 in human neutrophils were further investigated. Our results showed that compound 10 did not alter fMLF-induced phosphorylation of Src (Src family Y416). Notably, phosphorylation of Akt (S473) and mobilization of [Ca2+]i caused by fMLF was inhibited by compound 10. Further structural optimization of 10 is ongoing.

Entities: CellLine Chemical Disease Gene Species

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Year: 2015 PMID： 25807261 PMCID： PMC4394546 DOI： 10.3390/ijms16036532

Source DB: PubMed Journal: Int J Mol Sci ISSN： 1422-0067 Impact factor: 5.923

30 in total

1. Identification of furo[3', 2':3,4]naphtho[1,2-d]imidazole derivatives as orally active and selective inhibitors of microsomal prostaglandin E(2) synthase-1 (mPGES-1).

Authors: Chih-Hua Tseng; Cherng-Chyi Tzeng; Pin-Keng Shih; Chia-Ning Yang; You-Chung Chuang; Shin-I Peng; Chang-Sheng Lin; Jih-Pyang Wang; Chih-Mei Cheng; Yeh-Long Chen
Journal: Mol Divers Date: 2011-12-09 Impact factor: 2.943

2. Isolation and synthesis of melodamide A, a new anti-inflammatory phenolic amide from the leaves of Melodorum fruticosum.

Authors: Hsiu-Hui Chan; Tsong-Long Hwang; Tran Dinh Thang; Yann-Lii Leu; Ping-Chung Kuo; Bui Thi Minh Nguyet; Do Ngoc Dai; Tian-Shung Wu
Journal: Planta Med Date: 2013-01-23 Impact factor: 3.352

3. The hederagenin saponin SMG-1 is a natural FMLP receptor inhibitor that suppresses human neutrophil activation.

Authors: Tsong-Long Hwang; Chien-Chiao Wang; Yao-Haur Kuo; Hui-Chi Huang; Yang-Chang Wu; Liang-Mou Kuo; Yi-Hsiu Wu
Journal: Biochem Pharmacol Date: 2010-06-25 Impact factor: 5.858

4. Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.

Authors: Chih-Hua Tseng; Yeh-Long Chen; Sheng-Huei Yang; Shin-I Peng; Chih-Mei Cheng; Chein-Hwa Han; Shinne-Ren Lin; Cherng-Chyi Tzeng
Journal: Bioorg Med Chem Date: 2010-06-10 Impact factor: 3.641

5. The signaling mechanisms mediating the inhibitory effect of TCH-1116 on formyl peptide-stimulated superoxide anion generation in neutrophils.

Authors: Ya-Ru Tsai; Li-Jiau Huang; Miau-Rong Lee; Yeh-Long Chen; Sheng-Chu Kuo; Cherng-Chyi Tzeng; Mei-Feng Hsu; Jih-Pyang Wang
Journal: Eur J Pharmacol Date: 2012-02-21 Impact factor: 4.432

6. Anti-inflammatory effects of glycyrol isolated from Glycyrrhiza uralensis in LPS-stimulated RAW264.7 macrophages.

Authors: Eun Myoung Shin; Hong Yu Zhou; Lian Yu Guo; Jeong Ah Kim; Seung Ho Lee; Irmgard Merfort; Sam Sik Kang; Hak Sung Kim; Sanghee Kim; Yeong Shik Kim
Journal: Int Immunopharmacol Date: 2008-07-11 Impact factor: 4.932

7. Substituted phenanthrene imidazoles as potent, selective, and orally active mPGES-1 inhibitors.

Authors: Bernard Côté; Louise Boulet; Christine Brideau; David Claveau; Diane Ethier; Richard Frenette; Marc Gagnon; André Giroux; Jocelyne Guay; Sébastien Guiral; Joseph Mancini; Evelyn Martins; Frédéric Massé; Nathalie Méthot; Denis Riendeau; Joel Rubin; Daigen Xu; Hongping Yu; Yves Ducharme; Richard W Friesen
Journal: Bioorg Med Chem Lett Date: 2007-10-17 Impact factor: 2.823

8. Effects of resveratrol and its derivatives on lipopolysaccharide-induced microglial activation and their structure-activity relationships.

Authors: Xue-Lian Meng; Jing-Yu Yang; Guo-Liang Chen; Li-Hui Wang; Li-Jia Zhang; Shu Wang; Jie Li; Chun-Fu Wu
Journal: Chem Biol Interact Date: 2008-04-22 Impact factor: 5.192

Discovery of benzo[f]indole-4,9-dione derivatives as new types of anti-inflammatory agents.

1. Identification of furo[3', 2':3,4]naphtho[1,2-d]imidazole derivatives as orally active and selective inhibitors of microsomal prostaglandin E(2) synthase-1 (mPGES-1).

2. Isolation and synthesis of melodamide A, a new anti-inflammatory phenolic amide from the leaves of Melodorum fruticosum.

3. The hederagenin saponin SMG-1 is a natural FMLP receptor inhibitor that suppresses human neutrophil activation.

4. Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.

5. The signaling mechanisms mediating the inhibitory effect of TCH-1116 on formyl peptide-stimulated superoxide anion generation in neutrophils.

6. Anti-inflammatory effects of glycyrol isolated from Glycyrrhiza uralensis in LPS-stimulated RAW264.7 macrophages.

7. Substituted phenanthrene imidazoles as potent, selective, and orally active mPGES-1 inhibitors.

8. Effects of resveratrol and its derivatives on lipopolysaccharide-induced microglial activation and their structure-activity relationships.

9. RV09, a novel resveratrol analogue, inhibits NO and TNF-alpha production by LPS-activated microglia.

10. Synthesis and anti-inflammatory evaluations of β-lapachone derivatives.

1. Crystal structure of methyl (2Z)-3-(4-chloro-phen-yl)-2-[(3-methyl-1H-indol-1-yl)meth-yl]prop-2-enoate.

2. Crystal structure of 2-[2-phenyl-1-(phenyl-sulfon-yl)eth-yl]-1-phenyl-sulfonyl-1H-indole.

3. Discovery of Indeno[1,2-c]quinoline Derivatives as Potent Dual Antituberculosis and Anti-Inflammatory Agents.

4. Synthesis and Biological Evaluation of Thalidomide Derivatives as Potential Anti-Psoriasis Agents.