Design, synthesis and bioactivity study of N-salicyloyl tryptamine derivatives as multifunctional agents for the treatment of neuroinflammation

Fan, Xiaohong; Li, Junfang; Deng, Xiaojie; Lu, Yuanqing; Feng, Yiyue; Ma, Shumeng; Wen, Huaixiu; Zhao, Quanyi; Tan, Wen; Shi, Tao; Wang, Zhen

doi:10.1016/j.ejmech.2020.112217

Cited by 35 publications

(39 citation statements)

References 74 publications

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“…On the other hand, compounds 26a and 26b reduced GFAP and Iba-1 levels in the hippocampus and displayed neuroprotection in Nissl staining in vivo . Besides, both compounds 26a and 26b had remarkable safety with LD 50 > 1000 mg/kg 41 .…”

Section: Recent Development In Anti-inflammatory Agentsmentioning

confidence: 95%

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Bian

Wu³

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Inflammation and disease are closely related. Inflammation can induce various diseases, and diseases can promote inflammatory response, and two possibly induces each other in a bidirectional loop. Inflammation is usually treated using synthetic anti-inflammatory drugs which are associated with several adverse effects hence are not safe for long-term use. Therefore, there is need for anti-inflammatory drugs which are not only effective but also safe. Several researchers have devoted to the research and development of effective anti-inflammatory drugs with little or no side effects. In this review, we studied some small molecules with reported anti-inflammatory activities and hence potential sources of anti-inflammatory agents. The information was retrieved from relevant studies published between January 2019 and May, 2021 for review. This review study was aimed to provide relevant information towards the design and development of effective and safe anti-inflammation agents.

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Section: Recent Development In Anti-inflammatory Agentsmentioning

confidence: 95%

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Bian

Wu³

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…NaBH 4 Reduction of Limonin (1). Limonin (1; 150 mg) was dissolved in dichloromethane (DCM) (15 mL), and 2.0 mL of a NaBH 4 solution (70 mg in anhydrous CH 3 OH) were added dropwise.…”

Section: Synthesis Of Compounds 1a-1gmentioning

confidence: 99%

“…[2] Lipopolysaccharide (LPS) can induce the phenotype of microglia to change and release a series of inflammatory factors, such as TNF-α, NO, iNOS, PGE2, which can cause inflammation and tissue damage. [3,4] The inflammation related diseases are still big threatens to human health, and more targeted drugs yet remain to be urgently developed.…”

Section: Introductionmentioning

confidence: 99%

“…Microglia mediated inflammatory response plays a key role in the occurrence and development of brain ischemia, neurodegenerative diseases and other diseases [2] . Lipopolysaccharide (LPS) can induce the phenotype of microglia to change and release a series of inflammatory factors, such as TNF‐ α , NO, iNOS, PGE2, which can cause inflammation and tissue damage [3,4] . The inflammation related diseases are still big threatens to human health, and more targeted drugs yet remain to be urgently developed.…”

Section: Introductionmentioning

confidence: 99%

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Chemical Constituents from Citrus changshan‐huyou and Their Anti‐Inflammatory Activities

Hu¹,

Liu

et al. 2020

Chemistry & Biodiversity

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“…In contrast, while another melatonin derivative with a 4-bromobenzoyl amide substitution at the N -acyl side chain (4-bromo- N -(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide, EBM) was predicted to be a substrate of CYP1A2, it displayed a potent antioxidant and neuroprotective effect [ 20 , 23 ]. Fan et al [ 24 ] also reported that N -salicyloyl tryptamine derivatives are potential anti-neuroinflammation agents that act by decreasing the production of proinflammatory mediators, NO, PGE 2 and TNF-α. These considerations prompted us to investigate and evaluate the anti-inflammatory activity of the BBM and EBM lipophilic melatonin derivatives.…”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory Comparison of Melatonin and Its Bromobenzoylamide Derivatives in Lipopolysaccharide (LPS)-Induced RAW 264.7 Cells and Croton Oil-Induced Mice Ear Edema

et al. 2021

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The pineal gland is a neuroendocrine organ that plays an important role in anti-inflammation through the hormone melatonin. The anti-inflammatory effects of melatonin and its derivatives have been reported in both in vitro and in vivo models. Our previous study reported the potent antioxidant and neuroprotective activities of bromobenzoylamide substituted melatonin. In silico analysis successfully predicted that melatonin bromobenzoylamid derivatives were protected from metabolism by CYP2A1, which is a key enzyme of the melatonin metabolism process. Therefore, the anti-inflammatory activities of melatonin and its bromobenzoylamide derivatives BBM and EBM were investigated in LPS-induced RAW 264.7 macrophages and croton oil-induced ear edema in mice. The experiments showed that BBM and EBM significantly reduced production of the inflammatory mediators interleukin-6 (IL-6), prostaglandin E2 (PGE2), and nitric oxide (NO) in a dose-dependent manner, but only slightly affected TNF-α in LPS-induced RAW 264.7 macrophages. This suggests that modifying melatonin at either the N1-position or the N-acetyl side chain affected production of NO, PGE2 and IL-6 in in vitro model. In the croton oil-induced mouse ear edema model, BBM, significantly decreased ear edema thickness at 2–4 h. It leads to conclude that bromobenzoylamide derivatives of melatonin may be one of the potential candidates for a new type of anti-inflammatory agent.

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Design, synthesis and bioactivity study of N-salicyloyl tryptamine derivatives as multifunctional agents for the treatment of neuroinflammation

Cited by 35 publications

References 74 publications

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Chemical Constituents from Citrus changshan‐huyou and Their Anti‐Inflammatory Activities

Anti-Inflammatory Comparison of Melatonin and Its Bromobenzoylamide Derivatives in Lipopolysaccharide (LPS)-Induced RAW 264.7 Cells and Croton Oil-Induced Mice Ear Edema

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