Synthesis and evaluation of new α-methylene-γ-lactone carbamates with NO production inhibitory effects in lipopolysaccharide-induced RAW 264.7 macrophages

Shao, Wen‐Hao; Chen, Bingyang; Cheng, Xiang‐Rong; Yuan, Haichao; Chen, Hao; Chang, Wanlin; Ye, Ji; Lin, Shuo; Sun, Qian; Zhang, Weidong

doi:10.1016/j.ejmech.2015.02.016

Cited by 8 publications

(4 citation statements)

References 20 publications

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“…). This survey reveals that only four molecules adopt the same structural motif, namely HOQKAC [35], HOTZOH [36], PEQVOZ [37] and USAJIK [38]. In these X-ray structures, the I•••C interactions appear much weaker than in I-azo-NH-MMA, since the I•••CH 2 =C distances are in the range of 3.526-3.692 Å (Figure S1, Supplementary Materials).…”

Section: Table 2 Parameters Of Halogen and Hydrogen Bonds Inmentioning

confidence: 99%

“…This intriguing contact convinced us to make a Cambridge Structural Database (CSD version 5.42 updates, Sep 2021) analysis on the interaction between an iodine and a double bond (I•••CH 2 =C, C•••I distances between 3.0 and 4.0 Å). This survey reveals that only four molecules adopt the same structural motif, namely HOQKAC[35], HOTZOH[36], PEQVOZ[37] and USAJIK[38]. In these X-ray structures, the I•••C interactions appear much weaker than in I-azo-NH-MMA, since the I•••CH 2 =C distances are in the range of 3.526-3.692 Å (FigureS1, Supplementary Materials).…”

mentioning

confidence: 99%

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Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Frangville¹,

Kumar²,

Gelbcke³

et al. 2021

Molecules

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Smart materials represent an elegant class of (macro)-molecules endowed with the ability to react to chemical/physical changes in the environment. Herein, we prepared new photo responsive azobenzenes possessing halogen bond donor groups. The X-ray structures of two molecules highlight supramolecular organizations governed by unusual noncovalent bonds. In azo dye I-azo-NO2, the nitro group is engaged in orthogonal H···O···I halogen and hydrogen bonding, linking the units in parallel undulating chains. As far as compound I-azo-NH-MMA is concerned, a non-centrosymmetric pattern is formed due to a very rare I···π interaction involving the alkene group supplemented by hydrogen bonds. The Cambridge Structural Database contains only four structures showing the same I···CH2=C contact. For all compounds, an 19F-NMR spectroscopic analysis confirms the formation of halogen bonds in solution through a recognition process with chloride anion, and the reversible photo-responsiveness is demonstrated upon exposing a solution to UV light irradiation. Finally, the intermediate I–azo–NH2 also shows a pronounced color change due to pH variation. These azobenzenes are thereby attractive building blocks to design future multi-stimuli responsive materials for highly functional devices.

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Section: Table 2 Parameters Of Halogen and Hydrogen Bonds Inmentioning

confidence: 99%

mentioning

confidence: 99%

Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Frangville¹,

Kumar²,

Gelbcke³

et al. 2021

Molecules

View full text Add to dashboard Cite

show abstract

“…). This survey reveals that only four molecules adopt the same structural motif, namely HOQKAC, [35] HOTZOH, [36] PEQVOZ [37] and USAJIK. [38] In these X-ray structures, the I•••C interactions appear much weaker than in I-azo-NH-MMA, since the I•••CH2=C distances are in the range of 3.526-3.692 Å (Figure S1).…”

Section: X-ray Structure Analysis Of Xb Azobenzenesmentioning

confidence: 99%

“…X-ray structure of I-azo-NH-MMA developing undulating parallel chains due to C•••I halogen bonds This intriguing contact convinced us to make a Cambridge Structural Database (CSD version 5.42 updates, Sep 2021) analysis on the interaction between an iodine and a double bond (I•••CH2=C). This survey reveals that only four molecules adopt the same structural motif, namely HOQKAC,[35] HOTZOH,[36] PEQVOZ[37] and USAJIK [38]. In these X-ray structures, the I•••C interactions appear much weaker than in I-azo-NH-MMA, since the…”

mentioning

confidence: 93%

Multi Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Frangville¹,

Kumar²,

Gelbcke³

et al. 2021

Preprint

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Smart materials represent an elegant class of (macro)-molecules endowed with the ability to react to chemical/physical changes in the environment. Herein, we prepared new photo responsive azobenzenes possessing halogen bond donor groups. The X-ray structures of two molecules highlight supramolecular organizations governed by unusual noncovalent bonds. In azo dye I-azo-NO2, the nitro group is engaged in orthogonal H···O···I halogen and hydrogen bonding, linking the units in parallel undulating chains. As concern parent I-azo-NH-MMA, a non-centrosymmetric pattern is formed due to a very rare I···π interaction involving the alkene group supplemented by hydrogen bonds. The Cambridge Structural Database contains only four structures with the same I···CH2=C contact. For all compounds, a 19F NMR spectroscopic analysis confirms the formation of halogen bonds in solution through a recognition process with chloride anion, and the reversible photo-responsiveness is demonstrated upon exposing a solution to UV light irradiation. Finally, intermediate I-azo-NO2 also shows a pronounced color change due to pH variation. These azobenzenes are thereby attractive building blocks to design multi-stimuli responsive materials for highly functional devices.

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Design, Synthesis and Biological Evaluation of Novel (E)‐Hydroxystyryl Aralkyl Sulfones as Neuroprotective Agents

Chen

Liu

et al. 2020

ChemistrySelect

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A novel class of (E)‐hydroxystyryl aralkyl sulfones were designed and synthesized as neuroprotective agents. Their neuroprotective properties were assessed by several antioxidant models including 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) free radicals scavenging model, neuronal protective effects against neurotoxins such as hydrogen peroxide (H2O2), 6‐hydroxydopamine (6‐OHDA) and 1‐methyl‐4‐phenylpyridinium iodide (MPP+). Besides, the anti‐inflammatory activity was evaluated by lipopolysaccharide (LPS)‐induced nitric oxide (NO) release model in BV2 microglial cells. The result demonstrated that cinnamyl substituted compound 5 h exhibited prominent antioxidant activity in H2O2 and 6‐OHDA models and higher anti‐inflammatory potency (IC50=7.3 μM) than lead compound 1 (IC50=13.4 μM). Furthermore, compound 5 h displayed predicted CNS (+) blood‐brain barrier permeability (Pe=5.66×10−6 cm s−1) in PAMPA model and low toxicity in PC12 and BV2 cells. These multifunctional properties highlight compound 5 h is a promising candidate for further development against neurodegenerative diseases.

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Synthesis and evaluation of new α-methylene-γ-lactone carbamates with NO production inhibitory effects in lipopolysaccharide-induced RAW 264.7 macrophages

Cited by 8 publications

References 20 publications

Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Multi Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction

Design, Synthesis and Biological Evaluation of Novel (E)‐Hydroxystyryl Aralkyl Sulfones as Neuroprotective Agents

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