Novel cephalosporin derivatives possessing a substituted cinnamoyl moiety at the 7β-position. Synthesis, structural characterization and antibacterial activity of 3-acetoxymethyl cephalosporin derivatives

López, José Miguel Túñez; Rodríguez, Zalua; González, Maritza; Tolón, Blanca; Avila, Rizette; gonzalez, ileana; Garmendía, Leonor; Mamposo, Taimirys; Carrasco, Ramón; Pellón, Raiza Texidor; Vélez, Hermán; Fini, Adamo

doi:10.1016/j.ejmech.2004.02.016

Cited by 10 publications

(7 citation statements)

References 18 publications

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“…2) by modifying the reported methods. [23][24][25] The protecting group tertbutyloxycarbony (Boc) in 3 was removed and the resulting species was reacted with Boc-protected Phe to make 4. This molecule contained P1-lactam ring, P2-Boc-Phe, and P1 0 -a,b-unsaturated ethyl ester.…”

Section: Synthesis Of Inhibitorsmentioning

confidence: 99%

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Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents

Kuo

Shie

Fang

et al. 2008

Bioorganic & Medicinal Chemistry

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Human enterovirus (EV) belongs to the picornavirus family, which consists of over 200 medically relevant viruses. A peptidomimetic inhibitor AG7088 was developed to inhibit the 3C protease of rhinovirus (a member of the family), a chymotrypsin-like protease required for viral replication, by forming a covalent bond with the active site Cys residue. In this study, we have prepared the recombinant 3C protease from EV71 (TW/2231/98), a particular strain which causes severe outbreaks in Asia, and developed inhibitors against the protease and the viral replication. For inhibitor design, the P3 group of AG7088, which is not interacting with the rhinovirus protease, was replaced with a series of cinnamoyl derivatives directly linked to P2 group through an amide bond to simplify the synthesis. While the replacement caused decreased potency, the activity can be largely improved by substituting the alpha,beta-unsaturated ester with an aldehyde at the P1' position. The best inhibitor 10b showed EC(50) of 18 nM without apparent toxicity (CC(50)>25 microM). Our study provides potent inhibitors of the EV71 3C protease as anti-EV71 agents and facilitates the combinatorial synthesis of derivatives for further improving the inhibitory activity.

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Section: Synthesis Of Inhibitorsmentioning

confidence: 99%

“…25 To a solution of HCl in 1,4-dioxane (4.0 M, 2 mL) was added a solution of 4 (190 mg, 0.4 mmol) in 1,4-dioxane (2 mL) at room temperature. The mixture was stirred for 10 min at 0°C, and then for 30 min at room temperature to prepare an acid chloride solution.…”

Section: Ethyl 4-{2-[34-(methylenedioxy)cinnamoyl]amino-1oxo-3-phenymentioning

confidence: 99%

Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents

Kuo

Shie

Fang

et al. 2008

Bioorganic & Medicinal Chemistry

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“…As previously described, esters and amides of coumaric, ferulic and caffeic acid possess numerous biological activities, e.g., antioxidant [ 82 , 83 , 86 , 89 , 94 , 95 , 96 ], anticancer [ 78 , 87 , 92 ], antibacterial [ 82 , 97 , 98 , 99 ], antifungal [ 100 , 101 , 102 ], antiviral [ 82 , 90 , 103 ], anti-inflammatory [ 104 , 105 , 106 ], and many other activities [ 84 , 107 , 108 ]. The most commonly described health beneficial properties of HCAs and their derivatives is antioxidant activity due to the phenolic hydroxyl group(s) on the main aromatic ring, which possess(es) the ability to react with free radicals and reactive oxygen species forming a resonance-stabilized phenoxyl radical.…”

Section: Synthesis and Properties Of Natural And Synthetic Hydroxymentioning

confidence: 99%

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

et al. 2020

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This review presents the main properties of hydroxycinnamic acid (HCA) derivatives and their potential application as agents for the prevention and treatment of neurodegenerative diseases. It is partially focused on the successful use of these compounds as inhibitors of amyloidogenic transformation of proteins. Firstly, the prerequisites for the emergence of interest in HCA derivatives, including natural compounds, are described. A separate section is devoted to synthesis and properties of HCA derivatives. Then, the results of molecular modeling of HCA derivatives with prion protein as well as with α-synuclein fibrils are summarized, followed by detailed analysis of the experiments on the effect of natural and synthetic HCA derivatives, as well as structurally similar phenylacetic and benzoic acid derivatives, on the pathological transformation of prion protein and α-synuclein. The ability of HCA derivatives to prevent amyloid transformation of some amyloidogenic proteins, and their presence not only in food products but also as natural metabolites in human blood and tissues, makes them promising for the prevention and treatment of neurodegenerative diseases of amyloid nature.

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“…18 All NMR experiments were performed at 298 K for a solution of 35 mg of compound dissolved in 0.5 ml of DMSO-d 6 on a Bruker AMX 400 instrument. The 1 H NMR spectra were recorded at a proton frequency of 250.13 MHz with a spectral width of 4 kHz and a 7.7 µs (90°) pulse.…”

Section: Experimental Spectramentioning

confidence: 99%

¹H and ¹³C spectral assignments of 7β‐(cinnamoyl‐substituted)amino‐3‐acetoxymethyl‐cephalosporins

López¹,

Rodríguez²,

González³

et al. 2004

Magnetic Reson in Chemistry

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Novel cephalosporin derivatives possessing a substituted cinnamoyl moiety at the 7β-position. Synthesis, structural characterization and antibacterial activity of 3-acetoxymethyl cephalosporin derivatives

Cited by 10 publications

References 18 publications

Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents

Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

¹H and ¹³C spectral assignments of 7β‐(cinnamoyl‐substituted)amino‐3‐acetoxymethyl‐cephalosporins

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Novel cephalosporin derivatives possessing a substituted cinnamoyl moiety at the 7β-position. Synthesis, structural characterization and antibacterial activity of 3-acetoxymethyl cephalosporin derivatives

Cited by 10 publications

References 18 publications

Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents

Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

1H and 13C spectral assignments of 7β‐(cinnamoyl‐substituted)amino‐3‐acetoxymethyl‐cephalosporins

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¹H and ¹³C spectral assignments of 7β‐(cinnamoyl‐substituted)amino‐3‐acetoxymethyl‐cephalosporins