Inhibition of LDL oxidation and inflammasome assembly by nitroaliphatic derivatives. Potential use as anti-inflammatory and anti-atherogenic agents

Cataldo, Nicolás; Musetti, Bruno; Celano, Laura; Carabio, Claudio; Cassina, Adriana; Cerecetto, Hugo; González, Mercedes; Thomson, Leonor

doi:10.1016/j.ejmech.2018.09.062

Cited by 4 publications

(2 citation statements)

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“…[27] The Henry reaction was performed utilizing ammonium acetate (NH 4 OAc) and benzaldehyde 14, resulting in the formation of nitroethene 15 with a remarkable yield. [28] Finally, nitroethene 15 was reduced with lithium aluminum hydride (LAH), resulting in a yield of 98 % of the desired primary amine 8. Amide 6 was synthesized with a 68 % yield by coupling carboxylic acid 7 and amine 8 using ethyl-(N',N'-dimethylamino) propylcarbodiimide hydrochloride (EDC) and 1-hydroxybenzotriazole (HOBt) as coupling reagents, as shown in Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

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Trifluoroacetyl‐Containing Scaffolds Assisted in Total Synthesis of Oxostephanine and Thailandine and Their Antimicrobial Activity

Vijitphan,

Makarasen,

Baicharoen

et al. 2024

Asian J Org Chem

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This study is the first to fully synthesize oxostephanine (1) and thailandine (2), two aporphine alkaloids that were originally found in Stephania venosa (Blume) Spreng. The synthesis described in this study utilized commercially available starting materials, namely 2‐bromo‐6‐methoxybenzaldehyde and 3,4‐dihydroxybenzaldehyde. The B‐ring moiety of aporphines was successfully synthesized through the utilization of the Bischler‐Napieralski cyclization process. The synthesis of the C ring in oxoaporphine was accomplished using an order of crucial steps, namely biaryl coupling, incorporation of trifluoroacetyl‐containing scaffolds, and palladium coupling, followed by oxidation using Fremy's salt. The synthesis of oxostephanine (1) and thailandine (2) was successfully achieved in 11 and 12 steps, respectively, resulting in equivalent overall yields of 11.7%. This study aimed to increase amount of interested compounds and explore the biological activity of those compounds. In this study, both compounds were subjected to testing for antibacterial activity using the CLSI standard M100 guideline. Oxostephanine (1) has shown significant antibacterial efficacy against gram‐positive bacteria and bacterial biofilms, as seen by minimum inhibitory concentration (MIC) values ranging from 7.8 to 125 µg/mL. Conversely, higher MIC values of 250 µg/mL indicated that thailandine (2) exhibited limited antimicrobial activity.

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Section: Resultsmentioning

confidence: 99%

“…The Henry reaction was performed utilizing ammonium acetate (NH 4 OAc) and benzaldehyde 14 , resulting in the formation of nitroethene 15 with a remarkable yield [28] . Finally, nitroethene 15 was reduced with lithium aluminum hydride (LAH), resulting in a yield of 98 % of the desired primary amine 8.…”

Section: Resultsmentioning

confidence: 99%