Synthesis of 1‐(substituted phenylcarbonyl/sulfonylamino)‐1,2,3,6‐tetrahydropyridine‐5‐carboxylic acid diethylamides as potential anti‐inflammatory agents

The pharmacological activities of tetrahydropyridine (THP) derivatives are dependent on the substituent ring moiety. In this study, we investigate the anti-inflammatory activities of 12 newly synthesized substituted N-[3-(1H-pyrrol-1-yl)methyl]-1,2,5,6-tetrahydrobenzamide/benzene sulfonamides (9a–l) in murine BV-2 microglial cells. All compounds were initially screened for attenuation of nitric oxide (NO) production in lipopolysaccharide (LPS) (1 μg/mL)-activated microglial cells. The data show that only SO2-substituted THPs were effective at sub-lethal concentrations (IC50 values of 12.92 μM (9i), 14.64 μM (9j), 19.63 μM (9k)) relative to L-N6-(1-iminoethyl)lysine positive control (IC50 = 3.1 μM). The most potent SO2-substituted compound (9i) also blocked the LPS-inducible nitric oxide synthase (iNOS) and attenuated the release of several cytokines including IL-1α, IL-10, and IL-6. These findings establish the moderate immunomodulating effects of SO2-substituted THP derivatives.

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“…New THP derivatives were synthesized using the methods described . The synthetic routes for the title compounds are outlined in Scheme .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Substituted N‐[3‐(1H‐Pyrrol‐1‐yl)methyl]‐1,2,5,6‐tetrahydropyridin‐1‐yl]benzamide/benzene Sulfonamides as Anti‐Inflammatory Agents

Gangapuram

Mazzio

Eyunni

et al. 2014

Archiv der Pharmazie

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“…Schizophrenia [18,19], Parkinson's disease [20,21], obesity, and diabetes [22,23]. Nitrogen heterocyclic tetrahydro-pyridine moiety is abundant in synthetic bioactive molecules as well as in various natural products [24] which exhibit a plethora of biological properties such as analgesic [25], anticonvulsant [26], antimalarial [27], hyperglycemic [28], nicotinic [29] and antiin uenza [30].…”

Section: Introductionmentioning

confidence: 99%

Application of a novel Deep Eutectic Solvent as a capable and new catalyst for the synthesis of tetrahydropyridines and 1,3-thiazolidin-4-ones

Goodarzi

Habibi

Monem

2023

Preprint

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A novel Deep Eutectic Solvent (ETPP-Br/THF-TCA-DES) was prepared by a mixture of ethyl triphenylphosphonium bromide (MTPP-Br) and tetrahydrofuran-2,3,4,5-tetra-carboxylic acid (THF-TCA, mole ratio 7:3) in a cheap, simple, and non-toxic method, characterized by FT-IR, TGA/DTA, densitometer, eutectic point, and 1H NMR techniques and used as a capable and new catalyst for the synthesis of two sets of compounds: i) the four new [a(1-4)] and the ten [a(5-15)] known alkyl 1,2,6-trisubstituted-4-[(hetero)arylamino]-1,2,5,6-tetrahydropyridine-3-carboxyl-ates, and ii) the two new [b(1-2)] and the eight [b(3-10)] known 1,3-thiazolidin-4-ones in solvent-free conditions, short reaction time, high yields, and easy recycling and separation of the DES catalyst. There is a nice consistency between the proposed structure of the DES compound, the integration values of the 1H NMR peaks and the ratio of ETPP-Br to THF-TCA obtained from the eutectic point phase diagram. Also, the decrease in splitting patterns of the peaks in DES, compared to the two starting materials can be a good evidence of hydrogen bond formation between the two components.

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“…Piperidines and their derivatives comprise a major class of N- heterocycles of biological interest. Compounds bearing the piperidine moiety exhibit a broad range of biological properties, including anti-hypertensive [3] , antibacterial [4] , antimalarial [5] , anti-inflammatory [6] , analgesic [7] , [8] , antioxidant [9] , and antiproliferative activities [10] .…”

Section: Introductionmentioning

confidence: 99%

Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity

Das

Silva

et al. 2018

Journal of Advanced Research

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Synthesis of 1‐(substituted phenylcarbonyl/sulfonylamino)‐1,2,3,6‐tetrahydropyridine‐5‐carboxylic acid diethylamides as potential anti‐inflammatory agents

Cited by 23 publications

References 19 publications

Synthesis and Biological Evaluation of Substituted N‐[3‐(1H‐Pyrrol‐1‐yl)methyl]‐1,2,5,6‐tetrahydropyridin‐1‐yl]benzamide/benzene Sulfonamides as Anti‐Inflammatory Agents

Synthesis and Biological Evaluation of Substituted N‐[3‐(1H‐Pyrrol‐1‐yl)methyl]‐1,2,5,6‐tetrahydropyridin‐1‐yl]benzamide/benzene Sulfonamides as Anti‐Inflammatory Agents

Application of a novel Deep Eutectic Solvent as a capable and new catalyst for the synthesis of tetrahydropyridines and 1,3-thiazolidin-4-ones

Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity

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