Anti-inflammatory effect of natural and semi-synthetic phthalides

Del-Ángel, Mayela; Nieto, Antonio; Ramírez‐Ápan, Teresa; Delgado, Guillermo

doi:10.1016/j.ejphar.2015.01.026

Cited by 25 publications

(20 citation statements)

References 47 publications

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“…1 H NMR (DMSO-d 6 ): δ = 1.87 (t, 4H, CH 2 -CH 2 pyrrolidine), 2.55 (s, 3H, CH 3 ), 3.25 (t, 4H, CH 2 -N-CH 2 pyrrolidine), 7.65, 8.26 (dd, 4H, Ar-H, AB system, J = 9.41 Hz). 13 C NMR (DMSO-d 6 ): δ = 24.7 (2C, CH 2 -CH 2 pyrrolidine), 28…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (DMSO-d 6 ): δ = 1.99 (t, 4H, CH 2 -CH 2 pyrrolidine), 3.27 (t, 4H, CH 2 -N-CH 2 pyrrolidine), 4.56 (s, 2H, CH 2 ), 7.84, 8.22 (dd, 4H, Ar-H, AB system, J = 8.57 Hz). 13 N-(4-Fluorobenzylidene)-4-(4-(pyrrolidin-1-ylsulfonyl)…”

Section: -Bromo-1-(4-(pyrrolidin-1-ylsulfonyl)phenyl)ethanone (2)mentioning

confidence: 99%

“…1 H NMR (DMSO-d 6 ): δ = 1.29 (t, 3H, CH 3 -CH 2 ), 1.92 (t, 4H, CH 2 -CH 2 pyrrolidine), 3.24 (t, 4H, CH 2 -N-CH 2 pyrrolidine), 4.20 (q, 2H, CH 3 -CH 2 ), 6.73 (s, 1H, CH-thiazole), 6.90 -8.62 (m, 9H, Ar-H). 13…”

Section: ) Ethyl 2-cyano-2-(3-phenyl-4-(4-(pyrrolidin-1-ylsulfonyl)pmentioning

confidence: 99%

“…Sulfonamides have been demonstrated to possess antibacterial [1]- [3], antifungal [4], insulin-releasing [5] [6], carbonic anhydrase inhibitory [7]- [9], hypoglycemic [10], anesthetic [11], anti-inflammatory [12] [13], andanticarcinogenic [14] [15] activities. Liver cancer (hepatocellular carcinoma) remains one of the most important health problems in the world because it is the third foremost cause of cancer-related deaths worldwide [16].…”

Section: Introductionmentioning

confidence: 99%

“…H NMR (DMSO-d 6 ): δ = 1.91 (t, 4H, CH 2 -CH 2 pyrrolidine),3.57 (t, 4H, CH 2 -N-CH 2 pyrrolidine), 7.67 -8.50 (m, 8H, Ar-H), 8.99 (s, 1H, CH-quinoxaline) 13. C NMR (DMSO-d 6 ): δ = 20.9 (2C, CH 2 -CH 2 pyrrolidine), 62.7 (2C, CH 2 -N-CH 2 pyrrolidine), [121.0 (2C), 124.4 (2C), 126.8 (2C), 130.4 (2C), 139.3, 140.5, 141.2 (2C), 153.0, 160.2] (14 ArC's + quinoxaline).…”

mentioning

confidence: 99%

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1-(4-(Pyrrolidin-1-ylsulfonyl)phenyl) ethanone in Heterocyclic Synthesis: Synthesis, Molecular Docking and Anti-Human Liver Cancer Evaluation of Novel Sulfonamides Incorporating Thiazole, Imidazo[1,2-a]pyridine, Imidazo[2,1-c] [1,2,4]triazole, Imidazo[2,1-b]thiazole, 1,3,4-Thiadiazine and 1,4-Thiazine Moieties

Bashandy¹

2015

IJOC

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This article describes the synthesis of some novel sulfonamides having the biologically active, thiazole 4-6, 8, 10-12a,b, 20, 22, 34, 35, imidazo[1,2-a]pyridine 14, imidazo[2,1-c][1,2,4]triazole 15, imidazo[2,1-b]thiazole 23, 24, 33, nicotinonitrile 25, 1,3,4-thiadiazine 27, quinoxaline 30 and 1,4thiazine 31 moieties, starting with 1-(4-(pyrrolidin-1-ylsulfonyl)phenyl)ethanone (1). The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1 H NMR, 13 C NMR and Ms spectral data. All the compounds were tested in-vitro antihuman liver hepatocellular carcinoma cell line (HepG2). Compounds 8, 11, 4, 22, 12a, 33, 35, 27 and 24 with selectivity index (SI) values of 33.21, 30.49, 19.43, 14.82, 10.29, 7.3, 6.87, 6.15 and 4.62, respectively, exhibited better activity than methotrexate (MTX) as a reference drug with SI value of 4.14. Molecular Operating Environment (MOE) performed virtual screening using molecular docking studies of the synthesized compounds. The results indicated that some synthesized compounds are suitable inhibitors against dihydrofolate reductase (DHFR) enzyme (PDB ID: 4DFR) with further modification. M. S. Bashandy 167

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Section: Methodsmentioning

confidence: 99%

Section: -Bromo-1-(4-(pyrrolidin-1-ylsulfonyl)phenyl)ethanone (2)mentioning

confidence: 99%

Section: ) Ethyl 2-cyano-2-(3-phenyl-4-(4-(pyrrolidin-1-ylsulfonyl)pmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

1-(4-(Pyrrolidin-1-ylsulfonyl)phenyl) ethanone in Heterocyclic Synthesis: Synthesis, Molecular Docking and Anti-Human Liver Cancer Evaluation of Novel Sulfonamides Incorporating Thiazole, Imidazo[1,2-a]pyridine, Imidazo[2,1-c] [1,2,4]triazole, Imidazo[2,1-b]thiazole, 1,3,4-Thiadiazine and 1,4-Thiazine Moieties

Bashandy¹

2015

IJOC

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Pharmacodynamic interaction of 3α‐hydroxymasticadienonic acid and diligustilide against indomethacin‐induced gastric damage in rats

Pineda-Peña

Meza-Pérez

Chávez-Piña

et al. 2019

Drug Development Research

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The aims of the study were to evaluate the pharmacodynamic interaction between 3α-hydroxymasticadienonic acid and diligustilide (DLG), isolated from the plants Amphiptherygium adstringens and Ligusticum porteri, respectively, using the indomethacininduced gastric injury model, as well as their individual gastroprotective efficacy in this model. Male Wistar rats were orally administered with 3α-hydroxymasticadienonic acid, DLG or the mixture of 3α-hydroxymasticadienonic acid-DLG (at a fixed-ratio combination of 1:1, 1:3, and 3:1). Thirty minutes later, the gastric damage was induced by a single oral dose of indomethacin (30 mg/kg). Three hours later, the gastric injury (mm 2 ) was determined. 3α-hydroxymasticadienonic acid and DLG as individual compounds showed a gastroprotective effect against indomethacin-induced gastric damage (p < .05).The effective dose (ED 50 ) values for each compound were 6.96 ± 1.25 mg/kg for 3α-hydroxymasticadienonic acid and 2.63 ± 0.37 mg/kg for DLG. The isobolographic analysis performed showed that the combination exhibited super-additive interaction as the experimental ED 50 values (Zexp) were lower than theoretical additive dose values (Zadd; p < .05). Our results identify the super-additive (synergist) interaction between 3α-hydroxymasticadienonic acid and DLG and the gastric safety of both compounds in the indomethacin-induced gastric injury model, suggesting their potential in the future as a strategy to decrease the gastric damage associated to the chronic use of nonsteroidal anti-inflammatory drugs (NSAIDs). K E Y W O R D S3α-hydroxymasticadienonic acid, diligustilide, gastric injury, isobolographic analysis, NSAIDs

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Chemistry and Biology of Selected Mexican Medicinal Plants

Mata

Figueroa

Navarrete

et al. 2019

Progress in the Chemistry of Organic Natural Products

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Anti-inflammatory effect of natural and semi-synthetic phthalides

Cited by 25 publications

References 47 publications

Pharmacodynamic interaction of 3α‐hydroxymasticadienonic acid and diligustilide against indomethacin‐induced gastric damage in rats

Chemistry and Biology of Selected Mexican Medicinal Plants

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