Trioxsalen derivatives with lipoxygenase inhibitory activity

Hadjipavlou‐Litina, Dimitra; Bariamis, Stavros E.; Militsopoulou, Maria; Athanassopoulos, Constantinos M.; Papaioannou, Dionissios

doi:10.3109/14756360902932776

Cited by 10 publications

(7 citation statements)

References 27 publications

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“…Specifically, the synthesis of cinnamic esters 1c – d was actually based on a condensation reaction using the Meldrum acid reagent under basic conditions, as it is reported in the literature [ 25 ]. The synthesis of cinnamic esters 1e – f was based on one pot reaction using BOP as a coupling reagent [ 24 , 26 ].…”

Section: Resultsmentioning

confidence: 99%

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Multifunctional Cinnamic Acid Derivatives

et al. 2017

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Our research to discover potential new multitarget agents led to the synthesis of 10 novel derivatives of cinnamic acids and propranolol, atenolol, 1-adamantanol, naphth-1-ol, and (benzylamino) ethan-1-ol. The synthesized molecules were evaluated as trypsin, lipoxygenase and lipid peroxidation inhibitors and for their cytotoxicity. Compound 2b derived from phenoxyphenyl cinnamic acid and propranolol showed the highest lipoxygenase (LOX) inhibition (IC50 = 6 μΜ) and antiproteolytic activity (IC50 = 0.425 μΜ). The conjugate 1a of simple cinnamic acid with propranolol showed the higher antiproteolytic activity (IC50 = 0.315 μΜ) and good LOX inhibitory activity (IC50 = 66 μΜ). Compounds 3a and 3b, derived from methoxylated caffeic acid present a promising combination of in vitro inhibitory and antioxidative activities. The S isomer of 2b also presented an interesting multitarget biological profile in vitro. Molecular docking studies point to the fact that the theoretical results for LOX-inhibitor binding are identical to those from preliminary in vitro study.

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Section: Resultsmentioning

confidence: 99%

“…To a stirred solution of the appropriate cinnamic acid 1 , 2 or 3 (1 equivalent) and propranolol or atenolol (1.1 equivalents) in dichloromethane (25 mL), BOP (1.2 equivalents) and triethylamine (4 equivalents) were added [ 24 , 26 ]. The end of the reaction was monitored by TLC.…”

Section: Methodsmentioning

confidence: 99%

Multifunctional Cinnamic Acid Derivatives

et al. 2017

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“…The latter, would allow for the replacement of either three or two conjugated double bonds of the spacer by the isosteric structural units NH-CO-C(R)]CH-N(R)-CO (analogs 1-7) and CO-N(R)-CH]C(R) (analogs [8][9][10][11]13), respectively. Finally, the implication of tert-butyl esters in the present study was thought of interest because we had observed, from biological studies of other types of a,b-unsaturated acids, that their corresponding tert-butyl esters were more potent inhibitors of lipoxygenase (LOX) than the free acids [6].…”

Section: Introductionmentioning

confidence: 82%

“…We had observed, from biological studies of other types of a,bunsaturated acids, that their corresponding tert-butyl esters were more potent inhibitors of lipoxygenase (LOX) than the free acids [6]. Several esters of a non-steroidal anti-inflammatory drug have been synthesized and showed long acting anti-inflammatory activity [26].…”

Section: Anti-inflammatory Activity In Vivomentioning

confidence: 99%

Syntheses and evaluation of the antioxidant activity of acitretin analogs with amide bond(s) in the polyene spacer

Hadjipavlou‐Litina

Magoulas

Krokidis

et al. 2010

European Journal of Medicinal Chemistry

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“…Then, it was dried over Na 2 SO 4 and finally evaporated to dryness to leave a solid residue. [54] The pure final product is obtained by recrystallization from ethyl acetate initially and then from 95% aqueous ethanol.…”

Section: Methodsmentioning

confidence: 99%

Multitarget Molecular Hybrids of Cinnamic Acids

et al. 2014

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Abstract:In an attempt to synthesize potential new multitarget agents, 11 novel hybrids incorporating cinnamic acids and paracetamol, 4-/7-hydroxycoumarin, benzocaine, p-aminophenol and m-aminophenol were synthesized. Three hybrids-2e, 2a, 2g-and 3b were found to be multifunctional agents. The hybrid 2e derived from the phenoxyphenyl cinnamic acid and m-acetamidophenol showed the highest lipoxygenase (LOX) inhibition and analgesic activity (IC50 = 0.34 μΜ and 98.1%, whereas the hybrid 3b of bromobenzyloxycinnamic acid and hymechromone exhibited simultaneously good LOX inhibitory activity (IC50 = 50 μΜ) and the highest anti-proteolytic activity (IC50= 5 μΜ). The hybrid 2a of phenyloxyphenyl acid with paracetamol showed a high analgesic activity (91%) and appears to be a promising agent for treating peripheral nerve injuries. Hybrid 2g which has an ester and an amide bond presents an interesting combination of anti-LOX and anti-proteolytic activity. The esters were found very potent and especially those derived from paracetamol and m-acetamidophenol. The amides follow. Based on 2D-structure-activity relationships it was observed that both steric and electronic parameters play major roles in OPEN ACCESSMolecules 2014, 19 20198 the activity of these compounds. Molecular docking studies point to the fact that allosteric interactions might govern the LOX-inhibitor binding.

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Trioxsalen derivatives with lipoxygenase inhibitory activity

Cited by 10 publications

References 27 publications

Multifunctional Cinnamic Acid Derivatives

Multifunctional Cinnamic Acid Derivatives

Syntheses and evaluation of the antioxidant activity of acitretin analogs with amide bond(s) in the polyene spacer

Multitarget Molecular Hybrids of Cinnamic Acids

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