Discovery and evaluation of piperid-4-one-containing mono-carbonyl analogs of curcumin as anti-inflammatory agents

Wu, Jianzhang; Zhang, Yali; Cai, Yuepiao; Wang, Jian; Weng, Bixia; Tang, Qinqin; Chen, Xiangjian; Pan, Zheer; Liang, Guang; Yang, Shulin

doi:10.1016/j.bmc.2013.03.057

Cited by 56 publications

(32 citation statements)

References 19 publications

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“…Some studies focused on the two phenol rings while others pointed it out that the β-diketone structure might be involved in the anti-inflammatory action of curcumin [41,42]. Previous studies have proven that the presence of bis-α,β-unsaturated β-diketone, two methoxy groups, two phenolic hydroxyl groups and two double-conjugated bonds to be critical in the anti-inflammatory activities assigned to curcumin [43].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, in vitro and Molecular Docking Studies of 1-(3,4-Dimethoxy-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-penta-1,4-dien-3-one as New Potential Anti-inflammatory

Sohilait¹,

Pranowo²,

Haryadi³

2018

Asian J. Chem.

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Synthesis of new asymmetrical curcumin analogue of 1-(3,4-dimethoxy-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-penta-1,4-dien-3-one via condensation reaction between vanillinacetone and veratraldehyde in ethanol has been performed. The in vitro anti-inflammatory activities of the synthesized compounds showed excellent anti-inflammatory activity. In vitro anti-inammatory activity by using inhibition of albumin denaturation technique compared to standard dichlorofenac. Molecular docking studies were performed, where docking of the compound into 6COX active site suggested that it could exert its anti-inflammatory potential by cyclooxygenase inhibition.

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Section: Resultsmentioning

confidence: 99%

Synthesis, in vitro and Molecular Docking Studies of 1-(3,4-Dimethoxy-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-penta-1,4-dien-3-one as New Potential Anti-inflammatory

Sohilait¹,

Pranowo²,

Haryadi³

2018

Asian J. Chem.

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“…However, its high metabolic instability and low bioavailability have dramatically limited its practical application [10]. Recently, our research group has synthesized a series of mono-carbonyl analogs of curcumin (MACs) by deleting b-diketone moiety [11][12][13]. The title compound, belongs to MACs and shown greater metabolic stability than that of curcumin.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (2E,6E)-2,6-bis[2-(trifluoromethyl)benzylidene]cyclohexanone, C22H16F6O

Zhang

Pan

et al. 2015

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of material (2E,6E)-2,6-bis[2-(trifluoromethyl)benzylidene]cyclohexanone was synthesized by an Aldol condesation between two molecules of 2-(trifluoromethyl)benzaldehyde and cyclohexanone, which was synthesized according our earlier published method [1,2]. An amount of 7.5 mmol cyclohexanone was added to a solution of 15 mmol 2-(tri-fluoromethyl)benzaldehyde in MeOH (10 ml). The solution was stirred at room temperature for 20 min, followed by dropwise addition of NaOMe/MeOH (1.5 ml, 7.5 mmol). The mixture was stirred at room temperature and monitored by TLC. When the reaction was finished, the residue was poured into saturated NH 4 Cl solution and filtered. The precipitate was washed with water and cold ethanol, and dried in vacuum. The solid was purified by chromatography over silica gel using CH 2 Cl 2 /CH 3 OH as the eluent to yield compound. All chemicals used for the synthesis were commercially available of AR grade, and were used as received. The yellow crystal of the title compound was obtained by slow evaporation of a CH 3 OH solution at room temperature. Experimental detailsPosition of the H atoms were calculated based on geometric criteria (C-H = 0.97 and 0.93 Å for methyl and aromatic atoms, respectively) then were placed in their calculated position and refined isotropically using a riding model with U iso (H) = 1.5 U eq (C) for methyl and U iso (H) = 1.2 U eq (C) for all others. DiscussionCurcumin has been demonstrated to possess a wide range of pharmaceutical activities, such as anti-tumor [3, 4], anti-inflammation [5], anti-oxidation [6], anti-bacterial [7], and cardiovascular protection [8,9]. However, its high metabolic instability and low bioavailability have dramatically limited its practical application [10]. Recently, our research group has synthesized a series of mono-carbonyl analogs of curcumin (MACs) by deleting b-diketone moiety [11][12][13]. The title compound, belongs to MACs and shown greater metabolic stability than that of curcumin. The crystal structure of the title compound is depicted in the figure. The asymmetric unit of this complex is constructed by two 2-(trifluoromethyl)benzylidene groups and a cyclohexanone linker. The C-C bond length of the cyclohexanone moiety ranging from 1.491 to 1.509 Å are quite normal single bonds. The C7-C8 and C12-C14 bond lengths of 1.328 and 1.324 Å conform to the value for a double bond. The C6-C7 and C14-C15 bond length of 1.466 Å are intermediate between the double and single bonds. The shortening of the C-C bonds showing the partial double-bond character of the C-C bonds, which are influenced by adjacent conjugated double bonds.

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“…NaOH (0.7 mL) and 95% EtOH (5 mL) was stirred at room temperature for 30 min, according to the partially modified procedure of a previous report [8]. The reaction mixture was subjected to microwave irradiation for 3 min at a power of 180 W and temperature of 60 °C.…”

Section: Synthesis Of 35-bis(2-hydroxybenzylidene)piperidin-4-one (3)mentioning

confidence: 99%

3,5-Bis(2-hydroxybenzylidene)piperidin-4-one

Eryanti

Herlina

Zamri

et al. 2014

Molbank

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Abstract:The title compound, 3,5-bis(2-hydroxybenzylidene)piperidin-4-one (3), was prepared via reaction of 2-hydroxybenzaldehyde (1) and 4-piperidone (2) under microwave irradiation in the presence of 10% NaOH solution. The compound was fully characterized from its UV, IR, NMR and MS data. Keywords: curcuminoids; aldol condensation; 4-piperidoneCurcumin is ubiquitous in many Curcuma species and is the major pigment found in the tumeric plant, Curcuma longa. Chemically, curcumin is a phenolic secondary metabolite known to possess anti-inflammatory [1], antioxidant [2], antiviral, anti-infective and anti-allergic activity [4], as well as anti-HIV [5] and anti-cancer [6] properties. Based on the wide range of its biological activities, curcumin has attracted much interst as a model for new target compounds to be synthesized. However, the isolation of curcuminoids from natural substances is low-yielding (3%-5% of the dry-weight), and in addition, the curcuminoids thus obtained possess limited structural variability. Indeed, this method presents an obstacle to optimize the function of curcumin [7]. Therefore, synthesis of curcumin OPEN ACCESS

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Discovery and evaluation of piperid-4-one-containing mono-carbonyl analogs of curcumin as anti-inflammatory agents

Cited by 56 publications

References 19 publications

Synthesis, in vitro and Molecular Docking Studies of 1-(3,4-Dimethoxy-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-penta-1,4-dien-3-one as New Potential Anti-inflammatory

Synthesis, in vitro and Molecular Docking Studies of 1-(3,4-Dimethoxy-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-penta-1,4-dien-3-one as New Potential Anti-inflammatory

Crystal structure of (2E,6E)-2,6-bis[2-(trifluoromethyl)benzylidene]cyclohexanone, C22H16F6O

3,5-Bis(2-hydroxybenzylidene)piperidin-4-one

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