Synthesis and electronic properties of alkyl- and alkyloxy-curcuminoids

Alsalim, Tahseen A.; Saeed, Bahjat A.; Elias, Rita S.; Abbo, Hanna S.; Titinchi, Salam J.J.

doi:10.5155/eurjchem.4.1.70-73.728

Cited by 5 publications

(3 citation statements)

References 19 publications

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“…These synthetic efforts were paired with the computational modeling of the relevant compounds. Previous computational studies of curcuminoids have been primarily focused on two veins: (1) prediction of the biological properties via docking studies and (2) prediction of their photophysical properties via TDDFT methods. , Additionally, computational methods were used to assess the validity of the catalytic role of the amine, as well as to ascertain the plausibility of an iminium ion intermediate in the proposed catalytic cycle. To the best of our knowledge, there has been no hybrid experimental–computational investigation of the relationship between isolated yields, structural features, and reaction conditions in the solvent-free synthesis of curcumin and its analogues.…”

Section: Introductionmentioning

confidence: 99%

Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids

et al. 2022

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A green and optimized protocol has been developed for the preparation of symmetric 1,7-bis(aryl)-1,6-heptadiene-3,5-diones and asymmetric 2-aryl-6-arylidenecyclohexanones with modified substrate scope and good functional group tolerance. Syntheses proceed smoothly under solvent-free conditions, providing moderate to excellent product yields with a minimal workup procedure. Control experiments, spectroscopic, and computational studies support a mechanism involving the boron-assisted in situ generation of imine intermediates. Crystal structures of three curcuminoids and isolated mechanistic intermediates are reported. The data provide insight for the further development of solvent-free protocols toward diverse curcumin derivatives in the fields of pharmaceutical and synthetic chemistries.

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Section: Introductionmentioning

confidence: 99%

Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids

et al. 2022

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“…Regardless of the many beneficial roles, the activities of curcuminoids are delimited due to the limited solubility in water and hydrolysis in an alkaline medium along with photochemical degradation [13]. These problems can be addressed by the modification of curcumin [14,15]. For decades, the researchers have been trying to design and synthesize super curcumin from curcumin derivatives and their analogues [16,17].…”

Section: Introdctionmentioning

confidence: 99%

Design and Synthesis of New Curcuminoid Compounds and their Derivatives as Antioxidant Agents

2021

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A series of new curcumin analogues and their derivatives were synthesized by reacting curcumin analogues with various substituted hydrazine compounds to afford new pyrazol derivatives. The preparation of ether and ester derivatives was also carried out. All synthesized compounds were characterized using FT-IR, 1 HNMR, 13 CNMR, and MS-ESI. The evaluations of these compounds have shown a good inhibition activity as antioxidant agents against the stable radical of diphenylpicrylhydrazyl (DPPH). Findings from this work demonstrated a high inhibition activity in compounds substituted with hydroxyl phenol groups in comparison with compounds with other groups.

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“…These properties give the curcuminoids a medical potency. But, their activities are limited due to their limited solubility in water and their short half-life, therefore, the researcher dream is to synthesize a super curcumin by the modification of the structure of curcumin to increase the activity [19,20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antioxidant study of new hydrazones derived from bisdemethoxycurcumin pyrazole

2017

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The antioxidant activity of new hydrazones derived from bisdemethoxycurcumin pyrazole was investigated. The study was divided into two main parts: The first one includes the synthesis and characterization of the target compounds from bisdemethoxycurcumin (BDMC), while the second step is devoted to the investigation of their antioxidant activities. In the first step of synthesis, the curcumin-pyrazole (2) was synthesized by the reaction of BDMC with hydrazine hydrate. Later, the obtained product treated with ethyl 2chloroacetate to produce curcumine ester (3), then the product was converted to hydrazide (4) by the reaction of curcumin ester (3) with hydrazine hydrate. Finally, curcumine hydrazones (5a-f) were synthesized from the reaction of hydrazide (4) with substituted aromatic aldehydes. All compounds were characterized with the aid of suitable spectroscopic techniques. The antioxidant activity of the prepared compounds was studied against the stable radical α,α-diphenyl-β-picrylhydrazyl. The study showed that only the phenolic OHcontaining compounds (2, 5b and 5f) have antioxidant activity.

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Synthesis and electronic properties of alkyl- and alkyloxy-curcuminoids

Cited by 5 publications

References 19 publications

Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids

Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids

Design and Synthesis of New Curcuminoid Compounds and their Derivatives as Antioxidant Agents

Synthesis and antioxidant study of new hydrazones derived from bisdemethoxycurcumin pyrazole

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