Synthesis and antiproliferative studies of curcumin pyrazole derivatives

Puneeth, Honnalagere Ramesh; Ananda, Hanumappa; Kumar, Kothanahally S. Sharath; Rangappa, Kanchugarakoppal S.; Sharada, A.C.

doi:10.1007/s00044-016-1628-5

Cited by 45 publications

(24 citation statements)

References 38 publications

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“…Nevertheless, the clinical translation of curcumin has been significantly hampered since it is poorly absorbed, improperly metabolized and shows poor systemic bioavailability, which mandates that patients consume up to 8–10 grams of free curcumin orally each day, in order for detectable levels in the circulation [ 109 , 118 ]. Thus, several strategies have been proposed to counter the bioavailability issue of curcumin involving (i) the use of adjuvants like piperine, which interferes with curcumin metabolism by glucuronidation, (ii) curcumin formulations based on nanotechnology with liposomes, micelles, phospholipid, among others, and (iii) use of curcumin analogues [ 117 , 121 , 122 , 123 ]. As result of the anticancer potential of curcumin and despite its clinical therapeutic limitations, there are currently 17 open clinical studies involving curcumin, mainly studies of combined curcumin therapy with other substances for the treatment of several types of cancer.…”

Section: Secondary Metabolites From Plants As Anticancer Agentsmentioning

confidence: 99%

Plant Secondary Metabolites as Anticancer Agents: Successes in Clinical Trials and Therapeutic Application

Seca

Pinto

2018

IJMS

536

303

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Cancer is a multistage process resulting in an uncontrolled and abrupt division of cells and is one of the leading causes of mortality. The cases reported and the predictions for the near future are unthinkable. Food and Drug Administration data showed that 40% of the approved molecules are natural compounds or inspired by them, from which, 74% are used in anticancer therapy. In fact, natural products are viewed as more biologically friendly, that is less toxic to normal cells. In this review, the most recent and successful cases of secondary metabolites, including alkaloid, diterpene, triterpene and polyphenolic type compounds, with great anticancer potential are discussed. Focusing on the ones that are in clinical trial development or already used in anticancer therapy, therefore successful cases such as paclitaxel and homoharringtonine (in clinical use), curcumin and ingenol mebutate (in clinical trials) will be addressed. Each compound’s natural source, the most important steps in their discovery, their therapeutic targets, as well as the main structural modifications that can improve anticancer properties will be discussed in order to show the role of plants as a source of effective and safe anticancer drugs.

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Section: Secondary Metabolites From Plants As Anticancer Agentsmentioning

confidence: 99%

Plant Secondary Metabolites as Anticancer Agents: Successes in Clinical Trials and Therapeutic Application

Seca

Pinto

2018

IJMS

536

303

View full text Add to dashboard Cite

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“…[65] 4,4'-(1E,1'E)-2,2'-(1-(3chlorophenyl)-1H-pyrazole-3,5-diyl)bis(ethene-2,1-diyl) bis(2-methoxyphenol) exhibited a high degree of cytotoxicity and cell proliferation inhibition against cancer cells can be selected for further in vitro and in vivo investigations. [66] Isoxazole analogs of curcumin exhibited significantly improved in vitro drug-like properties including solubility, metabolic stability, cell permeability and lack of nonspecific cytotoxicity when compared with curcumin. [67]…”

Section: Curcumin Pyrazole and Isoxazole Analogs As Anticancer Agentsmentioning

confidence: 99%

Recent Updates in Curcumin Pyrazole and Isoxazole Derivatives: Synthesis and Biological Application

Patel

Halpani

2019

Chemistry & Biodiversity

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Curcumin is an admired, plant-derived compound that has been extensively investigated for diverse range of biological activities, but the use of this polyphenol is limited due to its instability. Chemical modifications in curcumin are reported to seize this limitation; such efforts are intensively performed to discover molecules with similar but improved stability and better properties. Focal points of these reviews are synthesis of stable pyrazole and isoxazole analogs of curcumin and application in various biological systems. This review aims to emphasize the latest evidence of curcumin pyrazole analogs as a privileged scaffold in medicinal chemistry. Manifold features of curcumin pyrazole analogs will be summarized herein, including the synthesis of novel curcumin pyrazole analogs and the evaluation of their biological properties. This review is expected to be a complete, trustworthy and critical review of the curcumin pyrazole analogs template to the medicinal chemistry community.

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“…The hypolipidemic ability of plant extracts was tested by assessing the pancreatic lipase inhibition assay [9]. Plant extracts were individually incubated with 1 ml of reaction mixture containing 1 unit of lipase enzyme and 100 mM phosphate buffer (pH 7.2) with Triton-X-100 (0.5%).…”

Section: Inhibition Of Pancreatic Lipase Activitymentioning

confidence: 99%

In Vitro Evaluation of Hypolipidemic Effect of Extracts of Medicinal Dracaena Cinnabari Balf. F. Resin

Mohammed

Al-Ostoot

et al. 2019

Asian J Pharm Clin Res

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Objective: The objective of the study was to in vitro evaluate of hypolipidemic effect of extracts of medicinal Dracaena cinnabari Balf. f. resin. Methods: About 800 g of dry powder of the resin of dracaena cinnabar was taken in a Soxhlet apparatus and subjected for sequential extraction of solvents from non-polar to polar end (hexane, benzene, diethyl ether, dichloromethane, chloroform, ethyl acetate, acetone, ethanol, methanol, and water); the extract samples were kept at 4°C for further assays. All the extracts were subjected to glucose uptake assay. Results: The ethanol extract showed significant (p<0.05) hypolipidemic effect by decreasing the activity of enzyme such as significant reduction in the pancreatic lipase enzyme, malic dehydrogenase enzyme, and glucose-6-phosphate dehydrogenase enzyme with IC50~13, ~13, and ~14, respectively. This results were similar to the standard drug atorvastatin with IC50~12, ~16, and ~17, respectively. Ethanol extract exhibited significant atherogenic index and percentage protection against hyperlipidemia. The potential biological activity of ethanol extract may be attributed to the highest polarity which needs further investigation.

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Synthesis and antiproliferative studies of curcumin pyrazole derivatives

Cited by 45 publications

References 38 publications

Plant Secondary Metabolites as Anticancer Agents: Successes in Clinical Trials and Therapeutic Application

Plant Secondary Metabolites as Anticancer Agents: Successes in Clinical Trials and Therapeutic Application

Recent Updates in Curcumin Pyrazole and Isoxazole Derivatives: Synthesis and Biological Application

In Vitro Evaluation of Hypolipidemic Effect of Extracts of Medicinal Dracaena Cinnabari Balf. F. Resin

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