Synthesis, Biological Evaluation and Molecular Docking of Novel Curcumin Derivatives as Bcl‐2 Inhibitors Targeting Human Breast Cancer MCF‐7 Cells

Bhuvaneswari, K.; Sivaguru, Paramasivam; Lalitha, Appaswami

doi:10.1002/slct.201702406

Cited by 15 publications

(18 citation statements)

References 44 publications

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“…The fluorinated curcuminoids were synthesized to evaluate their inhibitory activities against HepG2 and compare with the activities of 1,3-diketone curcumin analogues. The presence of fluorine atom(s) in aromatic rings displayed close (7,9) or lower (8, 10) inhibitory activities respecting to compounds (1)(2)(3). As mentioned, the para-substituted À OH group is responsible for generating phenoxyl radical which is the crucial species for apoptosis.…”

Section: In Vitro Cytotoxicity Against Hepg2mentioning

confidence: 91%

“…Several possibilities have been proposed regarding the potential mechanisms of liver anticancer activities of curcumin (1) and among these, its ability to elevate the activities of Phase 2 detoxification enzymes (e. g. glutathione S-transferases (GST)) has received much attention. [13,27,33] Curcumin contains an electrophilic α,β-unsaturated ketone, as a Michael acceptor can react with nucleophilic centers such as À SH group and glutathione (GSH), which can detoxify toxic agents through enzyme-mediated (e. g., by GST) interactions.…”

Section: In Vitro Cytotoxicity Against Hepg2mentioning

confidence: 99%

“…Experimental and computational studies on curcumin structure demonstrated that the aromatic ring/substituents on it and β-diketone moieties are crucial for biological responses and kinetic stability. [1][2][3][4][5][6][7][8][9][10][11][12] Several synthetic curcumin analogues have been developed through chemical modifications on its pharmacophores such as pyrazole, [6,[13][14][15][16][17][18][19][20] 1,4-thiazepane, [7] monocarbonyl, [8] aza-aromatic, [9] N-alkyl β-enaminone curcuminoids. [10][11][12] to circumvent the limitations of curcumin.…”

Section: Introductionmentioning

confidence: 99%

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Curcuminoids versus Pyrazole‐Modified Analogues: Synthesis and Cytotoxicity against HepG2 Cancer Cell Line

et al. 2020

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Twenty compounds including curcuminoids and their pyrazolemodified analogues were synthesized in a two-step reaction: (i) condensation between benzaldehyde derivatives and pentane-2,4-dione and (ii) pyrazole cyclization of the 1,3-diketone group in the resulting curcuminoids with hydrazine hydrate. The synthesized compounds were assayed for in vitro anticancer activity against HepG2 cancer cell line by determining their half-maximal inhibitory concentration (IC 50). Pyrazole curcuminoid (1 a, IC 50 = 1.53 � 0.11 μM) was found to be the most potent molecule against the cancer cells. The pyrazole curcuminoids (1 a-3 a, 5 a) significantly exhibited between 2-to 23-fold higher anticancer activities when compared with their parent structures (1-3, 5). However, the class of fluorinated analogues (7-10; 7 a-10 a) displayed inactivities or activities close to those of respecting compounds (1-6; 1 a-6 a). Structure-activity relationship analysis indicated that the phenolic motif is responsible for inhibition of cell growth whereas the fluoro/methoxy substituents on the aromatic rings have insignificant contributions to inhibitory activities against HepG2.

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Section: In Vitro Cytotoxicity Against Hepg2mentioning

confidence: 91%

Section: In Vitro Cytotoxicity Against Hepg2mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Curcuminoids versus Pyrazole‐Modified Analogues: Synthesis and Cytotoxicity against HepG2 Cancer Cell Line

et al. 2020

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“…Compounds 7b (Ar (38) in ethanol at room temperature to afford functionalized curcumin derivatives 118 in 80−92% yield, Scheme 51. The construction of the cyclohexene ring proceeded through a Knoevenagel/Michael/cyclization sequence catalyzed by DABCO (10 mol%) [114]. Compounds 118j (R = 4-Me, R 1 = CO 2 Et) and 118k (R = 2-NO 2 , R 1 = CO 2 Et) were screened for their in vitro antitumor activity against human breast cancer cells (MCF-7) using the MTT assay.…”

Section: Curcumin Derivativesmentioning

confidence: 99%

“…Regioselective multicomponent synthesis of spiro-indeno[1,2-b]quinoxalin-pyrrolothiazoles 113 for antitumor screening.Very recently, an Ugi four-component synthesis of quinoline-coumarin hybrids 115 was described by Taheri et al[101]. This efficient and simple access to quinoline-coumarin derivatives involved coumarin-3-carboxylic acid(114), diverse 2-chloroquinoline-3-carbaldehydes 1, aniline derivatives 2 and aliphatic isocyanides 18 in methanol at room temperature (Scheme 48). Ugi multicomponent reaction for the synthesis of quinoline-coumarin derivatives 115 to be investigated against A2780 human Ovarian cancer cell line.Cytotoxic effects of fourteen products were investigated in A2780 human ovarian cancer cells.…”

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confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.Molecules 2020, 25, 505 2 of 71 acetylcholinesterase inhibitors, anti-HIV, antimicrobial, antioxidant, anti-mycobacterial and anticancer activities ( Figure 1). It is noteworthy that 64% and 16% of the supporting literature found for this review correspond to heterocyclic structures with anticancer and antimicrobial activities, respectively. Scheme 2. Three-component synthesis of 3,4-dihydropyrimidinones/thiones type 7 under microwave irradiation, for anti-inflammatory activity.Patil et al., reported a one-pot pseudo-five-component synthesis of highly functionalized tetrahydropyridines 9 using Cu(OTf) 2 as catalyst, Scheme 3. In vitro anti-inflammatory activity of the obtained compounds 9 was determined against matrix metalloproteinases (MMPs) as MMP-2 and MMP-9 by using gelatin zymography [29]. Scheme 3. Multicomponent Cu(OTf) 2 catalyzed synthesis of substituted tetrahydropyridines 9 for anti-inflammatory activity.A highly diastereoselective synthesis (exclusively the cis isomer is formed), of chromeno β-lactam hybrids 13/14 was also achieved by an efficient one-pot three-component reaction between either 5,5-dimethylcyclohexane-1,3-dione (10a) or 4-hydroxycoumarin (10b), diverse benzaldehydes 11 and malononitrile (12), in the presence of DABCO under reflux conditions (Scheme 4). Scheme 4. Three-component synthesis of β-lactam hybrids 13/14 for anti-inflammatory activity.The synthesized compounds (13 in 80-95% yield) and (14 in 82-95% yield) were screened for anti-inflammatory activity (as well as for anticancer activity, please see Section 3.13.13. Compound 13b (Ar = 4-ClC 6 H 4 , Ar 1 = 4-MeC 6 H 4 ) was the most active of all the chromeno β-lactam hybrids 13/14 tested, with a 19.8 anti-inflammatory ratio, although, it resulted less active than the reference drug dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation [30].

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Curcumin‐based bioactive heterocycles derived via multicomponent reactions

Nagargoje

Shaikh

Shingate

2023

Archiv der Pharmazie

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Curcumin is an important phytochemical, found in the Asian countries, especially in the Indian subcontinent. The use of this "privileged natural product" in the diversityoriented synthesis of curcumin-based heterocycles via multicomponent reactions (MCRs) is the subject of interest for many medicinal chemists across the globe. This review particularly focuses on the reactions involving curcuminoids as one of the reactants in the MCRs of curcuminoid to synthesize curcumin-based heterocycles.Also, the various pharmacological activities of curcumin-based heterocycles generated via the MCR approach are discussed. The research work published in the last 10 years is in the focus of this review article.

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Synthesis, Biological Evaluation and Molecular Docking of Novel Curcumin Derivatives as Bcl‐2 Inhibitors Targeting Human Breast Cancer MCF‐7 Cells

Cited by 15 publications

References 44 publications

Curcuminoids versus Pyrazole‐Modified Analogues: Synthesis and Cytotoxicity against HepG2 Cancer Cell Line

Curcuminoids versus Pyrazole‐Modified Analogues: Synthesis and Cytotoxicity against HepG2 Cancer Cell Line

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Curcumin‐based bioactive heterocycles derived via multicomponent reactions

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