Synthesis and anticancer activity of novel curcumin–quinolone hybrids

Raghavan, Saiharish; Manogaran, Prasath; Narasimha, Krishna Kumari Gadepalli; Kuppusami, Balasubramanian Kalpattu; Mariyappan, P.; Gopalakrishnan, Anjana; Venkatraman, Ganesh

doi:10.1016/j.bmcl.2015.06.068

Cited by 59 publications

(31 citation statements)

References 16 publications

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“…Condensation of N-alkylquinolines 56 with complex of feruloyl acetone diuoroboronite in the presence of n-butylamine followed by heating in a mixture of methanol/water afforded the respective 3-(5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trien-1-yl)-1,6-disubstituted-quinolin-2(1H)-ones 58 (Scheme 12). 69 On the other hand, 2-chloroquinoline-3-carbaldehyde (16a) reacted with thiomorpholine (59) by heating in ethanol containing anhydrous potassium carbonate to furnish 2thiomorpholino-quinoline-3-carbaldehyde (60). Compound 60 reacted with acetophenones 61a-j in ethanol containing anhydrous K 2 CO 3 under microwave (MW) irradiation conditions to afford the respective unsaturated ketones 62a-j, respectively (Scheme 13).…”

Section: Synthesis Of Ab-unsaturated Ketonesmentioning

confidence: 99%

Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs

et al. 2018

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Section: Synthesis Of Ab-unsaturated Ketonesmentioning

confidence: 99%

Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs

et al. 2018

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“…Isoxazole (2), N-substituted pyrazoles (3)(4)(5)(6)(7)(8)(9), and pyrimidine ring (10-12) containing curcumin derivatives were synthesized by interaction of curcumin with hydroxyl amine hydrochloride, hydrazine hydrate, phenyl hydrazine, 2,4-dinitrophenyl hydrazine, furoic hydrazide, isoniazid, semicarbazide, thiosemicarbazide, urea, thiourea, and guanidine, respectively. Synthetic route and structure of these curcumin derivatives are presented in Scheme 1, while the physiochemical data of synthesized compounds are shown in Table 1 (analytical data, see supplementary information, Table S1).…”

Section: S C H E M Ementioning

confidence: 99%

“…It has shown its pharmacological safety and wide range of biological activities such as antibacterial to anticancer agent [1][2][3][4] . Currently, curcumin is acclaimed to be one of the most widely researched naturally occurring chemopreventive agent which is cytoprotective to healthy human cells [5][6][7] . In spite of important therapeutic application, limited therapeutic utility concerns are associated with curcumin because of its poor absorption and fast metabolism under physiological conditions [8] .…”

mentioning

confidence: 99%

Screening of curcumin‐derived isoxazole, pyrazoles, and pyrimidines for their anti‐inflammatory, antinociceptive, and cyclooxygenase‐2 inhibition

et al. 2017

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Curcumin has shown pharmacological properties against different phenotypes of various disease models. Different synthetic routes have been employed to develop its numerous derivatives for diverse and improved therapeutic roles. In this study, we have synthesized curcumin derivatives containing isoxazole, pyrazoles, and pyrimidines and then the synthesized molecules were evaluated for their anti-inflammatory and antinociceptive activities in experimental animal models. Acute toxicity of synthesized molecules was evaluated in albino mice by oral administration. Any behavioral and neurological changes were observed at dose of 10 mg/kg body weight.Additionally, cyclooxygenase-2 (COX-2) enzyme inhibition studies were performed through in vitro assays. In vivo anti-inflammatory studies showed that curcumin with pyrimidines was the most potent anti-inflammatory agent which inhibited induced edema from 74.7% to 75.9%. Compounds 7, 9, and 12 exhibited relatively higher prevention of writhing episodes than any other compound with antinociceptive activity of 73.2%, 74.9%, and 71.8%, respectively. This was better than diclofenac sodium (reference drug, 67.1% inhibition). Similarly, COX-2 in vitro inhibition assays results revealed that compound 12 (75.3% inhibition) was the most potent compound.Molecular docking studies of 10, 11, and 12 compounds in human COX-2 binding site revealed the similar binding modes as that of other COX-2-selective inhibitors. K E Y W O R D Santi-inflammatory, COX-2 inhibition, curcumin derivatives, molecular modeling Chemically curcumin is diferuloylmethane which has attracted much attention of medicinal chemists for various diseases and therapeutic agents development. It has shown its pharmacological safety and wide range of biological activities such as antibacterial to anticancer agent [1][2][3][4] . Currently, curcumin is acclaimed to be one of the most widely researched naturally occurring chemopreventive agent which is cytoprotective to healthy human cells [5][6][7] . In spite of important therapeutic application, limited therapeutic utility concerns are associated with curcumin because of its poor absorption and fast metabolism under physiological conditions [8] . Active methylene and keto moiety are believed to be responsible for its rapid metabolism. In order to circumvent the problem of rapid metabolism and to improve its pharmacokinetics profile, several synthetic modifications have been studied on carbonyl and active methylene moiety [9] . In present study, isoxazole, N-substituted pyrazoles, and pyrimidine ring were incorporated in this focused segment of curcumin. Nitrogen heterocyclic moieties such as pyrazoles and pyrimidines containing derivatives gained considerable attention in medicinal chemistry for

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“…However, the difluoroboron complex of acetylacetone provides a pathway to dyes with the dioxaborine core incorporated into the polymethine chain as the central electron acceptor group of the D–π–A–π–D system. Only bis‐styryls of this type ― borondifluoride complexes of curcumin analogues ― have been reported hitherto (Figure ) . Their absorption maximum ranges from 450 to 650 nm, shifting bathochromically and gaining intensity with increasing electron‐donating ability of a substituent in the benzene rings , .…”

Section: Introductionmentioning

confidence: 99%

D–π–A–π–D Dyes with a 1,3,2‐Dioxaborine Cycle in the Polymethine Chain: Efficient Long‐Wavelength Fluorophores

et al. 2018

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The nitrile group in newly synthesized 5‐cyano‐2,2‐difluoro‐4,6‐dimethyl‐1,3,2‐dioxaborine is shown to significantly increase the acidity of the methyl groups. This allows the cyanine condensation with both methyl groups to form D–π–A–π–D dyes in which the dioxaborine cycle is a part of the polymethine chain. There, the reactivity of the remaining methyl group in the semi‐product is reduced enough to perform the reaction stepwise, giving access to nonsymmetric derivatives. The synthesis of dyes with various electron donor termini [indole, benzothiazole, pyran, 4‐(dialkylamino)phenyl] and with different polymethine chain lengths is reported. The obtained compounds show intense absorption and fluorescence in the red and NIR region, their fluorescence brightness (the product of the molar extinction and the fluorescence quantum yield) attaining a value of 200,000 m–1 cm–1. They are characterized by small‐scale positive solvatochromism, yet their fluorescence quantum yield is much more sensitive to ambient polarity. Time‐dependent (TD)DFT calculations have been performed to study the electronic structure of the new dioxaborines and reveal the nature of the long‐wavelength electronic transitions in those molecules.

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Synthesis and anticancer activity of novel curcumin–quinolone hybrids

Cited by 59 publications

References 16 publications

Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs

Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs

Screening of curcumin‐derived isoxazole, pyrazoles, and pyrimidines for their anti‐inflammatory, antinociceptive, and cyclooxygenase‐2 inhibition

D–π–A–π–D Dyes with a 1,3,2‐Dioxaborine Cycle in the Polymethine Chain: Efficient Long‐Wavelength Fluorophores

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