BF3·OEt2-promoted concise synthesis of difluoroboron-derivatized curcumins from aldehydes and 2,4-pentanedione

Liu, Kai; Chen, Jiangmin; Chojnacki, Jeremy E.; Zhang, Shijun

doi:10.1016/j.tetlet.2013.02.015

Cited by 49 publications

(34 citation statements)

References 18 publications

(15 reference statements)

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“…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). All the synthesized compounds were confirmed by performing IR, 1 HNMR, and 13 CNMR spectral studies (Supporting information).…”

Section: S C H E M Ementioning

confidence: 97%

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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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Section: S C H E M Ementioning

confidence: 97%

“…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] .…”

Section: Introductionmentioning

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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“…Subsequently Tomapatanaget et al [22] presented a detailed photophysical study for the curcumin boron complexes and also the cyanide detection ability of the difluoroboron curcumin analogs in aqueous media. In past few years novel difluoroboron analogs of curcumin with different donor groups conjugated to the difluoroboron enolate were reported [24][25][26][27] showing that the different structural modification well contributed in enhancement of the chemical and photophysical properties of these class of molecules.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent difluoroboron-curcumin analogs: An investigation of the electronic structures and photophysical properties

Margar

Rhyman

Ramasami

et al. 2016

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…A second, more recent approach first published by Rao et al relies on boron trifluoride as the complexing agent [13]. The reaction was altered by Zhang et al to be carried out in toluene (Scheme 1) [14]. This reaction produces the BF 2 complex of the corresponding curcuminoid in yields up to 98% and high purity as an insoluble solid, which requires only a minimum of work-up.…”

Section: Introductionmentioning

confidence: 99%

“…Although a range of papers reports the synthesis of BF 2 complexes of β-diketones such as curcuminoids [13–14] or dibenzoylmethanes [15–16], to our knowledge the reported procedures for the hydrolysis of these complexes are very limited and not always reproducible.…”

Section: Introductionmentioning

confidence: 99%

Curcuminoid–BF₂ complexes: Synthesis, fluorescence and optimization of BF₂ group cleavage

Weiss¹,

Reichel²,

Görls³

et al. 2017

Beilstein J. Org. Chem.

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Eight difluoroboron complexes of curcumin derivatives carrying alkyne groups containing substituents have been synthesized following an optimised reaction pathway. The complexes were received in yields up to 98% and high purities. Their properties as fluorescent dyes have been investigated. Furthermore, a strategy for the hydrolysis of the BF2 group has been established using aqueous methanol and sodium hydroxide or triethylamine.

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BF3·OEt2-promoted concise synthesis of difluoroboron-derivatized curcumins from aldehydes and 2,4-pentanedione

Cited by 49 publications

References 18 publications

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

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

Fluorescent difluoroboron-curcumin analogs: An investigation of the electronic structures and photophysical properties

Curcuminoid–BF₂ complexes: Synthesis, fluorescence and optimization of BF₂ group cleavage

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BF3·OEt2-promoted concise synthesis of difluoroboron-derivatized curcumins from aldehydes and 2,4-pentanedione

Cited by 49 publications

References 18 publications

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

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

Fluorescent difluoroboron-curcumin analogs: An investigation of the electronic structures and photophysical properties

Curcuminoid–BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage

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Curcuminoid–BF₂ complexes: Synthesis, fluorescence and optimization of BF₂ group cleavage