Novel enaminones as non-cytotoxic compounds with mild antibacterial activity: Synthesis and structure-activity correlations

Cindrić, Marina; Rubčić, Mirta; Hrenar, Tomica; Pisk, Jana; Cvijanović, Danijela; Lovrić, Jasna; Vrdoljak, Višnja

doi:10.1016/j.molstruc.2017.10.078

Cited by 17 publications

(3 citation statements)

References 46 publications

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“…To further demonstrate the value of this catalyst, the Fe‐N x /CNTs catalyst system was used for the synthesis of some pharmacologically active compounds. As shown in Equations (2) and (3) in Scheme , the condensation reactions proceeded smoothly to give the target products DM27 and H 2 L 4 in good yields; DM27 is a P‐glycoprotein efflux inhibitor that can enhance the oral bioavailability of antiviral drugs, and H 2 L 4 is a noncytotoxic compound with antibacterial activity …”

Section: Resultsmentioning

confidence: 99%

A Reusable CNT‐Supported Single‐Atom Iron Catalyst for the Highly Efficient Synthesis of C−N Bonds

Ding

Huang

et al. 2020

Chemistry A European J

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C−N bond formation is regarded as a very useful and fundamental reaction for the synthesis of nitrogen‐containing molecules in both organic and pharmaceutical chemistry. Noble‐metal and homogeneous catalysts have frequently been used for C−N bond formation, however, these catalysts have a number of disadvantages, such as high cost, toxicity, and low atom economy. In this work, a low‐toxic and cheap iron complex (iron ethylene‐1,2‐diamine) has been loaded onto carbon nanotubes (CNTs) to prepare a heterogeneous single‐atom catalyst (SAC) named Fe‐Nx/CNTs. We employed this SAC in the synthesis of C−N bonds for the first time. It was found that Fe‐Nx/CNTs is an efficient catalyst for the synthesis of C−N bonds starting from aromatic amines and ketones. Its catalytic performance was excellent, giving yields of up to 96 %, six‐fold higher than the yields obtained with noble‐metal catalysts, such as AuCl3/CNTs and RhCl3/CNTs. The catalyst showed efficacy in the reactions of thirteen aromatic amine substrates, without the need for additives, and seventeen enaminones were obtained. High‐angle annular dark‐field scanning transmission electron microscopy in combination with X‐ray absorption spectroscopy revealed that the iron species were well dispersed in the Fe‐Nx/CNTs catalyst as single atoms and that Fe‐Nx might be the catalytic active species. This Fe‐Nx/CNTs catalyst has potential industrial applications as it could be cycled seven times without any significant loss of activity.

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Section: Resultsmentioning

confidence: 99%

A Reusable CNT‐Supported Single‐Atom Iron Catalyst for the Highly Efficient Synthesis of C−N Bonds

Ding

Huang

et al. 2020

Chemistry A European J

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“…That is what made them very useful as intermediates in the synthesis of acyclic, cyclic, and heterocyclic systems [2][3][4][5][6]. Besides their use as precursors, β-enaminone-containing molecules have also been employed for medical purposes and remained very useful, showing several activities such as antibacterial [7], antitubercular [8], anti-inflammatory [9], anticonvulsant [10], antitumoral [11], antinociceptive [12], and antidepressant activities [13]. More recently, they have been identified as non-classical inhibitors of carbonic anhydrase [14] (Fig.…”

Section: Introductionmentioning

confidence: 99%

New efficient synthesis, spectroscopic characterization, and X-ray analysis of novel β-enaminocarboxamide derivatives

et al. 2023

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A new series of β-enaminocarboxamide was synthesized via the addition of chlorosulfonyl isocyanate to β-enaminones. The prepared intermediates were converted to corresponding β-enaminocarboxamides by removal of the chlorosulfonyl group using methanol. The resulting compounds were obtained in excellent yields in the range of (80-92%) and were characterized by 1 H, 13 C, HMBC, HSQC NMR spectroscopy, and IR spectroscopy as well as elemental analysis. 1 H-NMR spectrum showed a non-equivalence of the primary amide protons which was due to H-bonding. β-enaminocarboxamide 5h was obtained as a crystal and was subjected to X-ray analysis. Results showed that 5h crystallizes in the monoclinic crystal system with C2/c space group and the ORTEP confirmed the presence of intramolecular H-bonds.

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“…96 Being able to participate in either electrophilic or nucleophilic substitution reactions, enaminones present itself as an ideal synthetic intermediate for acyclic and numerous (hetero)aromatic compounds. 97 Drugs that bear the enaminone core fragment have been known to be efficacious as antibiotics, 97 anti-inflammatory, 98 antitubercular, 99 antinociceptive, 93a anticonvulsants, 100 antitumor, 101 antifungal, 102 and antidepressant 103 agents.…”

Section: Chemistry Of Enaminonesmentioning

confidence: 99%

Development of water-based C-X bond formation reactions

Goh¹

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Novel enaminones as non-cytotoxic compounds with mild antibacterial activity: Synthesis and structure-activity correlations

Cited by 17 publications

References 46 publications

A Reusable CNT‐Supported Single‐Atom Iron Catalyst for the Highly Efficient Synthesis of C−N Bonds

A Reusable CNT‐Supported Single‐Atom Iron Catalyst for the Highly Efficient Synthesis of C−N Bonds

New efficient synthesis, spectroscopic characterization, and X-ray analysis of novel β-enaminocarboxamide derivatives

Development of water-based C-X bond formation reactions

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