Novel functionalized β-nitrostyrenes: Promising candidates for new antibacterial drugs

Boguszewska-Czubara, Anna; Kula, Karolina; Wnorowski, Artur; Biernasiuk, Anna; Popiołek, Łukasz; Miodowski, Dawid; Demchuk, Oleg M.; Jasiński, Radomir

doi:10.1016/j.jsps.2019.02.007

Cited by 14 publications

(12 citation statements)

References 25 publications

(39 reference statements)

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“…The biological activity of these compounds can be additionally stimulated by the presence of the nitro group [18,19]. The NO 2 group gives interesting potential possibilities for different-type functionalization in amines, nitrosocompounds, oximes, nitronates and many other [20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

The Participation of 3,3,3-Trichloro-1-nitroprop-1-ene in the [3 + 2] Cycloaddition Reaction with Selected Nitrile N-Oxides in the Light of the Experimental and MEDT Quantum Chemical Study

et al. 2021

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The regioselective zw-type [3 + 2] cycloaddition (32CA) reactions of a series of aryl-substituted nitrile N-oxides (NOs) with trichloronitropropene (TNP) have been both experimentally and theoretically studied within the Molecular Electron Density Theory (MEDT). Zwitterionic NOs behave as moderate nucleophiles while TNP acts as a very strong electrophile in these polar 32CA reactions of forward electron density flux, which present moderate activation Gibbs free energies of 22.8–25.6 kcal·mol−1 and an exergonic character of 28.4 kcal·mol−1 that makes them irreversible and kinetically controlled. The most favorable reaction is that involving the most nucleophilic MeO-substituted NO. Despite Parr functions correctly predicting the experimental regioselectivity with the most favorable O-CCCl3 interaction, these reactions follow a two-stage one-step mechanism in which formation of the O-C(CCl3) bond takes place once the C-C(NO2) bond is already formed. The present MEDT concludes that the reactivity differences in the series of NOs come from their different nucleophilic activation and polar character of the reactions, rather than any mechanistic feature.

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Section: Introductionmentioning

confidence: 99%

The Participation of 3,3,3-Trichloro-1-nitroprop-1-ene in the [3 + 2] Cycloaddition Reaction with Selected Nitrile N-Oxides in the Light of the Experimental and MEDT Quantum Chemical Study

et al. 2021

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“…Nitro compounds and their derivatives are important in biological, pharmaceutical and industrial fields. 15,16 The reduction of nitro group under electrochemical conditions is another approach that has been widely explored but is not as frequently used. The reaction can be carried out under mild conditions and is often utilized to reduce nitro compounds that are challenging to reduce using alternative techniques.…”

Section: Introductionmentioning

confidence: 99%

Chitosan – hydrogen iodide salt supported graphite electrode: A simple and novel electrode for the reduction of nitro group under electrochemical condition

Deena,

Selvaraj,

Thomas

2024

10.5267/j.ccl

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The present investigation provides a unique, simple, selective and efficient method for the electrochemical reduction of aromatic nitro groups into amines using chitosan-hydrogen iodide salt supported graphite electrode. 3:1 tetrabutyl ammonium chloride and acetic acid mixture was used as the medium for electrolytic process and a constant voltage of 5 V applied between the modified electrodes. The reaction was found to be selective and further reduction of amines was not observed. The purity of the products was checked with HPLC and characterized using spectroscopic tools. The electrochemical synthesis resulted in moderate to good yields of amino compounds which were higher than the reduction using conventional graphite electrodes. Quaternary ammonium chloride behaved as supporting electrolyte during synthesis and the reaction did not progress in the absence of acetic acid. The redox characteristic of the process was studied by cyclic voltammetry of the reaction mixture.

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“…For the model of nitroalkene, we selected ( E )-3,3,3-trichloro-1-nitroprop-1-ene (TNP) ( 1 ). TNP can be characterized by a very reactive structure for organic synthesis and the ability to insert different CX 3 and NO 2 groups into the main product, which additionally stimulates many important biologically active functions [ 24 , 25 , 26 , 27 , 28 ]. Moreover, this nitroalkene was successfully tested in 32CA reactions with many organic compounds, such as nitrones [ 29 , 30 , 31 ], nitrile N -oxides [ 32 , 33 ], diazocompounds [ 2 , 3 , 34 ] and N -azomethine ylides [ 35 , 36 , 37 ], and in other reactions [ 38 , 39 , 40 ].…”

Section: Introductionmentioning

confidence: 99%

On the Question of the Formation of Nitro-Functionalized 2,4-Pyrazole Analogs on the Basis of Nitrylimine Molecular Systems and 3,3,3-Trichloro-1-Nitroprop-1-Ene

et al. 2022

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Experimental and theoretical studies on the reaction between (E)-3,3,3-trichloro-1-nitroprop-1-ene and N-(4-bromophenyl)-C-arylnitrylimine were performed. It was found that the title process unexpectedly led to 1-(4-bromophenyl)-3-phenyl-5-nitropyrazole instead of the expected Δ2-pyrazoline molecular system. This was the result of a unique CHCl3 elimination process. The observed mechanism of transformation was explained in the framework of the molecular electron density theory (MEDT). The theoretical results showed that both of the possible channels of [3 + 2] cycloaddition were favorable from a kinetic point of view, due to which the creation of 1-(4-bromophenyl)-3-aryl-4-tricholomethyl-5-nitro-Δ2-pyrazoline was more probable. On the other hand, according to the experimental data, the presented reactions occurred with full regioselectivity.

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Novel functionalized β-nitrostyrenes: Promising candidates for new antibacterial drugs

Abstract: Graphical abstract

Cited by 14 publications

References 25 publications

The Participation of 3,3,3-Trichloro-1-nitroprop-1-ene in the [3 + 2] Cycloaddition Reaction with Selected Nitrile N-Oxides in the Light of the Experimental and MEDT Quantum Chemical Study

The Participation of 3,3,3-Trichloro-1-nitroprop-1-ene in the [3 + 2] Cycloaddition Reaction with Selected Nitrile N-Oxides in the Light of the Experimental and MEDT Quantum Chemical Study

Chitosan – hydrogen iodide salt supported graphite electrode: A simple and novel electrode for the reduction of nitro group under electrochemical condition

On the Question of the Formation of Nitro-Functionalized 2,4-Pyrazole Analogs on the Basis of Nitrylimine Molecular Systems and 3,3,3-Trichloro-1-Nitroprop-1-Ene

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