Synthesis and biological evaluation of aminoketones

Sankappa, U.; Isloor, Arun M.; Shetty, Prakash; Isloor, Nishitha; Malladi, Shridhar; Fun, Hoong‐Kun

doi:10.1016/j.ejmech.2010.09.015

Cited by 12 publications

(5 citation statements)

References 24 publications

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“…The antibacterial activity of ketonic Mannich bases generated from arylamines and aromatic aldehydes was also investigated by several groups. Starting from cyclohexanone, a set of eleven compounds 107 was obtained, and screening against four common bacteria using serial dilution method showed that many of these candidates have excellent antibacterial activity, comparable to that of ceftriaxone [136]. However, the lack of rational design and systematic use of the aldehyde and amine components used to generate Mannich bases 107 ( Fig.…”

Section: Antibacterial Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

271

110

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The biological activity of Mannich bases, a structurally heterogeneous class of chemical compounds that are generated from various substrates through the introduction of an aminomethyl function by means of the Mannich reaction, is surveyed, with emphasis on the relationship between structure and biological activity. The review covers extensively the literature reports that have disclosed Mannich bases as anticancer and cytotoxic agents, or compounds with potential antibacterial and antifungal activity in the last decade. The most relevant studies on the activity of Mannich bases as antimycobacterial agents, antimalarials, or antiviral candidates have been included as well. The review contains also a thorough coverage of anticonvulsant, anti-inflammatory, analgesic and antioxidant activities of Mannich bases. In addition, several minor biological activities of Mannich bases, such as their ability to regulate blood pressure or inhibit platelet aggregation, their antiparasitic and anti-ulcer effects, as well as their use as agents for the treatment of mental disorders have been presented. The review gives in the end a brief overview of the potential of Mannich bases as inhibitors of various enzymes or ligands for several receptors.

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Section: Antibacterial Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

271

110

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“…The β‐aminocarbonyl compounds were predicted to be more effective for antibacterial [29] and antioxidant activities [30] . Hence, the docking method, molecular operating environment (MOE) was selected as it is user friendly and gives receptor‐ligand binding affinities with all possible binding geometries on the basis of a numerical value called S‐score.…”

Section: Methodsmentioning

confidence: 99%

Montmorillonite K10 Clay Catalyzed Synthesis of Novel β‐Aminocarbonyl Compounds and Their Biological Evaluation

Rambabu

Kiran²,

Tarakeswar³

et al. 2022

Chemistry & Biodiversity

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An efficient and reusable green catalyst for the synthesis of β-aminocarbonyl compounds has been developed. In this new and greener approach, β-aminocarbonyl compounds (1a -1r) were obtained by Montmorillonite K10 clay catalyzed reaction of aryl amines, aliphatic/aromatic aldehydes and β-ketoesters. Molecular docking investigations were performed for all compounds (1a -1r) with the proteins PDB ID: 1JIJ and 1KZN for S. aureus and E. coli, respectively. For all compounds good to strong interactions with the active sites were observed. The biological activities of β-aminocarbonyl compounds were further assessed for their antibacterial and antioxidant activities. The results confirmed that β-aminocarbonyl compounds could be further developed into new drugs with potent antibacterial and antioxidant activities.

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“…Over the past decades, the research on the new operationally simple, efficient, recyclable, and environmentally benign catalysts for the Mannich reaction has gained popularity in synthetic chemistry. Nowadays, it has been noted that this reaction can also be promoted by a wide array of catalysts, such as rare earth perfluorooctanoate (RE(PFO) 3 ) [7], Brönsted acidic ionic liquid [8], HClO 4 -SiO 2 [9], SalenZn complex [10], cerium (IV) ammonium nitrate (CAN) [11], Triton X10 (TX10) aqueous micelles [12], CeCl 3 ⋅7H 2 O [13], Tröger's base derivatives [14], Cbz protected [15], and PEG-OSO 3 H [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30]. However, they often suffer from the drawbacks of long reaction times, harsh reaction conditions, toxicity, and difficulty in product separation, which limit their use in the synthesis of complex molecules.…”

Section: Introductionmentioning

confidence: 99%

Full Kinetics and a Mechanistic Investigation of the Green Protocol for Synthesis of β-Aminoketone in the Presence of Saccharose as a Catalyst by a One-Pot Three-Component Reaction

Habibi‐Khorassani

Maghsoodlou

Shahraki

et al. 2014

Advances in Physical Chemistry

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For the first time, in a green protocol, an investigation of the kinetics and mechanism of the reaction between benzaldehyde 1, 4-chloroanilinne 2, and acetophenone 3 compounds in the presence of saccharose as a catalyst was performed for generating -aminoketone. For determining the kinetic parameters, the reaction was monitored by using the UV/Vis spectrophotometry technique. The second order rate constant ( 1 ) was automatically calculated by the standard equations contained within the program. In the studied temperature range, the second order rate constant (ln 1 , ln 1 / ) depended on reciprocal temperature that was in good consistent with Arrhenius and Eyring equations, respectively. These data provided the suitable plots for calculating the activation energy and parameters (Ea, Δ ‡ , Δ ‡ , and Δ ‡ ) of the reaction. Furthermore, useful information was obtained from studying the effects of solvent, concentration, and catalyst on the reaction mechanism. The results showed that the first step of the reaction mechanism is a rate determining step (RDS). The obtained experimental data and also the steady state assumption confirmed the proposed mechanism.

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Synthesis and biological evaluation of aminoketones

Cited by 12 publications

References 24 publications

Mannich bases in medicinal chemistry and drug design

Mannich bases in medicinal chemistry and drug design

Montmorillonite K10 Clay Catalyzed Synthesis of Novel β‐Aminocarbonyl Compounds and Their Biological Evaluation

Full Kinetics and a Mechanistic Investigation of the Green Protocol for Synthesis of β-Aminoketone in the Presence of Saccharose as a Catalyst by a One-Pot Three-Component Reaction

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