The chemistry of aminoguanidine derivatives – preparation, crystal structure, thermal properties, and molecular docking studies of aminoguanidinium salts of several carboxylic acids

Selvakumar, R.; Geib, Steven J.; Sankar, Aathi Muthu; Premkumar, Thathan; Sundararajan, G.

doi:10.1016/j.jpcs.2015.05.024

Cited by 17 publications

(4 citation statements)

References 32 publications

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“…Similarly [AgunH] + [HCOO] − assembly also exhibit asymmetric and symmetric stretching bands of the carboxylate group at 1569 cm −1 and 1350 cm −1 respectively (Figure S1b(1)).The presence of AgunH + cations in the both the salts is manifested in strong intensity peaks at 1680 and 1690 cm −1 which can be assigned to the C−N stretching vibrations. The N−N stretching frequency of hydrazinic moiety of aminoguanidinium cation is absorbed at 1103 cm −1 . The change in characteristic frequencies of parent materials compared with that of spectrum of the salts indicated molecular complex between the aminoguanidinium and carboxylates.…”

Section: Resultsmentioning

confidence: 96%

“…Moreover in aminoguanidinium cation the NH 2 group present in the imidinium portion at the protonated guanidine is stabilized by efficient resonance with the charge ( Figure a ), and makes a multiple sites for strong charge assisted hydrogen bonding patterns . It is because of this structural significance, aminoguanidinium resulted a stable salt formation with inorganic anions (NO 3 − , H 2 PO 4 − , Cl − , and SO 4 2− etc., ) and organic anions (tartrate, oxalate, squarate, malonate, fumarate, succinate, dipicolinate, benzoate, pyridine dicarboxylate, pyrazole −3,5 dicarboxylic acids etc.,) .In most of the reported crystal structures it is noticed that most aminoguanidine is in a monoprotonated (AgunH + ) form and in two crystal structures (dinitrate and sulphate anions) it acts as a di–cation (AgunH 2 + ). It has also been noted that depending on the nature of carboxylic acids, aminoguanidine undergone condensation reaction and form a zwitter ionic salts .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Experimental Studies on Supramolecular Synthons of Aminoguanidinium Carboxylates: A Case Study of π‐HoleBonded Carbon Bonding via Theoretical Approaches

et al. 2018

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New supramolecular salts of aminoguanidinium with mono and di-carboxylic acids (formate and maleate respectively) have been prepared and their crystal structures were solved using single crystal X-ray diffraction analysis. A crystal packing of both the ion pair assemblies are organized via various weak intermolecular interactions including NÀ H…O, OÀ H…O, CÀ H… O and NÀ H…N etc., hydrogen bonds and form 2D and 3D assemblies. The supramolecular viewpoint of the titled ion-pair assemblies are discussed interms of strong hydrogen bonded ring motifs generated between the aminoguanidininium and carboxylates and the homo synthons of aminoguanidine retained in these solid state assemblies. Interestingly both the ion pair assemblies are supported by the π-hole utilized carbon bonding (C…O, C…N &C…C) interactions. As compared to aminoguanidinium formate assembly, in amminoguanidinium hydrogenmaleate, π-hole utilized carbon bonding interactions were sustained between the cation and anion pair which affords the spatial arrangement for stacking the cation and anion through electrostatic interaction. In this respect, πhole interactions are function as a structure directing self-assembled force and regulate the aminoguandinium hydrogen maleate assembly. Apart from the X-ray diffraction studies, the geometrical parameters, interaction energy, its energy component contribution (LMOEDA analysis) and also the properties of weak interactions including carbon bonding present in the synthesized aminoguanidinium carboxylates assembly were analyzed systematically through wave functional analysis with MP2/6-31 + + g(d,p) level of theory. The role of hydrogen bonding and carbon bonding confirmation and their strength in terms of crystal packing were summarized through various theoretical calculations such as Atoms In Molecules (AIM), Hirshfeld surface analysis, NCI plot and Natural Bonding Orbital analysis (NBO).

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Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Synthesis and Experimental Studies on Supramolecular Synthons of Aminoguanidinium Carboxylates: A Case Study of π‐HoleBonded Carbon Bonding via Theoretical Approaches

et al. 2018

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“…Thus, in [ 61 ], the interaction of alkaloids with ChE was studied and, according to molecular modeling data, 7-epi-javaniside binds on the surface of BChE surrounded by amino acids Glu238, Arg242, Thr284, Pro359 and Pro281. According to molecular modeling data, one of the aminoguanidinium salts of carboxylic acids studied in [ 62 ] also binds on the surface of BChE in the vicinity of Val233, Glu238, Arg242 and Val288.…”

Section: Resultsmentioning

confidence: 99%

Anticholinesterase and Serotoninergic Evaluation of Benzimidazole–Carboxamides as Potential Multifunctional Agents for the Treatment of Alzheimer’s Disease

Belinskaia,

Voronina,

Krivorotov

et al. 2023

Pharmaceutics

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The etiology and pathogenesis of Alzheimer’s disease are multifactorial, so one of the treatment strategies is the development of the drugs that affect several targets associated with the pathogenesis of the disease. Within this roadmap, we investigated the interaction of several substituted 1,3-dihydro-2-oxo-1H-benzimidazol-2-ones with their potential molecular targets: cholinesterases (ChE) and three types of the Gs-protein-coupled serotonin receptors (5-HTR) 5-HT6, 5-HT4 and 5-HT7 (5-HT4R, 5-HT6R and 5-HT7R, respectively). A microplate modification of the Ellman method was used for the biochemical analysis of the inhibitory ability of the drugs towards ChE. Molecular modeling methods, such as molecular docking and molecular dynamics (MD) simulation in water and the lipid bilayer, were used to study the interaction of the compounds with ChE and 5-HTR. In vitro experiments showed that the tested compounds had moderate anticholinesterase activity. With the help of molecular modeling methods, the mechanism of interaction of the tested compounds with ChE was investigated, the binding sites were described and the structural features of the drugs that determine the strength of their anticholinesterase activity were revealed. Primary in silico evaluation showed that benzimidazole–carboxamides effectively bind to 5-HT4R and 5-HT7R. The pool of the obtained data allows us to choose N-[2-(diethylamino)ethyl]-2-oxo-3-(tert-butyl)-2,3-dihydro-1H-benzimidazole-1-carboxamide hydrochloride (compound 13) as the most promising for further experimental development.

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“…[9][10][11]33 The syntheses of guanidinium and/or aminoguanidinium salts of organic acids have been widely explored with a few examples of organic salts, viz. formate, 34 hemioxalate, 35 hydrogen Ltartrates, 36,37 squarates, 38,39 fumarates, [40][41][42][43] succinates, 44 oxalates, [45][46][47][48] benzoates, 49 maleates, 50,51 pyromellitate, 52 oxamate, 48 malonate, 48 sulfoacetate 48 and glutamate. 53 From our literature survey, we identified a small number of crystal structures with 6-membered heteroaromatic dicarboxylic acids; the guanidinium/aminoguanidinium salts of chelidamate dipicolinates and quinolinate [54][55][56] reveal that the guanidinium/aminoguanidinium ions in these salts exist solely in the mono-protonated form.…”

Section: Introductionmentioning

confidence: 99%

Structural and anti-oxidant properties of guanidinium pyrazole-3,5-dicarboxylates

et al. 2016

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The chemistry of aminoguanidine derivatives – preparation, crystal structure, thermal properties, and molecular docking studies of aminoguanidinium salts of several carboxylic acids

Cited by 17 publications

References 32 publications

Synthesis and Experimental Studies on Supramolecular Synthons of Aminoguanidinium Carboxylates: A Case Study of π‐HoleBonded Carbon Bonding via Theoretical Approaches

Synthesis and Experimental Studies on Supramolecular Synthons of Aminoguanidinium Carboxylates: A Case Study of π‐HoleBonded Carbon Bonding via Theoretical Approaches

Anticholinesterase and Serotoninergic Evaluation of Benzimidazole–Carboxamides as Potential Multifunctional Agents for the Treatment of Alzheimer’s Disease

Structural and anti-oxidant properties of guanidinium pyrazole-3,5-dicarboxylates

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