Anticonvulsant evaluation and mechanism of action of benzylamino enaminones

Edafiogho, Ivan O.; Ananthalakshmi, Kethireddy V.V.; Kombian, Samuel B.

doi:10.1016/j.bmc.2006.03.049

Cited by 64 publications

(37 citation statements)

References 17 publications

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“…Conformations that adopt a RE influence this distance may result in different activities [2–9]. In a previous study, we have performed a QSAR study on the activity of various RE in the active conformation [17].…”

Section: Introductionmentioning

confidence: 99%

QSAR Study and Molecular Design of Open-Chain Enaminones as Anticonvulsant Agents

Martínez

Duchowicz

Estrada

et al. 2011

IJMS

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Present work employs the QSAR formalism to predict the ED50 anticonvulsant activity of ringed-enaminones, in order to apply these relationships for the prediction of unknown open-chain compounds containing the same types of functional groups in their molecular structure. Two different modeling approaches are applied with the purpose of comparing the consistency of our results: (a) the search of molecular descriptors via multivariable linear regressions; and (b) the calculation of flexible descriptors with the CORAL (CORrelation And Logic) program. Among the results found, we propose some potent candidate open-chain enaminones having ED50 values lower than 10 mg·kg−1 for corresponding pharmacological studies. These compounds are classified as Class 1 and Class 2 according to the Anticonvulsant Selection Project.

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Section: Introductionmentioning

confidence: 99%

QSAR Study and Molecular Design of Open-Chain Enaminones as Anticonvulsant Agents

Martínez

Duchowicz

Estrada

et al. 2011

IJMS

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“…The compounds that are analyzed as possible active molecules are structurally related to the enaminones previously employed for establishing our QSAR equation. The 15 ringed enaminones from CC and the 11 enaminones classified by the ASP [9] were separated in families and substituents. By means of this set of compounds, different organizing diagrams are elaborated as follows: Figure 6 (aniline enami- Enaminones 63 -65 in Figure 6 do not belong to CC nor ASP.…”

Section: Resultsmentioning

confidence: 99%

Anticonvulsant Activity of Ringed Enaminones: A QSAR Study

et al. 2009

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The formalism of the QSAR Theory is employed to establish mathematical relationships that link the molecular structure of ringed enaminones to their observed antiepileptic activity. The design of predictive linear regression models, solely based on the available experimental information, involved the simultaneous analysis of 1312 theoretical descriptors calculated with Dragon software. This QSAR study that is based both on classic antiepileptics and second-generation anticonvulsant drugs, including compounds of the enaminone type, allowed the proposal of novel ringed enaminone derivatives as possible antiepileptic agents, posing a similar or even better predicted biological activity when compared to other commonly used drugs.

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“…Enaminones are an important class of organic synthetic intermediates for the synthesis of a variety of heterocycles and pharmaceutical compounds. Their basic structural units, N-C=C-C=O, are responsible for the synthesis of many therapeutic agents of both natural and synthetic sources, including taxol, anticonvulsants, anti-inflammatory agents and ducarmycin classes of anti-tumor agents, as well as quinoline antibacterial and quinoline antimalarial agents (Hogenkamp et al, 2007;Idafiogho et al, 2006;Ghandi and Jamea, 2011).…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study of the Proton Transfer in Enaminones

Elias¹

2012

American Journal of Applied Sciences

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Problem statement: Hydrogen bonding has a vital rule to unrevealed the nature of many different interactions both in gas phase and condensed media thus it is one of the most important concepts in chemistry. Enaminoes with their ability to form intrahydrogen bonded cheated rings represent one of the suitable compounds to study such concept. Approach: The three possible tautomers of eneminones were fully optimized at several theoretical levels including B3LYP with the 6-31+G(d,p), 6-311++G(d,p) and aug-cc-pVDZ basis sets as well as MP2/6-311++G(d,p) level of theory. Then a search for the possible transition state between the two most stable tautomers; the ketamine and the enolimine was done at the B3LYP/6-311++G(d,p) level of theory. Results: The ketamine is the most stable while the diketo is the less stable within the tautomeric mixture and the proton transfer occurs through a transition state that is energetically resemble the enolimine tautomer. Conclusion:The interconversion of the tautomers is preferable in the enolimine → ketamine direction.

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Anticonvulsant evaluation and mechanism of action of benzylamino enaminones

Cited by 64 publications

References 17 publications

QSAR Study and Molecular Design of Open-Chain Enaminones as Anticonvulsant Agents

QSAR Study and Molecular Design of Open-Chain Enaminones as Anticonvulsant Agents

Anticonvulsant Activity of Ringed Enaminones: A QSAR Study

Theoretical Study of the Proton Transfer in Enaminones

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