Synthesis, anticonvulsant and neurotoxicity evaluation of some new pyrimidine-5-carbonitrile derivatives

Shaquiquzzaman, Mohammad; Khan, Shahrukh Rafi; Amir, Mohd; Alam, Mohammad Mumtaz

doi:10.1016/j.jsps.2011.09.007

Cited by 26 publications

(14 citation statements)

References 14 publications

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“…In the present study, N-H stretching modes are observed at 3270, 3210cm -1 for dihydropyrimidine 32 . The νN 5 -H 8 ,νN 7 -H 6 stretching modes are observed at 3369 and 3277cm -1 respectively in FT-IR.…”

Section: Ringsupporting

confidence: 55%

Spectral Characterization and Vibrational Assignments of Ethyl 4-(3-(2,3-Dihydrobenzofuran-5-Carboxamido)Phenyl) -6-Methyl-2-Oxo-1,2,3,4-Tetrahydropyrimidine-5- Carboxylate by Ab Initio Density Functional Method

Adaikalaraj¹,

Manivarman²,

Bose³

2017

Orient. J. Chem

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In the present investigation, then novel compound ethyl 4-(3-(2,3-dihydrobenzofuran5carboxamido)phenyl-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate(DFOC) were synthesized .The synthesized compound have been characterized by using UV-visible, FT-IR, FT-Raman, 1 H-NMR and 13 CNMR spectral studies. The harmonic vibrational frequencies, optimized molecular geometry have been carried out with the help of B3LYP density functional theory method. The stability of the molecule was analyzed by means natural bond orbital analysis and delocalized p-p* interactions. Moreover, the frontier molecular orbital analysis, molecular electrostatic potential surface and thermodynamic properties of DFOC were investigated using DFT calculations.keywords: DFOC, NBO, NLO HOMO-LUMO and DFT.

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Section: Ringsupporting

confidence: 55%

Spectral Characterization and Vibrational Assignments of Ethyl 4-(3-(2,3-Dihydrobenzofuran-5-Carboxamido)Phenyl) -6-Methyl-2-Oxo-1,2,3,4-Tetrahydropyrimidine-5- Carboxylate by Ab Initio Density Functional Method

Adaikalaraj¹,

Manivarman²,

Bose³

2017

Orient. J. Chem

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“…(Figure 2). [21] In continuation of our work on cyanopyrimidine based hybrids [22,23] as anticancer agents [24] and in a search of new hits, it was envisaged to design and synthesize a series of novel compounds bearing both benzimidazole and cyanopyrimidine with expectations of very encouraging results. Hence, several analogs of benzimidazole pendant cyanopyrimidine derivatives ( Figure 3) were synthesized (7a-j) and evaluated for their in-vitro anticancer activity at National Cancer Institute (NCI) USA, against NCI-60 cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of benzimidazole pendant cyanopyrimidine derivatives as anticancer agents

Wang

Akhtar

Nainwal

et al. 2020

Journal of Heterocyclic Chem

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Thirteen new benzimidazole pendant cyanopyrimidine derivatives were synthesized. The compounds were synthesized through multistep reaction protocol. The structures of synthesized derivatives were studied by EI‐MS, 1H NMR, FT‐IR and elemental analysis. All the compounds were studied for their anticancer activity at National Cancer Institute. Except compound 7j, all the compounds unveiled cytotoxicity against cancer cells. The most active compound 7a had shown highest value of growth inhibition of 88.44% and 84.19% against HOP‐92 and T‐47D cancer cell lines.

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“…. Moreover, several researchers have worked on the anticonvulsant potential of pyrimidines and triazines in subsequent years and from their studies, it has been proved that both of these moieties contain antiseizure properties. The distance range such as A, D, and HBD, between the essential pharmacophoric elements of clinically used and designed compounds 4a–t are depicted in Table .…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Docking Study of Pyrimidine–Triazine Hybrids for GABA Estimation in Animal Epilepsy Models

Sahu

Siddiqui

Naim

et al. 2017

Archiv der Pharmazie

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A series of new pyrimidine-triazine hybrids (4a-t) was designed and synthesized, from which potent anticonvulsant agents were identified. Most of the compounds exhibited promising anticonvulsant activity against the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) tests, along with minimal motor impairment with higher safety compared to the standard drugs, phenytoin and carbamazepine. In the series, 5-(4-(4-fluorophenyl)-6-(4-hydroxyphenyl)-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl)-1,2-dihydro-1,2,4-triazin-3(6H)-one (4o) and 5-(6-(4-hydroxy-3-methoxyphenyl)-4-(4-hydroxyphenyl)-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl)-1,2-dihydro-1,2,4-triazin-3(6H)-one (4s) emerged as most potent anticonvulsant agents with median doses of 22.54 and 29.40 mg/kg (MES ED ), 285.02 and 293.42 mg/kg (scPTZ ED ), and 389.11 and 412.16 mg/kg (TD ), respectively. Docking studies were also performed for all synthesized compounds to get insight into the binding pattern toward the GABA receptor as a possible mechanism of their anticonvulsant action, and in silico ADME studies were carried out to predict the safety and stability of the molecules. The increased GABA level in the experimental animals in the neurochemical estimation assay confirmed their GABAergic modulating activity. The most potent compounds were also evaluated for their neurotoxic and hepatotoxic effects. Fortunately, they did not show any sign of neurotoxicity or hepatotoxicity, suggesting that they have a broad spectrum of anticonvulsant activity with a large safety margin. Together, this research suggested that 4o and 4s may serve as leads in the discovery and development of new anticonvulsant drugs.

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Synthesis, anticonvulsant and neurotoxicity evaluation of some new pyrimidine-5-carbonitrile derivatives

Cited by 26 publications

References 14 publications

Spectral Characterization and Vibrational Assignments of Ethyl 4-(3-(2,3-Dihydrobenzofuran-5-Carboxamido)Phenyl) -6-Methyl-2-Oxo-1,2,3,4-Tetrahydropyrimidine-5- Carboxylate by Ab Initio Density Functional Method

Spectral Characterization and Vibrational Assignments of Ethyl 4-(3-(2,3-Dihydrobenzofuran-5-Carboxamido)Phenyl) -6-Methyl-2-Oxo-1,2,3,4-Tetrahydropyrimidine-5- Carboxylate by Ab Initio Density Functional Method

Synthesis and biological evaluation of benzimidazole pendant cyanopyrimidine derivatives as anticancer agents

Design, Synthesis, and Docking Study of Pyrimidine–Triazine Hybrids for GABA Estimation in Animal Epilepsy Models

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