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Statements

Subject Item
n2:RIV%2F61388963%3A_____%2F12%3A00385875%21RIV13-AV0-61388963
rdf:type
n8:Vysledek skos:Concept
dcterms:description
Based on bioisosteric similarities with isoniazid, a series of 1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives has been designed. The target compounds have been synthesized by multicomponent reaction which involves one-pot organic reactions using ethylcyanoacetate, urea/thiourea and arylaldehydes in presence of ethanolic K2CO3. Two methodologies, conventional and microwave-assisted, have been adopted for the synthesis. The later strategy gave high yields in less than 10 min as compared to long hours using the former approach. Molecular docking of the target compounds into the enzyme Mycobacterium tuberculosis enoyl reductase (InhA) revealed important structural information on the plausible binding interactions. Major binding interactions were found to be of dispersion type (residues Tyr158, Ile215, Met103 and Met199) and a hydrogen bond with Tyr158. Binding poses of the all the compounds were energetically favorable and showed good interactions with the active site residues. Few selected compounds were also evaluated for antitubercular activity in vitro against drug-sensitive M. tuberculosis H37Rv strain and clinically isolated S, H, R and E resistant M. tuberculosis by luciferase reporter phage (LRP) assay method. Some compounds displayed promising antimycobacterial activity comparable or less than the standard drugs isoniazid and rifampicin. Based on bioisosteric similarities with isoniazid, a series of 1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives has been designed. The target compounds have been synthesized by multicomponent reaction which involves one-pot organic reactions using ethylcyanoacetate, urea/thiourea and arylaldehydes in presence of ethanolic K2CO3. Two methodologies, conventional and microwave-assisted, have been adopted for the synthesis. The later strategy gave high yields in less than 10 min as compared to long hours using the former approach. Molecular docking of the target compounds into the enzyme Mycobacterium tuberculosis enoyl reductase (InhA) revealed important structural information on the plausible binding interactions. Major binding interactions were found to be of dispersion type (residues Tyr158, Ile215, Met103 and Met199) and a hydrogen bond with Tyr158. Binding poses of the all the compounds were energetically favorable and showed good interactions with the active site residues. Few selected compounds were also evaluated for antitubercular activity in vitro against drug-sensitive M. tuberculosis H37Rv strain and clinically isolated S, H, R and E resistant M. tuberculosis by luciferase reporter phage (LRP) assay method. Some compounds displayed promising antimycobacterial activity comparable or less than the standard drugs isoniazid and rifampicin.
dcterms:title
Microwave-assisted synthesis, molecular docking and antitubercular activity of 1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives Microwave-assisted synthesis, molecular docking and antitubercular activity of 1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives
skos:prefLabel
Microwave-assisted synthesis, molecular docking and antitubercular activity of 1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives Microwave-assisted synthesis, molecular docking and antitubercular activity of 1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives
skos:notation
RIV/61388963:_____/12:00385875!RIV13-AV0-61388963
n8:predkladatel
n14:ico%3A61388963
n4:aktivita
n18:Z
n4:aktivity
Z(AV0Z40550506)
n4:cisloPeriodika
24
n4:dodaniDat
n15:2013
n4:domaciTvurceVysledku
Brahmkshatriya, Pathik
n4:druhVysledku
n7:J
n4:duvernostUdaju
n16:S
n4:entitaPredkladatele
n13:predkladatel
n4:idSjednocenehoVysledku
150454
n4:idVysledku
RIV/61388963:_____/12:00385875
n4:jazykVysledku
n12:eng
n4:klicovaSlova
antitubercular; binding interactions; luciferase reporter phage (LRP) assay; microwave-assisted; molecular docking
n4:klicoveSlovo
n9:luciferase%20reporter%20phage%20%28LRP%29%20assay n9:molecular%20docking n9:binding%20interactions n9:antitubercular n9:microwave-assisted
n4:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n4:kontrolniKodProRIV
[CDB6848D873F]
n4:nazevZdroje
Bioorganic and Medicinal Chemistry Letters
n4:obor
n17:CC
n4:pocetDomacichTvurcuVysledku
1
n4:pocetTvurcuVysledku
8
n4:rokUplatneniVysledku
n15:2012
n4:svazekPeriodika
22
n4:tvurceVysledku
Mohan, S. B. Dinda, S. C. Brahmkshatriya, Pathik Seenivasan, S. P. Naik, D. Rana, D. N. Kumar, V. Kumar, B. V. V. R.
n4:wos
000311425500051
n4:zamer
n5:AV0Z40550506
s:issn
0960-894X
s:numberOfPages
4
n10:doi
10.1016/j.bmcl.2012.10.032