SYNTHESIS, CRYSTAL STRUCTURE, DFT AND ANTIBACTERIAL ACTIVITY STUDIES OF (E)-2-BENZYL-3-(FURAN-3-YL)-6,7-DIMETHOXY-4-(2-PHENYL-1H-INDEN-1-YLIDENE)-1,2,3,4-TETRAHYDROISOQUINOLINE

The title compound (I), (E)-2-benzyl-3-(furan-3-yl)-6,7-dimethoxy-4-(2-phenyl-1H-inden-1-ylidene)-1,2,3,4-tetrahydroisoquinoline (C37H31NO3), was synthesized and structurally characterized by elemental analysis, ¹H NMR and 13C NMR and single crystal X-ray diffraction. In the compound, the N-containi...

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Autores principales:	MURUGAVEL,S, MANIKANDAN,N, LAKSHMANAN,D, NAVEEN,KANAGARAJ, PERUMAL,PARAMASIVAN THIRUMALAI
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2015
Materias:	X-ray structure determination Hydrogen bonds DFT calculations MEP antibacterial activity
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072015000300008
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spelling	oai:scielo:S0717-970720150003000082015-12-04SYNTHESIS, CRYSTAL STRUCTURE, DFT AND ANTIBACTERIAL ACTIVITY STUDIES OF (E)-2-BENZYL-3-(FURAN-3-YL)-6,7-DIMETHOXY-4-(2-PHENYL-1H-INDEN-1-YLIDENE)-1,2,3,4-TETRAHYDROISOQUINOLINEMURUGAVEL,SMANIKANDAN,NLAKSHMANAN,DNAVEEN,KANAGARAJPERUMAL,PARAMASIVAN THIRUMALAI X-ray structure determination Hydrogen bonds DFT calculations MEP antibacterial activity The title compound (I), (E)-2-benzyl-3-(furan-3-yl)-6,7-dimethoxy-4-(2-phenyl-1H-inden-1-ylidene)-1,2,3,4-tetrahydroisoquinoline (C37H31NO3), was synthesized and structurally characterized by elemental analysis, ¹H NMR and 13C NMR and single crystal X-ray diffraction. In the compound, the N-containing six-membered ring of the tetrahydroisoquinoline unit adopts a distorted half-chair conformation. In the crystal structure, supramolecular chains mediated by C-HO contacts along the b-axis are linked into a double layer via C-Hπ hydrogen bonds. The resulting double layer stacks along the c-axis without any specific interactions. The molecular geometry was also optimized using density functional theory using (DFT/B3LYP) method with the 6-311G(d,p) basis set and compared with the experimental data. In addition to the optimized geometrical structure, molecular orbital, molecular electrostatic potential (MEP) and chemical reactivity studies of the compound have been investigated by using DFT. The antibacterial activity of the compound for various concentrations were determined against eight test pathogens Bacillus cerus, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Acinetobacter baumannii, Staphylococcus epidermidis, Klebsiella pneumoniae and Proteus vulgaris. The results revealed that the compound exhibited good to moderate antibacterial activity.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.60 n.3 20152015-09-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072015000300008en10.4067/S0717-97072015000300008
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	X-ray structure determination Hydrogen bonds DFT calculations MEP antibacterial activity
spellingShingle	X-ray structure determination Hydrogen bonds DFT calculations MEP antibacterial activity MURUGAVEL,S MANIKANDAN,N LAKSHMANAN,D NAVEEN,KANAGARAJ PERUMAL,PARAMASIVAN THIRUMALAI SYNTHESIS, CRYSTAL STRUCTURE, DFT AND ANTIBACTERIAL ACTIVITY STUDIES OF (E)-2-BENZYL-3-(FURAN-3-YL)-6,7-DIMETHOXY-4-(2-PHENYL-1H-INDEN-1-YLIDENE)-1,2,3,4-TETRAHYDROISOQUINOLINE
description	The title compound (I), (E)-2-benzyl-3-(furan-3-yl)-6,7-dimethoxy-4-(2-phenyl-1H-inden-1-ylidene)-1,2,3,4-tetrahydroisoquinoline (C37H31NO3), was synthesized and structurally characterized by elemental analysis, ¹H NMR and 13C NMR and single crystal X-ray diffraction. In the compound, the N-containing six-membered ring of the tetrahydroisoquinoline unit adopts a distorted half-chair conformation. In the crystal structure, supramolecular chains mediated by C-HO contacts along the b-axis are linked into a double layer via C-Hπ hydrogen bonds. The resulting double layer stacks along the c-axis without any specific interactions. The molecular geometry was also optimized using density functional theory using (DFT/B3LYP) method with the 6-311G(d,p) basis set and compared with the experimental data. In addition to the optimized geometrical structure, molecular orbital, molecular electrostatic potential (MEP) and chemical reactivity studies of the compound have been investigated by using DFT. The antibacterial activity of the compound for various concentrations were determined against eight test pathogens Bacillus cerus, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Acinetobacter baumannii, Staphylococcus epidermidis, Klebsiella pneumoniae and Proteus vulgaris. The results revealed that the compound exhibited good to moderate antibacterial activity.
author	MURUGAVEL,S MANIKANDAN,N LAKSHMANAN,D NAVEEN,KANAGARAJ PERUMAL,PARAMASIVAN THIRUMALAI
author_facet	MURUGAVEL,S MANIKANDAN,N LAKSHMANAN,D NAVEEN,KANAGARAJ PERUMAL,PARAMASIVAN THIRUMALAI
author_sort	MURUGAVEL,S
title	SYNTHESIS, CRYSTAL STRUCTURE, DFT AND ANTIBACTERIAL ACTIVITY STUDIES OF (E)-2-BENZYL-3-(FURAN-3-YL)-6,7-DIMETHOXY-4-(2-PHENYL-1H-INDEN-1-YLIDENE)-1,2,3,4-TETRAHYDROISOQUINOLINE
title_short	SYNTHESIS, CRYSTAL STRUCTURE, DFT AND ANTIBACTERIAL ACTIVITY STUDIES OF (E)-2-BENZYL-3-(FURAN-3-YL)-6,7-DIMETHOXY-4-(2-PHENYL-1H-INDEN-1-YLIDENE)-1,2,3,4-TETRAHYDROISOQUINOLINE
title_full	SYNTHESIS, CRYSTAL STRUCTURE, DFT AND ANTIBACTERIAL ACTIVITY STUDIES OF (E)-2-BENZYL-3-(FURAN-3-YL)-6,7-DIMETHOXY-4-(2-PHENYL-1H-INDEN-1-YLIDENE)-1,2,3,4-TETRAHYDROISOQUINOLINE
title_fullStr	SYNTHESIS, CRYSTAL STRUCTURE, DFT AND ANTIBACTERIAL ACTIVITY STUDIES OF (E)-2-BENZYL-3-(FURAN-3-YL)-6,7-DIMETHOXY-4-(2-PHENYL-1H-INDEN-1-YLIDENE)-1,2,3,4-TETRAHYDROISOQUINOLINE
title_full_unstemmed	SYNTHESIS, CRYSTAL STRUCTURE, DFT AND ANTIBACTERIAL ACTIVITY STUDIES OF (E)-2-BENZYL-3-(FURAN-3-YL)-6,7-DIMETHOXY-4-(2-PHENYL-1H-INDEN-1-YLIDENE)-1,2,3,4-TETRAHYDROISOQUINOLINE
title_sort	synthesis, crystal structure, dft and antibacterial activity studies of (e)-2-benzyl-3-(furan-3-yl)-6,7-dimethoxy-4-(2-phenyl-1h-inden-1-ylidene)-1,2,3,4-tetrahydroisoquinoline
publisher	Sociedad Chilena de Química
publishDate	2015
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072015000300008
work_keys_str_mv	AT murugavels synthesiscrystalstructuredftandantibacterialactivitystudiesofe2benzyl3furan3yl67dimethoxy42phenyl1hinden1ylidene1234tetrahydroisoquinoline AT manikandann synthesiscrystalstructuredftandantibacterialactivitystudiesofe2benzyl3furan3yl67dimethoxy42phenyl1hinden1ylidene1234tetrahydroisoquinoline AT lakshmanand synthesiscrystalstructuredftandantibacterialactivitystudiesofe2benzyl3furan3yl67dimethoxy42phenyl1hinden1ylidene1234tetrahydroisoquinoline AT naveenkanagaraj synthesiscrystalstructuredftandantibacterialactivitystudiesofe2benzyl3furan3yl67dimethoxy42phenyl1hinden1ylidene1234tetrahydroisoquinoline AT perumalparamasivanthirumalai synthesiscrystalstructuredftandantibacterialactivitystudiesofe2benzyl3furan3yl67dimethoxy42phenyl1hinden1ylidene1234tetrahydroisoquinoline
_version_	1718445538992455680

SYNTHESIS, CRYSTAL STRUCTURE, DFT AND ANTIBACTERIAL ACTIVITY STUDIES OF (E)-2-BENZYL-3-(FURAN-3-YL)-6,7-DIMETHOXY-4-(2-PHENYL-1H-INDEN-1-YLIDENE)-1,2,3,4-TETRAHYDROISOQUINOLINE

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