Synthesis of 4-hydroxy-2(1H)-quinolone derived chalocones, pyrazolines and their

antimicrobial, in-silico antimalarial evaluations

S. Sarveswari a, , V. Vijayakumar a, R. Siva b and R. Priyab

a Centre for Organic and Medicinal Chemistry, VIT University, Vellore 632 014, India.b Plant Biotechnology Division, School of Biosciences and Technology, VIT University,

Vellore-632014, Tamil Nadu, India

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Fig .1.Molecular docking result of compound 5a (a) H-bond network with protein residues are shown

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Fig .2.Molecular docking result of compound 5b H-bond network with protein residues are shown

Fig .3.Molecular docking result of compound 5c H-bond network with protein residues are shown

Fig .4.Molecular docking result of compound 5d and its H-bond network with protein residues are shown

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Fig .5.Molecular docking result of compound 5e H-bond network with protein residues are shown

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Fig .6.Molecular docking result of compound 5f H-bond network with protein residues are shown

Fig .7.Molecular docking result of compound 5g H-bond network with protein residues are shown

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Fig .8.Molecular docking result of compound 5h H-bond network with protein residues are shown

Fig .9.Molecular docking result of compound 5i H-bond network with protein residues are shown

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Fig .10.Molecular docking result of compound 5j H-bond network with protein residues are shown

Fig .11.Molecular docking result of standard 1 and its H-bond network with protein residues are shown

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Fig .12.Molecular docking result of standard 2 and its H-bond network with protein residues are shown

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Fig .13.Molecular docking result of compound 4a and its H-bond network with protein residues are shown

Fig .14.Molecular docking result of compound 4j H-bond network with protein residues are shown

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Fig .15.Molecular docking result of compound 4c H-bond network with protein residues are shown

Fig .16.Molecular docking result of compound 4d H-bond network with protein residues are shown

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Fig .17 Molecular docking result of compound 4e H-bond network with protein residues are shown

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Fig .18 Molecular docking result of compound 4f H-bond network with protein residues are shown

Fig .19 Molecular docking result of compound 4g H-bond network with protein residues are shown

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Fig .20 Molecular docking result of compound 4h H-bond network with protein residues are shown

Fig .21 Molecular docking result of compound 4i H-bond network with protein residues are shown

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Fig .22 Molecular docking result of compound 4j H-bond network with protein residues are shown

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1H NMR spectrum of 4-hydroxy-3-(3-(2,4-dichlorophenyl)acryloyl)quinolin-2(1H)-one (4c)

Expanded aromatic region of 1H NMR spectrum of 4-hydroxy-3-(3-phenyl acryloyl)quinolin-

2(1H)-one (4c)

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1H NMR spectrum of 4-hydroxy-3-(3-(4-methoxyphenyl)acryloyl) quinoline-2(1H)-one (4d)

1H NMR spectrum of 4-hydroxy-3-(3-(3,4-dimethoxyphenyl)acryloyl)quinolin-2(1H)-one (4e)

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Expanded aromatic region of 1 H NMR 4-hydroxy-3-(3-(3,4-dimethoxyphenyl)acryloyl)quinolin-

2(1H)-one (4e)

Expanded aromatic region of 1H NMR spectrum of 4-hydroxy-3-(3-(thiophen-2-yl)acryloyl)

quinolin-2(1H)-one (4h)

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1H NMR spectrum of 4-hydroxy-3-(3-(thiophen-2-yl)acryloyl)quinolin-2(1H)-one (4h)

13C NMR spectrum of 4-hydroxy-3-(3-(thiophen-2-yl)acryloyl)quinolin-2(1H)-one (4h)

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1H NMR spectrum of 4-hydroxy-3-(3-(pyridin-2-yl)acryloyl)quinolin-2(1H)-one (4i)

Expanded aromatic region of 1H NMR spectrum of 4-hydroxy-3-(3-(pyridin-2-yl)acryloyl)

quinolin-2(1H)-one (4i)

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13C NMR of spectrum 4-hydroxy-3-(3-(pyridin-2-yl)acryloyl)quinolin-2(1H)-one (4i)

1H NMR spectrum of 4-hydroxy-3-(3-(furon-2-yl)acryloyl)quinolin-2(1H)-one (4j)

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Expanded aromatic region of 1H NMR spectrum of 4-hydroxy-3-(3-(furon-2-yl) acryloyl)

quinolin-2(1H)-one (4j)

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Spectra of 3-(4,5-dihydro-5-aryl-1-phenyl-1H-pyrazol-3-yl)-4-hydroxyquinolin-(1H)-ones (5a-j)

1H NMR spectrum of 3-(4,5-dihydro-1,5-diphenyl-1H-pyrazol-3-yl)-4-hydroxyquinolin-2(1H)-one (5a)

1H NMR spectrum of 3-(4,5-dihydro-5-(2,4-dichlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-4-hydroxyquinolin-2(1H)-one (5c)

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ESI mass spectrum of 3-(4,5-dihydro-5-(2,4-dichlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-4-

hydroxyquinolin-2(1H)-one (5c)

1H NMR spectrum of 3-(4,5-dihydro-5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)-4-

hydroxyquinolin-2(1H)-one (5d)

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ESI mass spectrum of 3-(4,5-dihydro-5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)-4-

hydroxyquinolin-2(1H)-one (5d)

1H NMR spectrum of 3-(4,5-dihydro-5-(3,4-dimethoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)-4-

hydroxyquinolin-2(1H)-one (5e)

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Expanded AMX region of 1H NMR spectrum of 3-(4,5-dihydro-5-(3,4-dimethoxyphenyl)-1-

phenyl-1H-pyrazol- 3-yl)-4-hydroxyquinolin-2(1H)-one (5e)

ESI Mass spectrum of 3-(4,5-dihydro-5-(3,4-dimethoxyphenyl)-1-phenyl-1H- pyrazol-3-yl)-4-

hydroxyquinolin-2(1H)-one (5e)

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ESI Mass spectrum of 3-(4,5-dihydro-5-(3-nitrophenyl)-1-phenyl-1H-pyrazol-3-yl-4-

hydroxyquinolin-2(1H)-one (5f)

1H NMR spectrum of 3-(4,5-dihydro-5-(thiophen-2-yl)-1-phenyl-1H-pyrazol-3-yl)-4-

hydroxyquinolin-2(1H)-one (5h)

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GCMS of 3-(4, 5-dihydro-5-(thiophen-2-yl)-1-phenyl-1H-pyrazol-3-yl)-4-hydroxyquinolin-

2(1H)-one (5h)

1H NMR spectrum of 3-(4,5-dihydro-5-(pyridin-2-yl)-1-phenyl-1H-pyrazol-3-yl)-4-

hydroxyquinolin-2(1H)-one (5i)

X

X

X

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1H NMR spectrum of 3-(4,5-dihydro-5-(furan-2-yl)-1-phenyl-1H-pyrazol-3-yl)-4-

hydroxyquinolin-2(1H)-one (5j)

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