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Synthesis, Characterization, Docking and antimicrobial evaluation of novel compounds of 2-phenoxy-1,3,2-benzodioxaphosphole-2-oxide-oxo azetidin and pyrazol-5-one-Mannich bases | Abstract

Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry, Pharmaceutical Sciences and Computational Chemistry

ISSN: 0975-413X

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Abstract

Synthesis, Characterization, Docking and antimicrobial evaluation of novel compounds of 2-phenoxy-1,3,2-benzodioxaphosphole-2-oxide-oxo azetidin and pyrazol-5-one-Mannich bases

Author(s): Madhavi Devarakonda*, B.Saritha, Y.N.Spoorthy and L.K.Ravindranath

The synthetic route of new mannich bases of 4-(3-chloro-1-(2-oxido-2-(4-substituted phenoxy)[d][1,3,2]dioxaphosphole-5-yl)-4-oxoazetidin-2-yl)-1-(morpholinomethyl)-3-(tri fluoromethyl)-1H-pyrazole-5(4H)-one(8a-f) was depicted in scheme:1. The mannich bases (8a-f) were prepared by condensation reaction between 4-(3-chloro-1-(3,4–dihydroxyphenyl)-4-oxaazetidin-2-yl)-1-(morpholinomethyl)-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one(6) and 4-Substituted-PhenylPhosphorodichlori date (7a-f). The synthon (6) was obtained by hydrolysis of 4-(3-chloro-1-(3,4-dimethoxyphenyl)-4-oxo azetidin-2-yl)-1-(morpholinomethyl)-3-(trifluoromethyl)-1H-pyrazol-5-(4H)-one(5). The synthon (5) was obtained by condensation reaction between 4-(((3,4-dimethoxyphenyl)imino)methyl)-1-(morpholinomethyl)-3-(trifluoro methyl)-1H-pyrazol-5-(4H)-one(4) and chloroacetyl chloride. The synthon (4) was obtained by Mannic reaction between 4-(((3,4-dimethoxy phenyl)imino)methyl)-3-(trifluoromethyl)-1-1H-pyrazol-5-(4H)-one(3) with formaldehyde and morpholine. The synthon (3) was obtained by condensation between 5-oxo-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-4-carbaldehyde (1) and 3-4-dimethoxy aniline(2). The structures of newly synthesized compounds (8a-f) were established by IR, 1HNMR, 13C-NMR, 31P-NMR, Mass spectral studies and Elemental analysis.


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