The synthesis of polysubstituted quinoline and its derivatives is the focus of a large number of pharmacological studies because of their wide range of biological applications. The quinoline moiety constitutes the main framework of several natural products such as Montelukast and Skimmianine. Quinoline was synthesized by Vilsmeier-Haack reagent which is a versatile reagent used in various synthetic transformation [1]. Quinine, amodiaquine, piperaquine, orimaquine, mefloquine and chloroquine are used as antimalarial drugs mainly consist quinoline moiety [2]. Quinoline nucleus shows good antitumor [3] and antifungal [4] activities. It is also reported that coordination polymer of quinoline ligand too showed antimicrobial activity [5]. Antimicrobial screening and molecular docking studies of some triazoloquinazolinone [6] has also been studied. On the other hand, thiazolidinones are also an important class of heterocyclic compounds which has been classified as 2,4,5thiazolidinones depending on the position of carbonyl group. Out of these 4-thiazolidinone is a five member ring with carbonyl
A series of 5-(benzofuran-2-yl)-N-(3-chloro-4-(2-(p-tolyloxy) substituted quinolin-3-yl)-2-oxoazetidin-1-yl)-1-phenyl-1H-pyrazole-3-carboxamide derivatives (4a-f) were synthesized with excellent yields by cyclocondensation reaction of 5-(benzofuran-2-yl)-N′-(2-(p-tolyloxy) substituted quinolin-3-yl)methylene)-1-phenyl-1H-pyrazole-3-carbohydrazide (3a-f) with chloroacetyl chloride in presence of triethylamine in DMF. One pot condensation of 5-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide (1) with 2-(p-tolyloxy) substituted quinoline-3-carbaldehyde (2a-f) in ethanol solvent in presence of catalytic amount of acetic acid gave intermediate compounds (3a-f). The structures of newly synthesized compounds have been substantiated through elemental analysis and spectral studies viz. 1H NMR, 13C NMR, IR and mass spectra. All the synthesized compounds were screened for their in vitro antibacterial activity against pathogenic bacteria such as S. aureus and E. coli at different
concentrations.
Based on the importance of heterocyclic rings in the field of medicinal chemistry, a new series of 4-arylidene-1-((6-methyl-2-(p-tolyloxy)quinolin-3yl)methyleneamino)-2-phenyl-1H-imidazol-5(4H)-one (3a-e) was designed, synthesized and screened for antimicrobial activity. In present investigation, 5-imidazolones (3a-e) have been synthesized by the condensation of 1-((6-methyl-2-(p-tolyloxy)quinolin-3-yl)methylene)hydrazine (1) with different 4-arylidene-2-phenyloxazol-5(4H)-ones (2a-e), in presence of dry pyridine as the solvent. Structure elucidation of the synthesized compounds was made on the basis of elemental analysis and spectral techniques such as IR, 1 HNMR, and further supported by Mass spectra. The title compounds were screened in-vitro for antibacterial and antifungal activity against different strains of bacteria and fungi. The result revealed that some of the title compounds exhibited significant antibacterial activity but were found to be inactive against the selected fungi.
An expeditious synthesis of series of novel 1,3,5-thiadiazine (5a-f) and (6a-f) derivatives have been
described. These compounds were synthesized by reaction of 1-(N-((6-methyl-2-(p-tolyloxy)quinoline-
3-yl)methylene)carbamimidoyl)-3-arylthiourea (3a-b) derivatives with N-aryl isocyanodichloride (4a-c)
in chloroform followed by basification with dilute NH4OH to give the target compounds 5a-f; which
were acetylated further to afford six novel 1,3,5-thiadiazin-3-(6H)-yl)ethanone (6a-f) derivatives. Synthesis
of intermediate compounds 3a-b was obtained by reacting 6-methyl-2-(p-tolyloxy)quinoline-3-
carbaldehyde (2a) and 1-carbamimidoyl-3-aryllthiourea (1a-b) in chloroform. Structures of compounds
5a-f and 6a-f were established by FTIR, 1H & 13C NMR, mass spectra and further supported by elemental
analysis. All synthesized compounds were investigated for their in vitro antimicrobial screening against
a panel of pathogenic microorganism comprising S. aureus as Gram positive while E. coli, P. vulgaris, S.
typhi as Gram-negative bacterial strains.
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