• Bulletin of the Korean Chemical Society
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• v.35 no.10
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• pp.2922-2928
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• 2014

To investigate the possible isosteric replacement of imidazolidinone moiety in 4-phenyl-1-arylsulfonylimidazolidinones (2) for broad and potent anti-cancer agents, a series of 5-phenyl-1H-pyrazol-3-yl 1-(acyl)indoline-5-sulfonates (4) and 1-(1-(acyl)indolin-5-ylsulfonyl)-5-phenylpyrazolidin-3-ones (5) were prepared and evaluated for their cytotoxicity against six human cancer cell lines. Although the pyrazoles 4 or pyrazolidinones 5 showed relatively good activity, still they showed lesser activity in comparison to imidazolidinones 2. These activity decreases could be interpreted with the effect of change of the hydrogen bonding characteristics and the substitution pattern on structural variations of five membered rings from imidazolidinones 2 to pyrazoles 4 and pyrazolidinones 5, respectively. Therefore, it can be concluded that 4-phenyl-1-arylsulfonylimidazolidinone is a basic pharmacophore of imidazolidinones 2.

• Archives of Pharmacal Research
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• v.13 no.2
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• pp.204-206
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• 1990

Certain pyrazolin-5-one and pyrazole derivatives bearing uracil-6-yl or tetrazol-5-yl moiety in position 1 have been synthesized. The anti-inflammatory activity of six representative compounds have been tested and the results are reported.

• Journal of the Korean Chemical Society
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• v.45 no.5
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• pp.454-460
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• 2001

The reaction of 3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(7) with hydrazine hydrate gave 3-hydrazinocarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(8). The reaction of compound 8 with alkyl (ethoxymethylene)cyanoacetates gave the [(quinoxalin-2-ylidene)ethanoyl]-1H-pyra-zoles(9). The reaction of compound 9b with N-alkylanilines provided the N-alkyl-(quinoxalin-2-ylidene)-N-phenylethanamides(10). Compounds 9 and 10 showed the tautomerism between the enamine and methylene imine forms in solution. The tautomer ratios were determined by the $^1H$ NMR.

• Journal of the Korean Chemical Society
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• v.47 no.3
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• pp.241-249
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• 2003

The reaction of 3-(1-ethoxycarbonyl)ethyl-1,2-dihydro-2-oxoquinoxaline (8) with hydrazine hydrate gave 3-(1-hydrazinocarbonyl)ethyl-2-hydroxyquinoxaline (9). The reaction of compound 9 with substituted benzaldehydes and heteroaryl aldehydes afforded 2-hydroxyquinoxalines (10-12), respectively. The reaction of compound 9 with alkyl (ethoxymethylene)cyanoacetates and ethoxymethylenemalononitrile resulted in the intramolecular cyclization to give the 5-amino-1-[2-(3-hydroxyquinoxalin-2-yl)propanoyl]-pyrazoles (13), respectively. Compounds 10-13 showed the tautomerism between the lactam and lactim forms in dimethyl sulfoxide solution. The tautomer ratios were determined by the $^1H$ NMR. The herbicidal and fungicidal activities of the synthesized compounds were investigated.

• Journal of the Korean Chemical Society
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• v.62 no.2
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• pp.87-92
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• 2018

A series of pyrimidine annulated dihydropyrano[2, 3-c]pyrazole derivatives were synthesized and screened for their antimicrobial activity. The precursor, dihydropyrano[2, 3-c]pyrazole was synthesised under catalyst free condition using PEG-400 as reaction medium which facilitated improved yield compared to base catalyzed reaction. Wide scope of substrates, simple workup procedure and high yield even in the absence of catalyst are the major highlights of the protocol. Dihydropyrano[2, 3-c]pyrazoles on condensation with formic acid formed pyrimidine annulated dihydropyrano[2, 3-c]pyrazole derivatives. All the products are characterized using FTIR, $^1H-NMR$ and $^{13}C-NMR$ spectroscopic techniques. The molecules have shown good to moderate activity as antimicrobial agents when compared to the standard drug ciprofloxacin.