AZETIDIN-2-ONE FUSED QUINOLINE ANALOGUES: SYNTHESIS AND BIOLOGICAL EVALUATION OF SOME NOVEL 2-CHLORO-3-FORMYL QUINOLINE DERIVATIVES
Keywords:
2-chloro-3-formyl-quinoline, Vilsmeier-Haack reagent, N-aryl acetamides, phenyl hydrazineAbstract
Objective: The aim of the present invention is to synthesize and find out the biological significance of the series of the designed azetidin-2-one fused 2-chloro-3-formyl quinoline derivatives.
Methods: A new series of 2-chloro-3-formyl quinolines derivatives 3-chloro-4-(2-chloro-8/7/6-methoxyquinolin-3-yl)-1-phenyl amino)azetidin-2-one, 3-chloro-4-(2-chloro-8/7/6-chloroquinolin-3-yl)-1-(phenylamino) azetidin-2-one, 3-chloro-4-(2-chloro-8/7/6-methylquinolin-3-yl)-1-(phenyl -amino)azetidin-2-one were synthesized by four steps. The cyclization is facilitated by N-aryl acetamides bearing electron donating groups at ortho-position. However yields of quinolines having electron donating groups in all cases. The structures of the synthesized compounds have been established on the basis of physical and spectral data and are screened for diuretic, some of the exhibited significant activity.
Results: The moderate yield of the proposed compounds was obtained. Spectral analysis and physical characteristic showed that the structural confirmation of the quinoline derivatives of the synthesized compounds. Some of the compounds showed lower to moderate level of significant activities.
Conclusion: From the result of spectral data and diuretic activity it has concluded that the compounds were found to exhibited significance activity.
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References
Spicer JA, Gamage SA, Finlay GJ, Denny WA. Structure-activity relationships for substituted bis(acridine-4-carboxamides): a new class of anticancer agents. J Med Chem 1997;42:2383-93.
Lyon MA, Lawrence S, William DJ, Jackson YA. Synthesis and structure verification of an analogue of kuanoniamine A. J Chem Soc: Perkin Trans 1999;1:437-42.
Kerry MA, Boyd GW, Mackay SP, Meth-cohn O, Platt L. Pyrazoles in comprehensive heterocyclic chemistry III. J Chem Soc: Perkin Trans; 1999. p. 2315.
Vlahov R, Parushev J, Nickel P, Snatzke G. Synthesis of some new quinoline derivatives-potential antimalarial drugs. J Pure Appl Chem Res 1990;7:1303-6.
Pramilla S, Garg SP, Nautiyal SR. Some new biologically active quinoline analogues. Indian J Heterocycl Chem 1998;7:201-4.
Heinz HP, Milhahn HC, Eckart E. Cycloalkane carboxylic esters derived from Lysergol, Dihydro lysergol-I, and elymoclavine as partial agonists and antagonists at rat 5-HT2AReceptors: pharmacological evidence that the Indolo[4,3-fg] quinoline system of the ergolines is responsible for high 5-HT2A receptor affinity. J Med Chem 1999;42:659-68.
Srivastava A, Singh MK, Singh RM. Synthesis of 1H-Pyrazolo quinolines and 3-amino-1H–pyrazolo quinoline. Indian J Chem 2005;45B;292:6.
Srivastava A, Singh RM. Facile synthesis of 2-chloro-3-formyl quinolines from N-aryl acetamides and transformation into different functionalities. Indian J Chem 2005;44B;1868:75.
John RD. Applications of absorption spectroscopy of organic compounds. New Delhi: prentice-Hall of India (P); 1969. p. 33-8.
Silverstein RM, Webster FX. Spectrometric Identification of Organic Compounds: John Wiley and Sons Inc; 1998.
McLafferty FW. Interpretation of Mass Spectra. New York: WA Benjamin. Inc. publishers; 1974.
Lipschitz NL, Hadidian Z, Kerpcsar A. Bioassay of diuretics. J Pharmacol Exp Ther 1943;79:97-110.
Tekale AS, Mukhedker SS, Shaikh SAL. A highly efficient synthesis of 2-chloro-3-formyl-8-methyl quinoline: Vilsmeier-haack reagent. Int J Chem Studies 2015;2:42-5.
Beniwal M, Jain N. Review article on vilsmeier haack reaction and its applications. Eur J Biomed Pharm Sci 2015;2:1340-74.