Synthesis and Biological Evaluation of Some Pyrrolidine-2-one Derivatives

nadia azeez betti, Redha Ib. Hussain, Sahar Ab. Kadhem

Abstract


In this research a number of pyrrolidine-2-one derivatives were prepared by lactamization of γ –butyrolactone (GBL) with hydrazine hydrate (80%) to produce (1-aminopyrrolidine-2-one) that undergoes several reactions to afford these derivatives that diagnosed by infrared, nuclear magnetic resonance and mass spectroscopy. Antibacterial activity has also been studied using some types of bacteria, some were found to have good antibacterial activity.


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Z.H. Zadeha, A. Ramazania, K. H. Zadehb, N. Razzaghi and F. Gouranloud," An overview on chemistry and biological importance of pyrrolidinone, "Curr. Org. Synth., vol.14, pp. 1-13, 2017.

F. Erik, H. David, R. Oliver and A. Jeffrey," Automated three-component synthesis of a library of γ-lactams, "J. Org. Chem., vol. 8, pp. 1804-1813, 2012. Crossref | PubMed

R. Vogelsang, R. Pinkos, U. Mahn, et al., Ullmann's, Encyclopedia of industrial chemistry, John Wiley and sons,2011.

K. Setrak, S. R. Tanielyan, R. L. More, T. T. Augustine, R. Kirk, S. Mark and G. Joseph," Hydrogenation of succinimide to 2-pyrrolidone over solid catalysts, "J. Top Cata., vol. 57, pp.1582-1587, 2014. Crossref

B. Robert, "Pyrrolidone-based surfactants (a literature review), "JAOCS, Vol. 72, pp. 759-760, 1995. Crossref

T. Takayama, N. Nambu and T. Nagai," Interactions of N-methyl-2-pyrrolidone with aminobenzoic acids in solution and solid states," Chem. pharm. Bull., vol.25, pp. 879-883, 1977. Crossref

L. Jiang, C. Cheng and L. Dong, "Synthesis and antitumor activity of a novel series of helicid-pyrrolidone derivatives," Chem. Nat. Compd., vol.51, pp. 121-126, 2015. Crossref

P. Hemalatha, M. Veeraiah, S.P. Kumar, K. Vanasuya, M. Manju and R. Naika, "Antibacterial properties of poly (N-vinyl pyrrolidone-co-acrylic acid)/diethyl amino ethanol ester, " IJACS, vol. 2, pp. 50-54, 2014.

Y. Mizushina, S. Kobayashi, K. Kuramochi, S. Nagata, F. Sugawara and K. Sakaguchi," Epolactaene, a novel neuritogenic compound in human neuroblastoma cells, selectively inhibits the activities of mammalian DNA polymerases and human DNA topoisomerase II. Biochem, "Biophys. Res. Commun., vol.273, pp. 784-788, 2000. Crossref | PubMed

C. Zhuang, Z.Miao, L. Zhu, G. Dong, Z. Guo and S. Wang," Discovery, synthesis, and biological evaluation of orally active pyrrolidone derivatives as novel inhibitors of p53−MDM2 protein− protein interaction, " J. Med. Chem.,vol.55,pp. 9630-9642, 2012. Crossref | PubMed

Z. Yang, T. Suomalainen, A. Mayra-Makinen and E. Huttunen," Antimicrobial activity of 2-pyrrolidone-5-carboxylic acid produced by lactic acid bacteria, " J. of Food Protec., vol. 60, pp. 786-790,1997. Crossref | PubMed

Y. Sangnoi, A. Plubrukarn, V. Arunpairojana and A. Kanjana," A new antibacterial amino phenyl pyrrolidone derivative from a novel marine gliding bacterium rapidithrix thailandica, " World J. of Micro. Biotech., vol. 30, pp. 1135-1139, 2014. Crossref | PubMed

J. Lee, S. Yoon, T. Hyeon, S.M. Oh and K.B. Kim," Synthesis of a new mesoporous carbon and its application to electrochemical double-layer capacitors, "J. Chem. Commun., vol. 21, pp. 2177-2178, 1999. Crossref

M. Enterría, F. Suárez-García, A. Martínez-Alonso and J.M.D. Tascón," Synthesis of ordered micro-mesoporous carbons by activation of SBA-15 carbon replicas, "J. Micro. Meso. Mater, vol. 151, pp. 390-396, 2012. Crossref

D. Michael, T. H. N. Thi and L. Jochen, "Investigations into the mechanism of lactamization of lactones yielding in a novel route to biologically active tryptamine derivatives," Tetrahedron, vol. 60, pp. 4567-4578, 2004. Crossref

R. A. A. Chawla, M. K. Parameswaran, P. C. S. Sharma, and T. K. Ravi,"Synthesis of novel 1, 3, 4-oxadiazole derivatives as potential antimicrobial agents, "J. Poli. Pharm. Soc., vol. 67, pp. 247-253, 2010.

H. A. Jawdat, S. H. Ayad and K. M. Aveen, "Synthesis, characterization of some new heterocyclic compounds containing, 3-oxazepine ring, " J. of (KUJSS), vol. 11, pp. 237-247, 2016.

G. K. Nadia, I. M. Mansoura and M. I. Hind, "Synthesis of new Schiff bases bearing 1, 2, 4-triazole, thiazolidine and chloroazetidine moieties and their pharmacological evaluation, " J. of Enz. Inhib. and Med. Chem., vol. 32, pp.191-129, 2017. Crossref | PubMed

O.O. Adnan and S.S Shymaa, "Synthesis of some novel pyrazole and quinolines from coumarin compounds," Raf. J. Sci., vol. 23, pp.108-116, 2012.

I. E. E. Magdy, A. Somaia and E.H. Mogedda,"Synthesis and cytotoxic evaluation of some novel 6-(benzofuran-2-yl)-4-(4-flurophenyl) pyridines," world J. of chem., vol.4, pp.182-194, 2009.

F. K. Mohamed, "Synthesis, reactions and antimicrobial activity on some novel phthalazinones derivatives," J. of D. Chem. Sin., vol.1, pp. 20-31, 2010.

N. H. Karam, J. H. Tomma and A. H. AL-Dujaili, "Synthesis and characterization of heterocyclic compounds derived from 4- hydroxy and 4-amino acetophenone," Ibn AL-Haitham J. for Pure and Applied Science, vol. 26, pp. 296-312, 2017.

M. S. Mohammed, "Synthesis of new 2-amino-5-mercapto-1, 3, 4-thiadiazole derivatives, " PhD., college of science for women/Baghdad University, pp. 40-41, 2010.

K. A. Nisreen, "Synthesis and characterization of 2-hydrazinyl 3H-imidazol [4,5b] pyridine derivatives, " Al- Mustansiriyah J. Sci., vol.26, pp. 43-50, 2015.




DOI: http://dx.doi.org/10.23851/mjs.v31i1.743

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