Journal of Chemical and Pharmaceutical Research

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1 Available on line Journal of Chemical and Pharmaceutical esearch J. Chem. Pharm. es.,, (): 1- ISS o: - Schiff s bases of piperidone derivative as microbial growth inhibitors Yatri. Shah*, Dhrubo Jyoti Sen and C Patel Department of Pharmaceutical and Medicinal Chemistry, Shri Sarvajanik Pharmacy College, Hemchandracharya orth Gujarat University, Mehsana, Gujarat, India Abstract Piperidones are a class of chemical compounds sharing the piperidone skeleton. A classic named reaction for the synthesis of piperidones is the Petrenko-Kritschenko Piperidone synthesis which involves combining a alkyl-1, -acetonedicarboxylate with benzaldehyde and an amine. This multicomponent reaction reaction related to the Hantzsch pyridine synthesis.some -piperidones give very good antimicrobial activity. So, here are some substituents of -piperidone to check whether I t give same activity or not. Introduction -Piperidinone is a derivative of piperidine with the molecular formula C H. - Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs (e.g., fentanyl)[1]. Its proven applications in Wittig eaction with Phosphorous Ylides, rganic Photoreceptor Synthesis, emoval of Sulphur Compounds from Gases, Pethidine Synthesis, Pharmaceutical Synthesis, Synthesis of Spiro Heterocycles & Fused ring Systems[]. -Phenethyl--piperidonePreparation -Phenethyl--piperidone can be prepared via a simple S substitution by reacting phenethyl bromide with -piperidinone in the presence of a phase transfer catalyst (PTC)[]. 1

2 Yatri. Shah et al J. Chem. Pharm. es.,, (): 1- Scheme of preparation of Phenyl ethyl -piperidone CH CH H -phenylethanamine CH =CHCCH methyl acrylate CCH CCH ame CCH methyl -((-methoxy-- oxoethyl)(phenethyl)ami no)propanoate methyl -oxo-1- phenethylpiperidin e--carboxylate H 1-phenethylpiperidin--one Procedure for reactions with different amines Phenyl ethyl -piperidone reacts with different amines [propylamine (I), isobutyl amine (II), methylamine (III)] respectively in presence of toluene as a solvent and water is removed and Schiff base is formed. Then this Schiff base undergoes reduction in presence of Zn-Hg /HCl and reduced product of Schiff base is obtained. Then it is reacted with benzoyl chloride and form benzoylated product, after benzoylation it reacts with two different azides: Hydrazide hydrate and semicarbazide.hcl and forms again Schiff base for both azides which further undergoes for clemensen reduction by reacting with ZnHg/HCl.the reduction product of both azides reacts with ethyl acetoacetate and undergoes cyclization and formed cyclized product[,].

3 Yatri. Shah et al J. Chem. Pharm. es.,, (): 1- General scheme for different synthesized products H reduction H 1-phenethylpiperidin--one (A) Zn/HgCl (B) CCl C H C H H reduction Zn/HgCl (D) -H H HCH. HCl (C) HH C HCH (Da) (E) CH CCH CC H reduction Zn/HgCl H HHCH (Db) H C (Ea) CH CCH CC H = CH, CH CH CH, CH CH(CH ) H C CH (Eb) Synthesized Compounds (IDb) -methyl-1-((1-phenethyl piperidin--yl)(propyl)amino-1,,dihydropyrazol--one H

4 Yatri. Shah et al J. Chem. Pharm. es.,, (): 1- (IEb) -methyl--oxo-1-((1-phenethyl piperidin--yl)(propyl)amino-1h-pyrazole-(h)-carboxamide H (IIDb) 1(isobutyl (1-phenethyl piperidin--yl)amino)-methyl-1,-dihydropyrazol--one H (IIEb) 1-(isobutyl(1-phenethylpiperidin--yl)amino)-metyl--oxo-1H-pyrazol-- (H)carboxamide H (IIIDb) -methyl-1-(methyl(1-phenethyl piperidin --yl)amino)-1,-dihydropyrazol--one H (IIIEb) -methyl-1-(methyl(1-phenethyl piperidin--yl)amino)--oxo-1h-pyrazol-(h)-carboxamide H

5 Yatri. Shah et al J. Chem. Pharm. es.,, (): 1- Physicochemical Parameters of Synthesis Compound Compound Mol.formula Mol.wt (g/mol) Polarity f a Composition C,H,(%) (cacltd.) Composition C, H, (%) (Found) PhenEthyl Piperidone C 1 H 1. Polar. C,.1;H,.;,.;,. C,.;H,.;,.;,. IDb C H. Semipolar. C,.1;H,.;,1.;,. C,.;H,.;,1.;,. IEb C 1 H 1. Semipolar. C,.;H,.11;,1.1;,. C,.;H,.1;,1.;,. IIDb C 1 H. Semipolar. IIEb C H. Semipolar. IIIDb C 1 H 1. Semipolar. IIIEb C 1 H 1. Semipolar. a-ethyl acetate: Hexane (:) Antibacterial activity C,.;H,.;,1.;,. C,.1;H,.;,1.;,.1 C,.;H,.;,1.;,. C,.;H,.1;,1.;,. C,1.;H,.;,1.;,. C,.1;H,.;,1.;,. C,.;H,.;,1.;,. C,.;H,.1;,1.;,. CMPUDS CC.(µg/ml) ZE F IHIBITI(mm) B.subtilis ±. ±. ±. (IDb) ±. ±.. ±. ±. ±. ±. ±. ±.1 ±.1 ±. ±. (IEb) ±. ±.1 ±. ±. ±.1 ±. ±. ±.1 ±. ±. ±.1 ±. (IIDb) ±. ±. ±. ±.1 ±.1 ±. ±. ±. ±. ±.1 ±. ±.

6 Yatri. Shah et al J. Chem. Pharm. es.,, (): 1- (IIEb) ±. ±. ±. ±. ±.1 ±. ±. ±. ±. ±. ±.1 ±. (IIIDb) ±. ±. ±. ±.1 ±.1 ±. ±. ±. ±. ±. ±. ±. (IIIEb) ±. ±. ±. ±.1 ±.1 ±. ±. ±. ±. ±.1 ±. 11±. Streptomycin 1±. 11±. 11±. 1±. 1±.1 1±. 1±.1 1±. 1±. ±. ±.1 ±. Ampicillin 11±. ±. 11±o. 1±. 1±. 1±. 1±. 1±. 1±. Histogram for Antimicrobial study of synthesized compounds Activity of Compound-IDb 1

7 Yatri. Shah et al J. Chem. Pharm. es.,, (): 1- Activity of Compound-IEb 1 Activity of Compound-IIDb 1 Activity of Compound-IIEb 1

8 Yatri. Shah et al J. Chem. Pharm. es.,, (): 1- Activity of Compound-IIIDb 1 Activity of Compound-IIIEb 1 Activity of Standard drug-streptomycin

9 Yatri. Shah et al J. Chem. Pharm. es.,, (): 1- Activity of standard drug Ampicillin B.cubtilus Conclusion All the newly synthesized compounds IDb, IEb, IIDb, IIEb, IIIDb, IIIEb were screened for antimicrobial activity. The test solutions of synthesized compounds of µg/ml, µg/ml, µg/ml and µg/ml were prepared in a methanol. Streptomycin was used as standard reference drug and methanol as a control. Among the all synthesized compounds, compound IIIEb gives a better antimicrobial activity against gram positive ( and B.subtilis) and gram negative () bacteria than other synthesized compounds. H eferences [1] Mieczyslaw Makosza, Pure Appl. Chem.. (): 1. [] Cunico W, Claudia B, Ferreira MG, Capri L, Soares M, ; : 1. [] V.Boekelheide and.j.windgassen, J. Am. Chem. Soc. 1.1:1. [] T.Kitsuki and Y.Fujikura, J.rg.Chem, 1.:1. [] Petrikaite V, Tarasevicius E, Pavilonis A. ; ():. [] Pelczar MJ, Chan ES, Pelczar J, Krieg. Microbiology.th ed. London: W.B. Saunders Co. Publisher; 1.p.-. [] Chakraborty P. A Text Book of Microbiology. nd ed. Sen M. (Kolkatta): ew central book agency (P) Ltd;.p.-, -.