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Synthesis and Antimicrobial Activity of Some New 5-Oxo-Imidazolidine Derivatives Vivek Gupta1*, A

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Synthesis and Antimicrobial Activity of Some New 5-Oxo-Imidazolidine Derivatives Vivek Gupta1*, A American Journal of Advanced Drug Delivery www.ajadd.co.uk Original Article Synthesis and Antimicrobial Activity of Some New 5-Oxo-Imidazolidine Derivatives Vivek Gupta1*, A. Pandurangan2 1Charak Institute of Pharmacy, Mandleshwar Dist. Khargone (M.P.) 2College of Pharmacy, MM University, Mullana, Ambala (Haryana) ABSTRACT Schiff bases are synthesized from paracetamol. 4- acetamidophenoxyacetylhydrazide is synthesized from paracetamol, which on reaction with various aldehydes gives Schiff bases. Schiff Address for bases treated with amino-acetic acid to produce Imidazolidine Correspondence derivatives. The entire synthesized compound characterized by Charak Institute of physical and analytical data. The chemical structures of synthesized Pharmacy, Mandleshwar Dist. compound were confirmed by means of IR, 1HNMR and MS. Khargone (M.P.) Antimicrobial activity of synthesized compounds evaluated by cup- Tel. +91‐9302255204 plate method. Synthesized compound showed good antimicrobial E-mail: Vivekg_srm06 activity. @yahoo.co.in Keywords: Antimicrobial, Paracetamol, Schiff bases. INTRODUCTION A Schiff base, named after Hugo requires the presence of organic reagents as Schiff, is a compound with a functional essential compounds of the measuring group that contains a carbon-nitrogen double system. They are used in optical and bond with the nitrogen atom connected to an electrochemical sensors, as well as in aryl or alkyl group, not hydrogen. Schiff various chromatographic methods, to enable bases in a broad sense have the general detection of enhance selectivity and formula R1R2C=NR3, where R is an organic sensitivity6-8. Imidazole nucleus has proved side chain. In this definition, Schiff base is to be a versatile moiety for a number of synonymous with azomethine1. Some medicinal agents. The various activities restrict the term to the secondary aldimines associated with the imidazole nucleus are (azomethines where the carbon is connected antiprotozoal, mutagenic properties, to a hydrogen atom), thus with the general anticancer, antiviral, enzyme inhibition and formula RCH=NR. Schiff bases derived broad spectrum antibacterial and antifungal from aromatic amines and aromatic activities. The aim of present study to make aldehydes have a wide variety of an efficient and less toxic antimicrobial applications in many fields, e.g., biological, agent with converting Schiff bases into inorganic and analytical chemistry1-5. imidazolone9. Application of many new analytical devices American Journal of Advanced Drug Delivery www.ajadd.co.uk Gupta et al_____________________________________________________ISSN-2321-547X MATERIALS AND METHODS temperature and allowed to stand for 5 hours. Solid product was separated out, filtered, Melting point is determine by open washed with ice cooled distilled water, dried capillary tube method and uncorrected. The and crystallized with ethanol. The Schiff Base IR spectrum was recorded by using KBr disc 1 was obtained. on FTIR 8010 Shimadzu model. The H- Percentage yield: 78%, melting point NMR spectra of the synthesized compounds : 146- 148OC were recorded on Brucker Spectrospin DPX 300 spectrophotometer. The solutions of the Procedure for Synthesis of 5-Oxo- test compounds were prepared in dimethyl Imidazolidine derivatives (2a-2l) sulfoxide DMSO-d6. Tetra Methyl Silane Schiff bases (1a-1l) (0.01 mol) and (TMS) was used as internal standard. amino acetic acid (0.75gm, 0.01 mol) was Molecular weight weights of the synthesized dissolved in 1:4 dioxane (25ml) with constant compounds were identified by Mass stirring. The content was transferred to round Spectrophotometer, LC-MSD-TrapSL (6300 bottom flask and heated under reflux for 5 Series Ion Trap LC/MS). hours. The mixture was allowed to cool at room temperature. The solid product was Procedure for the synthesis of ethyl-4- filtered, washed with ice cold water, dried and acetamidophenoxyacetate re-crystallised from ethanol. A mixture of paracetamol (1.51g, 0.01mol) and ethylchloroacetate (1.22ml, SCHEME 0.01mol) was refluxed in dry acetone in presence of anhydrous K2CO3 (1.38g, Step I: Synthesis of 4-acetamidophen- 0.01mol) for 6 hr and was then poured onto oxyacetylhy-drazide the crushed ice. Solid product obtained was crystallized from ethanol. Percentage yield: 80%, melting point H3COCHN OH O : 197- 199 C Paracetamol Procedure for the synthesis of 4- acetamidophenoxyacetylhydrazide ClCH COOC H Acetone / K2CO3 A mixture of ethyl-4- 2 2 5 acetamidophenoxyacetate (2.835g, 0.01mol) and hydrazine hydrate (2.0 ml, 0.04mol) in ethanol was refluxed for 5 hr. The solution H3COCHN O CH2COOC2H5 was then poured onto crushed ice. The separated solid was crystallized from ethanol. Percentage yield : 70%, Melting point Ethyl-4-acetamidophenoxyacetate : 155- 1570C NH2NH2H2O / EtOH Procedure for Synthesis of Schiff bases: (1a- 1l) In a round bottomed flask, 4- acetamidophenoxyacetylhydrazide (2.23 gm, H3COCHN O CH2CONHNH2 0.01mol), various aldehyde (5 ml) and ehanol (30-35 ml) was taken and refluxed for three 4-acetamidophenoxyacetylhydrazide hours. The solution was cooled at room AJADD[1][4][2013]413‐421 Gupta et al_____________________________________________________ISSN-2321-547X Rf = Distance run by solute / Distance run by Step II: Synthesis of Schiff bases solvent See Table 2 Spectral data of the synthesized compounds H3COCHN O CH2CONHNH2 2a: IR- 3390 (N-H Stre. Secondary Amide), 3350 (N-H Stre imidazolidine), 3050 (Aromatic -C-H Stre.), 1610 (acyclic C=O R-CHO stre.), 1340 (C-NH imidazolidine). 1 HNMR- 9.6 (m, 1H NH cyclic), 8.1 (s, 1H, NH amide), 7.6-7.2 (m, 8H, Ar-CH), 3.3 (d, 2H, -CH2- aromatic), 2.5 (m, 1H, aromatic –CH-). H COCHN O CH CONHN CHR 3 2 MS - 367(M+) 2b: IR- 3360 (O-H Stre.), 3340 (N-H Stre imidazolidine), 3040 (Aromatic -C-H Step- III: Synthesis of N-(5-oxo-2-aryl- Stre.), 1610 (acyclic C=O stre.), 1340 (C-NH imidazolidine-1-yl) 4-acetamidophen- imidazolidine). oxyacetamide derivatives 1HNMR- 9.6 (m, 1H NH cyclic), 8.1 (s, 1H, NH amide), 7.6-7.3 (m, 8H, Ar-CH), 5.2 (s, 1H, OH), 3.3 (d, 2H, -CH2- aromatic), 2.2 (s, 3H, CH3). H COCHN O CH CONHN CHR 3 2 MS- 384 (M+) 2c: IR- 3370 (N-H Stre. Secondary Amide), 3350 (N-H Stre imidazolidine), 3020 NH2CH2COOH (Aromatic -C-H Stre.), 1610 (acyclic C=O stre.), 1340 (C-NH imidazolidine), 810 (C- R Cl). 1HNMR- 9.6 (m, 1H NH cyclic), 8.1 H3COCHN O CH2CONH N NH (s, 1H, NH amide), 7.6-7.2 (m, 8H, Ar-CH), O 3.3 (2H, -CH2- aromatic), 2.5 (1H, aromatic – CH-), 2.2 (3H, CH3). 2a-2l MS – 401.1(M+) R = Various aromatic aldehyde 2d: IR- 3430 (N-H Stre of Primary Amine), 3390 (N-H Stre. Secondary Amide), Thin layer chromatography 3350 (N-H Stre imidazolidine), 3050 The purity of synthesized compound (Aromatic -C-H Stre.),1610 (acyclic C=O was ascertained by TLC stre.), 1490 (CH2 bend.), 1340 (C-NH imidazolidine). Absorbent - Precoated silica gel 1HNMR- : 9.6 (s, 1H, NH cyclic), 8.1 plate (s, 1H, NH amide), 7.6-7.2 (m, 8H, Ar-CH), Mobile phase - Carbon tetra 5.0 (d, 2H, NH2), 3.3 (2H, -CH2- aromatic), chloride:Chloroform: Methanol (6:2:2 v/v) 2.5 (1H, aromatic –CH-). Detecting agent - Iodine vapour MS – 383 (M+) 2e: IR- 3360 (N-H Stre. Secondary Amide), 3310 (N-H Stre imidazolidine), 3040 AJADD[1][4][2013]413‐421 Gupta et al_____________________________________________________ISSN-2321-547X (Aromatic -C-H Stre.), 2815 (C-H Stre MS – 432 (M+) OCH3), 1710 (acyclic C=O stre.), 1360 (C- 2j: IR- 3390 (N-H Stre. Secondary NH imidazolidine). Amide), 3350 (N-H Stre imidazolidine), 3050 1HNMR- 9.6 (s, 1H NH cyclic), 8.1 (Aromatic -C-H Stre.), 1610 (acyclic C=O (s, 1H, NH amide), 7.6-7.2 (m, 8H, Ar-CH), stre.), 1340 (C-NH imidazolidine). 1 4.1 (t, 3H, OCH3), 3.3 (2H, -CH2 - aromatic), HNMR- 9.6 (s, 1H NH cyclic), 8.1 2.5 (1H, aromatic –CH-). (s, 1H, NH amide), 7.6-7.2 (m, 8H, Ar-CH), + MS – 396 (M ) 5.0 (s, 4H, NH2), 3.3 (2H, -CH2 - aromatic), 2f: IR- 3360 (N-H Stre. Secondary 2.5 (1H, aromatic –CH-). Amide), 3310 (N-H Stre imidazolidine), 3010 MS – 396 (M+) (Aromatic -C-H Stre.), 2920 (Aliphatic C-H 2k: IR- 3360 (N-H Stre. Secondary Stre.), 1610 (acyclic C=O stre.), 1340 (C-NH Amide), 3310 (N-H Stre imidazolidine), 3020 imidazolidine). (Aromatic -C-H Stre.), 1610 (acyclic C=O 1HNMR- 9.6 (s, 1H NH cyclic), 8.1 stre.), 1490 (N-O Stre), 1340 (C-NH (s, 1H, NH amide), 7.6-7.2 (m, 8H, Ar-CH), imidazolidine). 1 3.3 (t, 3H, -CH3), 2.5 (1H, aromatic –CH-). HNMR- 9.6 (s, 1H NH cyclic), 8.1 MS – 381 (M+) (s, 1H, NH amide), 7.7-7.2 (m, 8H, Ar-CH), 2g: IR- 3360 (N-H Stre. Secondary 3.3 (2H, -CH2 - aromatic), 2.5 (1H, aromatic – Amide), 3320 (N-H Stre imidazolidine), 3040 CH-). (Aromatic -C-H Stre.), 1610 (acyclic C=O MS – 457 (M+) Stre.), 1490 (N-O Stre.), 1340 (C-NH 2l: IR- 3390 (N-H Stre. Secondary imidazolidine). Amide), 3350 (N-H Stre imidazolidine), 3050 1HNMR- 9.6 (s, 1H NH cyclic), 8.1 (Aromatic -C-H Stre.), 1610 (acyclic C=O (s, 1H, NH amide), 7.6-7.2 (m, 4H, Ar-CH), stre.), 1350 (C-NH imidazolidine), 820 (C-Cl 3.3 (2H, -CH2 - aromatic), 2.5 (1H, aromatic – Stre.) CH-). 1HNMR- 9.6 (s, 1H NH cyclic), 8.1 MS – 381 (M+) (s, 1H, NH amide), 7.7-6.8 (m, 8H, Ar-CH), 2h: IR- 3410 (O-H Stre.), 3370 (N-H 3.3 (2H, -CH2 - aromatic), 2.5 (1H, aromatic – Stre. Secondary Amide), 3310 (N-H Stre CH-). imidazolidine), 3050 (Aromatic -C-H Stre.), MS – 401 (M+) 1610 (acyclic C=O stre.), 1340 (C-NH imidazolidine).
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