Research Article EXPLORING THE EFFECTS OF NEWER THREE COMPONENT AMINOBENZYLATED REACTIONS OF TRIPHENYL IMIDAZOLE MOTIF AS POTENT ANTIMICROBIAL AND ANTIINFLAMMATORY AGENTS N.UMARANI*, K.ILANGO, GYANESH GARG, BOMPADA K. SRINIVAS AND V.HEMALATHA *Department of Pharmaceutical Chemistry, SRM College of Pharmacy, SRM University, Kattankulathur603203, Tamilnadu, India Email:umaarun79@gmail.com Received: 20 Nov 2010, Revised and Accepted: 24 Dec 2010 ABSTRACT An elegant synthesis of newer desired aminobenzylated triphenyl imidazole hybrids is described. Cyclization of benzil with appropriate aromatic aldehydes in the presence of ammonium acetate yielded 2‐substituted ‐ 4, 5‐diphenyl imidazole entities, which further undergoes mannich condensation reaction with benzaldehyde and various aromatic secondary amines afforded the title compounds. The constituents of the newly synthesised compounds have been established on the basis of their physical and spectral data. All the newly synthesised heterocycles have been screened for invitro antimicrobial and anti‐inflammatory activities. Among all the synthesized compounds, the compound TPI‐IV exhibited good anti‐inflammatory activity and better anti‐microbial activity against bacterial strains Staphylococcus aureus, Pseudomonas aeruginosa and fungal strain Candida albicans. Keywords: Triphenyl imidazole hybrids, Synthesised heterocycles, Mannich condensation, In vitro antimicrobial activity, Anti‐inflammatory activity. INTRODUCTION Triphenyl imidazole is a privileged structural motif, which has played a pivotal role in the drug discovery process. Nitrogen containing heterocycles paved way for the active research in Pharmaceutical Chemistry. The study of triphenyl imidazole derivatives has been a developing field within the realm of heterocyclic chemistry for the past several decades because of their ready accessibility through synthesis, wide range of chemical reactivity and manifold biological activities. This structural template shows remarkable pharmacological activities such as antibacterial 1,2 , anti‐inflammatory 3,4 , anticonvulsive 5 , anthelmintic 6 , antiulcer 7 , antiviral 8 , antitumour 9 , antispasmodic 10 , antioxidant 11 and antitubercular 12 . Intrigued by these investigations and as a part of our initial efforts to discover potentially active new agents, we decided to synthesise with this functionality coupled with mannich base could furnish better therapeutic results. To our knowledge mannich reaction using benzaldehyde have not been reported as yet. This initiated us to explore the aminobenzylated reaction as well as anti‐inflammatory and antimicrobial properties of target compounds. N N CH NH Ar H 3 CO H 3 CO H 3 CO Fig. 1: Parent nucleus of triphenyl imidazole MATERIALS AND METHODS All the reagents used were of analytical grade. Melting points of the title compounds were determined using Veego‐Digital VMP‐D melting point apparatus and are uncorrected. Infra red spectra (cm ‐ 1 ) were recorded on Perkin‐Elmer spectrophotometer as pellets on KBr discs. The 1 HNMR (400MHz) spectra were recorded on Bruker‐ Avance II spectrometer in DMSO‐d6 using TMS as an internal standard (chemical shifts in δ ppm). The splitting patterns are designated as follows: s, (singlet), d, (doublet), t, (triplet), m, (multiplet). Mass spectra were recorded on Shimadzu LCMS‐ SL2010A (70ev) mass spectrometer. The reactions were monitored by thin layer chromatography (TLC) using precoated silica gel G plates of E‐Merck. The spots were developed in iodine chamber. Synthesis of 4,5diphenyl2(2,3,4trimethoxyphenyl)4H imidazole DPI Benzil (25mmol, 5.25g) and 2,3,4‐trimethoxy benzaldehyde (25mmol) were refluxed with ammonium acetate (10g) and glacial acetic acid (5 ml) for 4 hr afforded 2‐substituted 4, 5‐diphenyl imidazole. After refluxing, the reaction mixture was left overnight and filtered. The filtrate was neutralized with ammonium hydroxide and the second crop of the precipitate were combined and recrystallised from ethanol. Yield 67%, m.p 136 o c, Rf value 0.69. Synthesis of N((4,5diphenyl2(2,3,4trimethoxyphenyl)1H imidazol1yl)phenyl)methyl)substituted amine (TPIITPIV) 4,5‐diphenyl‐2‐(2,3,4‐trimethoxyphenyl)‐4H‐imidazole derivatives were dissolved in methanol and undergoes mannich condensation reaction with benzaldehyde and appropriate aromatic secondary amines yielded the corresponding N,N‐disubstituted ‐ 2,4,5‐ triphenyl ‐1H‐imidazol‐1‐yl methanamine analogues by refluxing for 2 hr. Volatiles are removed under reduced pressure and the resulting dense oily product was recrystallised from ethanol to afford a white solid substance. The physicochemical parameters of the target compounds were tabulated in Table 1. N((4, 5 diphenyl2(2, 3, 4trimethoxyphenyl)1Himidazol1 yl) phenyl) methyl)Nphenyl benzenamine (TPII). IR (KBr) cm ‐1 : 3083.60 (Aromatic ‐CH stretching), 2933.57 (Aliphatic ‐CH stretching), 1519.64 (aromatic C=C stretching), 1432.44 (C=N stretching), 1041.84 (C‐N stretching), 1243.44 (C‐O‐C stretching). 1 HNMR(400 MHz,DMSO‐d6) δ ppm: 6.14 (s,1H,CH), 3.84 (s,9H,(OCH3)3), 6.54‐8.26 (m,27H,Ar‐H). Mass: m/z 643. International Journal of Pharmacy and Pharmaceutical Sciences ISSN- 0975-1491 Vol 3, Issue 2, 2011