www.ijpsonline.com This PDF is available for free download from a site hosted by Medknow Publications (www.medknow.com). Research Research Research Research Research Paper Paper Paper Paper Paper Synthesis and Pharmacological Studies of Aminoxy Synthesis and Pharmacological Studies of Aminoxy Synthesis and Pharmacological Studies of Aminoxy Synthesis and Pharmacological Studies of Aminoxy Synthesis and Pharmacological Studies of Aminoxy Containing 2,4,6- Containing 2,4,6- Containing 2,4,6- Containing 2,4,6- Containing 2,4,6-Trisubstituted-s- risubstituted-s- risubstituted-s- risubstituted-s- risubstituted-s-Triazine riazine riazine riazine riazine Derivatives Derivatives Derivatives Derivatives Derivatives SHILPI JAIN, D. BHAMBI, RANJANA SHARMA, AND G. L. TALESARA* Synthetic Organic Chemistry Laboratory, Department of Chemistry, M. L. Sukhadia University, Udaipur-313001, Arylamines on diazotization and further treatment with dicyandiamide yielded aryldicyandiamide (1a-d), which on addition with aminoxy compound (2) gave corresponding biguanides (3a-d). Cycloaddition of biguanide with ethylchloroacetate furnished 2,4,6-trisubstituted-s-triazines (4a-d). Subsequent treatment of these compounds with N-hydroxyphthalimide or N-hydroxysuccinimide in presence of triethylamine gave final compounds (5a-h). IR, 1 H NMR and mass spectra were used to confirm their structure. Compounds (5a-h) were screened for antibacterial (Escherichia coli, Proteus vulgaris, Klebsiella pneumoniae, Pseudomonas aureus and Staphylococcus aureus) and antifungal (Candida albicans and Aspergillus fumigatus) activities. Antibacterial activity revealed that compounds 5a, 5b, 5c, 5g showed comparable activity against bacteria P. vulgaris, P. aureus, where rest of the compounds showed weak activity against all the pathogenic bacteria. The fungicidal data indicated that compound 5d possess high level activity and rest of the compounds showed comparable to the standard. In the present communication, a series of 2-(2',4'- MATERIALS AND METHODS dinitroarylaminoxy)-4-methoxyphthalimido or methoxysucc- inimido-6-(4"-subs.anilino)-s-triazine (5a-h) have been Melting points of synthesized compounds were synthesized and tested for antimicrobial activities. The determined in open capillary tubes and are therefore synthesis of s-triazine 1 and their pharmacological uncorrected. The structures of compounds were are well documented. Some 2-arylamino-4- established on the basis of elemental analysis and spectral chloro-6-(pyrimidine-4-carboxyhydrazino)-1,3,5-triazines data. The IR spectra were recorded in the range of 4000- have been synthesized 6 and observed to possess 450 cm -1 using KBr pellets on a FTIR RXI Perkin-Elmer remarkable antitubercular activity. Several derivatives of s- spectrophotometer. 1 H NMR spectra were recorded on a triazine show antimicrobial 7 , antibacterial 8 and herbicidal 9 Bruker DRX 300 MHz spectrophotometer using CDCl activities. These are also used for treatment of HIV DMSO-d 6 as solvent. The FAB mass spectra were infection 10 . Phthalimidoxy derivatives represent one of the recorded on a Jeol SX-102/DA-6000 spectrometer data India. applications 2-5 / 3 most active class of compounds possessing biological activities 11,12 . N-phthalimidoxy-2-methacrylate, ethyl N- phthalimidoxy acetate containing phthalimidoxy group have been demonstrated to possess anticancer 13 , anticonvulsant 14 , antimalarial 15 , hypotensive 16 and antiamoebic 17 properties. Aminoxy moiety has a special place in the modern therapy of malaria 18 . Synthesis and antimicrobial properties of substituted 3-aminooxy propionyl and 3-aminooxy (E)-2-methoxyimino propionyl monolactams have been reported 19 . Combination of all these three biological moieties in one molecule might result in the overall enhanced biological activity. *For correspondence E-mail: gtalesara@yahoo.com system using argon/xenon (6KV,10 mA) as FAB gas. Purity of synthesized compounds was checked by silica gel-G plates of 2 mm thickness using benzene and ethyl acetate (9:1 and 1:9) as solvent system and iodine chamber as developer. N-Hydroxyphthalimide was prepared by reported method 20 . 4-Substituted aryl dicyandiamide (1a-d): Suspension of p-substituted aniline (0.01 mol) in hot 5 N HCl was cooled to 0-5°. It was diazotized by adding sodium nitrite (0.01 mol) solution in water, whether the reaction has completed or not was checked by starch-iodide paper 21 . Diazotized mixture was slowly added to a solution of dicyandiamide (0.01 mol) in water (25 ml) with stirring, Indian Journal of Pharmaceutical Sciences January - February 2007 28