Ultrasonic Assisted Synthesis, Characterization and Bioactivity Assessment of Novel Piperonal Based Schiff Base and Its Metal Complexes

Document Type : Research Article


1 Department of Chemistry, Hazara University Mansehra, PAKISTAN

2 Department of Biochemistry, Hazara University Mansehra, PAKISTAN

3 Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, PAKISTAN

4 Department of Physics, Hazara University, Mansehra, PAKISTAN


A novel Schiff base was synthesized by the reaction of piperonal and anthranilic acid, which was further utilized in the synthesis of five novel complexes by reaction with different metal salts ultrasonically. Time for the reaction was greatly reduced through ultrasound irradiations and the yield of reactions was also high as compared to the conventional methods using reflux conditions. The synthesized Schiff base and its metal complexes were characterized by spectroscopic techniques like UV-Visible, IR, and 1H NMR. The synthesized compounds were tested for their antibacterial and antioxidant activity. Good results were obtained in the case of antibacterial activities.


Main Subjects

[1] Cella R., Stefani H.A.,Ultrasound in Heterocyclic Chemistry, Tetrahedron. 65: 2619-2641 (2009).
[2] William T R, Loomis A L, The Chemical Effects of High Frequency Sound Waves, J.A.C.S, 49: 3086-3100 (1927).
[3] Li J., Wang S., Chen G., Tong-Shuang L., Some Applications of Ultrasound Irradiation in Organic Synthesis, Current Organic Synthesis 2: 415-436 (2005).  
[4] Mosslemin M.H., Nateghi M.R., Rapid and Efficient Synthesis of Fused Heterocyclic Pyrimidines under Ultrasonic Irradiation, Ultrasonic Sonochemistry 17 162-167 (2010).
[5] Nladhari A.G., Saki F., Ultrasound Synthesis of Five-Membered Heterocycles, Ultrasonic Sonochemistry , 20: 571-580 (2013).
[6] Sultan S., Anjum R., A Mild and Efficient Synthesis of 2-Substituted 2, 3-dihydro-4 (1H)-quinazolinones, Int. J. of Research in Pharmaceutical and Biomedical Science, 3: 1511-1512 (2012).
[8] Karthikeyan M.S.,Prasad D.J,Poojary B.,Bhat K.S.,Holla B.S., Kumari N.S, Synthesis and Biological Activity of Schiff and Mannich Bases Bearing 2, 4-Dichloro-5-Fluorophenyl Moiety, J. Med. Chem., 14: 7482-7489 (2006).
[10] Panneerselvam P., Nair R.R., Vijayalakshmi G., Subramanian E.H., Sridhar S.K., Synthesis of Schiff Bases of 4-(4-aminophenyl)-morpholine as Potential Antimicrobial Agents, Eur. J. Med. Chem., 40: 225-229 (2005).
[11] Sridhar S.K.,Saravanan M., Ramesh A., Synthesis and Antibacterial Screening of Hydrazones, Schiff and Mannich Bases of Isatin Derivatives, Eur. J. Med. Chem. 36: 615-625 (2001).
[13] Mladenova R., Ignatova M., Manolova N., Petrova T.,  Rashkov I., Preparation, Characterization and Biological Activity of Schiff Base Compounds Derived from 8-Hydroxyquinoline-2-Carboxaldehyde and Jeffamines ED®, Eur. Polym. J., 38: 989-999 (2002).
[14] Walsh O.M.,Meegan M.J.,Prendergast R.M.,  Nakib T.A., Synthesis of 3-Acetoxyazetidin-2-Ones and 3-Hydroxyazetidin-2-Ones with Antifungal and Antibacterial Activity, Eur. J. Med. Chem., 31: 989-1000 (1996).
[15] Cinarli A., Gürbüz1 D., Tavman A., Birteksöz A.S., Synthesis, Spectral Characterizations and Antimicrobial Activity of some Schiff Bases of 4-chloro-2-Aminophenol, Bull. Chem. Soc. Ethiop., 25: 407-417 (2011).
[17] El-ajaily M.M., Ben-Gweirif S., Maihub A.A., El-Tajoury A.N., Complexation  Behavior of Schiff Base Toward Transition Metal Ions, 1: 191-194 (2005).
[18] Morad F.M., El-Ajaily M.M., Gweirif S.B., Preparation, Physical Characterization and Antibacterial Activity of Ni (II) Schiff Base Complex, Journal of Science and Its Applications. J. Science. Appls., 1: 72-78 (2007).
[19] Sultan S., Anjum R., A Simple and Solvent Less Ammonium Chloride Catalyzed one- pot Synthesis of 3 - Substituted Indoles under Microwave Irradiation, Int. J. of Research in Pharmaceutical and Biomedical Science, 3: 1567-1569 (2012).
[20] Usharani M., Akila E., Rajavel R., Pharmacological Properties of Schiff Base Metal Complexes Derived from Subsituted Pyridine and Aromatic Amine: A Review, Int. J. Advanced Scientific Technical Research, 5: 198-206  (2013).
[21] Sing R.P., Murthy K.C.N., Jayaprakasha G.K., Studies on the Antioxidant Activity of Pomegranate (Punica granatum) Peel and Seed Extracts Using in Vitro Models, Agric. Food. Chem., 50: 81-86 (2002).