All organic solvents and chemicals were of analytical grade. Albendazole (Bandy Mankind Pharma Ltd., New Delhi) and Mebendazole (Mansukhlal Tribhovandas & Company, Mumbai) were used for anthelmintic activities. For synthesis of benzotriazole derivatives, a 12 mm wide and 140 mm long probe (of an UP 400S ultrasonic processor) was immersed directly into the reaction mixture at room temperature. The operating frequency and the output power were 24 kHz and 240 W respectively. The synthesized compounds were characterized by spectral studies using Perkin Elmer 1600 series Fourier transformer-infrared spectrophotometer in KBr-pellet method; 1H NMR, Bruker 400 MHz NMR spectrometer (Bruker Bioscience, Billerica, MA, USA)
in MeOD using TMS as internal standard. After suitable modifications to the classical synthesis selleck compound carried out by other workers,15, 16 and 17 sixteen new benzotriazole derivatives were synthesized under green conditions (viz., ultrasonication and solvent free conditions) by the addition of diazotization step (Fig. 1). In vitro anthelmintic activity for the synthesized compounds was studied with minor modifications to the standard method. 18Pheretima posthuma (earthworm) obtained from Agricultural Department, Guntur, India, of nearly equal size (length: 9 ± 1.5 cm
and width: 0.1–0.2 cm). Solutions of the all compounds and control drugs (albendazole and mebendazole) were prepared freshly. The drugs and synthesized compounds were dissolved in minimum quantity of DMF and adjusted to 15 ml volume with Tween-80 (3%) in normal saline. The test concentrations (1, 2.5 and 5% w/v) were taken in petri dishes (4 inches). A SAR405838 mw group of six earthworms were released in to each of 15 ml of control drugs and the test suspensions (1, 2.5 and 5% w/v each). Observations were made for the time taken to paralysis and death of individual worms up to 4 h of the test period. Each petri dish was placed with 6 worms and observed for paralysis (or) death. The mean time for paralysis was noted when no movement of any sort could be observed, except when the worm was shaken vigorously. The death time of worm (min) was recorded
after ascertaining that worms neither moved when shaken nor when given external stimuli. Death was concluded when the worms lost their motility followed with fading away of their Linifanib (ABT-869) body colors. All the newer 1,2,3-benzotriazole derivatives synthesized by ultrasound activation in solvent-free condition were obtained in moderate to good yields in the range of 71–82%. The synthesized derivatives were characterized by FTIR and 1H NMR values measured in cm−1 and δ (ppm) respectively. The data was interpreted with reference to standard values 19 and 20 and given in Table 1 for some of the synthesized compounds. All synthesized compounds were tested for anthelmintic activity and compared with the standard anthelmintic substances i.e., mebendazole and albendazole under the same conditions.