Silica-supported fluoroboric acid (HBF4–SiO2) catalyzed highly productive synthesis of thiomorpholides as activators of l-asparaginase as well as the antioxidant agent |
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| Authors: | Babasaheb P Bandgar Shrikant S Gawande Suchita C Warangkar Jalinder V Totre |
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| Institution: | 1. Medicinal Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur 413 255, India;2. Organic Chemistry Research Laboratory, School of Chemical Sciences, Swami Ramanand Teerth Marathawada University, Nanded 431 606, India;3. Biochemistry Research Laboratory, School of Life Sciences, Swami Ramanand Teerth Marathawada University, Nanded 431 606, India;4. Institute for Drug Research, Department of Medicinal Chemistry and Natural Products, School of Pharmacy, The Hebrew University of Jerusalem, 91120, Israel |
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| Abstract: | An efficient solvent-free procedure for the synthesis of thiomorpholides in the presence of a catalytic amount of solid-supported fluoroboric acid (HBF4–SiO2) is described. The advantages of this method are high yields, short reaction times, ease of product isolation, low cost, and the catalyst can be recycled for a number of times without significant loss of activity. Three thiomorpholides possessing electron-donating group (4c, 4g, and 4h) were exhibiting excellent stimulatory activities against Erwinia carotovora l-asparaginase. The most potent activator, compound 4h displayed the following kinetic parameters, Km = 75 μM and Vmax = 1000 μmol mg?1 min?1 and KA = 0.985 μM. Furthermore, these compounds (4g, 4h, 4c, 4f, 4a, and 4d) have also shown promising 2,2′-diphenyl-1-picrylhydrazyl (DPPH) reducing antioxidant activity (21–36%) at 1 mM concentration as compared to standard butylated hydroxyl anisole (72% at 1 mM). |
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