Abstract
A novel series of asymmetric of (E)-3-(4-(benzyloxy) phenyl)-2-((substituted benzylidene) amino)-1-(thiazolidin-3-yl) propan-1-one derivatives (AAP-1 to AAP-10) have been efficiently synthesized from (S)-2-amino-3-(4-(benzyloxy)phenyl)-1-(thiazolidin-3-yl)propan-1-one (4) and various substituted aldehydes by conventional as well as microwave irradiation method. The structure of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, and Mass spectroscopic methods, further evaluated for their in vitro antimicrobial activities. Among these series, the compounds AAP-2, AAP-4, AAP-5, AAP-7, AAP-8 AAP-9, and AAP-10, showed excellent antibacterial activities against Gram-positive bacteria like Staphylococcus aureus (SA), Lysinibacillus sphaericus (LS), Bacillus subtilis (BS) and Klebsiella aerogenes (KA), Pseudomonas Aeruginosa (PA), Chromobacterium violaceum (CV) as Gram-negative bacteria as compared to standard Ciprofloxacin. The compounds AAP-1, AAP-4, AAP-5, AAP-6, AAP-7, and AAP-8 exhibited good antifungal activities against Fusarium oxysporum (FO), Rhizoctonia solani (RS), Colletotrichum capsici (CC) strains as compared to standard Fluconazole. Molecular docking studies of final compounds were performed using Auto Dock Vina software against Lanosterol 14α-demethylase (CYP51A1) enzyme and crystal 4WMZ and showed effective binding affinity of these molecules with enzymes. Quantitative structure toxicity relationship study of target compounds were studied by various computational animal models and defined oral rat LD50 values for cytotoxicity. The AAP-2, AAP-4, AAP-5, and AAP-7 to AAP-10 showed low toxicity. In addition, the pharmacokinetic of target compounds were studied and revealed acceptable good drug-likeness score properties as well as follow Lipinski's rule of five.
Graphical Abstract
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Acknowledgements
This research work is dedicated to my dear father late Mr. Ashok Trambak Pund and friends late Mr. Somanath Darkunde and late Dr. Nilesh Patil. Authors are thankful to Principal, Shivaji Arts, Commerce and Science College Kannad, District Aurangabad (M.S.) for availing research laboratory and FTIR facilities. Authors also thankful to Mr. Prathmesh Pramod Deshpande for support and Mr. Vijay Maskar, Sprint testing solution, Mumbai for characterization of samples.
Disclosure statement
No potential conflict of interest was reported by the authors.