A facile Single Pot Synthesis of Highly Functionalized Tricyclic Heterocycle Compounds Via Sequential Knoevenagel-michael Addition and Their ?-glucosidase Inhibition, Antioxidants and Antibacterial Studies. | [Journal of Chemical Society of Pakistan • 2018]

Author(s):

1. Faiz Ahmed: Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan; Institute of Chemistry, University of Punjab, Lahore Pakistan; Institute of Chemistry, University of São Paulo, 05508-000 São Paulo, Brazil

2. Abdul Rauf: Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

3. Ahsan Sharif: Institute of Chemistry, University of Punjab, Lahore Pakistan

4. Ejaz Ahmad: Institute of Chemistry, University of Punjab, Lahore Pakistan

5. Muhammad Arshad: Institute of Chemistry, University of Punjab, Lahore Pakistan

6. Breno Pannia Esposito: Institute of Chemistry, University of São Paulo, 05508-000 São Paulo, Brazil

7. Telma Mary Kaneko: Faculty of Pharmaceutical Sciences, University of São Paulo, 05508-000 São Paulo, Brazil

8. Ashfaq Mahmood Qureshi: Department of Chemistry, The Government Sadiq College Women University, Bahawalpur, Pakistan, 63100

Abstract:

Summary: A facile methodology was developed which involved multicomponent single pot reaction which yielded the synthesis of highly functionalized tricyclic-heterocycle compounds (1c6c) and (1d-7d) in good yields (60-80%). The discovered novel methodology involved sequential multicomponent reactions; consisting of Knoevenagel reaction followed by Michael addition; moreover, the proposed mechanism is consistent with the stepwise methodology which also availed the same tricyclic heterocycle compounds (1c-6c) and (1d-7d). In-silico (a-glucosidase inhibitory studies only) and in-vitro biological evaluation was extensively performed for all the synthesized compounds. Tricyclic-heterocycle compounds (1c-6c) and (1d-7d) showed excellent interacting affinity with receptor protein (PDB ID: 3A47) which were further complemented and confirmed through in-vitro a-glucosidase inhibitory studies which were found to be comparable with standard acarbose. Whereas, 3c, 3d and 5d exhibited IC50 value (111.8, 99.4, 108.7 µmol/L) as compared to standard acarbose (135.6 µmol/L) making them excellent a-glucosidase inhibition candidates among the lot. Furthermore, all the novel synthesized compounds were screened for in-vitro antibacterial, and antioxidant studies, which revealed that all these compounds show mild bacteriostatic properties at 200 µM concentration against 105 CFU/200 µL of three bacterial strains; Pseudomonas aeruginosa, Escherichia coli, and Staphylococcus aureus, while compounds (2d, 3d, 4d, 6c, 6d) are found more potent antioxidants than the standard ascorbic acid.

Page(s): 761-772

DOI: DOI not available

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 40, Issue: 4, Year: 2018

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