In vitro biological assessment of 1,3,4-oxadiazole sandwiched by azinane and acetamides supported by molecular docking and BSA binding studies

Virk, N.; Iqbal, J.; Aziz-ur-Rehman, A.; Abbasi, M.; Siddiqui, S.; Rasool, S.; Mehr-un-Nisa, M.; Abid, M.; Khalid, H.; Zafar, F.; Javaid, H.

Growing Science » Current Chemistry Letters » In vitro biological assessment of 1,3,4-oxadiazole sandwiched by azinane and acetamides supported by molecular docking and BSA binding studies

Journals

CCL Volumes

Volume 1 (23)
- Issue 1 (7)
- Issue 2 (5)
- Issue 3 (6)
- Issue 4 (5)

Volume 2 (26)
- Issue 1 (7)
- Issue 2 (6)
- Issue 3 (6)
- Issue 4 (7)

Volume 3 (30)
- Issue 1 (7)
- Issue 2 (10)
- Issue 3 (8)
- Issue 4 (5)

Volume 4 (21)
- Issue 1 (5)
- Issue 2 (5)
- Issue 3 (6)
- Issue 4 (5)

Volume 5 (20)
- Issue 1 (5)
- Issue 2 (5)
- Issue 3 (5)
- Issue 4 (5)

Volume 6 (20)
- Issue 1 (5)
- Issue 2 (5)
- Issue 3 (5)
- Issue 4 (5)

Volume 7 (15)
- Issue 1 (4)
- Issue 2 (4)
- Issue 3 (4)
- Issue 4 (3)

Volume 8 (20)
- Issue 1 (5)
- Issue 2 (5)
- Issue 3 (5)
- Issue 4 (5)

Volume 9 (20)
- Issue 1 (5)
- Issue 2 (5)
- Issue 3 (5)
- Issue 4 (5)

Volume 10 (43)
- Issue 1 (5)
- Issue 2 (7)
- Issue 3 (17)
- Issue 4 (14)

Volume 11 (43)
- Issue 1 (14)
- Issue 2 (11)
- Issue 3 (10)
- Issue 4 (8)

Volume 12 (78)
- Issue 1 (21)
- Issue 2 (22)
- Issue 3 (20)
- Issue 4 (15)

Volume 13 (68)
- Issue 1 (23)
- Issue 2 (17)
- Issue 3 (16)
- Issue 4 (12)

Countries

Current Chemistry Letters

ISSN 1927-730x (Online) - ISSN 1927-7296 (Print) Quarterly Publication Volume 12 Issue 2 pp. 353-368 , 2023

In vitro biological assessment of 1,3,4-oxadiazole sandwiched by azinane and acetamides supported by molecular docking and BSA binding studies Pages 353-368 Download PDF

Authors: Naeem A. Virk, Javed Iqbal, Aziz-ur-Rehman Aziz-ur-Rehman, Muhammad A. Abbasi, Sabahat Z. Siddiqui, Shahid Rasool, Mehr-un-Nisa Mehr-un-Nisa, Muhammad Amin Abid, Hira Khalid, Fatiqa Zafar, Huraiza Javaid

DOI: 10.5267/j.ccl.2022.12.004

Keywords: Antibacterial activity, Azinane, Enzyme inhibition, BSA binding

Abstract: The 1,3,4-Oxadiazole is an aromatic heterocyclic moiety recognized in drug research for its low lipophilicity. The multiple functionalities, heterocyclic azinane, sulfonamide, 1,3,4-oxadiazole and acetamide, are combined collectively to enhance the bioactivity potential of synthesized molecules. All the compounds were acquired by following microwave assisted and conventional techniques in a comparative way. The synthesized derivatives were screened for their antibacterial and enzyme inhibition potential. Furthermore, BSA binding analysis was executed to infer about the interaction with serum albumin. The spectral data of IR, EI-MS, ¹H-NMR and ¹³C-NMR were used to elucidate the final structures of compounds. The synthesized compounds had a modest antibacterial potential. Compound 8f bearing 2-methyl-4,5-dinitrophenyl group was the most active one against all the bacterial strains taken into account and α-glucosidase enzyme. Compound 8d bearing 4-nitrophenyl group was the best acetyl cholinesterase inhibitor and 8i bearing phenylethyl group was the best urease inhibitor.

How to cite this paper

 Virk, N., Iqbal, J., Aziz-ur-Rehman, A., Abbasi, M., Siddiqui, S., Rasool, S., Mehr-un-Nisa, M., Abid, M., Khalid, H., Zafar, F & Javaid, H. (2023). In vitro biological assessment of 1,3,4-oxadiazole sandwiched by azinane and acetamides supported by molecular docking and BSA binding studies.Current Chemistry Letters, 12(2), 353-368.

Refrences

1. Sharma P. C., and Jain S. (2008) Synthesis and antibacterial activity of certain novel 1-cyclopropyl-6-1,4-dihydro-7-4-substituted-piperazin-1-yl-4-oxoquinolin-3-carboxylates. Acta Pharm. Sci., 50 35-40.
2. Sharma P. C., and Jain S. (2008) Synthesis and in-vitro antibacterial activity of some novel N-nicotinoyl-1-ethyl-6-fluoro-1,4-dihydro-7-piperazin-1-yl-4-Oxoquinoline-3-carboxylates. Acta Pol. Pharm. Drug Res., 65 551-556.
3. Chou S. S. P., and Huang J. L. (2012) Tandem cross metathesis and intramolecular aza-Michael reaction to synthesize bicyclic piperidines and indolizidine 167E. Tetrahedron Lett., 53 5552-5554.
4. Vitnik V. D., and Vitnik Z. J. (2015) The spectroscopic (FT-IR, FT-Raman, l3C, 1H-NMR and UV) and NBO analyses of 4-bromo-1-(ethoxycarbonyl)piperidine-4-carboxylic acid. Spectrochimica Acta Part A: Mole Biom. Spec., 138 1-12.
5. Wagle S., Vasudeva A. A., and Suchetha N. K. (2008) Synthesis of some new 2-(3-methyl-7-substituted-2-oxoquinoxalinyl)-5-(aryl)-1,3,4-oxadiazoles as potential non-steroidal anti-inflammatory and analgesic agents. Indian J. Chem., 47B 439-448.
6. Tan T. M., Chen Y., Kong K. H., Bai J., Li Y., Lim S. G., Ang H., and Lam Y. (2006) Synthesis and the biological evaluation of 2-benzenesulfonylalkyl-5-substituted-sulfanyl-[1,3,4]-oxadiazoles as potential anti-hepatitis B virus agents. Antivir. Res., 71 7-14.
7. Aziz-ur-Rehman, Fatima A., Abbas N., Abbasi M. A., Khan K. M., Ashraf M., Ahmad I., and Ejaz S. A. (2013) Synthesis, characterization and biological screening of 5-substituted-1,3,4-oxadiazole-2yl-N-(2-methoxy-5-chlorophenyl)-2-sulfanyl acetamide. Pak. J. Pharm. Sci., 206 345-352.
8. Aziz-ur-Rehman, Fatima A., Abbasi M. A., Rasool S., Malik A., Ashraf M., Ahmad I., and Ejaz S. A. (2013) Synthesis of new N-(5-Chloro-2-methoxyphenyl)-4-(5-substituted-1,3,4-Oxadiazol-2-lthio) butanamide derivatives as suitable lipoxygenase inhibitors. J. Saudi. Chem. Soc., (Doi: http://dx.doi.org/10.1016/j.jscs.2013.02.006).
9. Khalid H., Aziz-ur-Rehman, Abbasi M. A., Malik A., Rasool S., Nafeesa K., Ahmad I., and Afzal S. (2013) Synthesis, spectral analysis and anti-bacterial study of N-substituted derivatives of 2-(5-(1-(phenylsulfonyl)piperidin-4-yl)-1,3,4-Oxadiazol-2-ylthio) acetamide. J. Saudi. Chem. Soc., (doi:http://dx.doi.org/ 10.1016/j.jscs.2013.05.001).
10. Feng Y., Tian N., Li Y., Jia C., Li X., Wang L., Cui X. (2017) Construction of Fused Polyheterocycles through Sequential [4 + 2] and [3 + 2] Cycloadditions. Org. Lett., 19 (7) 1658–1661. doi:10.1021/acs.orglett.7b00452.
11. Abd-Ella A., Metwally S., El-Ossaily Y., Elrazek F., Aref S., Naffea Y., and Abdel-Raheem S. (2022) A review on recent advances for the synthesis of bioactive pyrazolinone and pyrazolidinedione derivatives. Curr. Chem. Lett., 11 (2) 157-172.
12. Łapczuk-Krygier A., Kącka-Zych A., and Kula K. (2019) Recent progress in the field of cycloaddition reactions involving conjugated nitroalkenes. Curr. Chem. Lett., 8 (1) 13-38.
13. Siadati S. A., and Rezazadeh S. (2022) The extraordinary gravity of three atom 4π-components and 1,3-dienes to C20-nXn fullerenes; a new gate to the future of Nanotechnology. Sci. Rad., 1 46-68.
14. Baranowski M., Dyksik M., and Płochocka P. (2022) 2D Metal Halide Perovskites: A New Fascinating Playground for Exciton Fine Structure Investigations. Sci. Rad., 1 (1) 3-25
15. Barnes K. L., Koster A. K., Jeffrey, C. S. (2014) Trapping the elusive aza-oxyallylic cation: new opportunities in hetero cycloaddition chemistry. Tetrahedron Lett., 55 (34) 4690-4696.
16. Kula K., Dresler E., Demchuk O. M., and Jasiński R. (2015) New aldimine N-oxides as precursors for preparation of heterocycles with potential biological activity. Przem. Chem., 94 (1) 1385-1387.
17. Kula K., Dobosz J., Jasiński R., Kącka-Zych A., Łapczuk-Krygier A., Mirosław B., and Demchuk O. M. (2020) [3+2] Cycloaddition of diaryldiazomethanes with (E)-3,3,3-trichloro-1-nitroprop-1-ene: An experimental, theoretical and structural study. J. Mol. Struct., 1203 127473.
18. Kula K., Kącka-Zych A., Łapczuk-Krygier A., Wzorek Z., Nowak A. K., and Jasiński R. (2021) Experimental and theoretical mechanistic study on the thermal decomposition of 3,3-diphenyl-4-(trichloromethyl)-5-nitropyrazoline. Molecules, 26 (5) 1364.
19. Kula K., and Zawadzińska K. (2021) Local nucleophile-electrophile interactions in [3+2] cycloaddition reactions between benzonitrile N-oxide and selected conjugated nitroalkenes in the light of MEDT computational study. Curr. Chem. Lett., 10 (1) 9-16.
20. Fryźlewicz A., Olszewska A., Zawadzińska K., Woliński P., Kula K., Kącka-Zych A., Łapczuk-Krygier A., and Jasiński R. (2022) On the Mechanism of the Synthesis of Nitrofunctionalised Δ2-Pyrazolines via [3+2] Cycloaddition Reactions between α-EWG-Activated Nitroethenes and Nitrylimine TAC Systems. Organics, 3 (1) 59-76.
21. Fryźlewicz A., Łapczuk-Krygier A., Kula K., Demchuk O. M., Dresler E., and Jasiński R. (2020) Regio- and stereoselective synthesis of nitrofunctionalized 1,2-oxazolidine analogs of nicotine. Chem. Heterocycl. Compd., 56 (1) 120-122.
22. Zawadzińska K., Ríos-Gutiérrez M., Kula K., Woliński P., Mirosław B., Krawczyk T., and Jasiński R. (2021) The participation of 3,3,3-trichloro-1-nitroprop-1-ene in the [3+2] cycloaddition reaction with selected nitrile N-oxides in the light of the experimental and MEDT quantum chemical study. Molecules, 26 (22) 6774.
23. Zawadzińska K., and Kula K. (2021) Application of β-phosphorylated nitroethenes in [3+2] cycloaddition reactions involving benzonitrile N-oxide in the light of DFT computational study. Organics, 2 (1) 26-37.
24. Żmigrodzka M., Sadowski M., Kras J., Dresler E., Demchuk O. M., and Kula K. (2022) Polar [3+2] cycloaddition between N-methyl azomethine ylide and trans-3,3,3-trichloro-1-nitroprop-1-ene. Sci. Rad., 1 26-35.
25. Kaspady M., Narayanaswamy V. K., Raju M., and Rao G. K. (2009) Synthesis, antibacterial activity of 2,4-disubstituted oxazoles and thiazoles as bioisosteres. Lett. Drug Des. Discov., 6 21-28.
26. Ellman G. L., Courtney K. D., Andres K. D. (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol., 7 88-90.
27. Chapdelaine P., Tremblay R. R., Dube J. Y. (1978) P-Nitrophenol-alpha-D-glucopyranoside as substrate for measurement of maltase activity in human semen. Clin. Chem., 24 208-211.
28. Jain A. N. (2003) Fully automatic flexible molecular docking using a molecular similarity-based search engine. J. Med. Chem., 46 (4) 499-511.
29. Chohan T. A., Qian H. Y., Pan Y. L., Chen J. Z. (2016) Molecular simulation studies on the binding selectivity of 2-anilino-4-(thiazol-5-yl)-pyrimidines in complexes with CDK2 and CDK7. Mol. BioSyst., 12 (1) 145-161.
30. Chohan T. A., Chen J. J., Qian H. Y., Pan Y. L., Chen J. Z. (2016) Molecular modeling studies to characterize N-phenylpyrimidin-2-amine selectivity for CDK2 and CDK4 through 3D-QSAR and molecular dynamics simulations. Mol. BioSyst., 12 (4) 1250-1268.
31. Holt P. A., Chaires J. B., Trent J. O. (2008) Molecular docking of intercalators and groove-binders to nucleic acids using Autodock and Surflex. J. Chem. Inf. Model., 48 (8) 1602-1615.
32. Wu X. H., Liu J. J., Huang H. M., Xue W. W., Yao X. J. (2011) Interaction studies of aristolochic acid I with human serum albumin and the binding site of aristolochic acid I in subdomain IIA. Int. J. Biol. Macromol., 49 343-350.