Theoretical anti-tuberculosis activity and molecular docking investigation of N-silylated heterocyclic compounds with benzyl chloride catalyzed by ammonium sulfate-doped red algae (AS@CRA)

Barazzouq, A.; Ouzebla, D.; Hsissou, R.; Daoudi, M.; Bahkali, A.; Zeroual, A.; Wang, S.; Syed, A.; idrissi, M.

Growing Science » Current Chemistry Letters » Theoretical anti-tuberculosis activity and molecular docking investigation of N-silylated heterocyclic compounds with benzyl chloride catalyzed by ammonium sulfate-doped red algae (AS@CRA)

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)

Volume 14 (20)
- Issue 1 (20)

Keywords

Authors

Countries

Current Chemistry Letters

ISSN 1927-730x (Online) - ISSN 1927-7296 (Print) Quarterly Publication Volume 14 Issue 1 pp. 59-68 , 2025

Theoretical anti-tuberculosis activity and molecular docking investigation of N-silylated heterocyclic compounds with benzyl chloride catalyzed by ammonium sulfate-doped red algae (AS@CRA) Pages 59-68 Download PDF

Authors: Ali Barazzouq, Driss Ouzebla, Rachid Hsissou, Mohammed Daoudi, Ali H. Bahkali, Abdellah Zeroual, Shifa Wang, Asad Syed, Mohamed El idrissi

DOI: 10.5267/j.ccl.2024.10.001

Keywords:

Abstract: In this charge we designated a Hilbert-Johnson process by coupling of heterocyclic N-silylated with benzyl chloride at 100°C using the calcined red algae (CRA) doped with ammonium sulfate (AS), AS@CRA as a heterogeneous catalyst. The resulting examination systems, which included atomic absorption, BET methodology and X-ray diffraction (XRD), scanning electron microscopy (SEM/EDX), and Fourier transform infrared spectroscopy (FT-IR), were employed to describe these catalysts. The effect of catalyst and alkylated agent were extensively studied. This catalyst can also be recycled several times in this condensation, and lastly, we suggested a probable answer mechanism for this process. Moreover, our molecular docking investigation revealed the anti-tuberculosis potential of the synthesized compounds. Notably, the drug isoniazid exhibited higher binding energies compared to the products 2a, 2b, and 2c. Additionally, the ADME study suggests that highly efficacious synthetic compounds may possess anti-tuberculosis properties.

How to cite this paper

 Barazzouq, A., Ouzebla, D., Hsissou, R., Daoudi, M., Bahkali, A., Zeroual, A., Wang, S., Syed, A & idrissi, M. (2025). Theoretical anti-tuberculosis activity and molecular docking investigation of N-silylated heterocyclic compounds with benzyl chloride catalyzed by ammonium sulfate-doped red algae (AS@CRA).Current Chemistry Letters, 14(1), 59-68.

Refrences

1. (a) Zhilitskaya ,L.V., & Yarosh, O.N, (2024). The synthesis of salts of five-membered heterocyclic compounds based on N-containing cations /anions (microreview). Chem. Heterocycl. Compd.,60 (5/6),230–232.
(b) Dubina, T.F., Kosarevych, A.V., & Grygorenko, O.O. (2024) Synthesis and reactions of novel imidazo[4,5-b]pyridine building blocks
2. Brishty, S.R., Hossain, M.J., Khandaker, M.U., Faruque, M.R.I., Osman, H., & Rahman, S.A. (2021) A comprehensive account on recent progress in pharmacological activities of benzimidazole derivatives. Front. Pharmacol., 12, 762807.
3. Hou, X.D., Guan, X.Q., Cao, Y.F., Weng, Z.M., Hu, Q., Liu, H.B., & Hou, J. (2020) Inhibition of pancreatic lipase by the constituents in St. John's Wort: In vitro and in silico investigations. Int. J. Biol. Macromol., 145, 620-633.
4. Akhtar, M.J., Yar, M.S., Sharma, V.K., Khan, A.A., Ali, Z., Haider, M.D., & Pathak, A. (2020) Recent progress of benzimidazole hybrids for anticancer potential. Curr. Org. Chem., 27, 5970-6014.
5. Vasava, M.S., Bhoi, M.N., Rathwa, S.K., Jethava, D.J., Acharya, P.T., Patel, D.B., & Patel, H.D. (2020) Benzimidazole: A milestone in the field of medicinal chemistry. Mini-Rev. Med. Chem., 20, 532-565.
6. Kaur, N., Bhardwaj, P., Devi, M., Verma, Y., Ahlawat, N., & Grewal P. (2019) Ionic liquids for the synthesis of five-membered N, N-, N, N, N-and N, N, N, N-heterocycles. Curr. Org. Chem., 23, 1214-1238.
7. Ankita, C., Sudipto, D., Tanmoy, G., Dilip, KM., & Swapan, M. (2018) An efficient strategy for N alkylation of benzimidazoles/imidazoles in SDS-aqueous basic medium and N-alkylation induced ring opening of benzimidazoles. Tetrahedron, 40, 5932-5941
8. Bhaskarjyoti, S., Rishi, R., Nimesh, R.C., Suman, M., Angshuman, R.C., & Komal, M.V. (2023) Highly active primary amine ligated Ru(II)-arene complexes as selective catalysts for solvent-free N-alkylation of Anilines. Mole. Catal., 548, 113440.
9. Elisabeth, M., Laurin, F., Christoph, K., & Ronald. (2019) Access to 3-Deazaguanosine Building Blocks for RNA Solid-Phase Synthesis Involving Hartwig–Buchwald C–N Cross-Coupling. M. Org. Lett, 21, 3900–3903.
10. Mikhail, V.M., & Marie, E.M. (2019). Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives. Beilstein J. Org. Chem, 15, 401–430.
11. Würfel, H., Kayser, M., & Heinze, T. (2019) Trimethylsilylation of polygalacturonic acid. Macromol. Chem. Phys., 220(9), 1900002.
12. Benjamin, W.J., & Lang, Xu. (2021) Computational Methods in Heterogeneous Catalysis. M. Chem. Rev, 121, 1007–1048
13. Charlotte, V., & Bert, M.W. (2022) The concept of active site in heterogeneous catalysis. Nat. Rev. Chem., 6, 89–11.
14. Onome, E., Abiodun, O., Charles, O.O., Victor, E., & Ebube, V.A. (2022) Green biodiesel based on non-vegetable oil and catalytic ability of waste materials as heterogeneous catalyst. Energy Sources A: Recovery Util. Environ. Eff., 44, 7432-7452
15. Yan L., Jun W., Dunru Z., Xiaoqian R., Hanqing GL. (2008) Heteropolyanion-Based Ionic Liquids: Reaction-Induced Self-Separation Catalysts for Esterification. Angew. Chem., 121, 174-177
16. Ejeromedoghene, O., Oladipo, A., Okoye, C.O., Enwemiwe, V., Anyaebosim, E.V., Olusola, M., & Adewuyi, S. (2022) Green biodiesel based on non-vegetable oil and catalytic ability of waste materials as heterogeneous catalyst. Energy Sources A: Recovery Util. Environ. Eff., 44, 7432-7452.
17. Ouzebla, D., Ourhriss, N., Eşme, A., El idrissi, M., & Zeroual A. (2024) Synthesis of some ribonucleosides derivatives and molecular docking analysis against variant corona virus omicrone. Curr. Chem. Lett., 13, 445-450.
18. Ouzebla, D., Ourhriss, N., Fadare, O.A., El Abdallaoui, H.E.A., & Zeroual, A. (2023). Efficient Synthesis of Acyclic Nucleosides by N-Alkylation Using K2CO3 Supported with Natural Phosphate (K2CO3@ NP) as Catalyst and Docking Study Against VIH. Chem. Africa, 6(2), 881-890.
19. Yuchao, C., Weili, D., Guangjun, W., Naijia, G., & Landong, L. (2021) Confinement in a Zeolite and Zeolite Catalysis, Confinement in a Zeolite and Zeolite Catalysis. Acc. Chem. Res, 54, 2894–2904
20. Nooshin, G., Zanjani, A., Kamran, P., & Elmira, Y. (2020) Biodiesel production in the presence of heterogeneous catalyst of alumina: Study of kinetics and thermodynamics. Int. J. Chem. Kinet., 52, 472-484
21. Sumit, H.D., Tarkeshwar, K., & Gopinath, H. (2018) Recent advancement and prospective of heterogeneous carbonaceous catalysts in chemical and enzymatic transformation of biodiesel. Energy Conv. Manag, 167, 176-202.
22. (a) Ouzebla, D., Ourhriss, N., Eşme, A., El idrissi, M., & Zeroual, A. (2024) Synthesis of some ribonucleosides derivatives and molecular docking analysis against variant corona virus omicrone. Curr. Chem, Lett., 13, 445-450(b) Chengyuan, L., Weihui, J., Shunjun, D., Han, S., & Gennian, M. (2017) Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction. Mol., 22, 84, 2-8
23. Atif, M., Barhoumi, A., Syed, A., & El idrissi, M. (2024) ADME Study, Molecular Docking, Elucidating the Selectivities and the Mechanism of [4 + 2] Cycloaddition Reaction Between (E)-N ((dimethylamino) methylene)benzothioamide and (S)-3-acryloyl-4-phenyloxazolidin-2-one. Mol Biotechnol, 1-12.
24. Barhoumi A., Ryachi K., Zeroual A., & El idrissi M. (2023) Chromatography Scrutiny, Molecular Docking, Clarifying the Selectivities and the Mechanism of [3 + 2] Cycloloaddition Reaction between Linallol and Chlorobenzene-Nitrile-oxide. J. Fluoresc, 1-17.
25. Żmigrodzka, M., Sadowski, M., Kras, J., Dresler, E., Demchuk, O.M., & Kula K. (2022) Polar [3+2] cycloaddition between N-methyl azomethine ylide and trans-3,3,3-trichloro-1-nitroprop-1-ene. Scientiae Radices, 1, 26-35.
26. Zeroual, A., Ríos-Gutiérrez, M., El idrissi, M., El Alaoui El Abdallaoui, H., & Domingo Luis, R. (2019) An MEDT study of the mechanism and selectivities of the [3+2] cycloaddition reaction of tomentosin with benzonitrile oxide. Int. J. Quantum Chem., 119, e25980.
27. Atif, M., Barhoumi, A., Syed, A., Bahkali, A.H., Chafi, M., Zeroual, A., Paray, B.A., Wang Sh., & El idrissi, M. (2024) ADME Study, Molecular Docking, Elucidating the Selectivities and the Mechanism of [4+ 2] Cycloaddition Reaction Between (E)-N ((dimethylamino) methylene) benzothioamide and (S)-3-acryloyl-4-phenyloxazolidin-2-one. Mol. Biotech., 1-12.