Synthesis, spectral study and antimicrobial activity of some new 2-n-butyl-4-chloro-5-formyl imidazole (BCFI) analogues

• Authors: Priyanka Pankhaniya , Nikhil P. Savaniya , Neha C. Bhoraniya , Heena K. Patel , Dipak M. Purohit
• Languages of publication: EN

Abstracts

EN

New chalcone derivatives (7a-7j) and thiosemicarbazone derivatives (9a-9j) containing 2-n-Butyl-4-chloro-5-formyl imidazole nucleus have been synthesized and their chemical structure were evaluated using Infrared spectroscopy (IR), Ultra-violet spectroscopy (UV-Vis.), 1H-NMR spectroscopy and mass spectroscopy. All the synthesized compounds were evaluated for their anti-bacterial activities against Gram-positive bacteria Bacillus subtilis & Staphylococcus epidermidis and gram-negative bacterial strain Pseudomonas aeruginosa & Porteous vulgaris. The anti-fungal activity was evaluated against Aspergillus niger. The activity of the compounds were compared with known standards such as streptomycin and nystatin. Among the synthesized chalcone derivatives 7d, 7g & 7h are potentially active against bacterial strains & fungi. Among the thiosemicarbazone derivatives 9a, 9g, 9j & 9i are moderately active against bacterial strains. While 9d & 9j shows good anti-fungal activity.

Keywords

EN

2-n-Butyl-4-chloro-5-formylimidazole (BCFI); Chalcones; Thiosemicarbazones; antimicrobial activity

Discipline

• CHEMISTRY: CHEMISTRY

• Publisher: Scientific Publishing House „DARWIN”
• Journal: World News of Natural Sciences
• Year: 2024
• Volume: 55
• Pages: 69-78

Contributors

author

Priyanka Pankhaniya

• Department of Chemistry, Shree M. & N. Virani Science College, Rajkot-360005, India

author

Nikhil P. Savaniya

• Department of Chemistry, Government Science College, Ahwa, Dist. Dang-394710, India

author

Neha C. Bhoraniya

• Department of Chemistry, Shree M. & N. Virani Science College, Rajkot-360005, India

author

Heena K. Patel

• Department of Chemistry, Shree M. & N. Virani Science College, Rajkot-360005, India

author

Dipak M. Purohit

• Department of Chemistry, Shree M. & N. Virani Science College, Rajkot-360005, India

References

• [1] Arora, P., Arora, V., Lamba, H. S., & Wadhwa, D. Importance of heterocyclic chemistry: a review. International Journal of Pharmaceutical Sciences and Research 3(9) (2012) 2947
• [2] Depa, N., & Erothu, H. Synthesis and biological active compounds of nitrogen-containing heterocyclic compounds: a review. Rasayan Journal of Chemistry 15(3) (2022)
• [3] Mermer, A., Keles, T., & Sirin, Y. Recent studies of nitrogen containing heterocyclic compounds as novel antiviral agents: A review. Bioorganic Chemistry 114 (2021) 105076
• [4] Feng, J., Geng, W. C., Jiang, H., & Wu, B. Recent advances in biocatalysis of nitrogen-containing heterocycles. Biotechnology Advances 54 (2022) 107813
• [5] Shukla, P. K., Verma, A., & Mishra, P. Significance of nitrogen heterocyclic nuclei in the search of pharmacological active compounds. New perspective in agricultural and human health (2017) 100-126
• [6] Kerru, N., Gummidi, L., Maddila, S., Gangu, K. K., & Jonnalagadda, S. B. A review on recent advances in nitrogen-containing molecules and their biological applications. Molecules 25(8) (2020) 1909
• [7] Lipshutz, B. H. Five-membered heteroaromatic rings as intermediates in organic synthesis. Chemical Reviews 86(5) (1986) 795-819
• [8] Shalini, K., Sharma, P. K., & Kumar, N. Imidazole and its biological activities: A review. Der Chemica Sinica 1(3) (2010) 36-47
• [9] Siwach, A., & Verma, P. K. Synthesis and therapeutic potential of imidazole containing compounds. BMC chemistry 15 (2021) 1-69
• [10] Alghamdi, S. S., Suliman, R. S., Almutairi, K., Kahtani, K., & Aljatli, D. Imidazole as a promising medicinal scaffold: Current status and future direction. Drug Design, Development and Therapy (2021) 3289-3312
• [11] Sadullayeva, G. G. The use of imidazole in medicine. Ta'lim va rivojlanish tahlili onlayn ilmiy jurnali 2(9) (2022) 41-47
• [12] Martin, C., Bonnet, M., Patino, N., Azoulay, S., Di Giorgio, A., & Duca, M. Design, Synthesis, and Evaluation of Neomycin‐Imidazole Conjugates for RNA Cleavage. ChemPlusChem 87(11) (2022) e202200250
• [13] Hamzeh-Mivehroud, M., Khoshravan-Azar, Z., & Dastmalchi, S. QSAR and molecular docking studies on non-imidazole-based histamine h3 receptor antagonists. Pharmaceutical Sciences 26(2) (2020) 165-174
• [14] López-Laguna, H., Voltà-Durán, E., Parladé, E., Villaverde, A., Vázquez, E., & Unzueta, U. Insights on the emerging biotechnology of histidine-rich peptides. Biotechnology Advances 54 (2022) 107817
• [15] Pandiarajan, S., Hajarabeevi, N., Shaikh, R. R., Raghunathan, S., & MubarakAli, D. Synthesis and Characterization of Novel Schiff Bases Derived from 2-Butyl-4-chloro Imidazole for the Enhanced Antimicrobial Property. Applied Biochemistry and Biotechnology 195(1) (2023) 253-263
• [16] Patel, H., Bhoraniya, N., Pankhaniya, P., Dave, D., & Purohit, D. M. Synthesis and antimicrobal screening of new chalcones, isoxazoles molecules bearing pyridine nucleus. World Journal of Pharmaceutical Research, 13(3) (2024) 899-908
• [17] Patel, H., Bhoraniya, N., Pankhaniya, P., & Purohit, D. M. Synthesis, spectral studies and antimicrobial activity of thiosemicarboximide derivatives containing pyridine nucleus. World News of Natural Sciences 54 (2024) 9-16
• [18] Kumar, C. P., Prathibha, B. S., Prasad, K. N. N., Raghu, M. S., Prashanth, M. K., Jayanna, B. K., ... & Kumar, K. Y. Click synthesis of 1, 2, 3-triazole based imidazoles: Antitubercular evaluation, molecular docking and HSA binding studies. Bioorganic & Medicinal Chemistry Letters 36 (2021) 127810.
• [19] Sahana, S., Vijayakumar, G. R., Sivakumar, R., Sriram, D., & Saiprasad, D. V. Synthesis, docking study and in-vitro evaluation of anti-tuberculosis activity of tri substituted imidazoles containing Quinoline Moiety. Journal of the Korean Chemical Society 66(3) (2022) 194-201
• [20] Sharma, P., LaRosa, C., Antwi, J., Govindarajan, R., & Werbovetz, K. A. Imidazoles as potential anticancer agents: an update on recent studies. Molecules 26(14) (2021) 4213
• [21] Kumar, N., & Goel, N. Recent development of imidazole derivatives as potential anticancer agents. Physical Sciences Reviews 8(10) (2023) 2903-2941
• [22] Al-Blewi, F., Shaikh, S. A., Naqvi, A., Aljohani, F., Aouad, M. R., Ihmaid, S., & Rezki, N. Design and synthesis of novel imidazole derivatives possessing triazole pharmacophore with potent anticancer activity, and in silico ADMET with GSK-3β molecular docking investigations. International journal of molecular sciences 22(3) (2021) 1162
• [23] Aruchamy, B., Kuruburu, M. G., Bovilla, V. R., Madhunapantula, S. V., Drago, C., Benny, S., & Ramani, P. Design, Synthesis, and Anti-Breast Cancer Potential of Imidazole–Pyridine Hybrid Molecules In Vitro and Ehrlich Ascites Carcinoma Growth Inhibitory Activity Assessment In Vivo. ACS omega, 8(43) (2023) 40287-40298
• [24] Tripathi, P., & Malviya, A. Imidazole Scaffold: A Review of Synthetic Strategies and Therapeutic Action. Biomedical and Pharmacology Journal 16(2) (2023) 1159-1168
• [25] Demchenko, S., Lesyk, R., Yadlovskyi, O., Zuegg, J., Elliott, A. G., Drapak, I., & Demchenko, A. Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5 H-pyrrolo [1, 2-a] imidazole and 5 H-Imidazo [1, 2-a] azepine Quaternary Salts. Molecules 26(14) (2021) 4253
• [26] Tippannanavar, M., Verma, A., Kumar, R., Gogoi, R., Kundu, A., & Patanjali, N. Preparation of nanofungicides based on imidazole drugs and their antifungal evaluation. Journal of agricultural and food chemistry 68(16) (2020) 4566-4578
• [27] Barry, A. L. Standardization of Antimicrobial Susceptibility Testing. Clinics In Laboratory Medicine 9(2) (1989) 203-219

• Document Type: article