全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...

Design, Synthesis and Antibacterial Activity Evaluation of 4,5-Diphenyl-1H-Imidazoles Derivatives

DOI: 10.4236/ojmc.2021.112002, PP. 17-26

Keywords: Synthesis, 4,5-diphenylimidazole-2-thiol, Benzimidazole, Antibacterial Activity, Drug-Resistant

Full-Text   Cite this paper   Add to My Lib

Abstract:

Due to the continuous emergence and rapid spread of drug-resistant strains of bacteria, there is an urgent need for the development of novel antimicrobials. Along this line, the synthesis and antibacterial activity of 4,5-diphenylimidazol-2-thiol derivatives 2a-g and 6a-e are reported. The structures of the synthesized compounds were confirmed by Nuclear Magnetic Resonance (NMR) and High Resolution Mass Spectrometry (HRMS). All compounds were screened in vitro for their antibacterial activity against Pseudomonas aeruginosa and Escherichia coli (Gram-negative bacteria) and also against Staphyloccocus aureus and Enterococcus faecalis (Gram-positive bacteria). The results showed most of the synthesized compounds have no antibacterial activity. However compound 6d was two-fold potent than ciprofloxacin against Staphylococcus aureus with Minimum Inhibitory Concentration (MIC) of 4 μg/mL and 6c showed moderate biological activity against Staphylococcus aureus (16 μg/mL) and Enterococcus faecalis (16 μg/mL).

References

[1]  Pituch, H., Obuch-Woszczatyński, P., Wultańska, D., Meisel-Mikołajczyk, F. and Łuczak, M. (2005) A Survey of Metronidazole and Vancomycin Resistance in Strains of Clostridium difficile Isolated in Warsaw, Poland. Anaerobe, 11, 197-199.
https://doi.org/10.1016/j.anaerobe.2005.01.006
[2]  Peláez, T., Alcalá, L., Marín, M., Martín-López, A., Martínez-Alarcón, J., et al. (2008) Metronidazole Resistance in Clostridium difficile Is Heterogeneous. Journal of Clinical Microbiology, 46, 3028-3032.
https://doi.org/10.1128/JCM.00524-08
[3]  Kusters, I. and Driessen, A.J. (2011) SecA, a Remarkable Nanomachine. Cellular and Molecular Life Sciences, 68, 2053-2066.
https://doi.org/10.1007/s00018-011-0681-y
[4]  Jeu, L., Piacenti, F.J., Lyakhovetskiy, A.G. and Fung, H.B. (2003) Voriconazole. Clinical Therapeutics, 25, 1321-1381.
https://doi.org/10.1016/S0149-2918(03)80126-1
[5]  Clercq, E. (2001) New Developments in Anti-HIV Chemotherapy. Current Medicinal Chemistry, 8, 1543-1572.
https://doi.org/10.2174/0929867013371842
[6]  Poole, K. (2001) Overcoming Antimicrobial Resistance by Targeting Resistance Mechanisms. Journal of Pharmacy and Pharmacology, 53, 283-294.
https://doi.org/10.1211/0022357011775514
[7]  Valls, A., Andreu, J.J., Falomir, E., Santiago, V.L., Atrián-Blasco, E., et al. (2020) Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids. Pharmaceuticals, 13, 482.
https://doi.org/10.3390/ph13120482
[8]  Liu, C., Shi, C., Mao, F., Xu, Y., Liu, J., et al. (2014) Discovery of New Imidazole Derivatives Containing the 2,4-Dienone Motif with Broad-Spectrum Antifungal and Antibacterial Activity. Molecules, 19, 15653-15672.
https://doi.org/10.3390/molecules191015653
[9]  Salahuddin, Shaharyar, M. and Mazumder, A. (2017) Benzimidazoles: A Biologically Active Compounds. Arabian Journal of Chemistry, 10, S157-S173.
https://doi.org/10.1016/j.arabjc.2012.07.017
[10]  Sharma. S., Sharma, V., Singh, G., Kaur, H., Srivastava, S. and Ishar, M.P.S. (2017) 2-(chromon-3-yl) Imidazole Derivatives as Potential Antimicrobial Agents: Synthesis, Biological Evaluation and Molecular Docking Studies. Journal of Chemical Biology, 10, 35-44.
https://doi.org/10.1007/s12154-016-0162-8
[11]  Tahlan, S., Kumar, S. and Narasimhan, B. (2019) Antimicrobial Potential of 1H-Benzo[d] Imidazole Scaffold: A Review. BMC Chemistry, 13, Article No. 18.
https://doi.org/10.1186/s13065-019-0521-y
[12]  Maduskuie, TP., Wilde, R.G., Billheimer, J.T., Cromley, D.A., Germain, S., et al. (1995) Design, Synthesis, and Structure-Activity Relationship Studies for a New Imidazole Series of J774 Macrophage Specific Acyl-CoA: Cholesterol Acyltransferase (ACAT) Inhibitors. Journal of Medicinal Chemistry, 38, 1067-1083.
https://doi.org/10.1021/jm00007a004
[13]  Moore, T.W., Sana, K., Yan, D., Krumm, S.A., Thepchatri, P., et al. (2013) Synthesis and Metabolic Studies of Host-Directed Inhibitors for Antiviral Therapy. ACS Medicinal Chemistry Letters, 4, 762-767.
https://doi.org/10.1021/ml400166b
[14]  Akpa, S.J., Say, M.V., Zoakouma, R.S.P., Fanté, B., Sissouma, D. and Adjou, A. (2016) Synthesis of 2-(benzylthio) Benzimidazole, 2-[(benzimidazol-2-yl) Methylthio] Benzimidazole and Structural Analogues against Haemoncus Contortus. African Journal of Pharmacy and Pharmacology, 10, 670-680.
https://doi.org/10.5897/AJPP2016.4557
[15]  Mahdavi, B., Rahimizadeh, M., Bakavoli, M., Rezaei-Seresht, E. and Fatemi, M. (2013) Unexpected Reduction of C-Cl Bond to C-H Bond by Hydrazine-Mediated Reaction during the Synthesis of Alkylbenzimidazoles Derivatives. Jordan Journal of Chemistry, 8, 63-69.
https://doi.org/10.12816/0001517
[16]  Bakshi, A. and Venkataramana, C.H.S. (2013) Synthesis of Some New Benzimidazole Derivatives Containing Pteridine Ring System and Their Antimicrobial Evaluation. Indian Research Journal of Pharmacy and Science, 1, 78-84.
[17]  Manju, P.T., Smith, A.A. and Padmaja, V. (2018) In-Silico Design, Synthesis and In-Vitro Anti-Tubercular and Anti-Microbial Screening of Novel Benzimidazole Derivatives. International Journal of Pharmaceutical Sciences and Research, 13, 3705-3711.
[18]  Thabaut, A. and Durosoir, J.L. (1979) L’Antibiogramme: Méthodes Classiques et Méthodes Automatisées. Médecine et Maladies Infectieuses, 9, 490-495.
https://doi.org/10.1016/S0399-077X(79)80006-2
[19]  Phillips, M.A. (1928) CCCXVII—The Formation of 2-Substituted Benziminazoles. Journal of the Chemical Society (Resumed), 2393-2399.
https://doi.org/10.1039/JR9280002393

Full-Text

comments powered by Disqus

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133