Synthesis, Characterization, and Preliminary Antimicrobial Evaluation of New Schiff Bases and Mannich Bases of Isatin

Authors

  • Mustafa Mahmood Mukhlif Ministry of Health and Environments, Department of 1Health in Alanbar/ Annah, Anbar, Iraq
  • May Mohammed Jawad Al-Mudhafar Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad, Baghdad, Iraq

DOI:

https://doi.org/10.31351/vol32issSuppl.pp156-163

Keywords:

Isatin, secondary amines, Mannich bases, Schiff bases, Antimicrobial activity.

Abstract

Till now, isatin derivatives have received a lot of interest in organic and medicinal chemistry due to their significant biological and pharmacological activities. Schiff’s and Mannich bases of isatins are an effective group of heterocyclic derivatives that play a significant role in medicinal chemistry as antimicrobial agents. In light of these facts, new Schiff bases and Mannich bases of isatin were synthesized. The monomer Mannich bases; 3(a-e) have been synthesized by reacting isatin with different secondary amines, piperidine, morpholine, and pyrrolidine, dimethylamine, diphenylamine, separately, and formaldehyde, while the dimer (5) formed by using piperazine and formaldehyde which then react separately with Phenylhydrazine to form new Schiff bases 4(a-e), and dimer Schiff base (6) as final products. The structures of the newly synthesized compounds were identified using two spectroscopic methods; (Fourier- transform infrared) FTIR and proton nuclear magnetic resonance spectroscopy (¹H-NMR) analysis. The preliminary in vitro antibacterial and antifungal screening results of new isatin derivatives [4(a-e) and 6] reported moderate to potent antimicrobial activity, the compound 4c exhibited moderate broad-spectrum antibacterial and antifungal activities compared to other derivatives. Moreover, compounds 4c and 6 have a good inhibitory effect against B. subtilis while amoxicillin (standard drug) shows no activity. For antifungal activity compounds (4a-c and 4e) have considerable activity towards C. albicans, whereas compound 4d exhibits slight activity and 6 of no activity.

References

Sulaiman AT, Sarsam SW. Synthesis, Characterization and Antibacterial Activity Evaluation of New Indole-Based Derivatives. Iraqi Journal of Pharmaceutical Sciences. 2020;29(1):207-15.

Rago AJ, Dong G. Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C–H activation. Green Synthesis and Catalysis. 2021;2(2):216-27.

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Published

2023-11-03

How to Cite

1.
Mustafa Mahmood Mukhlif, May Mohammed Jawad Al-Mudhafar. Synthesis, Characterization, and Preliminary Antimicrobial Evaluation of New Schiff Bases and Mannich Bases of Isatin. Iraqi Journal of Pharmaceutical Sciences [Internet]. 2023 Nov. 3 [cited 2024 Nov. 5];32(Suppl.):156-63. Available from: https://bijps.uobaghdad.edu.iq/index.php/bijps/article/view/2532