Synthesis and Evaluation of the in vitro Antimicrobial Activity of Triazoles, Morpholines and Thiosemicarbazones

Abstract

Background: Microbial infections is a global public health problem. The aim of this work was to synthesize and evaluate the antimicrobial activity of novel triazoles, morpholines and thiosemicarbazones. </P><P> Methods: Compounds were synthesized using 2,4-Dihydroxyacetophenone and 4-hydroxybenzaldehyde as starting materials. The antimicrobial activity of these compounds against bacteria and yeast was evaluated by the broth microdilution method. Results: The proposed route for synthesis gave high to moderate yields, moreover these compounds were successfully characterized by 1H NMR, 13C NMR and LC-MS. Antimicrobial testing indicated that the thiosemicarbazone and morphine derivatives had the best antimicrobial activity against the microorganisms tested with minimum inhibitory concentrations (MIC) between 0.29 and 5.30 µM. Thiosemicarbazone derivative (12) was able to inhibit the growth of C. tropicalis, with minimum fungicidal concentration (MFC) of 0.55 µM. In addition, this compound was active against E. coli, S. aureus and S. epidermidis, with MIC values ranging from 0.29 to 1.11 µM. Moreover, the morpholine derivative (15) had an MIC value of 0.83 µM against C. albicans and E. coli. Conclusion: We have efficiently synthesized a series of eleven novel triazoles, thiosemicarbazones and morpholine derivatives using 2,4-Dihydroxyacetophenone and 4-hydroxybenzaldehyde as starting materials. Thiosemicarbazone derivative (12) showed promising antifungal and antibacterial activity and these findings suggest that this compound can be used as scaffolds to design new antimicrobial drugs.

Influence of Complexation of Thiosemicarbazone Derivatives with Cu (II) Ions on Their Antitumor Activity against Melanoma Cells

“…A view of these molecules in conformation observed in the crystal is shown in Figure 1. The C2=S3, N4-N5, and N5=C6 bond lengths of 1.686(4), 1.373 (4), and 1.266(5) Å in T2, 1.6896(13), 1.3809 (14), and 1.2766 (17) Å in T3 and 1.693(3), 1.375 (3), and 1.272(3) Å in T5, respectively, are characteristic for those observed in other organic molecules containing thiosemicarbazone system [22,23] and confirming that the thione tautomeric form is observed in the crystalline state. In all analyzed molecules the thiosemicarbazone skeleton N1/C2/S3/N4/N5/C6 is slightly distorted from planarity with the largest deviation from the mean plane of 0.025(3) Å for N5 in T2, 0.0563 (12) Å for N4 in T3 and 0.015(2) Å for N4 in T5.…”

“…In all analyzed molecules the thiosemicarbazone skeleton N1/C2/S3/N4/N5/C6 is slightly distorted from planarity with the largest deviation from the mean plane of 0.025(3) Å for N5 in T2, 0.0563 (12) Å for N4 in T3 and 0.015(2) Å for N4 in T5. The torsion angles C7-N1-C2-N4, N1-C2-N4-N5, C2-N4-N5-C6, N4-N5-C6-C21 and N6-C6-C21-C22 of −179.5(4), −3.7(5), 179.2 (3), −178. 7(3) and −7.3 (6) • in T2, −177.01 (14), 5.86 (19), 178.25 (13), −177.95 (12) and 2.4 (2) • in T3 and −174.…”

“…The structure of thiosemicarbazones has a significant influence on biological activity. Their antiviral [1], antidiabetic [2], antifungal, and antibacterial [3] activity is known.…”

Synthesis, Modification and Biological Activity of Diosgenyl β-d-Glycosaminosides: An Overview

“…Hydroxy acids used in these explorations are structural analogs of some amino acids. N-Aminoacyl and N-hydroxyacyl derivatives of diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside (63)(64)(65)(66)(67)(68)(69)(70)(71)(72)(73)(74)(75)(76) were obtained using the solution-phase method of peptide synthesis in DCM/DMF mixture. Fmoc-protected amino acids were used for the synthesis, whereas N,N'-diisopropylcarbodiimide (DIC) and 1-hydroxybenzotriazole (HOBt) were used as the coupling agents (Scheme 6).…”

Synthesis, docking and evaluation of in vitro anti-inflammatory activity of novel morpholine capped β-lactam derivatives

“…[23] Another class of nitrogen ring compounds are the morpholine derivatives, often used as the building blocks, [24] selective norepinephrine reuptake inhibitors [25] and dopamine D4 receptor ligands. [26] Moreover, they have been shown anti-inflammatory, [27,28] antiparasitic, [29] antimicrobial, [30,31] antitumor, [32] and antioxidant activities. [33,34] Linezolid is an example of a commercially important antibacterial agent possessing a morpholine ring (Scheme 1).…”