Synthesis and Evaluation of 4-[5-((4-hydroxybenzylidene) amino)-1,3,4-thiadiazol-2-yl] Phenol Compound Biological Activities

Background and Aim: The 1,3,4-thiadiazole molecule has a heterocyclic structure in several medications and natural products.It is an essential part of several pharmacological classes, such as antibacterial, anti-inflammatory, analgesic, antiviral, antineoplastic, and anti-tubercular drugs.Thiadiazole compounds have attracted interest in the field of medicinal chemistry because of their biological and pharmacological activities, especially their anticancer capacities.This study aimed to synthesize a new phenol compound with antibacterial and anticancer efficacy.The relationship between Schiff-base and antibacterial and antitumor actions was studied. Materials and Methods:The microwave approach was employed to create the novel compound known as 4-[5-((4hydroxybenzylidene) amino)-1,3,4-thiadiazol-2-yl] phenol.Its composition was validated by analyzing several elements, including FT-IR, 1H-NMR, and 13 C-NMR.The biological activity of Gram-positive and Gram-negative bacteria was examined using four different bacterial isolates.This was observed through the plate-hole diffusion method.The anticancer efficacy of the compound was evaluated against prostate cancer cells. Results:The synthesized phenol compound demonstrated enhanced anticancer activity against prostate cancer cells in vitro but no effect on normal cells.Its minimum inhibitory concentration (MIC) for Klebsiella pneumoniae and Bacillus cereus was 1 mg/ml, while it was determined 3 and 5 mg/ml for Staphylococcus aureus and Escherichia coli, respectively. Conclusion:The synthesized compound showed favorable antibacterial and anticancer activities.It offers potential for subsequent research on a new Schiff-base with higher efficiency, lower toxicity, and higher selectivity in these activities.

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Publication Details

Journal
Iranian Journal of Medical Microbiology
Published
2025-03-30
DOI
https://doi.org/10.30699/ijmm.19.1.29
Citations
1
Primary Topic
Synthesis and biological activity
Type
article
Field-Weighted Citation Impact
0.94
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article

Synthesis and Evaluation of 4-[5-((4-hydroxybenzylidene) amino)-1,3,4-thiadiazol-2-yl] Phenol Compound Biological Activities

Shaker A.N. Al-Jadaan, Basil A. Abbas, Ban M.S. Saeed
1 citations
Iranian Journal of Medical Microbiology
Synthesis and biological activity
0.94
article

Synthesis and Evaluation of 4-[5-((4-hydroxybenzylidene) amino)-1,3,4-thiadiazol-2-yl] Phenol Compound Biological Activities

Shaker A.N. Al-Jadaan, Basil A. Abbas, Ban M.S. Saeed
article en
1 citations

Abstract

Background and Aim: The 1,3,4-thiadiazole molecule has a heterocyclic structure in several medications and natural products.It is an essential part of several pharmacological classes, such as antibacterial, anti-inflammatory, analgesic, antiviral, antineoplastic, and anti-tubercular drugs.Thiadiazole compounds have attracted interest in the field of medicinal chemistry because of their biological and pharmacological activities, especially their anticancer capacities.This study aimed to synthesize a new phenol compound with antibacterial and anticancer efficacy.The relationship between Schiff-base and antibacterial and antitumor actions was studied. Materials and Methods:The microwave approach was employed to create the novel compound known as 4-[5-((4hydroxybenzylidene) amino)-1,3,4-thiadiazol-2-yl] phenol.Its composition was validated by analyzing several elements, including FT-IR, 1H-NMR, and 13 C-NMR.The biological activity of Gram-positive and Gram-negative bacteria was examined using four different bacterial isolates.This was observed through the plate-hole diffusion method.The anticancer efficacy of the compound was evaluated against prostate cancer cells. Results:The synthesized phenol compound demonstrated enhanced anticancer activity against prostate cancer cells in vitro but no effect on normal cells.Its minimum inhibitory concentration (MIC) for Klebsiella pneumoniae and Bacillus cereus was 1 mg/ml, while it was determined 3 and 5 mg/ml for Staphylococcus aureus and Escherichia coli, respectively. Conclusion:The synthesized compound showed favorable antibacterial and anticancer activities.It offers potential for subsequent research on a new Schiff-base with higher efficiency, lower toxicity, and higher selectivity in these activities.

Iranian Journal of Medical MicrobiologyVol. 19(1)
University of Basrah (IQ)
Openalex Percentile: Top 26%
Synthesis and biological activity
0.94
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Synthesis and Evaluation of 4-[5-((4-hydroxybenzylidene) amino)-1,3,4-thiadiazol-2-yl] Phenol Compound Biological Activities — Shaker A.N. Al-Jadaan, Basil A. Abbas, et al. · Iranian Journal of Medical Microbiology (2025) | TGRS Research Map | TGRS