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

M. Saeed, Ban; A.N. Al-Jadaan, Shaker; A. Abbas, Basil

doi:10.30699/ijmm.19.1.29

year 19, Issue 1 (January - February 2025) Iran J Med Microbiol 2025, 19(1): 29-39 | Back to browse issues page

‎ 10.30699/ijmm.19.1.29

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M. Saeed B, A.N. Al-Jadaan S, A. Abbas B. Synthesis and Evaluation of 4-[5-((4-hydroxybenzylidene) amino)-1,3,4-thiadiazol-2-yl] Phenol Compound Biological Activities. Iran J Med Microbiol 2025; 19 (1) :29-39
URL: http://ijmm.ir/article-1-2559-en.html

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

Ban M. Saeed¹

, Shaker A.N. Al-Jadaan²

, Basil A. Abbas³

1- Department of Microbiology, Al-Zahraa College of Medicine, University of Basrah, Basrah, Iraq
2- Department of Pharmaceutical Chemistry, College of Pharmacy, University of Basrah, Basrah, Iraq
3- Microbiology Department, College of Veterinary Medicine, University of Basrah, Basrah, Iraq , basil.abbas@uobasrah.edu.iq

Abstract: (466 Views)

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-((4-hydroxybenzylidene) amino)-1,3,4-thiadiazol-2-yl] phenol. Its composition was validated by analyzing several elements, including FT-IR, 1H-NMR, and ¹³C-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.

Keywords: Antibacterial, Anticancer, MIC, Prostate Cancer Cell, Schiff-base

Full-Text [PDF 1075 kb] (67 Downloads) | | Full-Text (HTML) (33 Views)

Type of Study: Original Research Article | Subject: Antimicrobial Substances
Received: 2025/01/9 | Accepted: 2025/03/1 | ePublished: 2025/03/30

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