Abstract
BackgroundPyrazolines show different biological activities. In recent years, interest in the chemistry of hydrazonoyl halides has been renewed. 1,3,4-Thiadiazoles are one of the most common heterocyclic pharmacophores with a wide range of biological activities.ResultsEthyl 2-(5-(furan-2-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methyl-thiazole-5-carboxylate, 2-(5-(furan-2-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one, and 1-(2-(5-(furan-2-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazol-5-yl)ethan-1-one were synthesized from the reaction of 5-(furan-2-yl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide with different halogenated compounds. Thiazole, 1,3,4-thiadiazole and pyrano[2,3-d]thiazole derivatives were also synthesized. The structures of the newly synthesized compounds were elucidated based on elemental analysis, spectral data, and alternative synthetic routes whenever possible. Additionally, the newly synthesized compounds were screened for antimicrobial activity against various microorganisms.ConclusionsA new series of novel functionalized 1,3,4-thiadiazoles, 1,3-thiazoles, and pyrazoline-containing moieties were synthesized using hydrazonoyl halides as precursors and evaluated for their in vitro antibacterial, and antifungal activities. The antimicrobial results of the examined compounds revealed promising results and some derivatives have activities similar to the references used.
Highlights
Pyrazolines show a variety of biological activities
Streptococcus pneumonia, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli were resistant to compounds (10a and 11b)
Aspergillus fumigatus was susceptible to compounds (11a), (20a), (20b), (20d), and (22)
Summary
Pyrazolines show a variety of biological activities. They are antimicrobial [1–4], antifungal [5], anti-depressant [6], immunosuppressive [7], anticonvulsant [8–10], antitumor [11], anti-amoebic [12], antibacterial [13], antiinflammatory [14], anticancer [15], and MAO inhibitory activity [16]. Thiazoles are used in drugs developed for the treatment of allergies [19], hypertension [20], inflammation [21], schizophrenia [22], bacterial infections [23], HIV [24], sleep disorders [25] and more recently, for the treatment of pain [26]. They are used as fibrinogen receptor antagonists with antithrombotic activity [27], and as new inhibitors of bacterial DNA gyrase B [28]. 1,3,4-thiadiazoles are among the most common heterocyclic pharmacophores They display a broad spectrum of biological activities, including antimicrobial [29], anticancer [30, 31], antioxidant [32], anti-depressant [33], anticonvulsant [34, 35] and antihypertensive activities [36], as well as acetyl cholinesterase inhibition for the treatment of Alzheimer’s disease [37, 38]. Interest in the chemistry of hydrazonoyl halides has been renewed. 1,3,4-Thiadiazoles are one of the most common heterocyclic pharmacophores with a wide range of biological activities
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