Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivatives

Al‐Soud, Yaseen A.; Al‐Dweri, Mohammad N.; Al‐Masoudi, Najim A.

doi:10.1016/j.farmac.2004.05.006

Cited by 231 publications

(119 citation statements)

References 30 publications

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“…Melting points were determined in Fisher-Johns blocks (Fisher Scientific, Schwerte, Germany) and presented without any corrections. The 1 H NMR spectra were recorded on a Bruker Avance 300 apparatus (Bruker BioSpin GmbH, Rheinstetten/Karlsruhe, Germany) in DMSO-d 6 with TMS as internal standard. The …”

Section: Generalmentioning

confidence: 99%

“…Among all heterocyclic systems the therapeutic importance of 1,2,4-triazoles and their derivatives is well documented and they have been reported to possess various biological activities such as analgesic 1 , antifungal 2,3 , antibacterial 4,5 , antiviral 6 , antiphlogistic 7,8 , and antitubercular 9 . Therefore, 4,5-substituted 1,2,4-triazoles seems to be suitable candidates for further chemical modifications and might be of interest as pharmacologically active compounds.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, antiproliferative and antimicrobial activity of new Mannich bases bearing 1,2,4-triazole moiety

Popiołek

Rzymowska

Kosikowska

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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This study presents the synthesis, antiproliferative and antimicrobial evaluation of a new series of Mannich base derivatives containing 1,2,4-triazole system. New compounds were prepared by the reaction of 4,5-disubstituted 1,2,4-triazole-3-thiones with formaldehyde and various amines. The structures of the prepared compounds were confirmed by means of 1 H NMR, 13 C NMR and elemental analyses. Twelve compounds were evaluated for their in vitro antiproliferative activities against six chosen cancer cell lines. All synthesized compounds were screened for their in vitro antimicrobial activity by using the agar dilution technique. For 17 potentially active compounds, their antibacterial activity was confirmed on the basis of MIC (minimal inhibitory concentration) by broth microdilution method using the reference Grampositive and Gram-negative bacterial strains.

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Section: Generalmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, antiproliferative and antimicrobial activity of new Mannich bases bearing 1,2,4-triazole moiety

Popiołek

Rzymowska

Kosikowska

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The structures were solved by direct methods using the SHELXS97 program and refined by the full-matrix least-squares on F 2 using SHELXL97 [10]. In the crystal net of (II) the DMSO molecule is disordered between two positions with the site occupancy factors (sof's) of 0.815 (6):0.185 (6). All non-H atoms in (I) and (II) were refined with anisotropic displacement parameters.…”

Section: Instrumentationmentioning

confidence: 99%

“…IR spectrum was recorded on a FT-IR Perkin Elmer 1725X spectrophotometer (KBr pellet, 4,000-400 cm -1 ). 1 H NMR spectrum was recorded at room temperature on Bruker Avance (300 MHz) apparatus using DMSO-d 6 as a solvent and TMS as an internal standard. The apparent resonance multiplicity is described as: s = singlet and m = multiplet.…”

Section: Instrumentationmentioning

confidence: 99%

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2-(4-Phenyl-5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)cyclohexanecarboxylic Acid and Its DMSO Solvate: Synthesis, Crystal Structure and Biological Activity

Mazur

Kozioł

Modzelewska-Banachiewicz

et al. 2011

J Chem Crystallogr

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A new 1,2,4-triazole derivative, 2-(4-phenyl-5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)cyclohexanecarboxylic acid, C 20 H 20 N 4 O 2 (I), and its dimethyl sulfoxide solvate 1:1 (II) have been synthesized and their crystal structure was established. Compound (I) was screened for its antiproliferative and antiinflammatory activity. Structural analysis indicated the substantial difference between two symmetry independent molecules in (I) and this in (II), it manifests in the relative orientation of pyridine/phenyl and triazole rings, as well as in the orientation of carboxyl group with respect to cyclohexane ring. The molecules A and B in the crystal (I) form two hydrogen-bonded chains through O-H carboxyl and N triazole atoms, giving separate catemers of symmetry independent molecules. The catemer of (IA) running along the 2 1 axis is homochiral, while the catemer (IB) is racemic-formed about the c glide plane. In the crystalline solvate (II) complexation of (I) with DMSO induced enantiomeric self-resolution. Obtained crystals are racemic twins, in which each part is built of one enantiomer of (I) having the relative configuration 11S,12R or 11R,12S. A pair of host-guest molecules is linked by the O-H carboxyl _O DMSO hydrogen bond.

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Studying the Structure and Evaluating α‐Glucosidase Inhibition of Novel Acetamide Derivatives Incorporating 4‐Ethyl‐4H‐1,2,4‐Triazole Starting from 2‐(Naphthalen‐1‐yl)Acetic Acid

Le,

Nguyen,

Tran

et al. 2024

Asian J Org Chem

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This research aims to create innovative compounds that incorporate 1,2,4‐triazole and exhibit α‐glucosidase inhibitory potential. Similar to our previously reported series of N‐aryl 2‐{[5‐(naphthalen‐1‐ylmethyl)‐4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl]thio}acetamide compounds, we explore here 4‐ethyl instead of 4‐phenyl as substituent. The synthesis process effectively yielded these compounds, with the highest yield reaching up to 91% for compound N‐phenyl‐2‐{[5‐(naphthalen‐1‐ylmethyl)‐4‐ethyl‐4H‐1,2,4‐triazol‐3‐yl]thio}acetamide 5a. Their structures were validated through various spectroscopic techniques such as IR, 1H‐NMR, 13C‐NMR, and HR‐MS spectra, and for compounds 3, 5d, and 5e by X‐ray diffraction. In vitro experiments revealed that only compound 5g, marked by a 3‐hydroxy substitution on the N‐phenylacetamide moiety, demonstrated higher α‐glucosidase inhibitory potential (IC50 = 158.4 ± 3.4 μM) compared to the positive control, acarbose (IC50 = 351.3 ± 1.8 μM). Molecular docking studies also coincide with in vitro assay by uncovering a strong hydrogen bond with residue Asp1526 along with other hydrophobic interactions of compound 5g in the α‐glucosidase binding pocket. Compound 5g showed a free binding energy of ‐9.7 kcal/mol, contrasting with acarbose (‐8.0 kcal/mol). Despite the modest activity, this research underscores the simplicity and convenience of the procedure for synthesizing 1,2,4‐triazole‐based compounds, and contributes a key feature to the structure‐activity relationship of the triazole scaffold in the α‐glucosidase pocket.

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Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivatives

Cited by 231 publications

References 30 publications

Synthesis, antiproliferative and antimicrobial activity of new Mannich bases bearing 1,2,4-triazole moiety

Synthesis, antiproliferative and antimicrobial activity of new Mannich bases bearing 1,2,4-triazole moiety

2-(4-Phenyl-5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)cyclohexanecarboxylic Acid and Its DMSO Solvate: Synthesis, Crystal Structure and Biological Activity

Studying the Structure and Evaluating α‐Glucosidase Inhibition of Novel Acetamide Derivatives Incorporating 4‐Ethyl‐4H‐1,2,4‐Triazole Starting from 2‐(Naphthalen‐1‐yl)Acetic Acid

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