Synthesis and antimicrobial evaluation of some 1,2,4-triazolo[1,5-a]pyridine, pyrimidine sulfonamides and sulfinyl derivatives

Abdel-Motaal, Fatma F.; Raslan, Mohamed A.

doi:10.5155/eurjchem.5.3.481-487.1054

Cited by 7 publications

(2 citation statements)

References 55 publications

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“…Most anticancer drugs exert their cytotoxicity by cell cycle disturbance via DNA damage and/or cytoskeleton perturbation. [23,24] Therefore, the mode of action of pyrazole derivative 13 was investigated using apoptosis induction and cell cycle analysis in 4T1 cells. Cell cycle analysis revealed that pyrazole 13 was able to arrest 4T1 cells at the G1 phase (81.7 %) compared to the vehicle (57.4 %) with a subsequent increase in the SubG1 phase (8.3 % vs. 2.9 % for vehicle), indicating the possible induction of apoptosis (Figure 4).…”

Section: Cell Cyclementioning

confidence: 99%

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One‐Pot Synthesis and Anticancer Activity of Novel Pyrazole Hybrids

2021

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Novel pyrazole hybrids (3‐17) were synthesized via one‐pot reaction of thiocarbonyldihydrazide (1), ethyl 3‐phenyl‐3‐oxopropanoate (2), and different carbonyl reagents in good yields (68–98 %). Their structures were confirmed using IR, 1HNMR, 13CNMR, and Mass spectroscopy (MS), as well as elemental analysis. Pyrazole hybrids (3‐17) were screened for their cytotoxicity against three different breast cancer cell lines (e. g., MDA‐MB‐231, MCF‐7, and 4T1) and HepG2 liver cancer cells. Interestingly, 5‐oxo‐N′‐(2‐oxoindolin‐3‐ylidene)‐3‐phenyl‐4,5‐dihydro‐1H‐pyrazole‐1‐carbothiohydrazide (13) exhibited good anticancer activity (IC50=25±0.4 μM) against the aggressive, invasive, and tumorigenic 4T1 cells. Therefore, its therapeutic index was estimated in normal human skin fibroblast (HSF). Moreover, its possible mode of action was investigated using colony formation, wound healing, apoptosis induction, cell cycle, and DNA damage assays. Collectively, pyrazole 13 led to 4T1 cells cell death via inhibition of wound healing and colony formation as well as cell cycle delay in the G0/G1 phase, activation of p27 levels, and apoptosis probably via DNA intercalation.

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Section: Cell Cyclementioning

confidence: 99%

“…Most anticancer drugs exert their cytotoxicity by cell cycle disturbance via DNA damage and/or cytoskeleton perturbation [23,24] . Therefore, the mode of action of pyrazole derivative 13 was investigated using apoptosis induction and cell cycle analysis in 4T1 cells.…”

Section: Biologymentioning

confidence: 99%

One‐Pot Synthesis and Anticancer Activity of Novel Pyrazole Hybrids

2021

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Regioselective Synthesis of Novel [1,2,4]Triazolo[1,5‐a]pyridine Derivatives

et al. 2021

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Herein we report the reaction of 2‐(5‐aryl‐4H‐1,2,4‐triazol‐3‐yl)acetonitriles 1 a,b with appropriate Michael acceptors 2–4 to give novel [1,2,4]triazolo[1,5‐a]pyridines 5–8, whose antioxidant properties have been investigated. A plausible reaction mechanism, supported by DFT calculations, has been proposed to explain the total observed regioselective formation of [1,2,4]triazolo[1,5‐a]pyridine derivatives depending on the type of substituents on the Michael acceptor. Triazoles are well‐known agents exhibiting antimicrobial,[1] antitumor,[2] anti‐inflammatory,[3] antihypertensive,[4] anticonvulsant,[5] antiviral[6] and analgesic[7] biological activities. On the other hand, pyridine is the key core of heterocyclic derivatives showing a variety of pharmacological properties.[8–12] Several studies have revealed that a combination of different bioactive molecules, having different mechanisms of action, is a current strategy affording useful therapeutic agents.[13] This is the case of the [1,2,4]triazolo[1,5‐a] pyridine heterocyclic motif,[14] present in a number of bioactive compounds,[15] and largely used in materials chemistry.[16] Accordingly, diverse synthetic methods have been described for the synthesis of differently substituted [1,2,4]triazolo[1,5‐a]pyridines.[17–24] Our group has recently reported the ultrasound‐promoted facile and convenient “one‐pot” procedure for the synthesis of novel [1,2,4]triazolo[1,5‐a]pyridines in short reaction times and high yields, based on the reaction of 2‐(5‐aryl‐4H‐1,2,4‐triazol‐3‐yl)acetonitriles, malononitrile (or ethyl cyanoacetate) and aromatic aldehydes, in absolute ethanol, in the presence of IRA‐400.[25]

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