T:Toxic;
79-04-9Relevant articles and documents
Design, synthesis, biological evaluation and molecular docking of new 1,3,4-oxadiazole homonucleosides and their double-headed analogs as antitumor agents
EL Mansouri, Az-eddine,Oubella, Ali,Mehdi, Ahmad,AitItto, Moulay Youssef,Zahouily, Mohamed,Morjani, Hamid,Lazrek, Hassan B.
, (2021)
A novel series of homonucleosides and their double-headed analogs containing theophylline, 1,3,4-oxadiazole, and variant nucleobases was designed and synthesized. The new derivatives were fully characterized by HRMS, FT-IR, 1H NMR, and 13C NMR. The cytotoxic activities of all prepared compounds were screened in vitro against four cell lines, including fibrosarcoma (HT-1080), breast (MCF-7 and MDA-MB-231), and lung carcinoma (A-549). The double-headed analogue 18 showed marked growth inhibition against all the cell lines tested, specifically in HT-1080, with an IC50 values of 17.08 ± 0.97 μM. The possible mechanism of apoptosis was investigated using Annexin V staining, caspase-3/7 activity, and analysis cell cycle progression. The compound 18 induced apoptosis through caspase-3/7 activation and cell-cycle arrest in HT-1080 and A-549 cells. The molecular docking confirms that the compound 18 activated caspase-3 via the formation of hydrogen bonds and hydrophobic interactions.
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Van Eijck,Kalefeld
, p. 161,163-168 (1976)
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Synthesis and Fungitoxic Evaluation of Acylamino-1,2,4-Triazoles
Kaur, Gurinderjit,Kaur, Harleen,Kaur, Pardeep,Sharma, Sunita,Singh, Ravneet
, p. 389 - 395 (2021/11/22)
Ten different acylamino-1,2,4-triazoles were prepared by the reaction of differently substituted benzoyl chlorides and acetyl chlorides with 4-amino-1,2,4-triazole using catalytic amount of triethylamine. The synthesized compounds were characterized using UV, 1H-nuclear magnetic resonance spectroscopy, and infrared spectroscopy. All the compounds were tested for their fungicidal potential against three fungal species, that is, Fusarium verticillioides, Macrophomina phaseolina, and Rhizoctonia solani using poisoned food technique. The synthesized compounds were tested at various concentrations along with standard carbendazim 50 WP. The amides synthesized by reaction of substituted benzoyl chlorides and 4-amino-1,2,4-triazole exhibited greater fungicidal activity against all the tested fungi as compared to the amides synthesized using substituted acetyl chlorides. Among all the tested compounds, 4-nitro-N-(4-H-1,2,4-triazol-4-yl)benzamide showed the maximum fungicidal activity with the least median effective dose (ED50) values of 100, 93, and 146 μg ml-1 against F verticillioides, M. phaseolina, and R. solani, respectively. All the compounds were found to be less effective than the standard used.
3-Aminobenzenesulfonamides incorporating acylthiourea moieties selectively inhibit the tumor-associated carbonic anhydrase isoform IX over the off-target isoforms I, II and IV
Fattah, Tanzeela Abdul,Bua, Silvia,Saeed, Aamer,Shabir, Ghulam,Supuran, Claudiu T.
, p. 123 - 128 (2018/10/20)
We describe the synthesis of a series of novel 1-aroyl/acyl-3-(3-aminosulfonylphenyl) thioureas (4a–k) acting as human carbonic anhydrase (hCA, EC 4.2.1.1) inhibitors. Reaction of alkyl/aryl isothiocyanates with 3-aminobenzenesulfonamide afforded a series of the title compounds incorporating a variety of short as well as highly lipophilic long tails. The newly synthesized sulfonamides were evaluated against 4 physiologically relevant CA isoforms (hCA I, II, IV, and IX). Several compounds showed interesting inhibitory activity. The tumor-associated hCA IX was the most sensitive isoform to inhibition with these compounds, with KIs in the range of 21.5–44.0 nM and selectivity ratios over the major cytosolic isoform hCA II in the range of 3.35–37.3. The sulfonamides incorporating the phenylacetylthioureido and pentadecanoylthioureido moieties were the most hCA IX-selective inhibitors detected in this work, making them of interest for further investigations.
