116433-51-3Relevant articles and documents
Efficient synthesis, antitubercular and antimicrobial evaluation of 1,4-disubstituted 1,2,3-triazoles with amide functionality
Kaushik,Pahwa, Ashima,Singh, Dharmendra,Kumar, Krishan,Luxmi, Raj
, p. 1127 - 1136 (2019)
Abstract: A series of 21 amide linked 1,4-disubstituted-1,2,3-triazoles were achieved via one-pot synthesis through Cu(I) catalyzed click reaction between terminal alkynes and 2-azido-N-substituted acetamides. Newly formed triazoles were characterized by various spectroscopic techniques (FT-IR, 1H NMR, 13C NMR spectroscopy, and HRMS) and investigated for in vitro antitubercular evaluation against bacteria, i.e., Mycobacterium tuberculosis and antimicrobial evaluation against Bacillus subtilis, Staphylococcus epidermidis, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, and Aspergillus niger. Some of the synthesized triazole derivatives were found to exhibit moderate inhibitory activity against the tested antitubercular strain, whereas one compound displayed a significant inhibitory activity against most of the tested microbial strains. Graphical abstract: [Figure not available: see fulltext.].
Synthesis of novel 1,2,3-triazoles bearing 2,4 thiazolidinediones conjugates and their biological evaluation
Kulkarni, Pravin S.,Karale, Sanjay N.,Khandebharad, Amol U.,Agrawal, Brijmohan R.,Sarda, Swapnil R.
, p. 2035 - 2046 (2021/02/05)
Searching for new active molecules against M. Bovis BCG and Mycobacterium tuberculosis (MTB) H37Ra, a focused of 1,2,3-triazoles-incorporated 2,4 thiazolidinedione conjugates have been efficiently prepared via a click chemistry approach cyclocondensation of 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4), aryl aldehyde (5a–l), and mercapto acetic acid (6) with good to promising yields. The newly synthesized compounds were tested against drug-sensitive MTB and BCG. In particular, compounds 8g, 8h, 8j and 8l are highly potent against both the strains with IC90 values in the range of 1.20–2.70 and 1.24–2.65?μg/mL, respectively. Based on the results from the antitubercular activity, SAR for the synthesized series has been developed. Most of the active compounds were non-cytotoxic against MCF-7, HCT 116 and A549 cell lines. Most active compounds were having a higher selectively index, which suggested that these compounds were highly potent.
α-Glucosidase and α-amylase inhibition, molecular modeling and pharmacokinetic studies of new quinazolinone-1,2,3-triazole-acetamide derivatives
Yavari, Ali,Mohammadi-Khanaposhtani, Maryam,Moradi, Shahram,Bahadorikhalili, Saeed,Pourbagher, Roghayeh,Jafari, Nasrin,Faramarzi, Mohammad Ali,Zabihi, Ebrahim,Mahdavi, Mohammad,Biglar, Mahmood,Larijani, Bagher,Hamedifar, Haleh,Hajimiri, Mir Hamed
, p. 702 - 711 (2021/01/18)
In this study, a new series of quinazolinone-1,2,3-triazole-acetamide hybrids 8a–m, using by molecular hybridization of the potent α-glucosidase inhibitor pharmacophores, was designed and evaluated against carbohydrate-hydrolyzing enzymes α-glucosidase and α-amylase. All the synthesized compounds with IC50 values in the range of 45.3 ± 1.4 μM to 195.5 ± 4.7 μM were significantly more potent than standard inhibitor against α-glucosidase, while these compounds were not active against α-amylase in comparison to standard inhibitor. Representatively, compound 8a with IC50 = 45.3 ± 1.4 μM was around 17 times more potent than standard inhibitor acarbose (IC50 = 750.0 ± 12.5 μM). The inhibition kinetic analysis of the compound 8a indicated that this compound was a competitive α-glucosidase inhibitor. Molecular modeling analysis confirmed that the most potent inhibitors 8a and 8b well accommodated in the modeled α-glucosidase active site and it was also revealed that these compounds formed stable inhibitor–receptor complexes with the α-glucosidase in comparison to acarbose. In silico pharmacokinetic and toxicity of the most potent compounds were evaluated and obtained results were compared with acarbose. Furthermore, the most potent compounds were also evaluated against human normal cells and no cytotoxicity was observed.
