Abstract:Synthesis of 1,2,3-triazole-substituted coumarins and also 1,2,3-triazolyl or 1,2,3-triazolylalk-1-inyl-linked coumarin-2,3-furocoumarin hybrids was performed by employing the cross-coupling and copper catalyzed azide-alkyne cycloaddition reaction approaches. The synthesized compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, Bacillius subtilis, Actinomyces viscosus and Escherichia coli bacterial strains. Coumarin-benzoic acid hybrids 4с, 42с and 3-((4-acetylamino-… Show more
“…Esterification of nordentatin (1) was carried out by an acylation method [6,15] (Figure 1). First, around 100 mg of sample (1) was put in each flask.…”
Section: General Procedures For the Modification Of Nordentatin (1) Wimentioning
confidence: 99%
“…They possess a wide variety of biological activities. Coumarins and their derivatives are being extensively studied for their biological activities, low toxicity, and low drug resistance properties [6,7].…”
New derivatives were obtained from natural nordentatin (1) previously isolated from the methanol fraction of Clausena excavata by an acylation method. Herein, we report ten new pyranocoumarin derivatives 1a–1j. Their structures were elucidated based on UV-vis, FT-IR, NMR, and DART-MS data. The α-glucosidase inhibition and anticancer activities of nordentatin (1) and its derivatives were also evaluated. The α-glucosidase inhibition assay exhibited that the derivatives 1b, 1d, 1e, 1f, 1h, 1i, and 1j possess higher inhibitory activity for α-glucosidase with IC50 values of 1.54, 9.05, 4.87, 20.25, 12.34, 5.67, and 2.43 mM, whereas acarbose was used as the positive control, IC50 = 7.57 mM. All derivatives exhibited a weak cytotoxicity against a cervical cancer (HeLa) cell line with the IC50 between 0.25 and 1.25 mM. They also showed moderate to low growth inhibition of a breast cancer (T47D) cell line with IC50 values between 0.043 and 1.5 mM, but their activity was lower than that of the parent compound, nordentatin (1) (IC50 = 0.041 mM).
“…Esterification of nordentatin (1) was carried out by an acylation method [6,15] (Figure 1). First, around 100 mg of sample (1) was put in each flask.…”
Section: General Procedures For the Modification Of Nordentatin (1) Wimentioning
confidence: 99%
“…They possess a wide variety of biological activities. Coumarins and their derivatives are being extensively studied for their biological activities, low toxicity, and low drug resistance properties [6,7].…”
New derivatives were obtained from natural nordentatin (1) previously isolated from the methanol fraction of Clausena excavata by an acylation method. Herein, we report ten new pyranocoumarin derivatives 1a–1j. Their structures were elucidated based on UV-vis, FT-IR, NMR, and DART-MS data. The α-glucosidase inhibition and anticancer activities of nordentatin (1) and its derivatives were also evaluated. The α-glucosidase inhibition assay exhibited that the derivatives 1b, 1d, 1e, 1f, 1h, 1i, and 1j possess higher inhibitory activity for α-glucosidase with IC50 values of 1.54, 9.05, 4.87, 20.25, 12.34, 5.67, and 2.43 mM, whereas acarbose was used as the positive control, IC50 = 7.57 mM. All derivatives exhibited a weak cytotoxicity against a cervical cancer (HeLa) cell line with the IC50 between 0.25 and 1.25 mM. They also showed moderate to low growth inhibition of a breast cancer (T47D) cell line with IC50 values between 0.043 and 1.5 mM, but their activity was lower than that of the parent compound, nordentatin (1) (IC50 = 0.041 mM).
“…Zhengkaichen et al reported a metal-free synthesis of 1,3,5-trisubstituted-1,2,4-triazoles in the presence of iodine as catalyst (Scheme 7 ). And it can be synthesized from hydrazones and aliphatic amines under oxidative conditions via a cascade C–H functionalization, double C–N bond formation, and oxidative aromatization [ 28 ]. Scheme 7 Metal-free synthesis of 1,3,5-trisubstituted-1,2,4-triazoles in the presence of iodine as catalyst …”
Background
A large number of studies have recently reported that, because of their significant biological and pharmacological properties, heterocyclic compounds and their derivatives have attracted a strong interest in medicinal chemistry. The triazole nucleus is one of the most important heterocycles which has a feature of natural products as well as medicinal agents. Heterocyclic nitrogen is abundantly present in most medicinal compounds. The derivatization of triazole ring is based on the phenomenon of bio-isosteres in which substituted the oxygen atom of oxadiazole nucleus with nitrogen triazole analogue.
Main text
This review focuses on recent synthetic procedure of triazole moiety, which comprises of various pharmacological activities such as antimicrobial, anticonvulsant, anti-inflammatory, analgesic, antitubercular, anthelmintic, antioxidant, antimalarial, antiviral, etc..
Conclusion
This review highlights the current status of triazole compounds as different multi-target pharmacological activities. From the literature survey, triazole is the most widely used compound in different potential activities.
“…[ 91 ] Dimers 37a,b (MIC: 16–32 µg/ml), which showed equal activity against drug‐sensitive S. aureus and MRSA strains, were more potent than ceftazidime and ceftriaxone (MIC: 32 to >256 µg/ml). [ 92,93 ] The dimers 37 (MIC: 31.2–125 µg/ml) displayed considerable activity against two Gram‐positive bacteria ( S. pneumoniae and S. aureus ) and three Gram‐negative bacteria ( E. coli , E. aerogenes , and S. typhi ), and these two dimers 37a,b (MIC: 31.2–62.5 µg/ml) were not inferior to streptomycin (MIC: 31.2–62.5 µg/ml), kanamycin (MIC: 62.5–125 µg/ml), and vancomycin (MIC: 31.2–250 µg/ml) against all tested organisms.…”
Infections caused by Gram-positive and -negative bacteria are one of the foremost causes of morbidity and mortality globally. Antibiotics are the mainstay of therapy for bacterial infections, but the emergence and wide spread of drug-resistant pathogens have already become a huge issue for public healthcare systems. The coumarin moiety, which is ubiquitous in nature, could bind to the B subunit of DNA gyrase in bacteria and inhibit DNA supercoiling by blocking the ATPase activity; hence, coumarin derivatives possess potential antibacterial activity. Several coumarin-containing hybrids such as coumermycin A1, clorobiocin, and novobiocin have already been used in clinical practice for the treatment of various bacterial infections; thus, it is conceivable that hybridization of the coumarin moiety with other antibacterial pharmacophores may provide opportunities for the development of novel antibiotics. This review outlines the advances in coumarin-containing hybrids with antibacterial potential in the recent 5 years and the structure-activity relationships are also discussed. K E Y W O R D S antibacterial, coumarin, hybrid compounds, structure-activity relationships
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