Recent Advances in the One-Pot Synthesis of Coumarin Derivatives from Different Starting Materials Using Nanoparticles: A Review

Adimule, Vinayak; Nandi, Santosh S.; Kerur, S. S.; Kadapure, Santosh Ashok; Chinnam, Sampath

doi:10.1007/s11244-022-01571-z

Cited by 26 publications

(8 citation statements)

References 146 publications

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“…Coumarins are a class of naturally occurring O -heterocyclic compounds with 2 H -1-benzopyran-2-one as a core framework ( Figure 1 ) [ 6 , 7 ] Coumarins are widely recognized for their pharmacological effects in both natural and synthetic forms. They possess antifungal, antibacterial, anti-inflammatory, antioxidant, anti-cholinesterase, antidiabetic, antineoplastic, anti-HIV, anticoagulant, and anticancer bioactivities ( Figure 2 ) [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Recent Trends in the Synthesis and Bioactivity of Coumarin, Coumarin–Chalcone, and Coumarin–Triazole Molecular Hybrids

Rohman,

Ardiansah,

Wukirsari

et al. 2024

Molecules

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Molecular hybridization represents a new approach in drug discovery in which specific chromophores are strategically combined to create novel drugs with enhanced therapeutic effects. This innovative strategy leverages the strengths of individual chromophores to address complex biological challenges, synergize beneficial properties, optimize pharmacokinetics, and overcome limitations associated with single-agent therapies. Coumarins are documented to possess several bioactivities and have therefore been targeted for combination with other active moieties to create molecular hybrids. This review summarizes recent (2013–2023) trends in the synthesis of coumarins, as well as coumarin–chalcone and coumarin–triazole molecular hybrids. To cover the wide aspects of this area, we have included differently substituted coumarins, chalcones, 1,2,3– and 1,2,4–triazoles in this review and considered the point of fusion/attachment with coumarin to show the diversity of these hybrids. The reported syntheses mainly relied on well-established chemistry without the need for strict reaction conditions and usually produced high yields. Additionally, we discussed the bioactivities of the reported compounds, including antioxidative, antimicrobial, anticancer, antidiabetic, and anti-cholinesterase activities and commented on their IC50 where possible. Promising bioactivity results have been obtained so far. It is noted that mechanistic studies are infrequently found in the published work, which was also mentioned in this review to give the reader a better understanding. This review aims to provide valuable information to enable further developments in this field.

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Section: Introductionmentioning

confidence: 99%

Recent Trends in the Synthesis and Bioactivity of Coumarin, Coumarin–Chalcone, and Coumarin–Triazole Molecular Hybrids

Rohman,

Ardiansah,

Wukirsari

et al. 2024

Molecules

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“…Apricots, cherries, cinnamon, strawberries, and other foods are some excellent sources of coumarins 12 . Natural and synthetic coumarins demonstrated a broad range of therapeutic applications 13 , including antimicrobial 14 – 16 , anti-HIV 17 , 18 , antioxidant 19 , anticoagulant 20 , 21 , anti-infammatory 22 , 23 , anticonvulsant 24 , 25 , anticancer 26 – 28 and antiviral 29 . Also, they attract the major interest of chemists due to their wide variety of uses such as laser dyes 30 , cosmetics 31 , fluorescence probes 32 , photosensitizers 33 , food and perfumes 34 .…”

Section: Introductionmentioning

confidence: 99%

“…Its 1 H NMR spectrum recorded triplet and quartet signals at δ 1.2 and 4.19 ppm due to ethoxy group, beside a singlet signal due to NH proton at δ 8.59 ppm. In the 13 C NMR spectrum of compound 12 one CH 3 and one CH 2 appeared at 14.93 and 45.02 ppm, respectively. Signals at 154.06, 158.76 and 164.03 are attributed to three carbonyl groups.…”

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confidence: 98%

Synthesis and antimicrobial activity of new series of thiazoles, pyridines and pyrazoles based on coumarin moiety

Sayed

Elsharabasy

Abdel‐Aziem

2023

Sci Rep

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Microbial infections are currently a widespread disease in hospitals and community health centres and are a major cause of death worldwide. In pursuit of searching new antimicrobial agents, coumarin linked to thiazoles, pyridines and pyrazoles have been developed and evaluated for their antimicrobial properties against two Gram + bacteria, two Gram − bacteria as well as two fungi. Some of the prepared coumarins displayed high to moderate activity against the tested microorganisms with respect to the reference drugs. However, compound 3 exhibited antimicrobial effect equal to the reference drug Ciprofloxacin for Gram − baceria Enterobacter cloacae. Compound 12 was found to be the most potent compound against Bacillus pumilis with MIC of 7.69 (µmol/ml). Compounds 3, 4 and 12 showed remarkable activity against Streptococcus faecalis with MIC of 14.34, 3.67 and 15.36 (µmol/ml), respectively. Regarding Escherichia coli, most compounds recorded high to moderate MIC values (4.73–45.46 µmol/ml). Moreover, in case of E. cloacae compound 9 was the most potent compound with MIC value of 22.76 (µmol/ml).

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“…Coumarins, which are well-known condensed benzoheterocycles, are used as medicinal chemicals because they are easily synthetically transformed into a large variety of functionalized structures 7 . They have various purposes, such as synthesis of medicines 8 ; laser dyes; and compounds with antifungal 9 , antibacterial 10 , anti-inflammatory 11 , and anticancer activities 11 , 12 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of coumarin derivatives and investigation of their inhibitory effects on lung cancer cell motility

Zhou

Kim

et al. 2022

Sci Rep

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Based on the pharmaceutical potentials of coumarins, which have antitumor activity, we synthesized new coumarin derivatives and evaluated their biological activities. The new coumarin derivatives were chemically synthesized from 4-hydroxycoumarin, and their structures were confirmed by nuclear magnetic resonance data. Ten of the synthesized compounds were investigated for antimetastatic activity against lung carcinoma cells. Several of the tested compounds showed good to mild inhibitory effects on lung cancer cell motility. There were no cytotoxic effects related to the use of these compounds. 4-Hydroxycoumarin derivatives, 4h and 4i, elicited the significant inhibitory effect on lung cancer cell motility by suppressing expression of the epithelial–mesenchymal transition markers N-cadherin, Snail, and Twist.

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Recent Advances in the One-Pot Synthesis of Coumarin Derivatives from Different Starting Materials Using Nanoparticles: A Review

Cited by 26 publications

References 146 publications

Recent Trends in the Synthesis and Bioactivity of Coumarin, Coumarin–Chalcone, and Coumarin–Triazole Molecular Hybrids

Recent Trends in the Synthesis and Bioactivity of Coumarin, Coumarin–Chalcone, and Coumarin–Triazole Molecular Hybrids

Synthesis and antimicrobial activity of new series of thiazoles, pyridines and pyrazoles based on coumarin moiety

Synthesis of coumarin derivatives and investigation of their inhibitory effects on lung cancer cell motility

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