Microwave-assisted synthesis of some new coumarin derivatives including 1,2,4-triazol-3-one and investigation of their biological activities

Kahveci, Bahittin; Yılmaz, Fatih; Menteşe, Emre; Ülker, Serdar

doi:10.1007/s10593-015-1714-5

Cited by 32 publications

(22 citation statements)

References 53 publications

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“…Compound 3 was prepared by simple alkylation of compound 1 with ethyl bromoacetate and K 2 CO 3 in anhydrous acetone and then was transformed to acetohyrazide 4 by treatment with hydrazine monohydrate in ethanol. Coumarin‐3‐carboxylic acid derivatives were reacted with 1 H ‐benzotriazole in the presence of SOCl 2 in dichloromethane to prepare 3‐(1 H ‐benzotriazol‐1‐ylcarbonyl)‐2 H ‐chromen‐2‐ones ( 2a–d ) . Compound 4 is the first intermediate on the route to the other target compounds as shown in Scheme .…”

Section: Resultsmentioning

confidence: 99%

“…Our research group has a long standing interest in research to identify whether hybrid molecules which include benzimidazole, coumarin, 1,2,4‐triazole and 1,2,4‐thiadiazole moieties, show a high biological effect especially enzyme inhibitions such as urease, lipase, α‐glucosidase, and xanthine oxidase . In the view of above facts, the current study describes the synthesis and urease inhibition studies of different quinazolinone hybrid compounds containing coumarin, isothiocyanate, furan, 1,2,4‐triazole and 1,2,4‐thiadiazole moieties.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors

Menteşe

Akyüz

Yılmaz

et al. 2018

Archiv der Pharmazie

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A new series of quinazolinone hybrid molecules containing coumarin, furan, 1,2,4triazole and 1,2,4-thiadiazole rings was designed, synthesized, and screened for their urease inhibition activities. All newly synthesized compounds showed outstanding urease inhibitory potentials with IC 50 values ranging between 1.26 ± 0.07 and 7.35 ± 0.31 μg/mL. Among the series, coumarin derivatives (10a-d) exhibited the best inhibitory effect against urease in the range of IC 50 = 1.26 ± 0.07 to 1.82 ± 0.10 μg/mL, when compared to standard urease inhibitors such as acetohydroxamic acid and thiourea (IC 50 = 21.05 ± 0.96 and 15.08 ± 0.71 μg/mL, respectively). Molecular docking studies were also performed to analyze the binding mode of compound 10b, and supported the experimental results. K E Y W O R D S coumarin, furan, molecular docking, quinazolin-4(3H)-one, thiadiazole, triazole, urease inhibition

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors

Menteşe

Akyüz

Yılmaz

et al. 2018

Archiv der Pharmazie

Self Cite

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“…Also, the microwave irradiation technique was not suitable for this type of reaction because, in this type of reactions, the discharge of HCl gas causes the increase of reaction pressure and that is very dangerous. Therefore, we have chosen to synthesize coumarin-benzotriazole derivative instead of acyl chloride derivative because benzotriazole derivatives are more stable and benzotriazole is an easy leaving group (26,30,37).…”

Section: Resultsmentioning

confidence: 99%

“…In these works, we have found that coumarin has a positive effect on antitumor, antilipase and α- glucosidase activities. In the present study, we focused on the synthesis of coumarin hydrazides and investigation of their antioxidant and lipase inhibition activities (27,30).…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides

Yılmaz¹,

Faiz

2018

Journal of the Turkish Chemical Society Section A: Chemistry

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In this work, 15 different coumarin hydrazides were successfully synthesized and screened for their antioxidant and antilipase activities. To do this, firstly, salicylaldehyde derivatives and Meldrum's Acid were reacted in absolute ethanol with catalytic amount of pyridine to obtain coumarin-3-carboxylic acid derivatives (1a-e). Then, these compounds were treated with 1H-benzotriazole in dichloromethane by using thionyl chloride to synthesize benzotriazole derivatives (2a-e). Then, compounds 2a-e were reacted with three commercial hydrazides (nicotinic hydrazide, benzhydrazide,and phenyl acetichydrazide) in ethanol by using microwave irradiation and conventional heating procedures to obtain final products (3-5a-e). Finally, these compounds were tested for their anti-oxidant and anti-lipase activities. The structure of newly synthesized compounds was identified by IR, 1 H NMR, 13 C NMR, and elemental analysis data.

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“…The coumarin–1,2,4‐triazole‐5‐one hybrids 14 and 15 as well as 1,2,4‐triazole‐5‐thione 16 and 17 also displayed some antimicrobial activity, although most of them were less potent than the references, these kinds of hybrids provided an alternative strategy for searching new antimicrobial agents.…”

Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

Coumarin–triazole Hybrids and Their Biological Activities

Fan

Xing

Liu

2018

Journal of Heterocyclic Chem

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Hybridization is emerged as a promising strategy in the discovery of new drugs, especially these with complimentary activities and multiple pharmacological targets that are the potential weapons to prevent the drug resistance. Currently, several hybrids are under different stages of clinical trial, and may be introduced into clinical practice to treat various diseases in the near future. Triazoles including 1,2,3‐triazole and 1,2,4‐triazole as well as coumarins occupy an important position in medicinal chemistry attribute to their various biological activities, and some of them have been used in clinical practice. Obviously, hybridization of these two pharmacophores may lead to novel candidates with broader spectrum, more effective, lower toxicity, and multiple mechanisms of action. This review aims to outline the biological activities of coumarin–triazole hybrids, and discuss their structure–activity relationship to pave the way for the further rational development of this kind of hybrids.

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Microwave-assisted synthesis of some new coumarin derivatives including 1,2,4-triazol-3-one and investigation of their biological activities

Cited by 32 publications

References 53 publications

Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors

Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors

Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides

Coumarin–triazole Hybrids and Their Biological Activities

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