29310-88-1Relevant articles and documents
A new and efficient method for conjugate addition of trialkylphosphites to 3-acylsubstituted coumarins
Nikolova, Rositca D.,Bojilova, Anka G.,Rodios, Nestor A.
, p. 10335 - 10342 (2004)
A new and efficient conjugate addition of trialkylphosphites to 3-ω-bromoacetylcoumarin 1 catalysed by p-toluenesulfonic acid (TsOH) has been studied. Under the same conditions, an enolphosphate gave the corresponding esters of 3-acetyl-4-phosphono-2-oxochromans in high yields. The use of TsOH in the reaction of 3-acetyl-, 3-benzoyl-, and 3-ethoxycarbonyl coumarins led mainly to 1,4-addition products - the corresponding 3-acyl-4-dialkylphosphono-2- oxochromans - in very good yields. Graphical Abstract
Tetrabutylammonium tribromide: An effective green reagent for the one-pot reaction of 3-acetyl-2H-chromen-2-ones with o-phenylenediamines
Kavitha, Kotthireddy,Srikrishna, Devulapally,Dubey, Pramod Kumar,Aparna, Pasula
, p. 172 - 185 (2018)
An efficient and completely greener approach has been outlined for the reaction of 3-acetyl-2H-chromen-2-ones with o-phenylenediamines using tetrabutylammonium tribromide (TBATB) to obtain 3-(quinoxalin-2-yl)-2H-chromen-2-ones in one-pot. Alternatively, a step-wise method has also been demonstrated for the synthesis of 3-(quinoxalin-2-yl)-2H-chromen-2-ones, where 3-acetyl-2H-chromen-2-ones has first treated with TBATB to give 3-(2-bromoacetyl)-2H-chromen-2-one followed by its nucleophilic substitution reaction with o-phenylenediamines. Use of polyethylene glycol-600 (PEG-600) as the solvent media, mild reaction conditions and easy isolation procedure of products are the added advantages for this synthesis. Both the one-pot and step-wise methods have been compared in terms of their reaction yields and one-pot synthesis was found to be superior. All the synthesized compounds were confirmed by characterization with 1HNMR, 13CNMR, HRMS, IR spectroscopy.
DFT-based molecular modeling, NBO analysis and vibrational spectroscopic study of 3-(bromoacetyl)coumarin
Sajan,Erdogdu,Reshmy,Dereli,Kurien Thomas,Joe, I. Hubert
, p. 118 - 125 (2011)
The NIR-FT Raman and FT-IR spectra of 3-(bromoacetyl)coumarin (BAC) molecule have been recorded and analyzed. Density functional theory (DFT) calculation of two BAC conformers has been performed to find the optimized structures and computed vibrational wavenumbers of the most stable one. The obtained vibrational wavenumbers and optimized geometric parameters were seen to be in good agreement with the experimental data. Characteristic vibrational bands of the pyrone ring and methylene and carbonyl groups have been identified. The lowering of HOMO-LUMO energy gap clearly explains the charge transfer interactions taking place within the molecule.
PEG-600 mediated one-pot reaction of 3-acetyl-2: H -chromen-2-one with heterylthiols and phenylthioureas using tetrabutylammonium tribromide as an efficient green reagent
Srikrishna, Devulapally,Kumar Dubey, Pramod
, p. 5168 - 5175 (2017)
A simple method for the one-pot reaction of 3-acetyl-2H-chromen-2-one with different heterylthiols and phenylthioureas under green conditions using tetrabutylammonium tribromide (TBATB) as an efficient reagent has been described. 3-Acetyl-2H-chromen-2-one
Design, synthesis and biological evaluation of novel coumarin thiazole derivatives as α-glucosidase inhibitors
Wang, Guangcheng,He, Dianxiong,Li, Xin,Li, Juan,Peng, Zhiyun
, p. 167 - 174 (2016)
A new series of coumarin thiazole derivatives 7a-7t were synthesized, characterized by 1H NMR, 13C NMR and element analysis, evaluated for their α-glucosidase inhibitory activity. The majority of the screened compounds displayed potent inhibitory activities with IC50 values in the range of 6.24 ± 0.07-81.69 ± 0.39 μM, when compared to the standard acarbose (IC50 = 43.26 ± 0.19 μM). Structure-activity relationship (SAR) studies suggest that the pattern of substitution in the phenyl ring is closely related to the biological activity of this class of compounds. Among all the tested molecules, compound 7e (IC50 = 6.24 ± 0.07 μM) was found to be the most active compound in the library of coumarin thiazole derivatives. Enzyme kinetic studies showed that compound 7e is a non-competitive inhibitor with a Ki of 6.86 μM. Furthermore, the binding interactions of compound 7e with the active site of α-glucosidase were confirmed through molecular docking. This study has identified a new class of potent α-glucosidase inhibitors for further investigation.
Novel 3-substituted coumarins as selective human carbonic anhydrase IX and XII inhibitors: Synthesis, biological and molecular dynamics analysis
Abdelrahman, Mohamed A.,Ibrahim, Hany S.,Nocentini, Alessio,Eldehna, Wagdy M.,Bonardi, Alessandro,Abdel-Aziz, Hatem A.,Gratteri, Paola,Abou-Seri, Sahar M.,Supuran, Claudiu T.
, (2021)
In this study, diverse series of coumarin derivatives were developed as potential carbonic anhydrase inhibitors (CAIs). A “tail” approach was adopted by selecting the coumarin motif as a tail that is connected to the ZBG benzenesulfonamide moiety via a hy
Coumarin-thiazole and -oxadiazole derivatives: Synthesis, bioactivity and docking studies for aldose/aldehyde reductase inhibitors
Ibrar, Aliya,Tehseen, Yildiz,Khan, Imtiaz,Hameed, Abdul,Saeed, Aamer,Furtmann, Norbert,Bajorath, Jürgen,Iqbal, Jamshed
, p. 177 - 186 (2016)
In continuation of our previous efforts directed towards the development of potent and selective inhibitors of aldose reductase (ALR2), and to control the diabetes mellitus (DM), a chronic metabolic disease, we synthesized novel coumarin-thiazole 6(a–o) and coumarin-oxadiazole 11(a–h) hybrids and screened for their inhibitory activity against aldose reductase (ALR2), for the selectivity against aldehyde reductase (ALR1). Compounds were also screened against ALR1. Among the newly designed compounds, 6c, 11d, and 11g were selective inhibitors of ALR2. Whereas, (E)-3-(2-(2-(2-bromobenzylidene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one 6c yielded the lowest IC50 value of 0.16 ± 0.06 μM for ALR2. Moreover, compounds (E)-3-(2-(2-benzylidenehydrazinyl)thiazol-4-yl)-2H-chromen-2-one (6a; IC50 = 2.94 ± 1.23 μM for ARL1 and 0.12 ± 0.05 μM for ARL2) and (E)-3-(2-(2-(1-(4-bromophenyl)ethylidene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one (6e; IC50 = 1.71 ± 0.01 μM for ARL1 and 0.11 ± 0.001 μM for ARL2) were confirmed as dual inhibitors. Furthermore, compounds 6i, 6k, 6m, and 11b were found to be selective inhibitors for ALR1, among which (E)-3-(2-(2-((2-amino-4-chlorophenyl)(phenyl)methylene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one (6m) was most potent (IC50 = 0.459 ± 0.001 μM). Docking studies performed using X-ray structures of ALR1 and ALR2 with the given synthesized inhibitors showed that coumarinyl thiazole series lacks the carboxylate function that could interact with the anionic binding site being a common ALR1/ALR2 inhibitors trait. Molecular docking study with dual inhibitor 6e also suggested plausible binding modes for the ALR1 and ALR2 enzymes. Hence, the results of this study revealed that coumarinyl thiazole and oxadiazole derivatives could act as potential ALR1/ALR2 inhibitors.
New thiazolyl-coumarin hybrids: Design, synthesis, characterization, X-ray crystal structure, antibacterial and antiviral evaluation
Osman, Hasnah,Yusufzai, Samina Khan,Khan, Mohammad Shaheen,Abd Razik, Basma M.,Sulaiman, Othman,Mohamad, Suriyati,Gansau, Jualang Azlan,Ezzat, Mohammed Oady,Parumasivam, Thaigarajan,Hassan, Mohd Zaheen
, p. 147 - 154 (2018)
A series of thiazole containing coumarin derivatives (2a-o) were efficiently synthesized as pharmacophore hybrids through Hantzsch cyclisation of 3-(2-bromoacetyl)-2H-chrome-2-ones with different N-substituted thiourea/N,N-di-substituted thiourea. All the
Synthesis, antioxidant and carbonic anhydrase I and II inhibitory activities of novel sulphonamide-substituted coumarylthiazole derivatives
Kurt, Belma Zengin,S?nmez, Fatih,Bilen, ?i?dem,Ergun, Adem,Gen?er, Nahit,Arslan, Oktay,Kucukislamoglu, Mustafa
, p. 991 - 998 (2016)
New secondary benzenesulphonamide-substituted coumarylthiazole derivatives were synthesized and their inhibitory effects on purified carbonic anhydrase I and II were evaluated using CO2 as a substrate. The result showed that all the synthesized
A highly selective and sensitive chemosensor derived coumarin–thiazole for colorimetric and fluorimetric detection of CN?ion in DMSO and aqueous solution: synthesis, sensing ability, Pd(II)/Pt(II) complexes and theoretical studies
?ahin, ?mer,?zdemir, ümmühan ?zmen,Sefero?lu, Nurgül,Ayd?ner, Burcu,Sar?, Musa,Tun?, Tuncay,Sefero?lu, Zeynel
, p. 5843 - 5852 (2016)
A colorimetric and fluorescence turn-on cyanide probe, including coumarin–thiazole and imine (azomethine) group, has been designed and synthesized. It showed an immediate visible color change from yellow to deep red only in DMSO, and an appearance of strong yellow and green fluorescence when CN?was added to DMSO, and a mixture of DMSO:H2O (9:1), respectively. Thus, the sensor can be used to detect CN?in aqueous solution. The sensing mechanism of chemosensor 4 reactions with CN?ion was observed with the deprotonation and addition mechanisms at the same time. The mechanisms of reactions of chemosensor 4 with; CN?, F?, and AcO?were examined using1H NMR spectroscopy, and were also theoretically supported by DFT and TD-DFT calculations. In addition, the metal complexes of chemosensor 4 with Pd(II) and Pt(II) were also synthesized and all the synthesized compounds were characterized using general spectroscopic methods (FTIR,1H/13C NMR, and mass spectrometry), magnetic susceptibilities, and conductivity measurements. Also, the molecular structure of 4 was determined using single crystal X-ray analysis.
Proton Sensitive Functional Organic Fluorescent Dyes Based on Coumarin-imidazo[1,2-a]pyrimidine; Syntheses, Photophysical Properties, and Investigation of Protonation Ability
Ayd?ner, Burcu,Sefero?lu, Zeynel
, p. 5921 - 5934 (2018)
A novel series of 2-coumarin-3-yl-imidazo[1,2-a]pyrimidines have been synthesized with functionalized coumarin and pyrimidine units of the different architecture to give various fluorescent compounds. A new additional series bearing unsubstituted coumarin and 7-dialkylaminocoumarin as fluorophore were obtained by palladium-catalyzed cross-coupling reactions, through coupling of 6-bromo-2-coumarin-3-yl-imidazopyrimidine derivatives with various arylboronic acids. In the all reaction step, microwave irradiation (MWI) method was used and compared with the conventional method (CM). Photophysical properties of synthesized compounds were studied by a combination of UV/Vis and fluorescence spectroscopy in various solvents having different polarities. The protonation abilities of all compounds were investigated by titration with trifluoroacetic acid (TFA) in dichloromethane. In both series, the compounds bearing 7-dialkylaminocoumarin are fluorescently active even in daylight and showed maximum absorption wavelengths (λabs–max) in the visible region in all solvents used. In addition, they showed drastic color and emission change in acidic environment. Moreover, for the investigation of protonation ability of three selected compounds bearing 7-dialkylaminocoumarin have been studied using a buffer solution with various pH and determinated their pKa values. The compound bearing morpholine has the potential to use as colorimetric and luminescence pH sensor. The thermal properties of all the synthesized compounds were also evaluated with TGA to test their usability as optic dyes.
Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives
Kurt, Belma Zengin,Gazioglu, Isil,Sonmez, Fatih,Kucukislamoglu, Mustafa
, p. 80 - 90 (2015)
A newly series of coumarylthiazole derivatives containing aryl urea/thiourea groups were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. The result showed that all the synthesized compounds exhibited inhibitory activity to both cholinesterases. Among them, 1-(4-(8-methoxy-2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-(4-chlorophenyl)thiourea (f8, IC50 = 4.58 μM) was found to be the most active compound against AChE, and 1-(4-fluorophenyl)-3-(4-(6-nitro-2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea (e31) exhibited the strongest inhibition against BuChE with IC50 value of 4.93 μM, which was 3.5-fold more potent than that of galantamine. The selectivity of f8 and e31 were 2.64 and 0.04, respectively. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized compounds were investigated for antioxidant activity. Among them, f8, f4 and f6 (IC50 = 1.64, 1.82 and 2.69 μM, respectively) showed significantly better ABTS cation radical scavenging ability than standard quercetin (IC50 = 15.49 μM).
Synthesis, spectroscopic, thermal and electrochemical studies on thiazolyl azo based disperse dyes bearing coumarin
?zkütük, Müjgan,Ipek, Ezgi,Aydiner, Burcu,Mama?, Serhat,Sefero?lu, Zeynel
, p. 521 - 532 (2016)
In this study, seven novel thiazolyl azo disperse dyes (6a-g) were synthesized and fully characterized by FT-IR, 1H NMR, 13C NMR, and mass spectral techniques. The electronic absorption spectra of the dyes in solvents of different polarities cover a λmax range of 404-512 nm. The absorption properties of the dyes changed drastically upon acidification. This was due to the protonation of the nitrogen in the thiazole ring, which in turn increased the donor-acceptor interplay of the π system in the dyes, and therefore increased the absorption properties of the prepared dyes. Thermal analysis showed that these dyes are thermal stable up to 269°C. Additionally, the electrochemical behavior of the dyes (6a-g) were investigated using cyclic voltammetric and chronoamperometric techniques, in the presence of 0.10 M tetrabutylammonium tetrafluoroborate, in dimethylsulfoxide, at a glassy carbon electrode. The number of transferred electrons, and the diffusion coefficient were determined by electrochemical methods. The results showed that, for all the dyes, one oxidation peak and two reduction peaks were observed.
Synthesis and potential antimicrobial activity of novel α-aminophosphonates derivatives bearing substituted quinoline or quinolone and thiazole moieties
Boukhari, Abbes,Djahoudi, Abdelghani,Litim, Bilal,Meliani, Saida
, p. 60 - 74 (2021/11/09)
To develop novel antimicrobial agents, and based on the biologically active heterocyclic quinoline and thiazole substituted, a series of novel α-aminophosphonates (9a–h) and (10i–l) derivatives that incorporated quinoline or quinolone, and coumarylthiazole or 5-phenylthiazol-2-amine moieties were designed and synthesized via Kabachnik–Fields reaction in the presence of ionic liquid under ultrasound irradiation. All the new compounds were obtained in good yield with a simple workup and were confirmed using various spectroscopic methods. The in vitro antimicrobial activity of all synthesized compounds were screened in terms of MIC values against the selected strains of Gram-negative and Gram-positive bacteria and two fungal strains using the broth micro-dilution method. The results showed that most of the tested compounds showed moderate inhibitory activities against both Gram‐positive and ‐negative bacteria compared with reference drugs. The following compounds 9e, 9g, 9h, 9i and 9f, 9g, 9h, 10k, 10l are the most active against Gram-positive and Gram-negative bacteria strains, respectively, with MIC values ranging between 0.25 and 128 μg/mL. The synthesized compounds 9b, 9c, 9f, 9g, 9h, 10k, and 10l exhibited excellent antifungal inhibition with MIC values ranging between 0.25 and 32 μg/mL. Structure–activity relationship revealed that the presence of coumarylthiazole moiety and hydroxyl in the quinoline group increased the inhibitory activity against microbial strains pathogens. These results confirm that the synthesized compounds can be potential antimicrobial drugs candidate. [Figure not available: see fulltext.]
