- PhI(OAc)2 mediated an efficient Knoevenagel reaction and their synthetic application for coumarin derivatives
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A phenyliododiacetate (PhI(OAc)2) mediated an efficient and novel protocol for the Knoevenagel reaction has been successfully accomplished. A base free, simple and straightforward method afforded wide substrate scope and good functional group tolerance, having high yields (80–92%) under environmentally benign and mild reaction conditions.
- Khan, Danish,Mukhtar, Sayeed,Alsharif, Meshari A.,Alahmdi, Mohammed Issa,Ahmed, Naseem
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- Synthesis and antiproliferative evaluation of novel biheterocycles based on coumarin and 2-aminoselenophene-3-carbonitrile unit
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A series of novel coumarins with 2-amino-3-cyanoselenophen-5-yl unit on C-3 have been synthesized. These compounds prepared easily at room temperature, in a short time and in high yield. The importance of biheterocyclic units as dominant structural motif of coumarin derivatives has been well recognized. Anti-cancer activity screening on MCF-7 cell line allowed identification of 2-amino-5-(6-bromo-2-oxo-2H-chromen-3-yl)selenophene-3-carbonitrile with the highest level of cytotoxic activity with mean IC50 and cLogP (partition co-efficient) values 10.84 μM and 3.18, respectively. The most radical scavenging compound was also recognized. Graphic abstract: [Figure not available: see fulltext.].
- Er?at?r, Mehmet,Giray, Elife Sultan,Y?ld?r?m, Metin,Yal?n, Serap
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- Gastroprotective activity of synthetic coumarins: Role of endogenous prostaglandins, nitric oxide, non-protein sulfhydryls and vanilloid receptors
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Natural or synthetic coumarins showed gastroprotective and antiulcer activity in animal models. In this study, we have synthetized twenty coumarins using classic methods to evaluate their gastroprotective effects on the ethanol/HCl-induced gastric lesion model in mice at 20?mg/kg. Among the coumarins synthetized, compounds 6 and 10 showed the greatest gastroprotective activity being as active as lansoprazole at 20?mg/kg and reducing gastric lesions by 75 and 76%, respectively. Then, in a second experiment, compounds 6 and 10 were re-evaluated in order to understand the possible mode of gastroprotective activity. Regarding coumarin 6, the protective effect was reduced by pre-treatment of the mice with N-ethylmaleimide and l-NAME suggesting that sulfhydryl compounds and endogenous nitric oxide are involved in its gastroprotective activity. While for coumarin 10 the effect was reduced by pre-treatment with indomethacin suggesting that prostaglandins are positively involved in its gastroprotective activity.
- Sepulveda, Beatriz,Quispe, Cristina,Simirgiotis, Mario,Torres-Benítez, Alfredo,Reyes-Ortíz, Johanna,Areche, Carlos,García-Beltrán, Olimpo
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- Design, synthesis, and structure–activity relationship study of O-prenylated 3-acetylcoumarins as potent inhibitors of soybean 15-lipoxygenase
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In this work, the design, synthesis, and structure–activity relationships of a novel array of geranyloxy and farnesyloxy 3-acetylcoumarins were reported as potent soybean 15-lipoxygenase inhibitors. Among the prepared coumarins, 7-farnesyloxy-3-acetylcoumarin (12b) was found to be the most potent inhibitor by IC50?= 0.68 μM while O-geranyl substituents at positions 5 and 6 of 3-acetylcoumarin (10a and 11a) were not inhibitors. Using docking studies, the binding affinity and the preferred pose of synthetic compounds were considered. It was found that lipoxygenase inhibitory activity and prenyl length chain were directly related. The hydrophobic cavity of the enzyme was more effectively occupied by the farnesyl moiety of the potent inhibitor 12b rather than other derivatives. Also, with this pose of farnesyl chain in 7-farnesyloxy-3-acetylcoumarins, the acetyl group could be directed to the hydrophilic pocket in the active site.
- Zerangnasrabad, Sara,Jabbari, Atena,Khavari Moghadam, Elahe,Sadeghian, Hamid,Seyedi, Seyed Mohammad
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- Microwave-assisted synthesis and photophysical studies of novel fluorescent N-acylhydrazone and semicarbazone-7-OH-coumarin dyes
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A microwave-assisted synthesis of novel N-acylhydrazone and semicacarbazone-7-hidroxy-coumarins derivatives, starting from 3-acetyl-7-hydroxy-2H-chromen-2-one, is described. This optimized protocol led to higher yields and considerable reduction in reaction time from ~24 to ~1 hour. Aqueous solutions of these compounds showed bright blue to cyan emission and maximum quantum yields of 0.244. The stereoelectronic effects of the attached groups led to modulation of the spectral characteristics by favoring syn or anti amide conformers. The synthesized compounds showed pH dependent luminescence and a strong batochromic shift up to 65 nm in a low polarity medium (methanol) due to a better stabilization of the syn-conformer promoting this redshifted emission. These characteristics can be exploited for designing new luminescent probes for pH as well as polar microenvironments.
- Pereira, Thiago Moreira,Vitório, Felipe,Amaral, Ronaldo Costa,Zanoni, Kassio Papi Silva,Murakami Iha, Neyde Yukie,Kümmerle, Arthur Eugen
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- A multi-signal mitochondria-targeted fluorescent probe for real-time visualization of cysteine metabolism in living cells and animals
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In this study, we developed a multi-signal mitochondria-targeted fluorescent probe (NIR-Cys) for simultaneous detection of Cys and its metabolite, SO2. In the design of the probe, the acrylate group and the CC of the coumarin ring were used as the recognizing moiety for Cys and SO2, respectively. The probe exhibited high sensitivity, excellent specificity, and fast response. NIR-Cys was found to precisely target and visualize Cys metabolism in mitochondria of living cells with a multi-fluorescence signal. This probe is expected to be a useful tool for understanding Cys metabolism.
- Yang, Xiaopeng,Liu, Wenya,Tang, Jun,Li, Ping,Weng, Haibo,Ye, Yong,Xian, Ming,Tang, Bo,Zhao, Yufen
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- Design, synthesis and evaluation of novel multi-target-directed ligands for treatment of Alzheimer's disease based on coumarin and lipoic acid scaffolds
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A novel series of coumarin-lipoic acid conjugates were synthesized via cycloaddition click reaction to find out new multi-target-directed ligands (MTDLs) for treatment of Alzheimer's disease (AD). All of synthesized compounds were screened for neuroprotec
- Jalili-Baleh, Leili,Forootanfar, Hamid,Kü?ükk?l?n?, Tuba Tüylü,Nadri, Hamid,Abdolahi, Zahra,Ameri, Alieh,Jafari, Mandana,Ayazgok, Beyza,Baeeri, Maryam,Rahimifard, Mahban,Abbas Bukhari, Syed Nasir,Abdollahi, Mohammad,Ganjali, Mohammad Reza,Emami, Saeed,Khoobi, Mehdi,Foroumadi, Alireza
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- A Fluorogenic and Chromogenic Probe Distinguishes Fluoride Anions and Thiols: Implications for Discrimination of Fluoride-Containing G Series and Sulfur-Containing V Series Nerve Agents
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A coumarin-based probe, FP2, was designed for the differential detection of fluoride anions and thiols, i.e., the corresponding nucleophilic substitution products from fluorine-containing G agents and sulfur-containing V agents, thus having the potential to discriminate between these two nerve agents. FP2 with two functional reaction groups, α, β-unsaturated ketone and silyl groups, can react selectively with fluoride anions and thiols at the μM level respectively. Intriguingly, in the THF solution, FP2 reacts with the fluoride anion but not with the thiol, whereas in the EtOH/HEPES solution, FP2 reacts with the thiol but not with the fluoride anion. As a result, FP2 can produce different fluorophores in the two detection solutions, thus displaying significant fluorescence changes. In addition, the FP2 detection system can show a significant color change from colorless to yellow within seconds when detecting fluoride anions in THF detection solutions, and from yellow to light blue when detecting thiols in EtOH/HEPES solutions, which will facilitate visual detection by emergency responders at the scene of an incident involving a nerve agent.
- Wu, Wei-hui,Wang, Xin,Zong, Liang,Li, Dan,Xiao, Yan-hua,Sui, Shao-hui,Li, Jian,Liu, Meng,Chen, Gao-yun,Luo, Teng,Liu, Min,Wang, Xin-ming,Jiang, Zhi-gang
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- Improved one-pot synthetic conditions for synthesis of functionalized fluorescent coumarin-thiophene hybrids: Syntheses, DFT studies, photophysical and thermal properties
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We have synthesized coumarin-thiophene hybrids using stepwise and one-pot methods under MWI and CM conditions, and then report the findings and conclusions: one-pot is better than stepwise in terms of high yields and fastness of getting products, and MWI is better than CM in terms of purity of compounds, better yields, and reaction period. Even though both protocols were found to be efficient, the microwave-assisted irradiation reactions were identified to be better, environmentally friendly, cost-effective, mild, more efficient, less time consuming but with high purity. The two protocols were employed for the synthesis of the target coumarin-thiophene hybrids via the Gewald reaction in stepwise and in one-pot three-component. The dyes 3a-j were prepared in good to excellent yields. Although, we recorded better yields via the stepwise protocol (80–96%), for the synthesis of the target molecules, as compared to the one-pot (82–90%), the stepwise condition is fraught with many changes such as long reaction conditions, extra use of solvents for purification of intermediates, and long reaction durations. Photophysical activities of all the target derivatives were investigated using a combination of UV–vis and fluorescence spectroscopies in different solvents. The umbelliferon-like derivative 3g was further investigated for possible use as a pH sensor via deprotonation (using TBAOH) and reverse protonation (using TFA), and was found to be applicable as pH sensor both in organic medium (DMSO) and partial aqueous binary (DMSO/H2O, v/v, 9:1) medium. Again, the ground and the excited state properties of the umbelliferon-like derivative 3g and its deprotonated form were also studied using the quantum chemical calculations. Finally, the thermal properties of all the target compounds were investigated using TGA in order to test their potency and applicability as optical dyes. All the dyes 3a-j have high thermal stability therefore they can be applicable as optical dyes.
- Yahaya, Issah,Sefero?lu, Nurgül,Sefero?lu, Zeynel
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- Synthesis and biological evaluation of some new triazolo[1,5-a]quinoline derivatives as anticancer and antimicrobial agents
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In the present study, versatile multifunctional unreported triazolo[1,5-a]quinoline derivatives were prepared. Compounds 1-19 were synthesized by adopting appropriate synthetic routes and were pharmacologically evaluated for their in vitro anticancer acti
- Bassyouni, Fatma A.,Abu-Baker, Sherifa M.,Mahmoud, Khaled,Moharam, Maysa,El-Nakkady, Sally S.,Abdel-Rehim, Mohamed
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- Synthesis, X-ray crystallographic study, pharmacology and docking of hydrazinyl thiazolyl coumarins as dengue virus NS2B/NS3 serine protease inhibitors
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A series of total twenty-one thiazole-coumarin derivatives 7a-u, linked via hydrazine linkage were synthesized through Hantzsch cyclisation. Out of twenty-one derivatives, fourteen derivatives viz. 7b-d, 7g, 7i-k, 7n and 7p-u are the novel derivatives. The structures of the synthesized compounds were established by extensive spectroscopic studies (FTIR, 1H NMR, 13C NMR, 2D NMR, LC-MS) and elemental analysis. The structure of (E)-6-methoxy-3-(1-(2-(4-p-tolylthiazol-2-yl)hydrazono)ethyl)-2H-chromen-2-one (7d) was unambiguously confirmed by X-ray crystallography analysis. Hybrid molecules were evaluated for their potential as anti-tubercular agents against Mycobacterium tuberculosis H37Rv ATCC 25618, and anti-bacterial agents against Eschericia coli, Enterobacter aerogenes, Salmonella typhi, Streptococcus pneumoniae and Staphylococcus aureus. All the compounds displayed considerable potency against all the pathogens with MIC values ranging from 31.25 to 250 μg/mL, therein compounds 7i, 7j, 7k, 7q and 7t displayed superior inhibitory activities compared to standard drugs streptomycin, kanamycin, vancomycin and isoniazid. Molecular docking studies were performed to check the potential as dengue virus NS2B/NS3 serine protease inhibitors, by comparing to standards 4-hydroxypanduratin, panduratin and ethyl 3-(4-(hydroxymethyl)-2-methoxy-5-nitrophenoxy)propanoate with DS of ?3.379, ?3.189 and ?3.381, respectively. All the compounds were found to exhibit potency against the DENV virus. In particular, compound 7c (DS –5.141) and 7l (DS –3.894) were found to be even better than the standards followed by compounds 7j (DS –3.113) and 7q (DS –3.561).
- Yusufzai, Samina Khan,Osman, Hasnah,Khan, Mohammad Shaheen,Razik, Basma M. Abd,Mohamad, Suriyati,Sulaiman, Othman,Gansau, Jualang Azlan,Johansah, Norhaniza,Ezzat, Mohammed Oday,Parumasivam, Thaigarajan,Rosli, Mohd Mustaqim,Razak, Ibrahim Abdul
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- Raman spectroscopy as a tool for monitoring mesoscale continuous-flow organic synthesis: Equipment interface and assessment in four medicinally-relevant reactions
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An apparatus is reported for real-time Raman monitoring of reactions performed using continuous-flow processing. Its capability is assessed by studying four reactions, all involving formation of products bearing α,β-unsaturated carbonyl moieties; synthesi
- Hamlin, Trevor A.,Leadbeater, Nicholas E.
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- Regioselectivity of aminomethylation in 3-acetyl-7-hydroxycoumarins: Mannich bases and Betti bases
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7-Hydroxycoumarin is a privileged structure for anti-inflammatory drug development. In this study, several new 3-acetyl-7-hydroxycoumarin derivatives were designed, synthesized and tested as anti-inflammatory agents. Interestingly, Mannich bases and Betti bases were separately obtained under acidic or neutral conditions. The regioselectivity of aminomethylation was studied based on the atomic electron density distribution by analysing the Voronoi deformation density (VDD) atomic charges, which reasonably explained the experimental outcome. Detection of nitric oxide (NO) and tumour necrosis factor alpha (TNF-α) release revealed that Mannich bases displayed stronger anti-inflammatory activity than the corresponding Betti bases.
- Gao, Fan,Tao, Deng,Ju, Cheng,Yang, Bei-Bei,Bao, Xiu-Qi,Zhang, Dan,Zhang, Tian-Tai,Li, Li
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- A coumarin-boronic ester derivative as fluorescent chemosensor for detecting H2O2 in living cells
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A coumarin derivative CBE fluorescent chemosensor based on boronic ester elimination by introducing boronic ester moiety as sensing site for efficient detecting H2O2 in living cells was developed. The probe can specifically recognize H2O2 in PBS buffer solution (containing 1% DMSO, pH = 7.4) with fluorescence enhancement response at 454 nm without interference from other substances. After H2O2 addition, the absorption band is red-shifted from 360 nm to 415 nm, and fluorescence is enhanced with fluorescence quantum yield increasing from 5.1% to 58.7%. The response is sensitive with detection limit being 0.17 nM within 16 min. The mechanism is that H2O2 triggers oxidative hydrolysis of the boronic ester and subsequent 1,6-elimination, causing C-O bond to break, thereby forming 7-hydroxycoumarin-3-acetyl and 5-cyclohexadien-1-one, 4-methylene-. The probe also has high photostability and excellent potential application in monitoring H2O2 in living cells.
- Cao, Duxia,Feng, Fei,Ma, Shuyue,Pan, Qiling,Wang, Kang-Nan,Xing, Miaomiao
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- Synthesis and in-vitro antimycobacterial activity of fluoroquinolone derivatives containing a coumarin moiety
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A series of gatifloxacin, ciprofloxacin, and 8-OCH3 ciprofloxacin coumarin derivatives with remarkable improvement in lipophilicity as compared to the parent fluoroquinolones was designed, synthesized, and characterized by 1H-NMR, MS, and HRMS. These derivatives were evaluated for their in-vitro activity against Mycobacterium smegmatis CMCC 93202 and MTB H37Rv ATCC 27294. All of the synthesized compounds were less active than the parent compounds against M. smegmatis CMCC 93202, but the activity of compound 6 was found to be 2-8-fold more potent than ciprofloxacin, 8-OCH 3 ciprofloxacin, moxifloxacin, and rifampin, and comparable to gatifloxacin against MTB H37Rv ATCC 27294. These results indicated that the lipophilicity of the tested compounds is not the sole parameter affecting antimycobacterial activity. A series of gatifloxacin, ciprofloxacin, and 8-OCH3 ciprofloxacin coumarin derivatives was designed, synthesized, characterized and evaluated for their in-vitro activity. The activity of one compound (6) was found to be 2-8-fold more potent than the respective parent GTFX, CPFX, and 8-OCH3 CPFX, indicating that the lipophilicity of the tested compounds is not the sole parameter affecting antimycobacterial activity. Copyright
- Guo, Qiang,Liu, Ming-Liang,Feng, Lian-Shun,Lv, Kai,Guan, Yan,Guo, Hui-Yuan,Xiao, Chun-Ling
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- Coumarin derivatives act as novel inhibitors of human dipeptidyl peptidase III: Combined in vitro and in silico study
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Dipeptidyl peptidase III (DPP III), a zinc-dependent exopeptidase, is a member of the metalloproteinase family M49 with distribution detected in almost all forms of life. Although the physiological role of human DPP III (hDPP III) is not yet fully elucida
- ?ubari?, Domagoj,Agi?, Dejan,Be?lo, Drago,Kara?i?, Zrinka,Karna?, Maja,Lisjak, Miroslav,Lon?ari?, Melita,Molnar, Maja,Popovi?, Boris M.,Rastija, Vesna,Tomi?, Sanja
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- Coumarin substituted symmetric diaminopyridine molecules: Synthesis, mesomorphic characterizations and DFT studies
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The 2, 6-diaminopyridine was symmetrically substituted with coumarins from a lateral side of the molecules. All the molecules characterized by standard spectroscopic methods such as infrared spectroscopy, and nuclear magnetic resonance spectroscopy techniques. Mesomorphic properties are evaluated by the differential scanning calorimetry and the polarized optical microscope. The measurements show that the lower members did not favour liquid crystal formation, while higher members are exhibiting liquid crystalline, namely Nematic mesophase. The DFT computations manifest the nature of liquid crystal geometrical aspects.
- Al-Mohammed, Mohammad Hameed,Ameen, Wissam Ahmed,Mohammad, AbdulKarim-Talaq,Srinivasa, H. T.
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- Design, characterization, in vitro antibacterial, antitubercular evaluation and structure–activity relationships of new hydrazinyl thiazolyl coumarin derivatives
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Herein, we describe the synthesis of 11new thiazolyl coumarin derivatives and evaluation of their potential role as antibacterial and antituberculosis agents. The structures of the synthesized compounds were established by extensive spectroscopic studies (Fourier transform infrared spectroscopy, 1H-nuclear magnetic resonance, 13C-nuclear magnetic resonance, 2D-nuclear magnetic resonance and liquid chromatography–mass spectrometry) and elemental analysis. All synthesized compounds were assayed for their in vitro antibacterial activity against a few gram positive and gram negative bacteria and antituberculosis activity against Mycobacterium tuberculosis H37Rv ATCC 25618 by using colorimetric microdilution assay method. Nine derivatives showed moderate anti-bacterial and anti-tuberculosis activities against all the tested strains. The highest activity against all the pathogens including Mycobacterium tuberculosis was observed by compound 7c with MIC values ranging between 31.25–62.5 μg/mL, indicating that coumarin skeleton could indeed provide useful scaffold for the development of new anti-microbial drugs.
- KhanYusufzai, Samina,Osman, Hasnah,Khan, Mohammad Shaheen,Mohamad, Suriyati,Sulaiman, Othman,Parumasivam, Thaigarajan,Gansau, Jualang Azlan,Johansah, Norhaniza,Noviany
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- Discovery of coumarin Mannich base derivatives as multifunctional agents against monoamine oxidase B and neuroinflammation for the treatment of Parkinson's disease
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Due to the complexity of the pathogenesis of Parkinson's disease (PD), multimodal treatment may achieve better results. In this study, a series of coumarin Mannich base derivatives were designed and synthesized as multifunctional agents for PD treatment. Among the derivatives, 3-(3-(dimethylamino)propanoyl)-7-hydroxy-5-methyl- 2H-chromen-2-one hydrochloride (24) exhibited the most potent and selective hMAO-B inhibitory activity, and anti-inflammatory and neuroprotective effects in the in vitro studies. It significantly attenuated PD-associated behavioural deficits in a 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced mouse model of PD. Furthermore, preliminary mechanistic studies indicated that 24 could selectively inhibit MAO-B activity, decrease the neuroinflammatory process, and protect tyrosine hydroxylase-immunopositive dopaminergic neurons. These results suggest that 24 is a promising multifunctional agent for effective therapy for PD.
- Tao, Deng,Wang, Yue,Bao, Xiu-Qi,Yang, Bei-Bei,Gao, Fan,Wang, Lin,Zhang, Dan,Li, Li
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- A smart mitochondria-targeting TP-NIR fluorescent probe for the selective and sensitive sensing of H2S in living cells and mice
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Hydrogen sulfide (H2S) is one of the important gaseous signalling molecules, which plays key roles in various critical biological processes. In this work, we report a novel two-photon near-infrared (TP-NIR) fluorescent probe (MNIR-H2S) for the sensing of mitochondrial H2S in living cells, tissues, zebrafish and nude mice. Using a xanthene dye as a TP-excitation (810 nm) NIR-emission (668 nm) fluorophore, a well-known H2S response moiety with a robust intramolecular charger transfer (ICT) effect can quickly respond to H2S and effectively quench the fluorescence intensity, and an oxonium cation structure serves as a mitochondria-targeting site. Notably,MNIR-H2Sdisplays high sensitivity, high selectivity, low cytotoxicity, powerful mitochondrial localization ability, deep tissue penetration, and a very minimal imaging background. Biological imaging results show the biological application ofMNIR-H2Sas a robust new tool for use in H2S imaging in biological systems.
- Yang, Qiaomei,Zhou, Liyi,Peng, Longpeng,Yuan, Gangqiang,Ding, Haiyuan,Tan, Libin,Zhou, Yizhuang
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- Thiourea dioxide promoted efficient organocatalytic one-pot synthesis of a library of novel heterocyclic compounds
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The utility of thiourea dioxide as an efficient organocatalyst for the library synthesis of novel heterocyclic compounds via one-pot multicomponent coupling reactions is disclosed. Thiourea dioxide is an inexpensive and readily accessible catalyst, resulting in better product yields as compared to the corresponding thiourea as catalyst. Thiourea dioxide is found to be insoluble in various organic solvents and therefore at the end of the reaction products can be separated by extraction with diethyl ether and the recovered catalyst can be used several times with consistent catalytic activity.
- Verma, Sanny,Kumar, Subodh,Jain, Suman L.,Sain, Bir
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- Development of hydrogelator-based gel-entrapped base catalysts (GEBCs) as heterogeneous basic catalysts for the synthesis of 3-acetylcoumarins
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New gel entrapped base catalysts (GEBCs) have been prepared by entrapping some organic and inorganic bases into a solid aqueous gel matrix. Sodium alginate, gelrite and carboxymethyl chitosan were studied for the preparation of GEBCs. The phase behaviour of binary systems (gelator + water) is well studied, but ternary systems (gelator + water + base) are not much studied. Addition of a base to a (gelator + water) system drastically affected the behaviour of the gel. The phase behaviour of ternary systems (gelator + water + base) was studied by developing the corresponding ternary phase diagrams. From this study, the promising homogeneous viscous phases were converted into hard, irreversible gel beads by cross-linking the gelator with divalent cations Ca2+, Ba2+ and Sr2+. These gel beads were studied for base entrapment efficiency and leaching of the base. The GEBCs were used for the condensation of salicylaldehydes and methyl/ethyl acetoacetate to obtain 3-acetylcoumarins.
- Korgavkar, Nilesh N.,Samant, Shriniwas D.
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- A facile one pot multi component synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetates and their antiviral activity
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An efficient one-pot synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetate derivatives has successfully been achieved via a three component cyclization reaction of various substituted 3-acetyl coumarins, thiosemicarbazide and dialkyl acetylenedicarboxylates, in presence of acetic acid. The isolated products were obtained in pure form with high yields through simple workup. The newly synthesised compounds structure was established on the basis of spectral (IR, 1H NMR, 13C NMR, ESI- mass) elemental analysis and single crystal X-ray data. All synthesised compounds were screened for their antiviral activity against a broad spectrum of human viruses in different cell cultures. Of the novel synthesised compounds, thirteen compounds exerted activity against Punta Toro virus, including compound IV-19, for which an antiviral potency was noted against a broad panel of DNA and RNA viruses as well.
- Kulkarni, Chandrashekhar V.,Vaarla, Krishnaiah,Vedula, Rajeswar Rao,Vermeire, Kurt,Vishwapathi, Vinod
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- Synthesis and mesomorphic properties of bis ester derivatives of coumarin containing chalcone linkage
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Bis ester derivatives of coumarin containing chalcone linkage with various terminal alkoxy groups were designed, synthesized and characterized. Compounds 11a-m were studied for their mesomorphic properties using polarizing optical microscope & differential scanning calorimetry and photophysical properties using UV-vis & fluorescence spectroscopy. In this particular homologous series, compounds having lower flexible alkoxy chains showed very good mesogenic property with nematic mesophase formation, while analogues with higher chains failed to show any liquid crystalline property. Compound 11a with methoxy group showed very good absorbance and fluorescence as compared to higher chain length analogues.
- Shah, Priyanka,Soni, Rina,Soman, Shubhangi S
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- Novel fluorescent probe for sequentially detecting hydrazine hydrate and bisulfite as well as synthesis and application of novel fluorescent probe
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The invention relates to a novel fluorescent probe for sequentially detecting hydrazine hydrate and bisulfite as well as synthesis and application of the novel fluorescent probe, which belongs to the technical field of analytical chemistry. The chemical structure of the probe is shown as a formula (I), and the probe can be used for sequentially detecting hydrazine hydrate and bisulfite on the basis of ESIPT and ICT mechanisms. The ESIPT and the ICT are inhibited, so that the probe has no fluorescence in an aqueous solution; after the hydrazine hydrate solution is added, the effects of the ESIPT and the ICT are recovered, so that the fluorescence at 615 nm is obviously enhanced; and when the bisulfite solution is continuously added into the 'probe+hydrazine hydrate' system, the ICT effect is inhibited, so that the maximum emission wavelength is blue-shifted to 508 nm. Through obvious fluorescence change, sequential detection of the two substances is realized. The fluorescent probe is easy and convenient to operate, good in selectivity, high in sensitivity and stable in optical performance, and an important thought is provided for development of the multifunctional fluorescent probe.The formula (I) is as shown in the specification.
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Paragraph 0007; 0016
(2021/05/15)
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- A novel dual-site ICT/AIE fluorescent probe for detecting hypochlorite and polarity in living cells
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A novel dual-site fluorescent probe (CTPA) was rationally designed and synthesized for the detection of hypochlorite (ClO-) and polarity. CTPA displayed an excellent sensitivity (LOD = 11.9 nM) and selectivity as well as a rapid response within 30 s to Cl
- Chen, Ligong,Cui, Siqian,Du, Yuchao,Fang, Wangwang,Hou, Yuqing,Li, Mingrui,Li, Yang,Wang, Bowei,Yan, Xilong
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supporting information
p. 21406 - 21414
(2021/12/09)
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- Coumarin-chalcone hybrids as inhibitors of MAO-B: Biological activity and in silico studies
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Fourteen coumarin-derived compounds modified at the C3 carbon of coumarin with an α,β-unsaturated ketone were synthesized. These compounds may be designated as chalcocoumarins (3-cinnamoyl-2H-chromen-2-ones). Both chalcones and coumarins are recognized scaffolds in medicinal chemistry, showing diverse biological and pharmacological properties among which neuro-protective activities and multiple enzyme inhibition, including mitochondrial enzyme systems, stand out. The evaluation of monoamine oxidase B (MAO-B) inhibitors has aroused considerable interest as therapeutic agents for neurodegenerative diseases such as Parkinson’s. Of the fourteen chalcocumarins evaluated here against MAO-B, ChC4 showed the strongest activity in vitro, with IC50 = 0.76 ± 0.08 μM. Computational docking, molecular dynamics and MM/GBSA studies, confirm that ChC4 binds very stably to the active rMAO-B site, explaining the experimental inhibition data.
- Moya-Alvarado, Guillermo,Ya?ez, Osvaldo,Morales, Nicole,González-González, Angélica,Areche, Carlos,Nú?ez, Marco Tulio,Fierro, Angélica,García-Beltrán, Olimpo
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supporting information
(2021/05/28)
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- Synthesis and mesomorphic properties of coumarin derivatives with chalcone and imine linkages
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We report here design and synthesis of two new mesogenic homologous series of coumarin derivatives consisting of chalcone and imine central linkages along with terminal n-alkoxy chain. All the compounds were synthesized and characterized by combination of elemental analysis and standard spectroscopic methods. All compounds were screened under polarising optical microscope (POM) for liquid crystalline properties, thermogram of all compounds were studied using differential scanning calorimetry (DSC) to get phase transition temperatures, enthalpy and entropy. X-ray single crystal study of n-octyloxy coumarin derivative 16 g was resolved with imine central linkage, which showed linear rod like geometry.
- Durgapal, Sunil Dutt,Soni, Rina,Soman, Shubhangi S.,Prajapati
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- Bifunctional fluorescent probe for identifying hypochlorite and bisulfite as well as preparation method and application of bifunctional fluorescent probe
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The invention discloses a bifunctional fluorescent probe for identifying hypochlorite and bisulfite as well as a preparation method and application of the bifunctional fluorescent probe, which can beused for identifying hypochlorite and bisulfite respecti
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Paragraph 0036; 0041; 0046
(2020/08/30)
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- An enzyme-responsive and photoactivatable carbon-monoxide releasing molecule for bacterial infection theranostics
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Infections caused by pathogenic bacteria, especially the drug-resistant bacteria, are posing a devastating threat to public health, which underscores the urgent needs for advanced strategies to effectively prevent and treat these intractable issues. Here
- Wang, Xianghong,Chen, Xin,Song, Lingjie,Zhou, Rongtao,Luan, Shifang
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p. 9325 - 9334
(2020/11/03)
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- Electrochemistry and Reactivity against Superoxide Anion Radicals of Hydroxycoumarins and Its Derivatives
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The present studies reveal superoxide radical anion reactivity against synthesized coumarins. Free radicals play an important role in many diseases and they have a protective function also. Therefore, we must keep a balance in their concentration, and thi
- Barrientos, C.,Navarrete-Encina, P.,Squella, J. A.
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- Mitochondria-targeted two-photon excited near-infrared emission hydrogen sulfide fluorescent probe, preparation method and application thereof
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The invention discloses a hydrogen sulfide fluorescent probe capable of being directly used for mitochondrial targeting two-photon excited near-infrared emission, a preparation method and applicationthereof, and belongs to the field of chemical and biological analysis and detection, wherein the molecular structural formula is represented by a formula I. The two-photon excited near-infrared emission fluorescent probe has the advantages of strong selectivity, excellent anti-interference capability, high sensitivity, strong imaging penetrability and high imaging resolution, can be used for rapiddetection and imaging of H2S in cancer cells and tissues, and has a good application prospect.
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Paragraph 0044; 0048-0051
(2020/09/16)
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- Natural and semisynthetic oxyprenylated aromatic compounds as stimulators or inhibitors of melanogenesis
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It has been very recently shown how naturally occurring oxyprenylated coumarins are effective modulators of melanogenesis. In this short communication we wish to generalize the potentialities as skin tanning or whitening agents of a wider panel of natural and semisynthetic aromatic compounds, including coumarins, cinnamic and benzoic acids, cinnamaldehydes, benzaldehyde, and anthraquinone derivatives. A total number of 43 compounds have been tested assaying their capacity to inhibit or stimulate melanin biosynthesis in cultured murine Melan A cells. The wider number of chemicals herein under investigation allowed to depict a detailed structure-activity relationship, as the following: (a) benzoic acid derivatives are slightly pigmenting agent, for which the effect is more pronounced in compounds with longer O-side chains; (b) independently from the type of substitution, cinnamic acids are able to increase melanin biosynthesis, while benzaldehydes are able to decrease it; (c) coumarins with a 3,3-dimethylallyl or shorter skeletons as substituents in position 7 are tanning agents, while coumarins with farnesyloxy groups are whitening ones; (d) double oxyprenylation in position 6 and 7 and 3,3-dimethylallyl or geranyl skeletons have slight depigmenting capacities, while farnesyl skeletons tend to marginally increase the tanning effect; (e) the presence of electron withdrawing groups (acetyl, COOH, and -Cl) and geranyl or farnesyl oxyprenylated chains respectively in positions 3 and 7 of the coumarin nucleus lead to a whitening effect, and finally (f) oxyprenylated anthraquinones have only a weak depigmenting capacity.
- Genovese, Salvatore,Epifano, Francesco,Medina, Philippe de,Caron, Nicolas,Rives, Arnaud,Poirot, Marc,Poirot, Sandrine Silvent,Fiorito, Serena
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p. 181 - 190
(2019/03/23)
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- Applications of coumarin mannich alkali in preventing and treating neurodegenerative diseases
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The invention relates to a novel coumarin mannich alkali and a pharmaceutically acceptable salt thereof, a preparation method of the coumarin mannich alkali and the pharmaceutically acceptable salt, apharmaceutical composition containing the coumarin mannich alkali or the pharmaceutically acceptable salt, and applications of the coumarin mannich alkali or the pharmaceutically acceptable salt in preventing or treating neurodegenerative diseases, and especially in preparation of drugs used for preventing or treating Alzheimer's disease, Parkinson's disease, Amyotrophic lateral sclerosis, and multiple sclerosis.
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Paragraph 0037; 0038
(2018/07/10)
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- Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer's disease: Design, synthesis and biological evaluation
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A series of new coumarin-dithiocarbamate hybrids were designed and synthesized as multitarget agents for the treatment of Alzheimer's disease. Most of them showed potent and clearly selective inhibition towards AChE and MAO-B. Among these compounds, compound 8f demonstrated the most potent inhibition to AChE with IC50 values of 0.0068 μM and 0.0089 μM for eeAChE and hAChE, respectively. Compound 8g was identified as the most potent inhibitor to hMAO-B, and it is also a good and balanced inhibitor to both hAChE and hMAO-B (0.114 μM for hAChE; 0.101 μM for hMAO-B). Kinetic and molecular modeling studies revealed that 8g was a dual binding site inhibitor for AChE and a competitive inhibitor for MAO-B. Further studies indicated that 8g could penetrate the BBB and exhibit no toxicity on SH-SY5Y neuroblastoma cells. More importantly, 8g did not display any acute toxicity in mice at doses up to 2500 mg/kg and could reverse the cognitive dysfunction of scopolamine-induced AD mice. Overall, these results highlighted 8g as a potential multitarget agent for AD treatment and offered a starting point for design of new multitarget AChE/MAO-B inhibitors based on dithiocarbamate scaffold.
- He, Qi,Liu, Jing,Lan, Jin-Shuai,Ding, Jiaoli,Sun, Yongbing,Fang, Yuanying,Jiang, Neng,Yang, Zunhua,Sun, Liyuan,Jin, Yi,Xie, Sai-Sai
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supporting information
p. 512 - 528
(2018/09/29)
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- Compounds for treating spinal muscular atrophy
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Provided herein are compounds, compositions thereof and uses therewith for treating spinal muscular atrophy. In a specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN2 into mRNA that is transcribed from the SMN2 gene. In another specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 into mRNA that is transcribed from the SMN1 gene. In yet another embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 and SMN2 into mRNA that is transcribed from the SMN1 and SMN2 genes, respectively.
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Page/Page column 417; 418
(2017/05/02)
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- Synthesis, electronic absorption, fluorescence and live time spectroscopic study of some new 3,7-disubstituted coumarin derivatives as new fluorescent probes
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The synthesis of several novel 3-heterocyclic substituent-7-methoxycoumarin derivatives were carried out starting from 3-acetyl-7-hydroxy-2H-chromen-2-one (3), which reacted with DMF-DMA affords enaminone 4 which transformed into pyranone 8, pyridine deri
- Altalbawy,Abdelkader,Darwish,Elnagdi
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p. 2303 - 2310
(2016/07/20)
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- SKIN PIGMENTATION MODIFIERS TO DARKEN OR LIGHTEN THE SKIN
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The present invention relates to a method for changing the pigmentation of a skin, a mucous membrane or hair with a compound of general formula (I), a cosmetic use of said compound of general formula (I), to cosmetic compositions comprising said compound of general formula (I), and to new depigmenting agents.
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Page/Page column 29
(2016/12/22)
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- Some new indole-coumarin hybrids; Synthesis, anticancer and Bcl-2 docking studies
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Hybrid molecules have attracted attention for their improved biological activity, selectivity and lesser side effects profile, distinct from their individual components. In the quest for novel anticancer drug entities, three series of indole-coumarin hybrids - 3-(1-benzyl-1H-indol-2-yl)-2H-chromen-2-ones, 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carbaldehydes and 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carboxylic acids were synthesized. All the synthesized compounds were characterized by spectral techniques like IR, 1H NMR, 13C NMR, mass spectrometry and elemental analysis. In silico docking studies of synthesized molecules with apoptosis related gene Bcl-2 that is recognized to play an important role in tumerogenesis were carried out. Dose-dependent cytotoxic effect of the compounds in human breast adenocarcinoma (MCF-7) and normal cell lines were assessed using MTT assay and compared with that of the standard marketed drug, Vincristine. Compound 4c had a highly lipophilic bromine substituent capable of forming halogen bond and was identified as a potent molecule both in docking as well as cytotoxicity studies. Flow cytometric cell cycle analysis of 4c exhibited apoptotic mode of cell death due to cell cycle arrest in G2/M phase. Structure activity relationship of these hybrid molecules was also studied to determine the effect of steric and electronic properties of the substituents on cell viability.
- Kamath, Pooja R.,Sunil, Dhanya,Ajees, A. Abdul,Pai,Das, Shubhankar
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p. 101 - 109
(2015/10/28)
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- Design, synthesis, and biological evaluation of novel benzimidazole derivatives and their interaction with calf thymus DNA and synergistic effects with clinical drugs
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A series of new benzimidazole derivatives was synthesized and characterized by IR, 1H NMR, 13C NMR, MS, and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by a twofold serial dilution technique. The bioactive evaluation showed that 3,5-bis(trifluoromethyl)phenyl benzimidazoles were comparably or even more strongly antibacterial and antifungal than the reference drugs Chloromycin, Norfloxacin, and Fluconazole. The combination of 2,4-difluorobenzyl benzimidazole derivative 5l and its hydrochloride 7 respectively with the antibacterials Chloromycin, Norfloxacin, and the antifungal Fluconazole was more sensitive to methicillin-resistant MRSA and Fluconazole-insensitive A. flavus. In addition, the interaction of compound 5l with calf thymus DNA demonstrated that this compound could effectively intercalate into DNA to form a compound 5l-DNA complex that might block DNA replication and thereby exert good antimicrobial activity.
- Zhang, Huizhen,Lin, Jianmei,Rasheed, Syed,Zhou, Chenghe
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p. 807 - 822
(2014/06/24)
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- Synthesis and antibacterial activity of some novel coumarinyl oxadiazole derivatives
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A novel series of 3-[2-(5-pyridin-4-yl)-1,3,4-oxadiazol-2-yl thio] acetyl-2H-chromen- 2-ones IV(a-h) were synthesized by the reaction of 2-pyridyl-1,3,4-oxadiazol-2-thiol (III) and substituted 3-bromo acetyl coumarins II(a-h) in presence of sodium ethoxide. The purity of the synthesized compounds was confirmed by their physical constants and TLC. The structures of the synthesized compounds were further confirmed by IR, NMR and mass spectral data. All the synthesized compounds were screened for antibacterial activity using broth microdilution method and gentamycin as standard drug. Among the series IVb, IVc, IVg and IVh compounds showed good antibacterial activity.
- Kumar, M.R. Pradeep,Honnalli,Ashalatha
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p. 189 - 192
(2019/01/21)
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- Design, synthesis and antimicrobial evaluation of novel benzimidazole type of Fluconazole analogues and their synergistic effects with Chloromycin, Norfloxacin and Fluconazole
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A novel series of benzimidazole type of Fluconazole analogues were synthesized and characterized by 1H NMR, 13C NMR, IR, MS and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by two-fold serial dilution technique. The bioactive evaluation showed that 3,5-bis(trifluoromethyl)phenyl benzimidazoles gave comparable or even stronger antibacterial and antifungal efficiency in comparison with reference drugs Chloromycin, Norfloxacin and Fluconazole. The combination of 2,4-difluorobenzyl benzimidazole derivative 5m and its hydrochloride 7 respectively with antibacterial Chloromycin, Norfloxacin or antifungal Fluconazole showed better antimicrobial efficiency with less dosage and broader antimicrobial spectrum than the separated use of them alone. Notably, these combined systems were more sensitive to Fluconazole-insensitive Aspergillus flavus and methicillin-resistant MRSA.
- Zhang, Hui-Zhen,Damu, Guri L.V.,Cai, Gui-Xin,Zhou, Cheng-He
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p. 329 - 344
(2013/07/27)
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- Polyoxygenated cinnamoylcoumarins as conformationally constrained analogs of cytotoxic diarylpentanoids: Synthesis and biological activity
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A series of polyoxygenated cinnamoylcoumarins was synthesized as conformationally constrained analogs of cytotoxic diarylpentanoids. The title compounds were tested against the viability of human chronic myelogenous leukemia (K562), human acute lymphoblastic leukemia (MOLT-4) and human breast adenocarcinoma (MCF-7) cell lines by using MTT (3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide) assay. Among them, all 6- or 7-hydroxylated compounds 6a-h exhibited remarkable cytotoxic activity. Particularly, 7-hydroxycoumarin analog 6h showed good antiproliferative activity against all tested cell lines (IC50 values ≤ 5.5 μM). The preliminary study with selected compounds 6e and 6f showed that reactivity towards mitochondrial thiol compounds cab be considered as cytotoxic mechanism of designed compounds. Furthermore, the antioxidant activity evaluation of synthesized compounds showed that hydroxylated compounds had antioxidative potential at higher concentrations.
- Molaverdi, Fatemeh,Khoobi, Mehdi,Emami, Saeed,Alipour, Masoumeh,Firuzi, Omidreza,Foroumadi, Alireza,Dehghan, Gholamreza,Miri, Ramin,Shaki, Fatemeh,Jafarpour, Farnaz,Shafiee, Abbas
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p. 103 - 110
(2013/10/01)
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- Synthesis and biological evaluation of (6- and 7-Phenyl) coumarin derivatives as selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1
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17β-Hydroxysteroid dehydrogenase type 1 (17β-HSD1) is an enzyme that catalyzes NADPH-dependent reduction of the weak estrogen, estrone, into the most potent estrogen, estradiol, which exerts proliferative effects via the estrogen receptors. Overexpression of 17β-HSD1 in estrogen-responsive tissues is related to the development of hormone-dependent diseases, such as breast cancer and endometriosis; thus, 17β-HSD1 represents an attractive target for the development of new therapies. We have discovered that simple coumarines 1 and 2 significantly inhibit 17β-HSD1 in a recombinant enzyme assay, with high selectivity against 17β-HSD2. We postulated that the introduction of various p-substituted phenyl moieties to position 6 or 7 of the coumarin core using the Suzuki-Miyaura cross-coupling reaction would provide mimetics of steroidal structures with improved inhibition of 17β-HSD1. The best inhibitor in the series proved to be 6a, with an IC50 of 270 nM, and with exceptional selectivity for 17β-HSD1 over 17β-HSD2 and against the α and β estrogen receptors.
- Star?evi?, ?tefan,Bro?i?, Petra,Turk, Samo,Cesar, Jo?ko,Lani?nik Ri?ner, Tea,Gobec, Stanislav
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experimental part
p. 248 - 261
(2011/03/22)
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- The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study
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Two fluorescence probes for the detection of cysteine (Cys), glutathione (GSH) and other biothiols, such as homocysteine (Hcy) and cysteinyl-glycine (Cys-Gly), were developed. These molecular probes are coumarin-based derivatives containing a chalcone-like moiety that reacts with biothiols through a Michael addition reaction, leading to strong fluorescence enhancements. The reactivity of the tested biothiols toward both probes (ChC1 and ChC2) follows the order Cys > GSH > Hcy > Cys-Gly, ChC1 being less reactive than ChC2. Possible interference with other amino acids was assessed. ChC1 and ChC2 display a highly selective fluorescence enhancement with thiols, allowing these probes to be used for fluorimetric thiol determination in SH-SY5Y cells.
- García-Beltrán, Olimpo,Mena, Natalia,Pérez, Edwin G.,Cassels, Bruce K.,Nu?ez, Marco T.,Werlinger, Francisca,Zavala, Daniel,Aliaga, Margarita E.,Pavez, Paulina
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supporting information; scheme or table
p. 6606 - 6609
(2012/01/06)
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- Synthesis and free radical scavenging activity of coumarin derivatives containing a 2-methylbenzothiazoline motif
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Coumarin and benzothiazole scaffolds can be found in a number of natural or synthetic antioxidants. In an effort to develop a novel radical scavenger and potential antioxidant, a series of coumarin derivatives containing 2-methylbenzothiazoline motif and related compounds was synthesized and evaluated for their DPPH (1,1-diphenyl-2-picrylhydrazyl) and ABTS ?+ (2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radicals scavenging activities. Among them, 7-hydroxy-3-(2-methyl-2,3- dihydrobenzo[d]thiazol-2-yl)-2H-chromen-2-one (3e) has shown a significant free radical scavenging activity. From the structure-activity point of view, it was found that phenolic coumarin ring and benzothiazoline moiety in target compounds may contribute to the scavenging activity against free radicals. A series of coumarin derivatives containing a 2-methylbenzothiazoline motif and related compounds were synthesized and evaluated for their DPPH and ABTS ?+ radicals scavenging activities. 7-Hydroxy-coumarin derivative 3e showed a significant free radical scavenging activity. Copyright
- Khoobi, Mehdi,Emami, Saeed,Dehghan, Gholamreza,Foroumadi, Alireza,Ramazani, Ali,Shafiee, Abbas
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experimental part
p. 588 - 594
(2012/06/29)
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- Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives
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Several 3-carbonyl (1-26), 3-acyl (27-52), and 3-carboxyhydrazido (53-58) coumarins have been synthesized in high yields (72-99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.
- Secci, Daniela,Carradori, Simone,Bolasco, Adriana,Chimenti, Paola,Yá?ez, Matilde,Ortuso, Francesco,Alcaro, Stefano
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experimental part
p. 4846 - 4852
(2011/11/13)
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- DERIVATIVES OF CHROMEN-2-ONE AS INHIBITORS OF VEGF PRODUCTION IN MAMMALIAN CELLS
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The compounds of formula (I) wherein A and R1-R5 are as defined in the description, are inhibitors of Vascular Endothelial Growth Factor and are useful as angiogenesis inhibitors and antiproliferative agents.
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