10441-27-7Relevant articles and documents
PhI(OAc)2 mediated an efficient Knoevenagel reaction and their synthetic application for coumarin derivatives
Khan, Danish,Mukhtar, Sayeed,Alsharif, Meshari A.,Alahmdi, Mohammed Issa,Ahmed, Naseem
, p. 3183 - 3187 (2017)
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.
Gastroprotective activity of synthetic coumarins: Role of endogenous prostaglandins, nitric oxide, non-protein sulfhydryls and vanilloid receptors
Sepulveda, Beatriz,Quispe, Cristina,Simirgiotis, Mario,Torres-Benítez, Alfredo,Reyes-Ortíz, Johanna,Areche, Carlos,García-Beltrán, Olimpo
, p. 5732 - 5735 (2016)
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.
Microwave-assisted synthesis and photophysical studies of novel fluorescent N-acylhydrazone and semicarbazone-7-OH-coumarin dyes
Pereira, Thiago Moreira,Vitório, Felipe,Amaral, Ronaldo Costa,Zanoni, Kassio Papi Silva,Murakami Iha, Neyde Yukie,Kümmerle, Arthur Eugen
, p. 8846 - 8854 (2016)
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.
Design, synthesis and evaluation of novel multi-target-directed ligands for treatment of Alzheimer's disease based on coumarin and lipoic acid scaffolds
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
, p. 600 - 614 (2018)
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
Improved one-pot synthetic conditions for synthesis of functionalized fluorescent coumarin-thiophene hybrids: Syntheses, DFT studies, photophysical and thermal properties
Yahaya, Issah,Sefero?lu, Nurgül,Sefero?lu, Zeynel
, p. 2143 - 2154 (2019)
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.
Synthesis, X-ray crystallographic study, pharmacology and docking of hydrazinyl thiazolyl coumarins as dengue virus NS2B/NS3 serine protease inhibitors
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
, p. 1647 - 1665 (2018)
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).
Regioselectivity of aminomethylation in 3-acetyl-7-hydroxycoumarins: Mannich bases and Betti bases
Gao, Fan,Tao, Deng,Ju, Cheng,Yang, Bei-Bei,Bao, Xiu-Qi,Zhang, Dan,Zhang, Tian-Tai,Li, Li
, p. 9864 - 9871 (2021)
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.
Synthesis and in-vitro antimycobacterial activity of fluoroquinolone derivatives containing a coumarin moiety
Guo, Qiang,Liu, Ming-Liang,Feng, Lian-Shun,Lv, Kai,Guan, Yan,Guo, Hui-Yuan,Xiao, Chun-Ling
, p. 802 - 809 (2011)
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
Coumarin substituted symmetric diaminopyridine molecules: Synthesis, mesomorphic characterizations and DFT studies
Al-Mohammed, Mohammad Hameed,Ameen, Wissam Ahmed,Mohammad, AbdulKarim-Talaq,Srinivasa, H. T.
, (2020)
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.
Discovery of coumarin Mannich base derivatives as multifunctional agents against monoamine oxidase B and neuroinflammation for the treatment of Parkinson's disease
Tao, Deng,Wang, Yue,Bao, Xiu-Qi,Yang, Bei-Bei,Gao, Fan,Wang, Lin,Zhang, Dan,Li, Li
, p. 203 - 212 (2019)
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.
Thiourea dioxide promoted efficient organocatalytic one-pot synthesis of a library of novel heterocyclic compounds
Verma, Sanny,Kumar, Subodh,Jain, Suman L.,Sain, Bir
, p. 6943 - 6948 (2011)
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.
A facile one pot multi component synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetates and their antiviral activity
Kulkarni, Chandrashekhar V.,Vaarla, Krishnaiah,Vedula, Rajeswar Rao,Vermeire, Kurt,Vishwapathi, Vinod
, (2021/10/19)
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.
Synthesis and mesomorphic properties of bis ester derivatives of coumarin containing chalcone linkage
Shah, Priyanka,Soni, Rina,Soman, Shubhangi S
, (2021/05/04)
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.
