2555-29-5Relevant articles and documents
Microwave-assisted synthesis of derivatives of khellinone under phase-transfer catalytic conditions
Hejchman, Elzbieta,Maciejewska, Dorota,Wolska, Irena
, p. 1337 - 1348 (2008)
The microwave-assisted synthesis of four new 5-acetyl-4,7-dimethoxy-6- hydroxybenzofuran (khellinone) analogs is described. The structures of the obtained derivatives in the solid state are evaluated on the basis of 13C CP/MAS NMR spectra and theoretical calculations at DFT level. A single crystal X-ray diffraction structure is presented for 8-acetyl-7-hydroxy- 4-methylcoumarin. 1,4-Bis(5-acetyl-4,7-dimethoxybenzofuran-6-yloxy)butane was evaluated for potential anticancer activity in an in vitro screening panel of 60 human tumor cell lines. Selected leukemia, non-small cell lung cancer, CNS, melanoma, ovarian, and breast cancer cell lines were sensitive to this compound.
5-HT1A and 5-HT2A receptors affinity, docking studies and pharmacological evaluation of a series of 8-acetyl-7-hydroxy-4-methylcoumarin derivatives
Ostrowska, Kinga,Grzeszczuk, Dawid,G?uch-Lutwin, Monika,Grybo?, Anna,Siwek, Agata,Le?niak, Anna,Sacharczuk, Mariusz,Trzaskowski, Bartosz
, p. 527 - 535 (2018)
In this work we describe the synthesis, docking studies and biological evaluation of a focused library of novel arylpiperazinyl derivatives of 8-acetyl-7-hydroxy-4-methylcoumarin. The new compounds were screened for their 5-HT1A and 5-HT2A receptor affinity. Among the evaluated compounds, six displayed high affinities to 5-HT1A receptors (4a-0.9 nM, 6a-0.5 nM, 10a-0.6 nM, 3b-0.9 nM, 6b-1.5 nM, 10b-1 nM). Compound 6a and 10a bearing a bromo- or methoxy- substituent in ortho position of the piperazine phenyl ring, were identified as potent antagonists of the 5-HT1A receptors. In the tail suspension test, mice injected with 6a showed a dose-dependent increase in depressive-like behavior that was related to a decrease in locomotor activity. Compound 10a did not decrease or prolong immobility time nor did it affect home cage activity. Molecular docking studies using 5-HT1A and 5-HT2A homology models revealed structural basis of the high affinity of ortho-substituted derivatives and subtle changes in amino acid interactions patterns depending on the length of the alkyl linker.
Antitumor and multikinase inhibition activities of some synthesized coumarin and benzofuran derivatives
Abd Elmageed, Zakaria Y.,Abdelhafez, Omaima M.,Ahmed, Eman Y.,Ahmed, Yasmine H.,Ali, Hamed I.,El-Telbany, Rania Farag A.,Serry, Aya M.,Zaafar, Dalia
, (2022/03/17)
Two new series of coumarin and benzofuran derivatives were designed, synthesized, and assessed for their in vitro and in vivo antitumor activities against breast cancer. Compounds 8, 9, 14, 15, and 17 exhibited the best antiproliferative activities (IC50: 0.07?2.94 μM) against the MCF-7 cell line, compared with lapatinib (IC50: 4.69 μM). Compound 14, with the most potent cytotoxic activity against MCF-7 cells, was capable of enhancing preG1 apoptosis and triggering cell cycle arrest at the G2/M phase. The kinase inhibitory activity of compound 14 against a panel of 22 kinases was examined to reveal multikinase inhibition within ?39% to ?97%. Furthermore, compound 14 exhibited potent in vivo Ehrlich (mammary adenocarcinoma) tumor regression, positive caspase-3, and negative EGFR immunoreaction, and was capable of elevating the catalase level. The physicochemical properties and pharmacokinetic parameters of compound 14 were investigated in silico for its druglikeness.
(E)-4 - methyl -7 - hydroxyl -8 - (3 - (ferrocenyl) acryloyl) coumarin as well as preparation method and application thereof
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Paragraph 0025; 0037; 0058; 0061; 0063; 0066, (2021/10/20)
The invention discloses (E)-4 - methyl -7 - hydroxyl -8 - (3 - (ferrocenyl) acryloyl) coumarin as well as a preparation method and application thereof, and (E)-4 - methyl -7 - hydroxyl -8 - (3 - (ferrocenyl) acryloyl) coumarin has the following structural formula. The present disclosure uses resorcinol as a raw material and condenses with Knoevenagal. 7 (7) Fries-methyl 8 hydroxyl E (-4 - 3 -8 - (ferrocenyl) acryloyl) coumarin is added into ABTBTBTS?, DPPHPHI and galvinvinvinvinylisopropyl -7 -) coumarin to exhibit excellent antioxidation activity, and the antioxidant performance is E superior -4 - to -7 - the -8 - corresponding 3 - ferrocenyl chalcone and coumarin-based chalcone, and has potential application values and is excellent in anti-oxidation activity and excellent in anti-oxidation performance.
Synthesis and biological evaluation of new coumarin derivatives as cytotoxic agents
Ragab, Fatma A.,Eissa, Amal A. M.,Fahim, Samar H.,Salem, Mohammad A.,Gamal, Mona A.,Nissan, Yassin M.
, (2021/05/03)
New coumarin derivatives 9a–f, 10a–e, and 11a–f were synthesized and evaluated for their cytotoxic activity against a human breast cancer cell line (MCF-7). All compounds exhibited good activity in the nanomolar range, using doxorubicin and erlotinib as positive controls. The most active compound 9d with IC50 of 21 nM was tested against the HCT-116, HepG-2, A549, and SGC-7901 cell lines, with IC50 values of 0.021, 0.170, 0.028, and 0.11 μM, respectively. Compound 9d was further investigated for its ability to suppress the expression of epidermal growth factor receptor (EGFR). Compound 9d decreased the concentration of EGFR by 87%, using erlotinib as a positive control. A docking study revealed similar or higher scores than for erlotinib and similar binding poses providing interactions with the hinge region of the tyrosine kinase (TK). Besides the effect on expression, this in silico investigation predicts the possibility of direct binding between the new coumarin derivatives and the EGFR TK. Moreover, computational calculation for ADME properties for the most active compounds 9d, 9e, 10c, and 11c revealed the expected high gastrointestinal tract absorption, moderate water solubility with no central nervous system toxicity, and druglikeness.
A multi-responsive crown ether-based colorimetric/fluorescent chemosensor for highly selective detection of Al3+, Cu2+ and Mg2+
Zhang, Qiang,Ma, Ruifang,Li, Zhuying,Liu, Zizhong
, (2019/12/09)
A novel multi-response chemosensor L based on coumarin-chalcone-crown ether was designed and synthesized, which exhibited a high selectivity for the colorimetric detecting Al3+ and Cu2+ and fluorescent recognizing Al3+ and Mg2+ in ethanol. L can monitor Al3+ and Cu2+ via distinct color changes from a slight yellow to pink and to orange, respectively. The sensor L can also monitor Al3+ and Mg2+ by fluorescence emission responses at 592 nm and 547 nm with low detection limits of 0.31 μM and 0.23 μM, respectively. The selectivity of L toward Al3+, Cu2+ and Mg2+ was not interfered by a large number of coexisting ions and was found to be reversible. By means of spectrometric titration, Job's plot, mass spectrometry, 1H NMR titration and IR spectroscopy analysis, it was unanimously confirmed that the sensor L had a stoichiometric ratio of 1:1 with Cu2+ and Mg2+, and 1:2 with Al3+. The order of the stability of the complexes formed by L and Al3+, Cu2+, Mg2+ was as follows: L-Al3+ > L-Cu2+ > L-Mg2+. At the same time, some possible bonding modes and sensing mechanisms were further proposed, and the optimized structure of the sensor L and its sensing mechanism for Al3+, Cu2+ and Mg2+ were confirmed by the calculations of DFT/B3LYP and TD-DFT methods in a suite of Gaussian 09 programs.
Synthesis of pyrazole-4-carbaldehyde derivatives for their antifungal activity
Reddy, Vadiyala Naveen,Yamini, Lingala,Rao, Yerrabelly Jayaprakash,Rao, Chitneni Prasad
, p. 1664 - 1674 (2017/06/27)
A series of pyrazole-4-carbaldehyde containing coumarin derivatives (9a–l) were achieved starting from substituted 6-hydroxy-4-methyl coumarins in a facial manner by Vilsmeier–Haack Formylation reaction in good yields, and their chemical structures were determined by Fourier transform infrared, 1H, 13C-nuclear magnetic resonance and mass spectroscopic techniques. Compounds 9a–l were docked into monoamine oxidase from Aspergillus niger and shown strong π-stacking interactions with the cage forming amino acids of Trp430 and Phe466, and were also further evaluated against antifungal activity on Aspergillus niger by taking Clotrimazole as standard. Out of twelve synthesized compounds 9a, 9b, 9g, and 9h were showed good and 9c, 9d, 9e, 9i, 9j, and 9k were showed moderate antifungal activity.
Synthesis and biological evaluation of novel coumarin derivatives as potential antimicrobials agents
Amin, Kamilia M.,Abou-Seri, Sahar M.,Abdelnaby, Rana M.,Rateb, Heba S.,Khalil, Mahmoud A. F.,Hussein, Mohamed M.
, p. 109 - 116 (2016/04/10)
Objective: Synthesize new series of 7-hydroxy-4-methylcoumarin and 7-alkoxy-4-methylcoumarin derivatives featuring thiosemicarbazone or thiazolidin-4-one moieties and to evaluate their antimicrobial activity against two strains of Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), two Gram-negative bacteria (Escherichia Coli and Pseudomonas aeruginosa), and Candida albicans. Methods: Preparation of the new coumarin derivatives was done by adopting Pechmann condensation and attaching different isothiocyanates to give coumarin-thiosemicarbazone hybrids. Thiosemicarbazones were cyclized into thiazolidine-4-ones using chloroacetic acid or diethyl bromo malonate. Results: Compounds VIb, Xb, XIVb, and XVc gave the highest inhibition zones (>20 mm) against Staphylococcus aureus. Their MIC (minimum inhibitory concentration) values ranging from 0.19-0.36 μg/ml were better than the reference drug tobramycin with MIC= 2μg/ml. Conclusion: The newly synthesized compounds with the 7-hydroxyl group showed better antimicrobial activity than those with the 7-alkoxy groups.
Synthesis and photooxygenation of linear and angular furocoumarin derivatives as a hydroxyl radical source: Psoralen, pseudopsoralen, isopseudopsoralen, and allopsoralen
Elgogary, Sameh Ramadan,Hashem, Neveen Mohamed,Khodeir, Mohamed Nabeel
, p. 506 - 512 (2015/03/30)
Synthesis of linear and angular furocoumarins with new skeleton structure of potential photobiological feature interest was carried out through Williamson reaction of hydroxycoumarins with 3-chloro-2-butanone followed by cyclization with polyphosphoric acid or by heating in a strongly alkaline solution. The photooxygenation reactions of synthesized furocoumarins were performed in chloroform and in the presence of tetraphenylporphyrin as singlet oxygen sensitizer (1O2). The photooxygenation reactions afforded the photocleaved product through [2 + 2] cycloaddition and the photooxygenated products through ene reaction and [4 + 2] cycloaddition. The photoproducts were isolated and fully characterized by spectral analyses.
Synthesis of two-photon active cinnamoyl coumarins for high-contrast imaging of cancer cells and their photophysical characterization
Yadav, Preeti,Satapathi, Soumitra,Kumari, Meena,Chaturvedi, Akanksha,Li, Lian,Samuelson, Lynne A.,Kumar, Jayant,Sharma, Sunil K.
, p. 39 - 45 (2014/04/03)
A series of two-photon (TP) active 4-dimethylaminocinnamoyl coumarins were synthesized. These compounds exhibit red shift in absorption and considerable Stokes shift in emission spectra in comparison to the parent coumarin. Large TP absorption cross-sections were measured for all the coumarins in dilute solutions. A correlation between the chemical structure and TP characteristics was established. TP confocal microscopy revealed that these coumarin derivatives can be internalized by cancer cells rendering them a potential candidate as a label in TP confocal imaging.
