776-86-3Relevant articles and documents
6-PRENYLOXY-7-METHOXYCOUMARIN, A COUMARIN-HEMITERPENE ETHER FROM CARDUUS TENUIFLORUS
Cardona, Luz,Garcia, Begona,Pedro, Jose R.,Perez, Jose
, p. 3989 - 3992 (1992)
From the acetone extract of Carduus tenuiflorus, a new coumarin-hemiterpene ether was isolated, which was identified as 6-(3,3-dimethylallyloxy)-7-methoxycoumarin.The synthesis of this coumarin and that of its positional isomer 7-(3,3-dimethylallyloxy)-6-methoxycoumarin were carried out from esculetin.Two other coumarins, three lignans and three flavonoids were also isolated. Key Word Index: Carduus tenuiflorus; Compositae; prenyloxycoumarins; isolation; synthesis; lignans; flavonoids.
Synthesis and structure-activity relationship of coumarins as potent Mcl-1 inhibitors for cancer treatment
Xia, Yang-Liu,Wang, Jing-Jing,Li, Shi-Yang,Liu, Yong,Gonzalez, Frank J.,Wang, Ping,Ge, Guang-Bo
, (2020/11/25)
Myeloid cell leukemia-1 (Mcl-1) is a validated and attractive target for cancer therapy. Over-expression of Mcl-1 in many cancers allows cancer cells to evade apoptosis and contributes to their resistance to current chemotherapeutics. In this study, more than thirty coumarin derivatives with different substituents were designed and synthesized, and their Mcl-1 inhibitory activities evaluated using a fluorescence polarization-based binding assay. The results showed that the catechol group was a key constituent for Mcl-1 inhibitory activity of the coumarins, and methylation of the catechol group led to decreased inhibitory activity. The introduction of a hydrophobic electron-withdrawing group at the C-4 position of 6,7-dihydroxycoumarin, enhanced Mcl-1 inhibitory capacity, and a hydrophilic group in this position was unbeneficial to the inhibitory potency. In addition, the introduction of a nitrogen-containing group to the C-5 or C-8 position, which allowed an intramolecular hydrogen bond, was also unfavorable for Mcl-1 inhibition. Among all coumarins tested, 4-trifluoromethyl-6,7-dihydroxycoumarin (Cpd 4) displayed the most potent inhibitory activity towards Mcl-1 (Ki = 0.21 ± 0.02 μM, IC50 = 1.21 ± 0.56 μM, respectively), for which the beneficial effect on taxol resistance was also validated in A549 cells. A strong interaction between Cpd 4 and Mcl-1 in docking simulations further supported the observed potent Mcl-1 inhibition ability of Cpd 4. 3D-QSAR analysis of all tested coumarin derivatives further provides new insights into the relationships linking the inhibitory effects on Mcl-1 and the steric-electrostatic properties of coumarins. These findings could be of great value for medicinal chemists for the design and development of more potent Mcl-1 inhibitors for biomedical applications.
High-selectivity preparation method for 7-methoxy-6/8-hydroxy coumarin
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Paragraph 0028; 0029; 0030, (2017/08/28)
The invention provides a high-selectivity preparation method for 7-methoxy-6/8-hydroxy coumarin and belongs to the field of synthesis of natural medicines. The method comprises the steps of subjecting a catechol coumarin compound to a high-selectivity methylation reaction with a methylation reagent in a proper base catalyst added organic reaction system, so as to obtain a 7-hydroxyl mono-methylate, wherein the mole ratio of a base to the catechol coumarin compound is (2.0 to 7.0): 1, the mole ratio of the methylation reagent to the catechol coumarin compound is (1.0 to 3.0): 1, the temperature of the organic reaction system is 0 DEG C to 30 DEG C, and the reaction time is 1.0 to 5.0 hours. The method has the characteristics of simplicity in operation, moderate conditions, good selectivity, high yield and the like and can be applied to the preparation of mono-methylates of coumarin catechols with different types of substituents.
Synthesis and anti-acetylcholinesterase activity of scopoletin derivatives
Khunnawutmanotham, Nisachon,Chimnoi, Nitirat,Saparpakorn, Patchreenart,Techasakul, Supanna
, p. 137 - 145 (2016/03/09)
A series of scopoletin derivatives incorporated with the pyridinium moiety was synthesized and evaluated for their acetylcholinesterase (AChE) inhibitory activity by the colorimetric Ellman's method. A 2-fluorobenzylpyridinium derivative was the most potent among the tested compounds, with an IC50 value of 0.215 ± 0.015 μM, which was greatly improved from that of scopoletin. Docking studies revealed that the scopoletin portion of the mentioned compound was bound to the peripheral anionic site of the AChE, whereas the N-benzylpyridinium residue to the catalytic anionic site.
Diphenyl sulfate derivatives, preparation method of thereof and fluorophore sensor comprising thereof
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Paragraph 177-179, (2017/06/02)
The present invention relates to a diphenyl sulfate derivative, a method for preparing the same, and a fluorescence bio-sensor comprising the same. The diphenyl sulfate derivative having a novel structure according to the present invention traces cells and carries out immuno-fluorescence staining of the mitochondria of the cells satisfactorily. Thus, the diphenyl sulfate sulfate is useful in the glioma-related field and the research field including virus and DNA transfection, and can be used advisably as fluorescence bio-sensor for diagnosing diseases, such as glioma, sarcoma or leukemia.
Synthesis and evaluation of antibacterial and anti-inflammatory properties of naturally occurring coumarins
Azelmat, Jabrane,Fiorito, Serena,Taddeo, Vito Alessandro,Genovese, Salvatore,Epifano, Francesco,Grenier, Daniel
, p. 399 - 405 (2015/09/07)
Coumarins are a group of heterocyclic compounds naturally present in a large variety of plant families. Nevertheless, oxyprenylated coumarins have been only recently seen as valuable and promising biologically active phytochemicals. In this study, we synthesized three naturally occurring O-prenylcoumarins (1), (2), and (3), and evaluated their antibacterial and anti-inflammatory properties in view of their therapeutic potential against periodontal disease. The three O-prenylcoumarins were synthesized using well-known schemes leading to the chromen-2-one nucleus. The periodontal pathogen Porphyromonas gingivalis was found to be highly susceptible to all three O-prenylcoumarins with minimal inhibitory concentration values in the range of 12.5-25 mg/ml; the non-prenylated forms of the coumarins did not show any activity. The antibacterial activity of (1), (2), and (3) appeared to result from its ability to permeate the cell membrane. Using the U937-3xkB-LUC human monocytic cell line, compounds (2) and (3) dose-dependently inhibited lipopolysaccharide-induced NF-kB activation, while (1) did not. The non-prenylated forms of the coumarins were either inactive or much less potent. In conclusion, O-prenylcoumarins (2) and (3) by exhibiting a dual mode of action including antibacterial and anti-inflammatory activities may represent promising targeted therapeutic agents for localized treatment of periodontal diseases.
Lamellarins as inhibitors of P-glycoprotein-mediated multidrug resistance in a human colon cancer cell line
Plisson, Fabien,Huang, Xiao-Cong,Zhang, Hua,Khalil, Zeinab,Capon, Robert J.
supporting information; experimental part, p. 1616 - 1623 (2012/09/08)
Chemical analysis of a Didemnum sp. (CMB-01656) collected during scientific Scuba operations off Wasp Island, New South Wales, yielded five new lamellarins A1 (1), A2 (2), A3 (3), A4 (4) and A5 (5) and eight known lamellarins C (6), E (7), K (8), M (9), S (10), T (11), X (12) and χ (13). Analysis of a second Didemnum sp. (CMB-02127) collected during scientific trawling operations along the Northern Rottnest Shelf, Western Australia, yielded the new lamellarin A6 (14) and two known lamellarins G (15) and Z (16). Structures were assigned to 1-16 on the basis of detailed spectroscopic analysis with comparison to literature data and authentic samples. Access to this unique library of natural lamellarins (1-16) provided a rare opportunity for structure-activity relationship (SAR) investigations, probing interactions between lamellarins and the ABC transporter efflux pump P-glycoprotein (P-gp) with a view to reversing multidrug resistance in a human colon cancer cell line (SW620 Ad300). These SAR studies, which were expanded to include the permethylated lamellarin derivative (17) and a series of lamellarin-inspired synthetic coumarins (19-24) and isoquinolines (25-26), successfully revealed 17 as a promising new non-cytotoxic P-gp inhibitor pharmacophore. Copyright
New approach for the construction of the coumarin frame and application in the total synthesis of natural products
Jerezano, Alberto,Jimenez, Fabiola,Del Carmen Cruz, Maria,Montiel, Luisa E.,Delgado, Francisco,Tamariz, Joaquin
, p. 185 - 198 (2011/04/17)
A new synthetic approach is described for building the coumarin scaffold through the Lewis acid-promoted cyclization of novel aryl 3-(dimethylamino)prop- 2-enoates 2a - 2f. The latter precursors were prepared via aminomethylenation of the corresponding aryl acetates 4a - 4f with the Bredereck reagent. This approach was used for the synthesis of biologically active natural compounds 1a - 1f, through a three-step procedure starting from the corresponding phenols.
PROCESS FOR PREPARATION OF ESCULETIN COMPOUNDS, ESCULETIN COMPOUNDS AND INTERMEDIATES THEREOF, AND USE OF BOTH
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Page/Page column 8-9, (2010/01/31)
An esculetin compound, an intermediate thereof, a process for manufacturing an esculetin compound, and an antifungal composition for agriculture and horticulture and an herbicide comprising an esculetin compound or an intermediate thereof are provided. The process for manufacturing an esculetin compound is a low-cost, high-yield, and industrially practicable process, and comprises the following step.A process for manufacturing an esculetin compound of the formula (2): characterized by cyclizing a trihydroxybenzaldehyde compound of the formula (1): in an aprotic polar solvent in the presence of a weak base, with acetic anhydride or the like.
Monoalkylation of dihydroxycoumarins via Mitsunobu dehydroalkylation under high intensity ultrasound. The synthesis of ferujol
Cravotto, Giancarlo,Chimichi, Stefano,Robaldo, Bruna,Boccalini, Marco
, p. 8383 - 8386 (2007/10/03)
Monoalkylation of natural dihydroxycoumarins was carried out by Mitsunobu dehydroalkylation under sonochemical conditions. Aesculetin (6,7-dihydroxycoumarin) was selectively alkylated in good yield with prenyl alcohols at position 7, as clearly shown by N
