92-61-5Relevant articles and documents
Inhibition of catechol-O-methyltransferase (COMT) by some plant-derived alkaloids and phenolics
Yalcin, Dilek,Bayraktar, Oguz
, p. 162 - 166 (2010)
In this study, as an alternative to the medicines, natural compounds extracted from plant species (Peganum harmala, Cistus parviflorus and Vitex agnus-cactus) were investigated in order to inhibit the catechol-O-metyhltranferase (COMT) activity. In fluoro
OBTUSININ - A NEW COUMARIN FROM Haplophyllum obtusifolium
Matkarimov, A. D.,Batirov, E. Kh.,Malikov, V. M.,Seitmuratov, E.
, p. 240 - 242 (1980)
The epigeal part of Haplophyllum obtusifolium collected in Ustyurt has yielded β-sitosterol, isofraxetin, and a new coumarin - obtusinin - with the composition C15H18O6, mp 135-137 deg C (methanol), D20 +140.9 deg (c 0.44; chloroform).The structure of obtusinin has been established on the basis of the results of a study of UV, IR, PMR, and mass spectra and also of some chemical transformations (hydrolysis, acetylation).
A COUMARIN GLUCOSIDE FROM XEROMPHIS OBOVATA
Sibanda, S.,Ndengu, B.,Multari, G.,Pompi, V.,Galeffi, C.
, p. 1550 - 1552 (1989)
From root bark of Xeromphis obovata three coumarins have been isolated: scopoletin, its 7-β-D-glucopyranoside (scopolin) and the new β-D-apiosyl-(1" -> 6)-β-D-glucopyranoside of scopoletin, named xeroboside.Also two iridoids, deacetylasperulosidic acid methyl ester and gardenoside, have been isolated and identified as the corresponding acetyl derivetives. Key Word Index-Xeromphis obovata; Rubiaceae; coumarins; iridoids; xeroboside.
Glycosides of Atractylodes ovata.
Kitajima, Junichi,Kamoshita, Akane,Ishikawa, Toru,Takano, Akihito,Fukuda, Tatsuo,Isoda, Susumu,Ida, Yoshiteru
, p. 1106 - 1108 (2003)
A new coumarin glycoside and a new glycoside of an acetylene derivative were isolated from the water-soluble portion of the methanolic extract of Atractylodes ovata rhizome together with eight known compounds. Their structures were characterized as scopoletin beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside and (2E)-2-decene-4,6-diyne-1,8-diol 8-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside, respectively, based on chemical and spectroscopic investigations. A comparison of the polar constituents among Atractylodes japonica, Atractylodes lancea, and A. ovata is led to the conclusion that A. ovata is distinguishable from A. lancea and A. japonica, as also shown by phylogenetic analysis.
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.
Scopoletin benzene sulfonyl furazan oxynitride derivatives as well as preparation method and application thereof
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Paragraph 0039; 0048-0052, (2020/06/20)
The invention belongs to the field of biological medicines, and discloses scopoletin benzene sulfonyl furazan oxynitride derivatives as shown in a formula I, wherein R is selected from H, acetamido and amino, X is selected from -(CH2)n-, and n is an integer of 2-6. Compared with scopoletin, the derivatives have a stronger proliferation inhibition effect on MDA-MB-231, MCF-7, HepG2 and A549 cell strains, the proliferation inhibition effect on tumor cells is remarkably superior to that of scopoletin, and the derivatives are expected to become a new anti-tumor drug. The invention also discloses an application of the derivatives in the preparation of antitumor drugs.
Novel NO-releasing scopoletin derivatives induce cell death via mitochondrial apoptosis pathway and cell cycle arrest
Chen, Cheng,Chen, Li,Lei, Zhichao,Li, Na,Shi, Zhixian,Sun, Jianbo,Wang, Yujin
, (2020/05/19)
A series of phenylsulfonyfuroxan-based NO-releasing scopoletin derivatives were designed and synthesized in the study. All target compounds showed significantly improved antiproliferative activity against four cancer cell lines (MDA-MB-231, MCF-7, HepG2 and A459) and lower cytotoxicity toward normal liver LO2 cells. Derivative 47 concentration-dependently inhibited the colony formation of MDA-MB-231 cells. NO-releasing assessment indicated that the intracellular NO level was almost positively correlated with the antiproliferative ability. Compound 47, which released the highest amounts of NO, showed the best potency (IC50 = 1.23 μM) against MDA-MB-231 cells. Mechanism research revealed for the first time that 47 blocked the proliferation of MDA-MB-231 cells by activating mitochondrial apoptosis pathway and arresting cell cycle at G2/M phase. Taken together, as a novel scopoletin derivative, 47 exhibited excellent inhibitory effects against malignant cancer cells and lower toxicity on normal cells. Thus, an in-depth evaluation of 47 to explore its complete therapeutic potential for cancer treatment is warranted.
Escoparone chemical whole synthetic method
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Paragraph 0032; 0039-0041; 0045; 0052-0054, (2019/05/15)
The invention discloses escoparone chemical whole synthetic method, which belongs to the technical field of chemical synthesis, escoparone chemical full-synthetic method is 2, 4, 5 - trimethoxybenzaldehyde de-methyl generating 4 - dihydroxy - 5 - methoxybenzaldehyde; 4 - dihydroxy - 5 - methoxy benzaldehyde with malonic acid to generate the cyclization reaction to produce the 3 - carboxyl scopolamine lactone; 3 - carboxyl scopolamine lactone by microwave auxiliary decarboxylative generating scopolamine lactone; scopolamine lactone by methylation get escoparone, aims to solve the low efficiency of the plant extract, the disadvantage of low yield and the synthetic yield is low, high cost, is not suitable for the industrial application of the shortcomings.
Preparation method of scopoletin
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Paragraph 0048-0052, (2019/10/04)
The invention discloses a preparation method of scopoletin, which comprises the following steps: 1) with 2,4-dihydroxy-5-methoxybenzaldehyde as an initial raw material, adding a solvent and a catalyst, adding a malonic acid compound within a reaction temperature range of 0-300 DEG C, and carrying out a heat preservation reaction for 2-10 hours to obtain a reaction solution, the usage amount of the malonic acid compound being 1-10 equivalents; 2) cooling the reaction solution at a cooling temperature of -10 DEG C to 35 DEG C, wherein a large amount of solids is separated after the reaction solution is cooled, and carrying out reduced pressure suction filtration on the reaction solution from which the large amount of solids are separated out to obtain a crude product of the scopoletin and filtrate; and 3) recrystallizing the crude product of the scopoletin with ethyl acetate to obtain a pure product of the scopoletin. The method has the advantages of high yield, low cost and low pollution.
Synthesis and acaricidal activities of scopoletin phenolic ether derivatives: Qsar, molecular docking study and in silico Adme predictions
Luo, Jinxiang,Lai, Ting,Guo, Tao,Chen, Fei,Zhang, Linli,Ding, Wei,Zhang, Yongqiang
, (2018/05/04)
Thirty phenolic ether derivatives of scopoletin modified at the 7-hydroxy position were synthesized, and their structures were confirmed by IR,1H-NMR,13C-NMR, MS and elemental analysis. Preliminary acaricidal activities of these compounds against female adults of Tetranychus cinnabarinus (Boisduval) were evaluated using the slide-dip method. The results indicated that some of these compounds exhibit more pronounced acaricidal activity than scopoletin, especially compounds 32, 20, 28, 27 and 8 which exhibited about 8.41-, 7.32-, 7.23-, 6.76-, and 6.65-fold higher acaricidal potency. Compound 32 possessed the the most promising acaricidal activity and exhibited about 1.45-fold higher acaricidal potency against T. cinnabarinus than propargite. Statistically significant 2D-QSAR model supports the observed acaricidal activities and reveals that polarizability (HATS5p) was the most important parameter controlling bioactivity. 3D-QSAR (CoMFA: q2 = 0.802, r2 = 0.993; CoMSIA: q2 = 0.735, r2 = 0.965) results show that bulky substituents at R4, R1, R2 and R5 (C6, C3, C4, and C7) positions, electron positive groups at R5 (C7) position, hydrophobic groups at R1 (C3) and R2 (C4), H-bond donors groups at R1 (C3) and R4 (C6) will increase their acaricidal activity, which provide a good insight into the molecular features relevant to the acaricidal activity for further designing novel acaricidal agents. Molecular docking demonstrates that these selected derivatives display different bide modes with TcPMCA1 from lead compound and they interact with more key amino acid residues than scopoletin. In silico ADME properties of scopoletin and its phenolic ether derivatives were also analyzed and showed potential to develop as good acaricidal candidates.
