51061-83-7Relevant academic research and scientific papers
Synthesis of 6-methoxy-4H-1-benzopyran-7-ol, a character donating component of the fragrance of Wisteria sinensis
Demyttenaere, Jan,Van Syngel, Kris,Peter Markusse,Vervisch, Stijn,Debenedetti, Silvia,De Kimpe, Norbert
, p. 2163 - 2166 (2002)
6-Methoxy-4H-1-benzopyran-7-ol 7, a major impact flavor compound of Wisteria sinensis has been synthesized from 2,4,5-trimethoxybenzaldehyde 1 via scopoletin 3. The synthetic sequence comprised (i) bisdemethylation of 2,4,5-trimethoxybenzaldehyde 1, (ii) Wittig reaction with ethoxycarbonylmethylenetriphenylphosphorane, (iii) hydrogenation on palladium/carbon in glacial acetic acid, (iv) DIBAL-H reduction of the intermediate lactone and (v) dehydration of the lactol with anhydrous oxalic acid.
Design, synthesis, and cytotoxic evaluation of novel scopoletin derivatives
Shi, Wei,Zhang, Jinlu,Bao, Na,Guan, Fuqin,Chen, Li,Sun, Jianbo
, p. 641 - 646 (2018)
A series of scopoletin derivatives were designed and synthesized by introducing α-aminoacetamide, acrylamide and β-aminopropamide, respectively, to 3-position of scopoletin, and their chemical structures were confirmed by ESI-MS, IR, 1H NMR, an
Coumarin derivative as well as synthesis method and application thereof
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Paragraph 0043-0045, (2021/03/24)
The invention belongs to the field of medicinal chemistry, and discloses a coumarin derivative shown as a formula I, wherein R1 is selected from H, a C1-C4 alkyl group and a C1-C4 alkoxy group, R2 isselected from substituted or unsubstituted phenyl, and a
Design, synthesis and biological activity evaluation of novel scopoletin-NO donor derivatives against MCF-7 human breast cancer in vitro and in vivo
Chen, Li,Deng, Qi,Lei, Zhichao,Li, Na,Sun, Jianbo,Wang, Kun,Yu, Nairong
, (2021/07/28)
In this study, eleven new 3- and 7-positions modified scopoletin derivatives (18a-k) were designed, synthesized, and biologically evaluated against human breast cancer cell lines. Most compounds showed improved antiproliferative activity against MCF-7 and MDA-MB-231 cells and weaker cytotoxicity on human breast epithelial cell line MCF-10A than lead compound 5. Among them, compound 18e exhibited the most potent antiproliferative activity against MCF-7 cells (IC50 = 0.37 ± 0.05 μM). Particularly, 18e produced the highest levels of nitric oxide (NO) intracellularly, and its antiproliferation effect was attenuated by hemoglobin (an NO scavenger). Further pharmacological research showed that 18e blocked the cell cycle at the G2/M phase, downregulated the phosphorylation of PI3K and Akt in MCF-7 cells and regulated the expressions of the apoptosis proteins to induce apoptosis. Moreover, 18e inhibited the growth of MCF-7 in vivo. Overall, 18e is a novel anticancer agent with the abilities of high concentration of NO releasing and the inhibition of PI3K/Akt signaling pathway, and may be a promising agent against MCF-7 human breast cancer.
Scopoletin benzene sulfonyl furazan oxynitride derivatives as well as preparation method and application thereof
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Paragraph 0039-0043; 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 0032-0035; 0045-0048, (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.
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.
Enantioselective Total Synthesis and Assignment of the Absolute Configuration of the Meroterpenoid (+)-Taondiol
Dethe, Dattatraya H.,Mahapatra, Samarpita,Sau, Susanta Kumar
supporting information, p. 2766 - 2769 (2018/05/22)
The first enantioselective total synthesis of (+)-taondiol, a pentacyclic marine meroterpenoid, has been achieved, which in addition to confirming the structure also established the absolute configuration of the natural product. The notable points in the synthetic route are synthesis of a highly functionalized tricyclic diterpenoid moiety starting from an enantiopure Wieland-Miescher ketone derivative in concise manner via Robinson-type annulation and an elegant hydrogen atom transfer olefin reduction followed by Lewis acid-catalyzed Friedel-Crafts reaction for one-pot C-C and C-O bond formations resulting in construction of the pentacyclic meroterpenoid skeleton.
Design, synthesis and cytotoxic activities of scopoletin-isoxazole and scopoletin-pyrazole hybrids
Shi, Wei,Hu, Jinglin,Bao, Na,Li, Dongang,Chen, Li,Sun, Jianbo
supporting information, p. 147 - 151 (2016/12/27)
12 novel scopoletin-isoxazole and scopoletin-pyrazole hybrids were designed, synthesized and their chemical structures were confirmed by HR-MS, IR,1H NMR and13C NMR spectra. The anticancer activities of the newly synthesized compounds were evaluated in vitro against three human cancer cell lines including HCT-116, Hun7 and SW620 by MTT assay. The screening results showed that six compounds (9a, 9c, 9d, 12a, 18b and 18d) exhibited potent cytotoxic activities with IC50values below 20?μM. Besides, we have further evaluated the growth inhibitory activities of six compounds against the human normal tissue cell lines HFL-1. Especially, compound 9d displayed significant anti-proliferative activity with IC50values ranging from 8.76?μM to 9.83?μM and weak cytotoxicity with IC50value of 90.9?μM on normal cells HFL-1, which suggested that isoxazole-based hybrids of scopoletin were an effective chemical modification to improve the anticancer activity of scopoletin.
