- Synthesis of 6-methoxy-4H-1-benzopyran-7-ol, a character donating component of the fragrance of Wisteria sinensis
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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.
- Demyttenaere, Jan,Van Syngel, Kris,Peter Markusse,Vervisch, Stijn,Debenedetti, Silvia,De Kimpe, Norbert
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Read Online
- Design, synthesis, and cytotoxic evaluation of novel scopoletin derivatives
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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
- Shi, Wei,Zhang, Jinlu,Bao, Na,Guan, Fuqin,Chen, Li,Sun, Jianbo
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Read Online
- Coumarin derivative as well as synthesis method and application thereof
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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
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Paragraph 0043-0045
(2021/03/24)
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- Design, synthesis and biological activity evaluation of novel scopoletin-NO donor derivatives against MCF-7 human breast cancer in vitro and in vivo
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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.
- Chen, Li,Deng, Qi,Lei, Zhichao,Li, Na,Sun, Jianbo,Wang, Kun,Yu, Nairong
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- Scopoletin benzene sulfonyl furazan oxynitride derivatives as well as preparation method and application thereof
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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.
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Paragraph 0039-0043; 0052
(2020/06/20)
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- Novel NO-releasing scopoletin derivatives induce cell death via mitochondrial apoptosis pathway and cell cycle arrest
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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.
- Chen, Cheng,Chen, Li,Lei, Zhichao,Li, Na,Shi, Zhixian,Sun, Jianbo,Wang, Yujin
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- Escoparone chemical whole synthetic method
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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.
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Paragraph 0032-0035; 0045-0048
(2019/05/15)
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- Enantioselective Total Synthesis and Assignment of the Absolute Configuration of the Meroterpenoid (+)-Taondiol
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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.
- Dethe, Dattatraya H.,Mahapatra, Samarpita,Sau, Susanta Kumar
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p. 2766 - 2769
(2018/05/22)
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- Synthesis and acaricidal activities of scopoletin phenolic ether derivatives: Qsar, molecular docking study and in silico Adme predictions
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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.
- Luo, Jinxiang,Lai, Ting,Guo, Tao,Chen, Fei,Zhang, Linli,Ding, Wei,Zhang, Yongqiang
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- Design, synthesis and cytotoxic activities of scopoletin-isoxazole and scopoletin-pyrazole hybrids
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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.
- Shi, Wei,Hu, Jinglin,Bao, Na,Li, Dongang,Chen, Li,Sun, Jianbo
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supporting information
p. 147 - 151
(2016/12/27)
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- Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach
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Lamellarin K is a complex pyrrole natural product and member of the lamellarin family – a group of natural products known for their potent biological activities, such as, antiproliferative activity and inhibition of P-gp mediated drug efflux pumps. We herein describe the synthesis of the N-benzyl-des-D ring analogue of lamellarin K using a route that centres on an acyl-Claisen reaction to eventually prepare a highly-functionalised 1-aryl-4-methyl-1,4-diketone. Paal-Knorr pyrrole formation using this diketone undergoes auto-oxidation to give a fully-substituted 5-formyl pyrrole which was converted into the natural lactone B ring. Antiproliferative testing of the N-benzyl-des-D ring analogue gave an IC50 of 2.63?μM against the MDA-MB-231 breast cancer cell line.
- Dittrich, Nora,Pilkington, Lisa I.,Leung, Euphemia,Barker, David
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p. 1881 - 1894
(2017/03/11)
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- Searching for multi-targeting neurotherapeutics against Alzheimer's: Discovery of potent AChE-MAO B inhibitors through the decoration of the 2H-Chromen-2-one structural motif
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The need for developing real disease-modifying drugs against neurodegenerative syndromes, particularly Alzheimer's disease (AD), shifted research towards reliable drug discovery strategies to unveil clinical candidates with higher therapeutic efficacy than single-targeting drugs. By following the multi-target approach, we designed and synthesized a novel class of dual acetylcholinesterase (AChE)-monoamine oxidase B (MAO-B) inhibitors through the decoration of the 2H-chromen-2-one skeleton. Compounds bearing a propargylamine moiety at position 3 displayed the highest in vitro inhibitory activities against MAO-B. Within this series, derivative 3h emerged as the most interesting hit compound, being a moderate AChE inhibitor (IC50 = 8.99 μM) and a potent and selective MAO-B inhibitor (IC50 = 2.8 nM). Preliminary studies in human neuroblastoma SH-SY5Y cell lines demonstrated its low cytotoxicity and disclosed a promising neuroprotective effect at low doses (0.1 μM) under oxidative stress conditions promoted by two mitochondrial toxins (oligomycin-A and rotenone). In a Madin-Darby canine kidney (MDCK)II-MDR1 cell-based transport study, Compound 3h was able to permeate the BBB-mimicking monolayer and did not result in a glycoprotein-p (P-gp) substrate, showing an efflux ratio = 0.96, close to that of diazepam.
- Pisani, Leonardo,Farina, Roberta,Soto-Otero, Ramon,Denora, Nunzio,Mangiatordi, Giuseppe Felice,Nicolotti, Orazio,Mendez-Alvarez, Estefania,Altomare, Cosimo Damiano,Catto, Marco,Carotti, Angelo
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- Gastroprotective activity of synthetic coumarins: Role of endogenous prostaglandins, nitric oxide, non-protein sulfhydryls and vanilloid receptors
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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.
- Sepulveda, Beatriz,Quispe, Cristina,Simirgiotis, Mario,Torres-Benítez, Alfredo,Reyes-Ortíz, Johanna,Areche, Carlos,García-Beltrán, Olimpo
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p. 5732 - 5735
(2016/11/25)
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- Scopolamine lactone derivative and its preparation method and application
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The invention discloses a scopoletin derivative as well as a preparation method and an application thereof. The general formula of the scopoletin derivative is formula (I), wherein R is selected from C1-4 alkyl and X is selected from a halo substituent. The scopoletin derivative has a remarkable anticoagulation effect and can remarkably prolong the in vitro blood coagulation time. The scopoletin derivative orally taken can quickly enter into blood to have the anticoagulation effect. The onset time and the curative effect of the scopoletin derivative for treating venous thromboembolic diseases are equivalent to those of warfarin and the scopoletin derivative is smaller in dosage and easy to control. The scopoletin derivative has novel medical use of preventing and treating venous thromboembolic diseases and meanwhile provides a novel treatment candidate medicine for patients with venous thromboembolic diseases. The invention further discloses the preparation method of the scopoletin derivative and the application of the scopoletin derivative in preparing anticoagulation medicines.
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Paragraph 0050-0053
(2017/03/28)
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- Synthesis and anti-acetylcholinesterase activity of scopoletin derivatives
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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.
- Khunnawutmanotham, Nisachon,Chimnoi, Nitirat,Saparpakorn, Patchreenart,Techasakul, Supanna
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p. 137 - 145
(2016/03/09)
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- Synthesis, in vitro and in vivo antitumor activity of scopoletin-cinnamic acid hybrids
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A series of hybrids of scopoletin and substituted cinnamic acid were designed, synthesized and evaluated in vitro and in vivo against five human tumor cell lines [MCF-7, MDA-MB-231, A549, HCT-116, and HeLa] with doxorubicin as the positive control. Compounds 17a, 17b, 17c and 17g exhibited potent cytotoxic activity. Especially, compound 17b displayed broad spectrum activity with IC50 values ranging from 0.249 μ1/4M to 0.684 μ1/4M. Moreover, in a preliminary pharmacological study, 17b not only remarkably induced cellular apoptosis, but also clearly induced A549 cells cycle arrest at S phase. In vivo study showed that 17b significantly suppressed tumor growth in a dose-dependent manner without causing the loss of the mean body weight of mice, which was superior to doxorubicin. These preliminary results indicate that 17b is an optimal anti-cancer leading compound and merit further structural modification.
- Li, Linhu,Zhao, Peng,Hu, Jinglin,Liu, Jinhong,Liu, Yan,Wang, Zhiqiang,Xia, Yufeng,Dai, Yue,Chen, Li
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p. 300 - 307
(2015/03/04)
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- Synthesis and biological evaluation of scopoletin derivatives
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A series of new scopoletin derivatives were designed and synthesized. Their anti-proliferative effect was initially evaluated against various human cancer cell lines. Among the tested compounds, A1, A2, and D6 showed significant anti-proliferative activities. Angiogenesis was detected by endothelial cell migration assay and tube formation study. The results showed that A1, A2, and D6 inhibited the vascular endothelial growth factor (VEGF)-stimulated proliferation, migration, and tube formation of human umbilical vein endothelial cells in vitro. Moreover, they inhibited the vessel growth in the chorioallantoic membrane in vivo. This inhibition was correlated with a significant decrease in the VEGF-triggered phosphorylated forms of ERK1/2 and Akt. In summary, these findings strongly suggested that these scopoletin derivatives might be structurally novel angiogenesis inhibitors.
- Cai, Xueting,Yang, Jie,Zhou, Jinpei,Lu, Wuguang,Hu, Chunping,Gu, Zhenhua,Huo, Jiege,Wang, Xiaoning,Cao, Peng
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- Total synthesis of six 3,4-unsubstituted coumarins
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In this article we describe a new methodology for the total synthesis of 3,4-unsubstituted coumarins from commercially available starting materials. Six examples were prepared, including five naturally occurring coumarins-7-hydroxy- 6,8-dimethoxycoumarin (isofraxidin), 7-hydroxy-6-methoxycoumarin (scopoletin), 6,7,8-trimethoxycoumarin, 6,7-dimethoxycoumarin (scoparone), and 7,8-dihydroxycoumarin (daphnetin) and one synthetic coumarin, 7-hydroxy-6-ethoxycoumarin. Moreover, five important o-hydroxybenzaldehyde intermediates were also obtained, namely 2,4-dihydroxy-3,5- dimethoxybenzaldehyde, 2,4-dihydroxy-5-methoxybenzaldehyde, 5-ethoxy-2,4- dihydroxybenzaldehyde, 2-hydroxy-3,4,5-trimethoxybenzaldehyde, and 2-hydroxy-4,5-dimethoxybenzaldehyde. The method developed herein involves just three or four steps and allows for the rapid synthesis of these important molecules in excellent yields. This is the first synthesis of 6,7,8-trimethoxycoumarin and 7-hydroxy-6-ethoxycoumarin.
- Gao, Wenqing,Li, Qingyong,Chen, Jian,Wang, Zhichao,Hua, Changlong
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p. 15613 - 15623
(2014/01/17)
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- Synthesis and antitumor activity of scopoletin derivatives
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Studies have shown that natural product scopoletin has significant pharmacological activities, such as antiarthritic, spasmolytic, antitumoral, antidepressant-like, antifungal, antihyperglycemic and antioxidative. In search of new antitumor agents, twelve scopoletin derivatives were designed and synthesized by a systematic combinatorial chemical approach and their chemical structures were confirmed by MS, IR, 1H NMR spectra and elemental analysis. Preliminary screening against mammary cells HUVEC and MCF-7 indicated that three compounds (5a, 5b, 5e) displayed reasonable antitumor activity with IC50 values below 18 μM whereas scopoletin showed its IC 50 values above 100 7μM. These results clearly indicated that structural modification of scopoletin can greatly increase its antitumor activity in vitro.
- Zhou, Jinpei,Wang, Lei,Wei, Lijuan,Zheng, Yu,Zhang, Huibin,Wang, Yubin,Cao, Peng,Niu, Ao,Wang, Jing,Dai, Yue
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experimental part
p. 397 - 401
(2012/07/28)
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- Synthesis of 2,3-syn-diarylpent-4-enamides via acyl-Claisen rearrangements of substituted cinnamyl morpholines: Application to the synthesis of magnosalicin
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The acyl-Claisen rearrangement of substituted phenylacetyl chlorides and cinnamyl morpholines gives 2,3-syn-diarylpent-4-enamides. Electron-rich cinnamyl morpholines containing alkoxy substituents only reacted with phenylacetyl chlorides; replacement of t
- Dickson, Benjamin D.,Dittrich, Nora,Barker, David
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scheme or table
p. 4464 - 4468
(2012/09/25)
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- Synthesis and in vitro antitumor activity of novel scopoletin derivatives
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Twenty scopoletin derivatives were developed by a systematic combinatorial chemical approach and their chemical structures were confirmed by MS, IR, 1H NMR spectra and elemental analysis. Primary screening against mammary (MCF-7 and MDA-MB 231) and colon (HT-29) carcinoma cells indicated that five compounds (8d, 8g, 8j, 11b and 11g) displayed high antitumor potencies with IC50 values below 20 μM whereas scopoletin showed IC50 values above 100 μM. Moreover, the most promising compound 11g was more active than 5-fluorouracil. These results clearly indicated that the modification of the scopoletin structure could greatly increase its antitumor activity in vitro.
- Liu, Wukun,Hua, Jie,Zhou, Jinpei,Zhang, Huibin,Zhu, Haiyang,Cheng, Yanhua,Gust, Ronald
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scheme or table
p. 5008 - 5012
(2012/08/28)
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- Synthesis and topoisomerase i inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D
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A novel 5-oxa-6a,8-diazaindeno[2,1-b]phenanthren-7-one scaffold was designed and synthesized as an active analogue of the cytotoxic marine alkaloid Lamellarin D. The design was based on molecular modeling of the site of interaction of Lamellarin D with DNA-topoisomerase I cleavable complex, whereas the synthesis capitalized on a simple Friedel-Crafts cyclization of indole to a β-carbolinone nucleus. The product exhibited topoisomerase I poisoning activity and submicromolar cytotoxicity on human non-small cell lung cancer H460 cell line.
- Cananzi, Salvatore,Merlini, Lucio,Artali, Roberto,Beretta, Giovanni Luca,Zaffaroni, Nadia,Dallavalle, Sabrina
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experimental part
p. 4971 - 4984
(2011/10/05)
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- Optimization of the antioxidant activity of hydroxy-substituted 4-thiaflavanes: A proof-of-concept study
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The design and the synthesis of a new family of hydroxy-4-thiaflavanes, in which the reactive phenolic OH is ortho to the sulfur atom of the benzofused oxathiin ring, allowed to prepare antioxidants that show rate constants for the reaction with peroxyl radicals (kinh), and bond dissociation energies (BDE), of the ArO-H group identical to those of α-tocopherol, the main component of vitamin E and the most effective lipophilic antioxidant known in nature. The peculiar conformation of the six-membered heterocyclic ring prevents the formation of an intramolecular hydrogen bond between the OH group and the S atom, while ensuring a good stabilization by electron donation of the phenoxyl radical formed after the reaction with peroxyl radicals. The preparation of these compounds was achieved through an inverse electron demand hetero Diels-Alder reaction of styrenes with o-thioquinones, in turn prepared from accurately designed 1,3-dihydroxy arenes. Properly arranging the substitution pattern on the aromatic ring, as in derivatives 9 and 11, allowed to reach values of kinh up to 4.0× 106 M-1 s -1 and BDE(OH) of 77.2 kcal mol-1. This approach represents an innovative way to obtain highly active antioxidants without using strongly electron donating alkylamino groups which are associated with adverse toxicological profiles. Sulfur makes the difference (again): The stereoelectronic features triggered by the sulfur atom in the benzo-fused six-membered ring of 4-thiaflavanes have been exploited to design a new family of phenolic antioxidants that show an ability to react with peroxyl radicals identical to that of α-tocopherol, the main component of vitamin E and the most potent natural lipophilic antioxidant (see scheme). Copyright
- Viglianisi, Caterina,Bartolozzi, Maria Grazia,Pedulli, Gian Franco,Amorati, Riccardo,Menichetti, Stefano
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supporting information; experimental part
p. 12396 - 12404
(2011/11/29)
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- NEW PHARMACEUTICAL COMPOUNDS
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Compounds of formula (I), wherein R1-R4, X, Y and Z are as defined in claims, exhibit COMT enzyme inhibiting activity and are thus useful as COMT inhibitors.
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Page/Page column 30-31
(2008/06/13)
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- Synthesis and electronic absorption and fluorescence of 2-arylbenzothiazole derivatives
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A series of new 2-arylbenzothiazoles have been prepared in high yields by Jacobson's cyclization condensation of 2-aminobenzenethiol with benzoyl chloride or benzaldehyde derivatives under three different routes. These compounds have been fully characterized by EA, IR, NMR and MS. The electronic absorption and fluorescence of these compounds have been systematically investigated for the first time. The relationships between their photophysical properties and structures have been discussed. The alteration of absorption and emission wavelengths can be elucidated by Hammett's substituent constants.
- Chen, Lianqing,Yang, Chuluo,Li, Suyue,Qin, Jingui
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p. 317 - 322
(2008/02/13)
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- Synthesis of virgatol and virgatenol, two naturally occurring coumarins from Pterocaulon virgatum (L.) DC, and 7-(2,3-epoxy-3-methylbutoxy)-6- methoxycoumarin, isolated from Conyza obscura DC
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The synthesis of a number of naturally occurring coumarins from Pterocaulon virgatum (L.) and Conyza obscura DC is described for the first time. It concerns the synthesis of 7-(2-hydroxy-3-methoxy-3-methylbutoxy)-6- methoxycoumarin (virgatol, 1), 7-(2-hydroxy-3-methyl-3-butenyloxy)-6- methoxycoumarin (virgatenol, 2) and 7-(2,3-epoxy-3-methylbutoxy)-6- methoxycoumarin (3). In addition, a straightforward synthesis of scopoletin (4) (7-hydroxy-6-methoxycoumarin) is reported and the synthesis of a new coumarin derivative, 6-methoxy-7-(2-oxo-3-methylbutoxy)coumarin (7), is described.
- Demyttenaere, Jan,Vervisch, Stijn,Debenedetti, Silvia,Coussio, Jorge,Maes, Dominick,De Kimpe, Norbert
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p. 1844 - 1848
(2007/10/03)
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- An Expeditious Synthesis of (±)-Mimosifoliol Utilizing a Cascade Involving an o-Quinone Methide Intermediate
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An efficient synthesis of (±)-mimosifoliol is reported. The key transformation involves a domino sequence leading to an o-quinone methide and its subsequent consumption in 1,4-conjugate addition with a vinyl Grignard reagent.
- Tuttle, Kristin,Rodriguez, Andrew A.,Pettus, Thomas R. R.
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p. 2234 - 2236
(2007/10/03)
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- An Improved Synthesis of Naturally Occuring Coumarins: Synthesis of Herniarin, Scoparone and 7-Methoxy-6-methylcoumarin
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Vilsmeier-Haack reaction of methoxybenzenes (1a-c) gives aldehydes (2a-c), which on demethylation with AlCl3 in CH2Cl2 yield the hydroxyaldehydes (3a-c).These hydroxyaldehydes on reaction with carbethoxymethylenetriphenylphosphorane furnish the naturally occuring coumarins, herniarin (4a), scoparone (4b) and 7-methoxy-6-methylcoumarin (4c).
- Mali, R. S.,Yadav, V. J.,Zaware, R. N.
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p. 759 - 760
(2007/10/02)
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