4-hydroxy-4'-methoxystilbene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-hydroxy-4'-methoxystilbene
• 英文别名: 4-[2-(4-methoxyphenyl)ethenyl]phenol
• 化学式: C₁₅H₁₄O₂
• mdl: MFCD28954202
• 分子量: 226.275
• InChiKey: KKYPOVJDPNCJMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-4'-methoxystilbene 在 laccase from Trametes versicolor 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 以65%的产率得到
  参考文献：
  名称：

  白藜芦醇相关脱氢二聚体：漆酶介导的仿生合成和抗增殖活性

  摘要：

  在来自变色栓菌 (TvL) 的漆酶存在下，将七种白藜芦醇相关单体芪类化合物进行仿生氧化偶联，得到外消旋二氢苯并呋喃脱氢二聚体 (±)-15 至 (±)-21。在光谱表征之后，这些产品被提交给针对 SW480 人结肠癌细胞的抗增殖活性生物测定。发现五种外消旋体具有活性，并通过手性 HPLC 进行拆分。对纯对映异构体进行圆二色性测量以确定它们在 C-7 和 C-8 处的绝对构型。这些对映体纯化合物进行了针对 SW480 细胞的抗增殖活性测定，并且都显示出活性，IC50 值在大约 20-90 μM 的范围内。在某些情况下，7R、8R 和 7S 的活性之间存在显着差异，观察到 8S 对映异构体，但立体中心的确定构型似乎不是该活性的结构要求。最有活性的化合物和无活性的化合物之间的比较强烈表明，在 C-4 羟基的邻位存在甲氧基对活性非常有害。

  DOI：

  10.1002/ejoc.201200664
• 作为产物：
  描述：

  4-甲氧基苯乙烯 、 4-碘苯酚 在 三乙醇胺 、 palladium diacetate 作用下， 反应 1.0h， 生成 4-hydroxy-4'-methoxystilbene
  参考文献：
  名称：

  TRPA1 channels as targets for resveratrol and related stilbenoids

  摘要：

  A series of twenty resveratrol analogues was synthesized and tested on TRPA1 and TRPV1 channels. None was able to significantly modulate TRPV1 channels. Conversely, most of them exhibited remarkably higher TRPA1 modulating activity than resveratrol. Optimal potency was observed with ortho monoxy-genated stilbenes 6 and 17. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.065

文献信息

• Hydroxylated di- and tri-styrylbenzenes, a new class of antiplasmodial agents: discovery and mechanism of action
  作者：Naina Sharma、Dinesh Mohanakrishnan、Amit Shard、Abhishek Sharma、Arun K. Sinha、Dinkar Sahal

  DOI：10.1039/c6ra06059e

  日期：——

  showed IC50 values of 0.9, 2.0 and 2.7 against 3D7 (chloroquine sensitive), Dd2 and Indo (chloroquine resistant) strains of Plasmodium falciparum respectively. Moreover, 27 and 11, which exhibited selectivity indices of 40 and >111 were also found to be nontoxic to the HeLa cell line. Microscopic studies revealed that the rings and trophozoites obtained from the 27 and 11 (an octupolar tristyrylbenzene

  首次系统评价了天然产物和二/三苯乙烯基苯的羟基二苯乙烯家族的抗疟原虫活性。使用修饰的Knoevenagel-Perkin-脱羧化-Heck序列，从容易获得的起始材料（即，羟基苯甲醛-苯乙酸-芳基卤化物）中快速合成了27个不同取代的羟基类苯乙烯类化合物的文库。评价了这些化合物对三种不同菌株恶性疟原虫的体外抗血浆活性。值得注意的是，4,4'4'' - （（1- Ë，1' ë，1'' Ë） -苯-1,3,5-三基三（乙烯-2,1-二基））三（2,6-二甲氧基苯酚）（27），一种八极类芪，对3D7（对氯喹敏感），Dd2和I​​ndo（对氯喹抗性）菌株的IC 50（μM）值分别为0.6、0.5和1.36，而二苯乙烯基苯（11）的IC 50值为0.9、2.0和2.7。的恶性疟原虫分别。此外，还发现选择性指数为40和> 111的27和11对HeLa细胞系无毒。显微镜研究表明，从27和11获得的环和滋养体
• A Genomic DNA Reporter Screen Identifies Squalene Synthase Inhibitors That Act Cooperatively with Statins to Upregulate the Low-Density Lipoprotein Receptor
  作者：Alastair G. Kerr、Lawrence C. S. Tam、Ashley B. Hale、Milena Cioroch、Gillian Douglas、Sarina Agkatsev、Olivia Hibbitt、Joseph Mason、James Holt-Martyn、Carole J. R. Bataille、Graham M. Wynne、Keith M. Channon、Angela J. Russell、Richard Wade-Martins

  DOI：10.1124/jpet.116.239574

  日期：2017.6

  profile and showed in vivo efficacy. Compounds OX03050 and OX03771 were found to inhibit squalene synthase, the first committed step in cholesterol biosynthesis. These squalene synthase inhibitors were shown to act cooperatively with statins to increase LDLR expression in vitro. Overall, we demonstrated here a novel series of small molecules with the potential to be further developed to treat patients

  高胆固醇血症仍然是心血管疾病发展的主要危险因素之一。许多大型双盲研究表明，使用他汀类药物降低低密度脂蛋白（LDL）胆固醇可将发生心血管事件的风险降低约30％。然而，尽管他汀类药物获得了成功，但由于依从性或效力问题，一些患者人群仍无法降低其LDL胆固醇以满足目标脂质水平。对于患有杂合性家族性高胆固醇血症的患者尤其如此，他们可能需要额外上调低密度脂蛋白受体（LDLR）才能将LDL胆固醇水平降低到最大剂量他汀类药物可达到的水平。在这里，我们从基因组DNA报告分子筛选中鉴定出一系列小分子，它们以纳摩尔效价（EC50 = 39 nM）上调了小鼠和人肝细胞系中的LDLR。对铅化合物OX03771 [（E）-N，N-二甲基-3-（4-苯乙烯基苯氧基）丙-1-胺]进行的构效关系研究导致鉴定了化合物OX03050 [（E）- 3-（4-苯乙烯基苯氧基）丙-1-醇]，具有相似的效价（EC50 = 26 nM）
• Stilbene synthesis through decarboxylative cross-coupling of substituted cinnamic acids with aryl halides
  作者：Nelly Rameau、Baptiste Russo、Stéphane Mangematin、Catherine Pinel、Laurent Djakovitch

  DOI：10.1016/j.apcata.2018.04.031

  日期：2018.6

  acid and aryl iodide derivatives was studied using both homogeneous and heterogeneous Pd-catalysts. It was demonstrated that simple Pd(OAc)2 can catalyze this reaction with useful to high yields when engaging ferulic acid whatever the nature of the aryl iodide. However, limitations were found when varying the nature of the cinnamic acid derivatives mainly due to low decarboxylation process. This could

  使用均相和非均相钯催化剂，研究了肉桂酸与芳基碘化物衍生物之间的钯催化的脱羧交叉偶联反应。已证明，无论芳基碘化物的性质如何，当与阿魏酸接合时，简单的Pd（OAc）2都可以高产率地催化该反应。然而，当改变肉桂酸衍生物的性质时，发现局限性主要是由于低脱羧过程。在某些情况下，可以通过添加Cu（OH）2 / 1,10-菲咯啉作为助催化剂来克服这一问题。在存在非均相催化剂的情况下，研究表明，Pd / C和自制的Pd / SiO 2催化剂均可提供较高的产品收率。然而，尽管活性较低，但已证明Pd / SiO由于具有较高的稳定性，因此2种催化剂可在至少4个循环中重复使用。
• Non-linear and potential non-linear optical materials containing molybdenum or tungsten mononitrosyl redox centres. Stilbene derivatives containing ferrocenyl, methoxy or dimethylamino donor groups
  作者：Benjamin J. Coe、Thomas A. Hamor、Christopher J. Jones、Jon A. McCleverty、David Bloor、Graham H. Cross、Tony L. Axon

  DOI：10.1039/dt9950000673

  日期：——

  Kurtz powder test for second harmonic generation (SHG). The ferrocenyl derivatives have been found to exhibit SHG on irradiation at 1907 nm, whereas all of the derivatives containing NMe2 or OMe groups are SHG inactive. The crystal structure of [Mo(NO)HB(dmpz)3}ClOC6H4[CHCHC6H4(NMe2-4)]-4}] shows that, although the compound crystallises in a polar space group, the lattice contains pseudocentrosymmetrically

  化合物[M（NO）HB（dmpz）3 } X n EC 6 H 4（CH CHC 6 H 3 –R，R'）-4} 2- n ]（dmpz = 3,5-二甲基吡唑基，n = 1，E = NH，R = [（η 5 -C 5 H ^ 4）的Fe（η 5 -C 5 H ^ 5）] - 4，R'= H; E = O，R = R'= H，E ＝ O或NH，R ＝ 4-OMe，R′＝ H； R ＝ 4-NMe 2，R′＝ H； E ＝ NH，R ＝ 2-OMe，R′＝ 4-OMe； R ＝ 3-OMe ，R'= 4-OMe； R = 2-OMe，R'= 5-OMe； M = Mo，X = Cl或I； M = W，X = Cl；n = 2； E = O，R = R ′= H; E = O或NH，R = 4-OMe或-NMe 2，R′＝ H；E = NH，R = 2-OMe，R'= 4-OMe; R ＝
• Searching for New Tools to Counteract the Helicobacter pylori Resistance: The Positive Action of Resveratrol Derivatives
  作者：Paola Di Fermo、Silvia Di Lodovico、Rosa Amoroso、Barbara De Filippis、Simonetta D’Ercole、Emanuela Di Campli、Luigina Cellini、Mara Di Giulio

  DOI：10.3390/antibiotics9120891

  日期：——

  The drug-resistance phenomenon in Helicobacter pylori underlines the need of novel strategies to improve the eradication rate including alternative treatments combining antibiotic and non-antibiotic compounds with synergistic action. In this study, the antibacterial (MIC/MBC) and anti-virulence effects (biofilm reduction and swarming motility inhibition) of resveratrol-RSV and new synthetized RSV-phenol derivatives, with a higher bioavailability, alone and combined with levofloxacin-LVX were evaluated against resistant H. pylori clinical strains. The experiments were confirmed in vivo using the Galleria mellonella model. Among the studied RSV derivatives, RSV-3 and RSV-4 possessed higher antibacterial activity with respect to RSV (MICs from 6.25 to 200 µg/mL and from 3.12 to 200 µg/mL, respectively). RSV, RSV-3, and RSV-4 were able to synergize with LVX restoring its effect in two out of seven clinical resistant strains tested for the study. RSV, RSV-3, and RSV-4, alone and with LVX at sub-MIC and sub-synergistic concentrations, significantly reduced the biofilm formation. Moreover, RSV-3 and RSV-4 reduced the H. pylori swarming motility on soft agar. RSV, RSV-3, and RSV-4 were non-toxic for G. mellonella larvae and displayed a protective effect against H. pylori infection. Overall, RSV–phenol derivatives should be considered interesting candidates for innovative therapeutic schemes to tackle the H. pylori antibiotic resistance.

  幽门螺杆菌耐药现象强调了需要采用新策略来提高根除率，包括联合具有协同作用的抗生素和非抗生素化合物的替代治疗方法。本研究评估了白藜芦醇-RSV和新合成的具有更高生物利用度的RSV-酚衍生物，单独和与左氧氟沙星-LVX联合使用，对耐药的幽门螺杆菌临床菌株的抗菌效应（MIC/MBC）和抗毒力效应（生物膜减少和游走运动抑制）。使用Galleria mellonella模型在体内进行了确认实验。在研究的RSV衍生物中，RSV-3和RSV-4相对于RSV具有更高的抗菌活性（MIC分别为6.25至200 µg/mL和3.12至200 µg/mL）。RSV、RSV-3和RSV-4能够与LVX协同作用，恢复其在七种临床耐药菌株中的效果。RSV、RSV-3和RSV-4单独和与亚MIC和亚协同浓度的LVX联合使用，显著减少了生物膜的形成。此外，RSV-3和RSV-4减少了软琼脂上的幽门螺杆菌游走运动。RSV、RSV-3和RSV-4对G. mellonella幼虫无毒，并对幽门螺杆菌感染显示出保护效果。总体而言，RSV-酚衍生物应被视为创新治疗方案的有趣候选者，以解决幽门螺杆菌的抗生素耐药性。