12-hydroxy-3-methoxystilbene | 190182-38-8

• 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: 12-hydroxy-3-methoxystilbene
• 英文别名: 4-Hydroxy-3'-methoxystilbene；4-[2-(3-methoxyphenyl)ethenyl]phenol
• CAS: 190182-38-8
• 化学式: C₁₅H₁₄O₂
• mdl: MFCD00045789
• 分子量: 226.275
• InChiKey: ZVJLZUWCAUTTBS-UHFFFAOYSA-N

物化性质

• 沸点：
  377.7±11.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  12-hydroxy-3-methoxystilbene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3,4'-Dihydroxystilben
  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
• 作为产物：
  描述：

  3-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 12-hydroxy-3-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

• [EN] SQUALENE COMPOUNDS AS MODULATORS OF LDL-RECEPTOR EXPRESSION<br/>[FR] COMPOSÉS DE SQUALÈNE EN TANT QUE MODULATEURS DE L'EXPRESSION DU RÉCEPTEUR LDL
  申请人：ISIS INNOVATION

  公开号：WO2016042318A1

  公开（公告）日：2016-03-24

  The present invention relates to compounds that modify low density lipoprotein receptor (LDLR) expression. The compounds have the structural formula I shown below: wherein m, R1, n, R2 and R3 are each as defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of diseases or disorders associated with elevated levels of low density lipoprotein cholesterol (LDL-C).

  本发明涉及修改低密度脂蛋白受体（LDLR）表达的化合物。这些化合物具有下面所示的结构式I：其中m、R1、n、R2和R3如本文所定义。本发明还涉及制备这些化合物的方法，包括它们的药物组合物，以及它们在治疗与低密度脂蛋白胆固醇（LDL-C）水平升高相关的疾病或紊乱中的应用。
• 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）
• Substituted biphenylalkoxyamines
  申请人：Ortho Pharmaceutical Corporation

  公开号：US05192786A1

  公开（公告）日：1993-03-09

  Novel substituted biphenylalkoxyamines and their synthesis are described. These novel compounds possess antimicrobial activity against yeasts and molds, and also have anticonvulsant and antisecretory properties. The compounds are useful for the treatment of yeast and mold infections in mammals, as well as the treatment of seizures and gastrointestinal diseases in mammals.

  本文描述了一种新型的取代双苯基烷氧基胺化合物及其合成方法。这些新型化合物具有抗真菌活性，可用于治疗哺乳动物的酵母和霉菌感染，同时还具有抗惊厥和抗分泌作用，可用于治疗哺乳动物的癫痫和胃肠疾病。
• Regio- and Stereoselective Biomimetic Synthesis of Oligostilbenoid Dimers from Resveratrol Analogues: Influence of the Solvent, Oxidant, and Substitution
  作者：Saraswati S. Velu、Irmaizatussyehdany Buniyamin、Lee Kiew Ching、Fareeda Feroz、Ibrahim Noorbatcha、Lim Chuan Gee、Khalijah Awang、Ibtisam Abd. Wahab、Jean-Frédéric Faizal Weber

  DOI：10.1002/chem.200801575

  日期：——

  Oligostilbenoids are polyphenols that are widely distributed in nature with multifaceted biological activities. To achieve biomimetic synthesis of unnatural derivatives, we subjected three resveratrol analogues to oligomerization by means of one-electron oxidants. Upon varying the metal oxidant (AgOAc, CuBr(2), FeCl(3)6 H(2)O, FeCl(3)6 H(2)O/NaI, PbO(2), VOF(3)), the solvent (over the whole range of

  寡类类胡萝卜素是多酚，在自然界中广泛分布，具有多方面的生物活性。为了实现仿生合成非天然衍生物，我们通过单电子氧化剂对三种白藜芦醇类似物进行了低聚。改变金属氧化剂（AgOAc，CuBr（2），FeCl（3）6 H（2）O，FeCl（3）6 H（2）O / NaI，PbO（2），VOF（3））后，溶剂（在整个极性范围内），以及原料的氧化取代模式，获得具有完全不同的碳骨架的二苯乙烯类低聚物。在这里，我们建议解释借助硬酸和软酸/碱概念生产的骨架类型的确定性，以及溶剂的溶剂化特性和通过pi堆积效应产生的优选排列方式。
• EP3193850A1
  申请人：——

  公开号：EP3193850A1

  公开（公告）日：2017-07-26