(E,E)-2,5-bis(4’-hydroxy-3’-carboxystyryl)benzene

• 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: (E,E)-2,5-bis(4’-hydroxy-3’-carboxystyryl)benzene
• 英文别名: (E,E)-1,4-bis(3'-carboxy-4'-hydroxystyryl)benzene；2,5-bis(4-hydroxy-3-carboxystyryl)benzene；X-34；5-((E)-2-{4-[(E)-2-(3-carboxy-4-hydroxyphenyl)vinyl]phenyl}vinyl)-2-hydroxybenzoic acid；X:E:B34；5-((E)-2-{4-[(E)-2-(3-carboxy-4-hydroxyphenyl)vinyl]-phenyl}vinyl)-2-hydroxybenzoic acid；5-[(E)-2-[4-[(E)-2-(3-carboxy-4-hydroxyphenyl)ethenyl]phenyl]ethenyl]-2-hydroxybenzoic acid
• 化学式: C₂₄H₁₈O₆
• 分子量: 402.403
• InChiKey: MCBNOAYTZBUCSX-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,4-二甲基-2-碘苯 在 吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 偶氮二异丁腈 、 水 、 sodium methylate 、 三溴化硼 、 sodium hydroxide 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 188.58h， 生成 (E,E)-2,5-bis(4’-hydroxy-3’-carboxystyryl)benzene
  参考文献：
  名称：

  Tritium-labeled (E,E)-2,5-bis(4′-hydroxy-3′-carboxystyryl)benzene as a probe for β-amyloid fibrils

  摘要：

  Accumulation of A beta in the brains of Alzheimer disease (AD) patients reflects an imbalance between A beta production and clearance from their brains. Alternative cleavage of amyloid precursor protein (APP) by processing proteases generates soluble APP fragments including the neurotoxic amyloid A beta 40 and A beta 42 peptides that assemble into fibrils and form plaques. Plaque-buildup occurs over an extended time-frame, and the early detection and modulation of plaque formation are areas of active research. Radiolabeled probes for the detection of amyloid plaques and fibrils in living subjects are important for noninvasive evaluation of AD diagnosis, progression, and differentiation of AD from other neurode-generative diseases and age-related cognitive decline. Tritium-labeled (E, E)-1-[H-3]-2,5-bis(4'-hydroxy-3'-carbomethoxystyryl)benzene possesses an improved level of chemical stability relative to a previously reported radioiodinated analog for radiometric quantification of A beta plaque and tau pathology in brain tissue and in vitro studies with synthetic A beta and tau fibrils. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.075

文献信息

• Derivatives of 1,4-bis(3-hydroxycarbonyl-4-hydroxyl)styrylbenzene as PTP1B inhibitors with hypoglycemic activity
  作者：Suja Shrestha、Bharat Raj Bhattarai、Bhooshan Kafle、Keun-Hyeung Lee、Hyeongjin Cho

  DOI：10.1016/j.bmc.2008.07.090

  日期：2008.9

  Disalicylic acid derivatives with stilbene and bis-styrylbenzene skeleton were synthesized as PTP1B inhibitors. The most potent in this series exhibited a submicromolar IC(50) value. One of the compounds 7b was tested in an animal model for its efficacy as an anti-diabetic or an anti-obesity agent. In feeding compound 7b to diet-induced obese mice, no significant differences in weight gain and food

  合成具有二苯乙烯和双苯乙烯基骨架的二水杨酸衍生物作为PTP1B抑制剂。该系列中最有效的药物表现出亚微摩尔IC（50）值。在动物模型中测试了化合物7b之一作为抗糖尿病药或抗肥胖药的功效。在向饮食诱导的肥胖小鼠饲喂化合物7b时，在药物治疗的小鼠和肥胖的对照小鼠之间未观察到体重增加和食物消耗的显着差异。然而，在肥胖诱导的糖尿病小鼠中，7b显着降低了空腹血糖水平并改善了葡萄糖耐量。
• Methods of preparing ophthalmic formulations and uses of same
  申请人：Cognoptix, Inc.

  公开号：US10350309B2

  公开（公告）日：2019-07-16

  The present invention relates to a process for preparing an ointment comprising subjecting a mixture of a fluorescent molecular rotor compound, mineral oil, and grinding media to ball milling agitation and combining this mixture with a hydrophobic vehicle for an ointment. The invention also relates to an ophthalmic formulation comprising a pharmaceutically acceptable carrier and a compound of the following structural Formula (I), or a pharmaceutically acceptable salt thereof: Values and preferred values of the variables in structural Formula (I) are described herein.

  本发明涉及一种制备软膏的工艺，包括将荧光分子转子化合物、矿物油和研磨介质的混合物进行球磨搅拌，并将该混合物与软膏的疏水性载体结合。本发明还涉及一种眼科制剂，该制剂包含一种药学上可接受的载体和一种结构式（I）如下的化合物或其药学上可接受的盐： 结构式（I）中各变量的值和优选值在此描述。
• Synthesis of Analogues of Congo Red and Evaluation of Their Anti-Prion Activity
  作者：Shane Sellarajah、Tamuna Lekishvili、Claire Bowring、Andrew R. Thompsett、Helene Rudyk、Christopher R. Birkett、David R. Brown、Ian H. Gilbert

  DOI：10.1021/jm049922t

  日期：2004.10.1

  No cure as of yet exists for any of the transmissible spongiform encephalopathies. In this paper, we describe the synthesis of analogues of Congo red and evaluation against a cellular model of infection, the SMB (scrapie mouse brain) persistently infected cell line, for their ability to inhibit the infectivity of the abnormal form of prion protein (PrP-res). The compounds have also been tested for their ability to inhibit the polymerization of PrPC by PrP-res. A number of analogues showed inhibition of PrP-res infectivity at nanomolar concentrations. Several analogues show promise; the most active compound, 2a, inhibits the formation of PrP-res in SMB cells with an EC50 of 25-50 nM.
• [EN] ANALOGUES OF CONGO RED AND EVALUATION OF THEIR ANTI-PRION ACTIVITY<br/>[FR] COMPOSES
  申请人：MEDICAL RES COUNCIL

  公开号：WO2005085189A3

  公开（公告）日：2005-12-29
• ALKYL, ALKENYL AND ALKYNYL CHRYSAMINE G DERIVATIVES FOR THE ANTEMORTEM DIAGNOSIS OF ALZHEIMER'S DISEASE AND $i(IN VIVO) IMAGING AND PREVENTION OF AMYLOID DEPOSITION
  申请人：UNIVERSITY OF PITTSBURGH

  公开号：EP0977815A1

  公开（公告）日：2000-02-09