(E)-2-hydroxy-5-styrylbenzoic acid | 1072937-49-5

• 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)-2-hydroxy-5-styrylbenzoic acid
• 英文别名: 5-[(E)-2-Phenylvinyl]-2-hydroxybenzoic acid；2-hydroxy-5-[(E)-2-phenylethenyl]benzoic acid
• CAS: 1072937-49-5
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: JZELPKQSIAYAOP-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴-4-羟基苯甲醛 在 N-甲基二环己基胺 、 magnesium 、 1,2-二溴乙烷 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.67h， 生成 (E)-2-hydroxy-5-styrylbenzoic acid
  参考文献：
  名称：

  [EN] THERAPY
  [FR] THÉRAPIE

  摘要：

  该发明解决了涉及放射治疗的癌症治疗中的放射抗性问题，特别是与药物磺胺嘧啶的使用相关的限制。具体而言，它提供了一系列化合物，用作放射增敏剂治疗癌症，例如致命且固有对放射治疗具有抗性的胶质母细胞瘤。在一个实施例中，该发明提供了一般式(I)的化合物，它们的立体异构体和药学上可接受的盐，用作放射增敏剂治疗癌症，其中环A选自可选择取代的苯基、联苯基和芴基；每个X独立选自：-C1-6烷基（优选C1-3烷基，例如-CH3）、-O-C1-6烷基（优选-O-C1-3烷基，例如-OCH3）、-S-C1-6烷基（优选-S-C1-3烷基，例如-SCH3）、-OH、-SH、-CO2R1（其中R1为H或C1-6烷基，优选C1-3烷基，例如-CH3）、-SO2-C1-6烷基（优选-SO2-C1-3烷基，例如-SO2-CH3）、-SO2-NR2R3（其中R2为H且R3为可选择取代的苯基）、-NR4R5（其中R4和R5独立选自H、C1-6烷基（优选C1-3烷基，例如-CH3）和-CO-C1-6烷基（优选-CO-C1-3烷基，例如-CO-CH3）、卤素（例如F、Cl或Br）和可选择取代的四唑基；n为0到5的整数，优选为0到2，例如1或2；并表示E或Z双键。

  公开号：

  WO2021058979A1

文献信息

• Scope and limitations of the Heck–Matsuda-coupling of phenol diazonium salts and styrenes: a protecting-group economic synthesis of phenolic stilbenes
  作者：Bernd Schmidt、Nelli Elizarov、René Berger、Frank Hölter

  DOI：10.1039/c3ob40420j

  日期：——

  4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4′-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior

  4-苯酚重氮盐与各种苯乙烯进行Pd催化的Heck反应，生成4'-羟基苯乙烯。与类似的4-甲氧基苯重氮盐相比，几乎在所有情况下均观察到更高的收率和更少的副产物。相反，用2-和3-苯酚重氮盐使反应完全失败。对于这些取代方式，甲氧基取代的衍生物是优越的。
• [EN] COMPOUNDS FOR MODULATING DDAH AND ADMA LEVELS, AS WELL AS METHODS OF USING THEREOF TO TREAT DISEASE<br/>[FR] COMPOSÉS DESTINÉS À MODULER LES NIVEAUX DE DDAH ET D'ADMA, AINSI QUE LEURS MÉTHODES D'UTILISATION POUR TRAITER UNE MALADIE
  申请人：VASCULONICS LLC

  公开号：WO2019213148A1

  公开（公告）日：2019-11-07

  Disclosed are compounds that can modulate DDAH and the amount of asymmetric dimethylarginine (ADMA) in a subject. Also provided are pharmaceutical compositions comprising these compounds, as well as methods of using these compositions to treat and/or prevent diseases associated with elevated or low levels of DDAH and ADMA.

  揭示了能够调节DDAH和主体中不对称二甲基精氨酸（ADMA）含量的化合物。还提供了包含这些化合物的药物组合物，以及使用这些组合物治疗和/或预防与DDAH和ADMA水平升高或降低相关的疾病的方法。
• 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。
• AUTOPHAGY ENHANCER AND USE THEREOF
  申请人：Industry-Academic Cooperation Foundation, Yonsei University

  公开号：US20190336483A1

  公开（公告）日：2019-11-07

  Provided are a compound of chemical formula 1 or 2 and a use thereof. The compound can be advantageously used in the prevention or treatment of metabolic diseases including type 2 diabetes, insulin resistance, or obesity, on the basis of a mechanism of autophagy activation through the promotion of lysosome production.

  提供了化学式为1或2的化合物及其用途。该化合物可以有利地用于预防或治疗代谢性疾病，包括2型糖尿病、胰岛素抵抗或肥胖，其基础是通过促进溶酶体产生来激活自噬机制。
• METAL OXIDES NANOPARTICLES CONJUGATED WITH NAPHTHALENE DERIVATIVES AS CONTRAST AGENTS FOR THE DETECTION OF BETA AMYLOID PLAQUES BY MAGNETIC RESONANCE IMAGES
  申请人：Centro De Neurociencias De Cuba

  公开号：EP3878475A1

  公开（公告）日：2021-09-15

  This invention is related to Chemistry and Physics applied to the field of Medicine and refers to the use of compounds with magnetic properties, which belong to the category of metal oxide nanoparticles, coated and conveniently functionalized, which are conjugated with naphthalene compounds related to agglomerates and β-amyloid plaques present in neurodegenerative diseases. These new nanoparticles (NPs) are used for the non-invasive detection of agglomerates and amyloid plaques using the Magnetic Resonance Imaging (MRI) technique. The nanoparticles described here cross the blood-brain barrier (BBB), without the use of any membrane-disrupting agent. Likewise, they bind with high affinity and specificity to the agglomerates and β-amytoid plaques, and are used as contrast agents in MRI for the early detection of Alzheimer's disease (AD). The new nanoparticles, coated, functionalized and conjugated with the naphthalene derivatives, have general Formula I; wherein: R1: is an organic coating to the metal oxide core, of polymeric type, catechol derivatives and trialkoxyalkylaminosilane; R2: -NHCO-alkylenyl-C(O)NH-alkylenyl-R3; R3: -COO-, -CO-, -NH, -O-, -S-, -NH-alkylenyl-NH-, -NR4-CSS-; R4: -H, -CH3, -CH2-CH3, -CH2CH2CH3, and MxOy: iron oxide (Fe3O4/γFe2O3), gadolinium oxide(III), manganese oxide(II) and copper(II) oxide; wherein the conjugated, functionalized and coated magnetic nanoparticle is capable of, when it is administered to a mammal, crossing the blood-brain barrier and specifically binding to the agglomerates and amyloid plaques present in brain tissue; wherein with this nanoparticle bound to the agglomerates and β-amyloid plaques in the brain tissue, hypo- or hyper-intense signals are observed in the region of interest through MRI. The compounds of Formula I are capable of acting as positive (T1) and / or negative (T2) contrast agents for MRI for the early and non-invasive diagnosis of AD, through a hypo- or hyper-intense signal of the β-amytoid agglomerates or Aβ plaques. In the NPs of Formula I, the metallic oxide magnetic core is coated with a functionalized polymeric layer that allows conjugation to naphthalene compounds, the preparation of which has been previously described in CU 2010/0204, EP 2 436 666 A20, P58243ZA00, US 9,764,047, CA 2789869C, PI 2012003534. The covalent and stable bond between the two chemical units form, in the NPs, a carbon chain with a singular structure, which surprisingly facilitates the NPs passage through the BBB, without the use of a disrupting agent, what are not described in the current state-of-the-art. These NPs unexpectedly enhance the affinity and selectivity properties of the naphthalene derivatives towards the Aβ agglomerates and β-plaques, they are stable molecules and do not show toxicity. We are not aware that the compounds presented in this invention have been previously reported.

  本发明与应用于医学领域的化学和物理学有关，是指使用具有磁性的化合物，这些化合物属于金属氧化物纳米粒子的范畴，经过涂层和方便的功能化处理，与神经退行性疾病中存在的团聚体和β-淀粉样蛋白斑块相关的萘化合物共轭。这些新型纳米粒子（NPs）可用于利用磁共振成像（MRI）技术对团块和淀粉样蛋白斑块进行无创检测。这里描述的纳米粒子可穿过血脑屏障（BBB），无需使用任何膜破坏剂。同样，它们还能以高亲和力和特异性与团块和β-类淀粉样蛋白斑块结合，可用作核磁共振成像中的造影剂，用于早期检测阿尔茨海默病（AD）。 新的纳米粒子具有萘衍生物的涂层、功能化和共轭，其通式为 I； 其中 R1：是金属氧化物核心的有机涂层，聚合物类型，邻苯二酚衍生物和三烷氧基烷基氨基硅烷； R2：-NHCO-烯基-C(O)NH-烯基-R3； R3：-COO-、-CO-、-NH、-O-、-S-、-NH-烯基-NH-、-NR4-CSS-； R4：-H、-CH3、-CH2-CH3、-CH2CH2CH3，以及 MxOy：氧化铁（Fe3O4/γFe2O3）、氧化钆（III）、氧化锰（II）和氧化铜（II）； 其中，共轭、功能化和涂层的磁性纳米粒子在给哺乳动物用药时，能够穿过血脑屏障，并与脑组织中的团聚体和淀粉样斑块特异性结合； 其中，当该纳米粒子与脑组织中的团聚体和β-淀粉样蛋白斑块结合后，通过核磁共振成像可在相关区域观察到低强或高强信号。 式 I 的化合物能够作为磁共振成像的阳性（T1）和/或阴性（T2）造影剂，通过 β 淀粉样蛋白团块或 Aβ 斑块的低强或高强信号，进行 AD 的早期无创诊断。 在式 I 的 NPs 中，金属氧化物磁芯上涂有一层可与萘化合物共轭的官能化聚合物层，其制备方法已在 CU 2010/0204、EP 2 436 666 A20、P58243ZA00、US 9,764,047、CA 2789869C、PI 2012003534 中进行过描述。 两个化学单元之间的共价稳定键在 NPs 中形成了一个具有奇异结构的碳链，这出乎意料地促进了 NPs 通过 BBB，而无需使用干扰剂，这在目前的先进技术中还没有描述。 这些 NPs 意外地增强了萘衍生物对 Aβ 团聚体和β斑块的亲和性和选择性，它们是稳定的分子，没有毒性。我们不知道本发明中提出的化合物以前是否被报道过。