3,3',4',5,5'-pentahydroxystilbene | 35154-48-4

• 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: 3,3',4',5,5'-pentahydroxystilbene
• 英文别名: (E)-5-[2-(3,5-dihydroxyphenyl)vinyl]benzene-1,2,3-triol；1,3-dihydroxy-5-[(E)-3,4,5-trihydroxystyryl]benzene；3,3',4,5,5'-pentahydroxy-trans-stilbene；3,4,5,3',5'-pentahydroxy-trans-stilbene；trans-3,3',4,5,5'-pentahydroxystilbene；PHS；5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2,3-triol
• CAS: 35154-48-4
• 化学式: C₁₄H₁₂O₅
• 分子量: 260.246
• InChiKey: PBRNOKNVNSKDQZ-OWOJBTEDSA-N

物化性质

• 沸点：
  621.4±55.0 °C(Predicted)
• 密度：
  1.579±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3',4',5,5'-pentahydroxystilbene 以 乙醇 为溶剂， 生成 cis-3.3'.4.5.5'-Pentahydroxystilben
  参考文献：
  名称：

  Drewes,S.E.; Fletcher,I.P., Journal of the Chemical Society. Perkin transactions I, 1974, p. 961 - 962

  摘要：

  DOI：
• 作为产物：
  描述：

  [(3,4,5-trimethoxyphenyl)methyl]phosphoric acid diethyl ester 在 sodium methylate 、 三溴化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 3,3',4',5,5'-pentahydroxystilbene
  参考文献：
  名称：

  Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure–activity relationship

  摘要：

  Resveratrol (3,5,4'-trihydroxy-trans-stilbene) is found in grapes and various medical plants. Among cytotoxic, antifungal, antibacterial cardioprotective activity resveratrol also demonstrates non-selective cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) inhibition. In order to find more selective COX-2 inhibitors a series of methoxylated and hydroxylated resveratrol derivatives were synthesized and evaluated for their ability to inhibit both enzymes using in vitro inhibition assays for COX-1 and COX-2 by measuring PGE(2) production. Hydroxylated but not methoxylated resveratrol derivatives showed a high rate of inhibition. The most potent resveratrol compounds were 3,3',4',5-tetra-trans-hydroxystilbene (COX-1: IC50 = 4.713, COX-2: IC50 = 0.0113 muM, selectivity index = 417.08) and 3,3',4,4',5,5'-hexa-hydroxy-trans-stilbene (COX-1: IC50 = 0.748, COX-2: IC50 = 0.00104muM, selectivity index = 719.23). Their selectivity index was in part higher than celecoxib, a selective COX-2 inhibitor already established on the market (COX-1: IC50 = 19.026, COX-2: IC50 = 0.03482 muM, selectivity index = 546.41). Effect of structural parameters on COX-2 inhibition was evaluated by quantitative structure-activity relationship (QSAR) analysis and a high correlation was found with the topological surface area TPSA (r = 0.93). Docking studies on both COX-1 and COX-2 protein structures also revealed that hydroxylated but not methoxylated resveratrol analogues are able to bind to the previously identified binding sites of the enzymes. Hydroxylated resveratrol analogues therefore represent a novel class of highly selective COX-2 inhibitors and promising candidates for in vivo studies. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.08.008

文献信息

• CAJANINE STRUCTURE ANALOGOUS COMPOUND, PREPARATION METHOD AND USE
  申请人：INSTITUTE OF MEDICINAL BIOTECHNOLOGY. CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：US20140371232A1

  公开（公告）日：2014-12-18

  Provided are cajanine structure analogous compounds, synthesis method and pharmacological effects thereof, the compounds of the present invention having the structure as represented by general formulas I, II, III, IV and V. Also provided are pharmaceutical compositions containing the compounds as active ingredient, and uses thereof; the compounds of the present invention having the pharmacological activities such as anti-virus, anti-virus-infection, nerve protection, anti-metabolic-diseases and the like. Also provided is a chemical total synthesis preparation method of the natural products cajanine, cajanine A and cajanine C. The present invention lays a foundation for the in-depth study and development of the compounds as clinical drugs in the future.

  提供的是与咖啡碱结构类似的化合物、合成方法及其药理效果，本发明的化合物具有如公式I、II、III、IV和V所代表的结构。还提供了含有这些化合物的药物组合物，以及它们的使用方法；本发明的化合物具有诸如抗病毒、抗病毒感染、神经保护、抗代谢性疾病等药理活性。还提供了天然产物咖啡碱、咖啡碱A和咖啡碱C的化学全合成制备方法。本发明为这些化合物作为未来临床药物深入研究和发展奠定了基础。
• MOLECULARLY IMPRINTED POLYMERS
  申请人：Hearn Milton T. W.

  公开号：US20120052757A1

  公开（公告）日：2012-03-01

  The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.

  本发明提供了设计分子印迹聚合物（MIPs）的方法，这些方法在从各种生物加工原料和废弃物中提取生物活性化合物方面具有应用。本发明进一步针对由本发明方法设计的MIPs。
• Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor
  作者：Syuhei Nakao、Miyuki Mabuchi、Shenglan Wang、Yoko Kogure、Tadashi Shimizu、Koichi Noguchi、Akito Tanaka、Yi Dai

  DOI：10.1016/j.bmcl.2017.05.025

  日期：2017.7

  A series of 31 resveratrol derivatives was designed, synthesized and evaluated for activation and inhibition of the TRPA1 channel. Most acted as activators and desensitizers of TRPA1 channels like resveratrol or allyl isothiocyanate (AITC). Compound 4z (HUHS029) exhibited higher inhibitory activity than resveratrol with an IC50 value of 16.1 μM. The activity of 4z on TRPA1 was confirmed in TRPA1-expressing

  设计，合成和评估了一系列31种白藜芦醇衍生物，以激活和抑制TRPA1通道。大部分充当白藜芦醇或异硫氰酸烯丙酯（AITC）等TRPA1通道的激活剂和脱敏剂。化合物4z（HUHS029）的抑制活性高于白藜芦醇，IC 50值为16.1μM 。通过全细胞膜片钳记录，在表达TRPA1的HEK293细胞以及大鼠背根神经节神经元中证实了4z对TRPA1的活性。此外，用4z预处理对体内AITC引起的TRPA1相关的疼痛行为表现出镇痛作用。
• Stilbene derivatives and their use in medicaments
  申请人：Szekeres Thomas

  公开号：US20070191627A1

  公开（公告）日：2007-08-16

  The invention relates to stilbene derivatives of general formula (I), in which at least four of the substituents R 1 to R 6 do not represent hydrogen. The substituents are effective radical captors, anti-tumour active ingredients and selective cyclooxygenase-2 inhibitors.

  该发明涉及一般式(I)的stilbene衍生物，其中至少有四个取代基R1至R6不代表氢。这些取代基是有效的自由基捕获剂、抗肿瘤活性成分和选择性环氧合酶-2抑制剂。
• Utilisation d'au moins un hydroxistilbene dans une composition raffermissante
  申请人：L'OREAL

  公开号：EP0953346A1

  公开（公告）日：1999-11-03

  L'invention se rapporte à l'utilisation d'au moins un hydroxystilbène dans ou pour la préparation d'une composition en tant qu'agent raffermissant de la peau. L'invention a également pour objet une composition raffermissante comprenant au moins un hydroxystilbène.

  本发明涉及将至少一种羟基二苯乙烯用于或用于制备作为皮肤紧致剂的组合物。 本发明还涉及一种包含至少一种羟基二苯乙烯的紧致组合物。