3,5-dihydroxy-4'-nitro-trans-stilbene | 823804-68-8

• 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: 3,5-dihydroxy-4'-nitro-trans-stilbene
• 英文别名: 5-[2-(4-nitro-phenyl)-vinyl]-benzene-1,3-diol；5-(4-Nitrostyryl)benzene-1,3-diol；5-[(E)-2-(4-nitrophenyl)ethenyl]benzene-1,3-diol
• CAS: 823804-68-8
• 化学式: C₁₄H₁₁NO₄
• 分子量: 257.246
• InChiKey: JJNQRIBTBNZQBJ-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-diacetoxy-4'-nitro-trans-stilbene 在 甲醇 、 sodium methylate 作用下， 反应 10.0h， 以81%的产率得到3,5-dihydroxy-4'-nitro-trans-stilbene
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer

  摘要：

  A series of new resveratrol analogues were designed and synthesized and their inhibitory activities against aromatase were evaluated. The crystal structure of human aromatase (PDB 3eqm) was used to rationalize the mechanism of action of the aromatase inhibitor 32 (IC50 0.59 mu M) through docking, molecular mechanics energy minimization, and computer graphics molecular modeling, and the information was utilized to design several very potent inhibitors, including compounds 82 (IC50 70 nM) and 84 (IC50 36 nM). The aromatase inhibitory activities of these compounds are much more potent than that for the lead compound resveratrol, which has an IC50 of 80 mu M. In addition to aromatase inhibitory activity, compounds 32 and 44 also displayed potent QR2 inhibitory activity (IC50 1.7 mu M and 0.27 mu M, respectively) and the high-resolution X-ray structures of QR2 in complex with these two compounds provide insight into their mechanism of QR2 inhibition. The aromatase and quinone reductase inhibitors resulting from these studies have potential value in the treatment and prevention of cancer. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.042

文献信息

• Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods
  申请人：——

  公开号：US20030073712A1

  公开（公告）日：2003-04-17

  Cytoprotective compounds, many of which are phenolic derivatives characterized by a substituted phenol having certain conjugated bonds, are useful in the treatment of certain ischemic or inflammatory conditions, including but not limited to stroke, myocardial infarction, congestive heart failure, and skin disorders characterized by inflammation or oxidative damage. They are also useful in the manufacture of pharmaceutical and cosmetic formulations for the treatment of such conditions.

  细胞保护化合物，其中许多是酚类衍生物，其特点是具有特定共轭键的取代酚，对于治疗某些缺血或炎症性疾病非常有用，包括但不限于中风、心肌梗死、充血性心力衰竭以及以炎症或氧化损伤为特征的皮肤疾病。它们还可用于制造用于治疗这些疾病的药物和化妆品配方。
• Compositions for manipulating the lifespan and stress response of cells and organisms
  申请人：Howitz T. Konrad

  公开号：US20060084135A1

  公开（公告）日：2006-04-20

  Provided herein are methods and compositions for modulating the activity of sirtuin deacetylase protein family members; p53 activity; apoptosis; lifespan and sensitivity to stress of cells and organisms. Exemplary methods comprise contacting a cell with an activating compound, such as a flavone, stilbene, flavanone, isoflavone, catechin, chalcone, tannin or anthocyanidin; or an inhibitory compound, such as a sphingolipid, e.g., sphingosine.

  本文提供了一种调节sirtuin去乙酰化酶蛋白家族成员、p53活性、细胞和生物的凋亡、寿命和对压力敏感性的方法和组合物。其中一种示例方法包括使用活化化合物（如黄酮、双苯乙烯、黄烷酮、异黄酮、儿茶素、查尔酮、单宁或花青素）或抑制化合物（如鞘脂类化合物，例如鞘氨醇）与细胞接触。
• COMPOSITIONS FOR TREATING OR PREVENTING OBESITY AND INSULIN RESISTANCE DISORDERS
  申请人：The President and Fellows of Harvard College

  公开号：EP3031461A1

  公开（公告）日：2016-06-15

  Provided herein are methods and compositions for modulating the activity or level of a sirtuin, thereby treating or preventing obesity or an insulin resistance disorder, such as diabetes in a subject. Exemplary methods comprise contacting a cell with a sirtuin activating compound or an inhibitory compound to thereby increase or decrease fat accumulation, respectively.

  本文提供了调节sirtuin活性或水平的方法和组合物，从而治疗或预防受试者的肥胖或胰岛素抵抗疾病，如糖尿病。示例性方法包括使细胞与sirtuin激活化合物或抑制化合物接触，从而分别增加或减少脂肪积累。
• Formulation and process for modulating wound healing
  申请人：BioMendics, LLC

  公开号：US10426742B2

  公开（公告）日：2019-10-01

  Methods and compounds are disclosed for wound healing by modulating autophagy. A formulation for modulating autophagy comprises a first modulating compound (FAM) selected from compounds having the general structure (I): wherein: L represents a linker selected from —C≡C—, (a tolan), —CH═CH— (a stilbene, preferably trans); or —CRa═CRb— a stilbene derivative; where Ra and Rb are independently H or phenyl optionally substituted with —(R3)p or —(R4)q; R1 to R4 are independent substituents at any available position of the phenyl rings, preferably at 3, 3′, 4, 4′, and/or 5, 5′; and m, n, p, and q are independently 0, 1, 2, or 3 representing the number of substituents of the rings, respectively, but at least one of m or n must be ≥1. Each R1 to R2 is independently selected from substituents described herein, including but not limited to hydroxyl, alkoxy, halo, halomethyl and glycosides. The formulation may also include an auxiliary autophagy modulating compound (AAM) as described herein. The formulation may include a hydrogel formed by the compounds themselves or otherwise and may include salts and/or complexes.

  本发明公开了通过调节自噬促进伤口愈合的方法和化合物。用于调节自噬的制剂包括选自具有一般结构 (I) 的化合物的第一调节化合物 (FAM)： 其中L 代表选自-C≡C-（甲苯）、-CH═CH-（二苯乙烯，最好是反式）或-CRa═CRb-二苯乙烯衍生物的连接体；其中 Ra 和 Rb 独立地是 H 或任选被-(R3)p 或-(R4)q 取代的苯基； R1至R4是独立的取代基，位于苯基环的任何可用位置，优选位于3，3′、4，4′和/或5，5′；m、n、p和q分别独立地为0、1、2或3，代表环的取代基数目，但m或n中至少有一个必须≥1。每个 R1 至 R2 独立地选自本文所述的取代基，包括但不限于羟基、烷氧基、卤代、卤代甲基和苷。制剂还可包括本文所述的辅助自噬调节化合物（AAM）。制剂可包括由化合物本身或以其它方式形成的水凝胶，并可包括盐和/或复合物。
• Synthesis and biological evaluation of a library of resveratrol analogues as inhibitors of COX-1, COX-2 and NF-κB
  作者：Soo Sung Kang、Muriel Cuendet、Denise C. Endringer、Vicki L. Croy、John M. Pezzuto、Mark A. Lipton

  DOI：10.1016/j.bmc.2008.04.031

  日期：2009.2

  Resveratrol (4,30,50- trihydroxystilbene) is a naturally occurring antioxidant that inhibits cyclooxygenase-1 (COX-1), cyclooxygenase-2 (COX-2) and the transcription factor NF-kappa B. A 78-membered library of resveratrol analogues in which the substituents on the two aryl rings and alkene were varied was synthesized using a solid-phase Wittig olefination reaction. The library contains inhibitors against all three proteins that were more potent than resveratrol itself. Preliminary structure-activity relationships were also obtained from these data that permitted the derivation of pharmacophore models for each of the three targets. (C) 2008 Elsevier Ltd. All rights reserved.