cymopol | 62008-14-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: cymopol
• 英文别名: (E)-2-bromo-5-(3,7-dimethylocta-2,6-dien-1-yl)benzene-1,4-diol；2-bromo-5-[(2E)-3,7-dimethylocta-2,6-dienyl]benzene-1,4-diol
• CAS: 62008-14-4
• 化学式: C₁₆H₂₁BrO₂
• 分子量: 325.246
• InChiKey: IUFDABCKTYWJDR-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cymopol 在 N-溴代丁二酰亚胺(NBS) 、 1,3-双[3,5-双(三氟甲基)苯基]硫脲 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以41%的产率得到4-isocymobarbatol
  参考文献：
  名称：

  硫脲作为香叶菊衍生物仿生溴环化的高活性催化剂

  摘要：

  带有电子缺陷芳基的硫脲在香叶基衍生物的仿生溴环化中显示出高催化活性。香叶基衍生物与N-溴代琥珀酰亚胺（NBS）的反应在CH 2 Cl 2中迅速进行，从而以高收率得到相应的溴环化产物。内消旋异构体和外消旋异构体的1：1混合物。香叶基衍生物的反应性高度依赖于末端取代基：供电子取代基增加反应性，而吸电子取代基降低反应性。

  DOI：

  10.1021/acs.orglett.9b00352
• 作为产物：
  描述：

  5-bromo-2-geranyl-1,4-benzenediol 在 4-甲基苯磺酸吡啶 作用下， 以 叔丁醇 为溶剂， 反应 10.0h， 以80%的产率得到cymopol
  参考文献：
  名称：

  Tanaka, Akira; Oritani, Takayuki, Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 3, p. 516 - 517

  摘要：

  DOI：

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• [EN] SEAWEED EXTRACTS, ISOLATED COMPOUNDS, AND METHODS OF TREATMENT<br/>[FR] EXTRAITS D'ALGUES, COMPOSÉS ISOLÉS ET PROCÉDÉS DE TRAITEMENT
  申请人：UNIV FLORIDA

  公开号：WO2019113383A1

  公开（公告）日：2019-06-13

  The instant invention relates to seaweed extract compositions, processes for isolation, isolated active agents, and methods of treating disease, disorders and conditions in a subject, including, reactive oxygen species (ROS)-mediated diseases and diseases mediated through the activation of the Nrf2-ARE (antioxidant response element) pathway, including proliferative diseases and disorders, Alzheimer's disease, stroke, and certain diseases and disorders of aging and associated with aging and exposure, by use of the extracts, compounds, and compositions thereof.

  本发明涉及海藻提取物组合物、隔离工艺、隔离的活性成分以及治疗受试者疾病、疾病和病情的方法，包括通过使用提取物、化合物和其组合物治疗反应性氧化物种（ROS）介导的疾病和通过激活Nrf2-ARE（抗氧化剂反应元素）途径介导的疾病，包括增殖性疾病和疾病、老年痴呆症、中风以及与老化和暴露相关的某些疾病和疾病。
• Organocopper chemistry of quinone bisketals. Application to the synthesis of isoprenoid quinone systems
  作者：Bertrand L. Chenard、Michael J. Manning、Peter W. Raynolds、John S. Swenton

  DOI：10.1021/jo01291a002

  日期：1980.2
• Seaweed natural products modify the host inflammatory response via Nrf2 signaling and alter colon microbiota composition and gene expression
  作者：Michelle S. Bousquet、Ranjala Ratnayake、Jillian L. Pope、Qi-Yin Chen、Fanchao Zhu、Sixue Chen、Thomas J. Carney、Raad Z. Gharaibeh、Christian Jobin、Valerie J. Paul、Hendrik Luesch

  DOI：10.1016/j.freeradbiomed.2019.09.013

  日期：2020.1

  Seaweeds are an important component of human diets, especially in Asia and the Pacific islands, and have shown chemopreventive as well as anti-inflammatory properties. However, structural characterization and mechanistic insight of seaweed components responsible for their biological activities are lacking. We isolated cymopol and related natural products from the marine green alga Cymopolia barbata and demonstrated their function as activators of transcription factor Nrf2-mediated antioxidant response to increase the cellular antioxidant status. We probed the reactivity of the bioactivation product of cymopol, cymopol quinone, which was able to modify various cysteine residues of Nrf2's cytoplasmic repressor protein Keap1. The observed adducts are reflective of the polypharmacology at the level of natural product, due to multiple electrophilic centers, and at the amino acid level of the cysteine-rich target protein Keap1. The non-polar C. barbata extract and its major active component cymopol, reduced inflammatory gene transcription in vitro in macrophages and mouse embryonic fibroblasts in an Nrf2-dependent manner. Cymopol-containing extracts attenuated neutrophil migration in a zebrafish tail wound model. RNA-seq analysis of colonic tissues of mice exposed to non-polar extract or cymopol showed an antioxidant and anti-inflammatory response, with more pronounced effects exhibited by the extract. Cymopolia extract reduced DSS-induced colitis as measured by fecal lipocalin concentration. RNA-seq showed that mucosal-associated bacterial composition and transcriptional profile in large intestines were beneficially altered to varying degrees in mice treated with either the extract or cymopol. We conclude that seaweed-derived compounds, especially cymopol, alter Nrf2-mediated host and microbial gene expression, thereby providing poly-pharmacological effects.
• NON-STEROID PROGESTERONE RECEPTOR AGONIST AND ANTAGONIST COMPOUNDS AND METHODS
  申请人：LIGAND PHARMACEUTICALS, INC.

  公开号：EP0637296A1

  公开（公告）日：1995-02-08