2-((7-methoxynaphthalen-2-yl)oxy)acetic acid | 911677-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((7-methoxynaphthalen-2-yl)oxy)acetic acid
• 英文别名: 2-(7-Methoxynaphthalen-2-yl)oxyacetic acid
• CAS: 911677-40-2
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: ULEQEOAQBRTBNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((7-methoxynaphthalen-2-yl)oxy)acetic acid 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.25h， 生成
  参考文献：
  名称：

  螺naphthofuranone吡唑啉的区域选择性合成经由benzoaurones的腈亚胺[3 + 2]环加成

  摘要：

  DOI：

  10.1016/j.tet.2020.131355
• 作为产物：
  描述：

  methyl 2-((7-methoxynaphthalen-2-yl)oxy)acetate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以86%的产率得到2-((7-methoxynaphthalen-2-yl)oxy)acetic acid
  参考文献：
  名称：

  Synthesis and Biochemical Evaluation of Noncyclic Nucleotide Exchange Proteins Directly Activated by cAMP 1 (EPAC1) Regulators

  摘要：

  Exchange proteins directly activated by cAMP (EPAC) play a central role in various biological functions, and activation of the EPAC1 protein has shown potential benefits for the treatment of various human diseases. Herein, we report the synthesis and biochemical evaluation of a series of noncyclic nucleotide EPAC1 activators. Several potent EPAC1 binders were identified including 25g, 25q, 25n, 25u, 25e, and 25f, which promote EPAC1 guanine nucleotide exchange factor activity in vitro. These agonists can also activate EPAC1 protein in cells, where they exhibit excellent selectivity toward EPAC over protein kinase A and G protein-coupled receptors. Moreover, 25e, 25f, 25n, and 25u exhibited improved selectivity toward activation of EPAC1 over EPAC2 in cells. Of these, 25u was found to robustly inhibit IL-6-activated signal transducer and activator of transcription 3 (STAT3) and subsequent induction of the pro-inflammatory vascular cell adhesion molecule 1 (VCAM1) cell-adhesion protein. These novel EPAC1 activators may therefore act as useful pharmacological tools for elucidation of EPAC function and promising drug leads for the treatment of relevant human diseases.

  DOI：

  10.1021/acs.jmedchem.9b02094

文献信息

• Mechanism of Action of an EPAC1-Selective Competitive Partial Agonist
  作者：Hongzhao Shao、Hebatallah Mohamed、Stephen Boulton、Jinfeng Huang、Pingyuan Wang、Haiying Chen、Jia Zhou、Urszula Luchowska-Stańska、Nicholas G. Jentsch、Alison L. Armstrong、Jakob Magolan、Stephen Yarwood、Giuseppe Melacini

  DOI：10.1021/acs.jmedchem.9b02151

  日期：2020.5.14

  The exchange protein activated by cAMP (EPAC) is a promising drug target for a wide disease range, from neurodegeneration and infections to cancer and cardiovascular conditions. A novel partial agonist of the EPAC isoform 1 (EPAC1), I942, was recently discovered, but its mechanism of action remains poorly understood. Here, we utilize NMR spectroscopy to map the I942-EPAC1 interactions at atomic resolution and propose a mechanism for I942 partial agonism. We found that I942 interacts with the phosphate binding cassette (PBC) and base binding region (BBR) of EPAC1, similar to cyclic adenosine monophosphate (cAMP). These results not only reveal the molecular basis for the I942 vs cAMP mimicry and competition, but also suggest that the partial agonism of I942 arises from its ability to stabilize an inhibitionin-competent activation intermediate distinct from both active and inactive EPAC1 states. The mechanism of action of I942 may facilitate drug design for EPAC-related diseases.
• COMPOSITIONS AND METHODS FOR LARGE-SCALE IN VITRO PLANT BIOCULTURE
  申请人：BOOSHOOT, LLC

  公开号：US20200383331A1

  公开（公告）日：2020-12-10

  The present invention provides media, kits, systems, and methods for achieving large scale pistachio production within a short time via bioculture, large scale yam production within a short time via bioculture, high multiplication rate of plants including cannabis via in vitro micropropagation, high induction rates of somatic embryos from later buds in bamboo, reduced production of phenolic compounds in plants, high production of virus-free plants, including potato, and large scale hemp production via culturing. The present invention for pistachio and yam production results in shorter tuber development phase and higher yield. In some embodiments, the present invention provides compositions, methods, and systems for the micropropagation and mass production of perennials, grasses, bamboos, cannabis and phyto-pharmaceutical plants as well as hemp plants. In some embodiments, the present invention provides compositions, methods, and systems for reducing the production of a phenolic by a plant, such as bamboo.
• [EN] COMPOSITIONS AND METHODS FOR BAMBOO PULPING<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE FABRICATION DE PÂTE DE BAMBOU
  申请人：RED TRIANGLE LLC

  公开号：WO2012097380A1

  公开（公告）日：2012-07-19

  Disclosed herein are compositions, methods and systems for bamboo pulping. Bamboo biomass materials that are exclusively or largely uniform are used for bamboo pulping. In some embodiments, the bamboo biomass materials are derived from a pure stand or monoculture of bamboo. In some embodiments, the bamboo pure stand or monoculture is generated by micropropagation comprising meta-topolin or an analogue thereof and/or thidiazuron or an analogue thereof.
• [EN] COMPOSITIONS, METHODS, AND SYSTEMS FOR MICROPROPAGATION OF PLANTS<br/>[FR] COMPOSITIONS, PROCÉDÉS ET SYSTÈMES DE MICROPROPAGATION DE PLANTES
  申请人：BOOSHOOT LLC

  公开号：WO2013016198A1

  公开（公告）日：2013-01-31

  The present invention provides compositions, methods, and systems for achieving very high multiplication rate of plants in vitro micropropagation.
• [EN] SELECTIVE NON-CYCLIC NUCLEOTIDE ACTIVATORS FOR THE CAMP SENSOR EPAC1<br/>[FR] ACTIVATEURS NUCLÉOTIDIQUES NON CYCLIQUES SÉLECTIFS POUR LE CAPTEUR DE CAMP EPAC 1
  申请人：[en]THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM

  公开号：WO2021188728A1

  公开（公告）日：2021-09-23

  The invention relates generally to novel EPAC1 activators, such as Formula (I) and (II) and the preparation thereof as well as the use of EPAC1 activators disclosed herein as to selectively activate EPAC1 in cells.