4-(5-(hydroxymethyl)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl)-phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(5-(hydroxymethyl)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl)-phenol
• 英文别名: 4-[(1S,2S,5S)-5-(Hydroxymethyl)-8-methyl-3-oxabicyclo[3.3.1]non-7-EN-2-YL]phenol
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: XXIFNRNIQJKFLP-XHSDSOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-(hydroxymethyl)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl)-phenol 生成 4-((1S,2S,5S)-5-Hydroxymethyl-8-methyl-3-oxa-bicyclo[3.3.1]non-7-en-2-yl)-phenol 、 4-((1S,2S,5S)-5-Hydroxymethyl-8-methyl-3-oxa-bicyclo[3.3.1]non-7-en-2-yl)-phenol
  参考文献：
  名称：

  Structure–activity relationships and sub-type selectivity in an oxabicyclic estrogen receptor α/β agonist scaffold

  摘要：

  An oxabicyclic template for estrogen receptor alpha and beta agonists has been identified which can be tuned to provide moderate levels of selectivity for either receptor sub-type. Structure-activity relationships within this phenol-substituted oxabicyclo[3.3.1]nonene series are described. Select compounds from the present series showed activity in vivo after oral dosing in rodent models of uterine proliferation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.077
• 作为产物：
  描述：

  diethyl 4-methylcyclohex-3-ene-1,1-dicarboxylate 在 lithium aluminium tetrahydride 、 hafnium tetrakis(trifluoromethanesulfonate) 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 4-(5-(hydroxymethyl)-8-methyl-3-oxabicyclo[3.3.1]non-7-en-2-yl)-phenol
  参考文献：
  名称：

  [EN] COMPOUNDS FOR SELECTIVE BINDING TO ESTROGEN RECEPTORS ALPHA/BETA RELATIVE TO GPER/GPR30
  [FR] COMPOSÉS POUR LA LIAISON SÉLECTIVE À DES RÉCEPTEURS ALPHA/BÊTA DES ŒSTROGÈNES PAR RAPPORT À GPER/GPR30

  摘要：

  当前的发明属于分子生物学/药理学领域，提供了一种新颖的3-氧杂双环[3.3.1]壬烯化合物及其衍生物，能够调节经典雌激素受体α和β（ERα和ERβ）的效应，对G蛋白偶联雌激素受体GPER（也称为GPR30）几乎没有生物学或生理效应。这些化合物可能作为所披露的一个或多个经典雌激素受体的激动剂和/或拮抗剂。

  公开号：

  WO2021041107A1

文献信息

• Versatile method for the synthesis of 4-substituted 6-methyl-3-oxabicyclo[3.3.1]non-6-ene-1-methanol derivatives: Prins-type cyclization reaction catalyzed by hafnium triflate
  作者：Masayuki Nakamura、Kenji Niiyama、Takeru Yamakawa

  DOI：10.1016/j.tetlet.2009.08.120

  日期：2009.11

  A versatile method for the synthesis of 4-substituted 6-methyl-3-oxabicyclo[3.3.1]non-6-ene-1-methanol derivatives has been developed using Prins-type cyclization reaction between aldehydes and O-protected/unprotected cyclohex-3-ene-1,1-dimethanol. Under optimized reaction conditions using hafnium triflate, various substrates, including functionalized benzaldehydes and heteroaromatic carbaldehydes

  利用醛与O-保护/未保护的环己基之间的Prins型环化反应，开发了一种通用的合成4-取代的6-甲基-3-氧杂双环[3.3.1]非-6-烯-1-甲醇衍生物的方法-3-烯-1,1-二甲醇。在使用三氟甲磺酸ha的优化反应条件下，各种底物，包括官能化的苯甲醛和杂芳族甲醛，均能以高收率获得环化产物。
• [EN] COMPOUNDS FOR SELECTIVE BINDING TO ESTROGEN RECEPTORS ALPHA/BETA RELATIVE TO GPER/GPR30<br/>[FR] COMPOSÉS POUR LA LIAISON SÉLECTIVE À DES RÉCEPTEURS ALPHA/BÊTA DES ŒSTROGÈNES PAR RAPPORT À GPER/GPR30
  申请人：UNM RAINFOREST INNOVATIONS

  公开号：WO2021041107A1

  公开（公告）日：2021-03-04

  The current invention is in the field of molecular biology/pharmacology and provides novel 3-oxabicyclo [3.3.1] nonene compounds and derivatives that modulate the effects of the classical estrogen receptors alpha and beta (ERalpha and ERbeta) with little to no biological or physiological effects on the G protein-coupled estrogen receptor GPER (also known as GPR30). These compounds may function as agonists and/or antagonists of one or more of the disclosed classical estrogen receptors.

  当前的发明属于分子生物学/药理学领域，提供了一种新颖的3-氧杂双环[3.3.1]壬烯化合物及其衍生物，能够调节经典雌激素受体α和β（ERα和ERβ）的效应，对G蛋白偶联雌激素受体GPER（也称为GPR30）几乎没有生物学或生理效应。这些化合物可能作为所披露的一个或多个经典雌激素受体的激动剂和/或拮抗剂。
• A Selective Ligand for Estrogen Receptor Proteins Discriminates Rapid and Genomic Signaling
  作者：Chetana M. Revankar、Cristian G. Bologa、Richard A. Pepermans、Geetanjali Sharma、Whitney K. Petrie、Sara N. Alcon、Angela S. Field、Chinnasamy Ramesh、Matthew A. Parker、Nikolay P. Savchuk、Larry A. Sklar、Helen J. Hathaway、Jeffrey B. Arterburn、Tudor I. Oprea、Eric R. Prossnitz

  DOI：10.1016/j.chembiol.2019.10.009

  日期：2019.12

  Estrogen exerts extensive and diverse effects throughout the body of women. In addition to the classical nuclear estrogen receptors (ERα and ERβ), the G protein-coupled estrogen receptor GPER is an important mediator of estrogen action. Existing ER-targeted therapeutic agents act as GPER agonists. Here, we report the identification of a small molecule, named AB-1, with the previously unidentified activity

  雌激素在整个女性体内发挥着广泛而多样的作用。除了经典的核雌激素受体（ERα和ERβ）外，G蛋白偶联的雌激素受体GPER是雌激素作用的重要介体。现有的靶向ER的治疗剂可作为GPER激动剂。在这里，我们报告一个名为AB-1的小分子的鉴定，该分子具有与GPER结合的经典ER的高选择性活性，该活性先前未得到确认。AB-1还具有独特的功能活性谱，作为转录活性的激动剂，但却是通过ERα进行快速信号传递的拮抗剂。我们的结果定义了一类小分子，它们可以区分经典ER和GPER，以及经典ER中的信号传导模式。如果发展成ER拮抗剂，这种活性特征，
• IDENTIFICATION AND TARGETED MODULATION OF GENE SIGNALING NETWORKS
  申请人：CAMP4 THERAPEUTICS CORPORATION

  公开号：US20210254056A1

  公开（公告）日：2021-08-19

  The present invention provides methods and compositions for the evaluation, alteration and/or optimization of gene signaling. Methods and systems are also provided which exploit the information generated in the identification of new targets and non-canonical signaling pathways.
• Structure–activity relationships and sub-type selectivity in an oxabicyclic estrogen receptor α/β agonist scaffold
  作者：Lawrence G. Hamann、J. Hoyt Meyer、Daniel A. Ruppar、Keith B. Marschke、Francisco J. Lopez、Elizabeth A. Allegretto、Donald S. Karanewsky

  DOI：10.1016/j.bmcl.2004.12.077

  日期：2005.3

  An oxabicyclic template for estrogen receptor alpha and beta agonists has been identified which can be tuned to provide moderate levels of selectivity for either receptor sub-type. Structure-activity relationships within this phenol-substituted oxabicyclo[3.3.1]nonene series are described. Select compounds from the present series showed activity in vivo after oral dosing in rodent models of uterine proliferation. (c) 2005 Elsevier Ltd. All rights reserved.