8-Hydroxy-7-methoxy-2,2-dimethylchroman-4-one | 76970-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-Hydroxy-7-methoxy-2,2-dimethylchroman-4-one
• 英文别名: 8-hydroxy-7-methoxy-2,2-dimethyl-3H-chromen-4-one
• CAS: 76970-47-3
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: ANILNYHCDPWYKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  8-Hydroxy-7-methoxy-2,2-dimethylchroman-4-one 在 sodium tetrahydroborate 、 乙醇 、 copper(ll) bromide 作用下， 以 甲醇 、 氯仿 、 乙酸乙酯 为溶剂， 生成 3-Bromo-7-methoxy-2,2-dimethylchromen-8-ol
  参考文献：
  名称：

  面向多样性的合成途径构建具有不同核心骨架的多杂环苯并吡喃文库：第二部分

  摘要：

  正如我们以前的报告（的延续J.梳子。化学。2010，12（548-558），我们完成了具有特权的苯并吡喃亚结构的多杂环小分子文库的面向多样性的合成。为确保合成效率，我们利用固相平行平台和基于氟标签的溶液相平行平台，构建了一个由284个成员组成的具有6个不同核心骨架的多杂环文库，其平均纯度为87％。 5-10毫克。该库旨在最大程度地提高三维空间中离散核心骨架的骨架多样性，并使用四种不同的苯并吡喃基原料和各种结构单元来实现组合多样性。加上我们报道的苯并吡喃基文库，

  DOI：

  10.1021/co2001907
• 作为产物：
  描述：

  3-甲基-1-(2,3,4-三羟基苯基)-2-丁烯-1-酮 在 盐酸 、 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 8-Hydroxy-7-methoxy-2,2-dimethylchroman-4-one
  参考文献：
  名称：

  Timar, Tibor; Jaszberenyi, J. Csaba, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 871 - 877

  摘要：

  DOI：

文献信息

• Discovery of Novel Benzopyranyl Tetracycles that Act as Inhibitors of Osteoclastogenesis Induced by Receptor Activator of NF-κB Ligand
  作者：Mingyan Zhu、Myung Hee Kim、Sanghee Lee、Su Jung Bae、Seong Hwan Kim、Seung Bum Park

  DOI：10.1021/jm1011269

  日期：2010.12.23

  A novel benzopyran-fused molecular framework 7ai was discovered as a specific inhibitor of RANKL-induced osteoclastogenesis using a cell-based TRAP activity assay from drug-like small-molecule libraries constructed by diversity-oriented synthesis. Its inhibitory activity was confirmed by in vitro evaluations including specific inhibition of RANKL-induced ERK phosphorylation and NF-kappa B transcriptional activation. 7ai can serve as a specific small-molecule modulator for mechanistic studies of RANKL-induced osteoclast differentiation as well as a potential lead for the development of antiresorptive drugs.
• Antidiabetic and Antiobesity Effects of Ampkinone (<b>6f</b>), a Novel Small Molecule Activator of AMP-Activated Protein Kinase
  作者：Sangmi Oh、Sung Jin Kim、Jung Hwan Hwang、Hyang Yeon Lee、Min Jeong Ryu、Jongmin Park、Soung Jung Kim、Young Suk Jo、Yong Kyung Kim、Chul-Ho Lee、Ki Ryang Kweon、Minho Shong、Seung Bum Park

  DOI：10.1021/jm100565d

  日期：2010.10.28

  Adenosine 5'-monophosphate (AMP) activated protein kinase (AMPK) has emerged as an attractive target molecule for the treatment of metabolic disorders, including obesity and type 2 diabetes. In this study, we identified a novel small molecule, ampkinone (6f), as an indirect AMPK activator, which was derived from the small molecule library constructed by diversity-oriented synthesis. Ampkinone stimulated the phosphorylation of AMPK via the indirect activation of AMPK in various cell lines. Ampkinone-mediated activation of AMPK required the activity of LKB1 and resulted in increased glucose uptake in muscle cells. In addition, ampkinone-treated DIO mice significantly reduced total body weight and overall fat mass. Histological examination and measurement of lipid parameters showed that ampkinone effectively improved metabolic abnormalities in the DIO mice model. Our results demonstrate that ampkinone, a small molecule with a privileged benzopyran substructure, has a potential as a new class of therapeutic agent for antidiabetic and antiobesity treatment via the indirect stimulation of AMPK.
• TIMAR, TIBOR;JASZBERENYI, J. CSABA, J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 871-877
  作者：TIMAR, TIBOR、JASZBERENYI, J. CSABA

  DOI：——

  日期：——
• Timar, Tibor; Jaszberenyi, J. Csaba, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 871 - 877
  作者：Timar, Tibor、Jaszberenyi, J. Csaba

  DOI：——

  日期：——
• Construction of Polyheterocyclic Benzopyran Library with Diverse Core Skeletons through Diversity-Oriented Synthesis Pathway: Part II
  作者：Mingyan Zhu、Byung Joon Lim、Minseob Koh、Seung Bum Park

  DOI：10.1021/co2001907

  日期：2012.2.13

  diversity-oriented synthesis of polyheterocyclic small-molecule library with privileged benzopyran substructure. To ensure the synthetic efficiency, we utilized the solid-phase parallel platform and the fluorous-tag-based solution-phase parallel platform to construct a 284-member polyheterocyclic library with six distinct core skeletons with an average purity of 87% on a scale of 5–10 mg. This library was designed

  正如我们以前的报告（的延续J.梳子。化学。2010，12（548-558），我们完成了具有特权的苯并吡喃亚结构的多杂环小分子文库的面向多样性的合成。为确保合成效率，我们利用固相平行平台和基于氟标签的溶液相平行平台，构建了一个由284个成员组成的具有6个不同核心骨架的多杂环文库，其平均纯度为87％。 5-10毫克。该库旨在最大程度地提高三维空间中离散核心骨架的骨架多样性，并使用四种不同的苯并吡喃基原料和各种结构单元来实现组合多样性。加上我们报道的苯并吡喃基文库，