5'-methoxy-2'-methoxymethoxyacetophenone | 91971-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-methoxy-2'-methoxymethoxyacetophenone
• 英文别名: 1-(5-methoxy-2-(methoxymethoxy)phenyl)ethanone；1-[5-Methoxy-2-(methoxymethoxy)phenyl]ethanone
• CAS: 91971-19-6
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: YALWVOSELIVYNI-UHFFFAOYSA-N

物化性质

• 沸点：
  317.4±32.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-methoxy-2'-methoxymethoxyacetophenone 在 (R)-1,1'-Bi-2-naphthol 、 neodymium (III) isopropoxide 叔丁基过氧化氢 、 三苯胂氧化物 、 sodium methylate 作用下， 以 四氢呋喃 、 癸烷 、 乙醇 为溶剂， 反应 36.0h， 生成 (5-methoxy-2-(methoxymethoxy)phenyl)((2S,3R)-3-(3-methoxyphenyl)oxiran-2-yl)methanone
  参考文献：
  名称：

  Convergent Synthesis of a Complex Oxime Library Using Chemical Domain Shuffling

  摘要：

  yThe synthesis of a complex hybrid oxime library is reported utilizing convergent ligation of alkoxyamine and carbonyl monomers via "chemical domain shuffling". Initial biological screening of the library against human small cell lung carcinoma (A549) cells led to the identification of a novel hybrid dimer in contrast to the corresponding monomeric compounds which were found to be inactive.

  DOI：

  10.1021/ol051023r
• 作为产物：
  描述：

  2'-羟基-5'-甲氧基苯乙酮 、 氯甲基甲基醚 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 5'-methoxy-2'-methoxymethoxyacetophenone
  参考文献：
  名称：

  黄烷醇对巨噬细胞一氧化氮产生的立体特异性抑制：合成及其构效关系。第2部分

  摘要：

  为了探索黄烷醇对RAW 264.7细胞中一氧化氮（NO）产生的抑制作用的构效关系，我们制备了一系列合成黄烷醇。在我们先前的研究中，发现2'，3'-二羟基苯基亚结构是在以3,5,7-三羟基苯并吡喃-4-酮为A / C环的黄烷醇中最有效的B环亚结构。在这项研究中，我们研究了不同取代对2-（2,3-二羟基苯基）-3-羟基苯并二氢吡喃-4-酮骨架的A环的影响，即通过将B环固定在2'，3' -二羟基苯基亚结构。制备了18种立体异构体和4种外消旋混合物，并测试了它们对RAW 264.7细胞中NO产生的抑制作用。我们观察到在（2 R，3 R）立体异构体比（2 S，3 S）立体异构体。在7位羟基或甲氧基的存在增强了抑制效力，而在A环的6或8位上的其他取代增加了效力和立体特异性。代表性化合物（2 R，3 R）-2'，3'，7,8-四羟基黄酮醇5e的IC 50值为17 µM，而其化合物（2 S，3 S）立体异构体在100

  DOI：

  10.1016/j.bmc.2017.05.060

文献信息

• Synthesis of flavonoids and their effects on aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues
  作者：Soon Sung Lim、Sang Hoon Jung、Jun Ji、Kuk Hyun Shin、Sam Rok Keum

  DOI：10.1211/0022357011775983

  日期：2010.2.18

  chalcone derivatives and by examining the structure-activity relationships on the inhibition of rat lens aldose reductase as well as on antioxidant effects. A series of 35 flavonoid derivatives were synthesized by Winget's condensation, oxidation, and reduction of appropriate acetophenones with appropriate benzaldehydes. The inhibitory activity of these derivatives on rat lens aldose reductase and their

  已知醛糖还原酶，多元醇途径的关键酶和氧化应激在糖尿病并发症中起重要作用。因此，具有有效抑制醛糖还原酶和氧化应激作用的药物将是预防糖尿病并发症的最有前途的药物。这项研究的目的是通过合成查尔酮衍生物，并通过研究抑制大鼠晶状体醛糖还原酶以及抗氧化作用的构效关系，开发出具有上述双重作用的新化合物。通过Winget的缩合，氧化和适当的苯乙酮与适当的苯甲醛的还原反应，合成了35种黄酮类衍生物。这些衍生物对大鼠晶状体醛糖还原酶的抑制活性及其抗氧化作用，评估了使用Cu2 +螯合剂测得的化合物在体外的自由基清除活性。还评估了它们对链脲佐菌素诱发的糖尿病大鼠红细胞，晶状体和坐骨神经中山梨醇积累的影响。在合成的新类黄酮衍生物中，具有A环2'，4'-二羟基基团的衍生物，例如2,4,2'，4'-四羟基查耳酮（22），2,2'，4'-三羟基查耳酮（11 ），发现2'，4'-二羟基-2,4-二甲基查耳酮（21）和3,4
• PYRIDYLPHENOL COMPOUND AND USE THEREOF
  申请人：Sasaki Satoshi

  公开号：US20090156646A1

  公开（公告）日：2009-06-18

  The present invention provides a compound which has metastin receptor antagonist activity and is useful for preventing and treating hormone-dependent cancer, benign prostatomegaly, endometriosis, precocious puberty, uterine myoma or the like. More specifically, the present invention provides a compound, represented by the formula: or a salt thereof, a prodrug thereof, and a pharmaceutical agent containing the same; wherein Ring A represents a 5- to 8-membered homocyclic or heterocyclic group optionally having a substituent other than formula —X-R 1 wherein X represents a bond or a spacer, and R 1 represents optionally substituted amino or an optionally substituted nitrogen-containing heterocyclic group; Ring B represents an optionally substituted benzene ring; R 2 represents an optionally substituted homocyclic or heterocyclic group; and R 3 and R 4 independently represent a hydrogen atom, cyano, acyl or an optionally substituted hydrocarbon group.

  本发明提供了一种具有转移素受体拮抗活性的化合物，可用于预防和治疗激素依赖性癌症、良性前列腺增生、子宫内膜异位症、早熟、子宫肌瘤等。更具体地，本发明提供了一种化合物，其表示为以下公式：或其盐、前药及含有该化合物的药物制剂；其中环A表示一个5-至8-成员的同环或异环族群，可选地具有除公式—X-R1以外的取代基，其中X表示键或空间组分，而R1表示可选地取代的氨基或可选地取代的含氮杂环族群；环B表示可选地取代的苯环；R2表示可选地取代的同环或异环族群；而R3和R4独立地表示氢原子、氰基、酰基或可选地取代的碳氢基团。
• EP1921066
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and structure–activity relationships of 2-acylamino-4,6-diphenylpyridine derivatives as novel antagonists of GPR54
  作者：Toshitake Kobayashi、Satoshi Sasaki、Naoki Tomita、Seiji Fukui、Noritaka Kuroda、Masaharu Nakayama、Atsushi Kiba、Yoshihiro Takatsu、Tetsuya Ohtaki、Fumio Itoh

  DOI：10.1016/j.bmc.2010.04.036

  日期：2010.6.1

  GPR54 is a G protein-coupled receptor (GPCR) which was formerly an orphan receptor. Recent functional study of GPR54 revealed that the receptor has an essential role to modulate sex-hormones including GnRH. Though antagonists of GPR54 are expected to be novel drugs for sex-hormone dependent diseases such as prostate cancer or endometriosis, small molecule GPR54 antagonists have not been reported. We have synthesized a series of 2-acylamino-4,6-diphenylpyridines to identify potent GPR54 antagonists. Detailed structure-activity relationship studies led to compound 9l with an IC50 value of 3.7 nM in a GPR54 binding assay, and apparent antagonistic activity in a cellular functional assay. (C) 2010 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Evaluation of Orally Available Clioquinol-Moracin M Hybrids as Multitarget-Directed Ligands for Cognitive Improvement in a Rat Model of Neurodegeneration in Alzheimer’s Disease
  作者：Zhiren Wang、Yali Wang、Bo Wang、Wenrui Li、Ling Huang、Xingshu Li

  DOI：10.1021/acs.jmedchem.5b01222

  日期：2015.11.12

  A novel series of clioquinol-moracin hybrids were designed and synthesized by fusing the pharmacophores of clioquinol and moracin M, and their activities as multitarget-directed ligands against Alzheimer's disease were evaluated. Biological activity results demonstrated that these hybrids possessed significant inhibitory activities against phosphodiesterase 4D (PDE4D) and A beta aggregation as well as remarkable antioxidant effects and excellent blood brain barrier permeability. The optimal compound, 18d (WBQ5187), exhibited excellent PDE4D inhibitory potency (IC50 = 0.32 mu M), significant antioxidant effects, appropriate biometal chelating functions, and interesting properties that modulated self- and metal-induced A beta aggregation. Two-dimensional NMR studies revealed that 18d had significant interactions with A beta(1-42) at the R5, H6, H14, Q15, and F20 residues. Furthermore, this typical hybrid possessed preeminent neuroprotective effects against inflammation in microglial cells. Most importantly, oral administration of 18d center dot HCl demonstrated marked improvements in cognitive and spatial memory in a rat model of Alzheimer's disease and protected hippocampal neurons from necrosis.