1-[3-Methoxy-4-(oxan-2-yloxy)phenyl]ethanone | 164467-48-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[3-Methoxy-4-(oxan-2-yloxy)phenyl]ethanone
• CAS: 164467-48-5
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: AWVQQLQXAAGLPP-UHFFFAOYSA-N

物化性质

• 沸点：
  386.8±42.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-[3-Methoxy-4-(oxan-2-yloxy)phenyl]ethanone 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 60.0h， 生成 4'-hydroxy-3'-methoxychalcone
  参考文献：
  名称：

  新型吡唑啉类似物的单胺氧化酶抑制活性：姜黄素的设计与合成

  摘要：

  一系列新的2-甲氧基-4-（5-苯基-4,5-二氢-1- ħ吡唑-3-基）phenolderivatives，4 - 13，合成以及它们的人MAO抑制活性进行测试。发现除了hMAO-B的选择性抑制剂4和非选择性抑制剂12以外，所有化合物均对hMAO-A具有选择性和可逆性。发现化合物7是hMAO-A的有效抑制剂，K i = 0.06± 0.003μM ，选择性指数为（SI = 1.02×10 –5）。已发现它比标准药物莫氯贝胺（hMAO-A，K i =0.11±0.01μM），选择性指数SI = 0.049。进行分子对接模拟以了解负责选择性和效能的关键相互作用。

  DOI：

  10.1021/acsmedchemlett.5b00326
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 香草乙酮 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 1-[3-Methoxy-4-(oxan-2-yloxy)phenyl]ethanone
  参考文献：
  名称：

  新型吡唑啉类似物的单胺氧化酶抑制活性：姜黄素的设计与合成

  摘要：

  一系列新的2-甲氧基-4-（5-苯基-4,5-二氢-1- ħ吡唑-3-基）phenolderivatives，4 - 13，合成以及它们的人MAO抑制活性进行测试。发现除了hMAO-B的选择性抑制剂4和非选择性抑制剂12以外，所有化合物均对hMAO-A具有选择性和可逆性。发现化合物7是hMAO-A的有效抑制剂，K i = 0.06± 0.003μM ，选择性指数为（SI = 1.02×10 –5）。已发现它比标准药物莫氯贝胺（hMAO-A，K i =0.11±0.01μM），选择性指数SI = 0.049。进行分子对接模拟以了解负责选择性和效能的关键相互作用。

  DOI：

  10.1021/acsmedchemlett.5b00326

文献信息

• SYNTHESIS OF CALEBIN-A AND ITS BIOLOGICALLY ACTIVE ANALOGS
  申请人：Majeed Muhammed

  公开号：US20160002141A1

  公开（公告）日：2016-01-07

  Disclosed is a simple, economical, industrially scalable green synthetic process for Calebin-A and its biologically active analogs.

  本发明公开了一种简单、经济、工业可扩展的绿色合成过程，用于合成Calebin-A及其生物活性类似物。
• Synthesis of Calebin-A and its biologically active analogs
  申请人：Majeed, Muhammed

  公开号：EP2963007A1

  公开（公告）日：2016-01-06

  Disclosed is a simple, economical, industrially scalable green synthetic process for Calebin-A and its biologically active analogs.

  所公开的是一种简单、经济、可工业化扩展的 Calebin-A 及其生物活性类似物的绿色合成工艺。
• Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway
  作者：Pay-Chin Leow、Priti Bahety、Choon Pei Boon、Chong Yew Lee、Kheng Lin Tan、Tianming Yang、Pui-Lai Rachel Ee

  DOI：10.1016/j.ejmech.2013.10.073

  日期：2014.1

  Osteosarcoma is a primary bone malignancy with aggressive metastatic potential and poor prognosis rates. In our earlier work we have investigated the therapeutic potential of curcumin as an anti-invasive agent in osteosarcoma by its ability to regulate the Wnt/beta-catenin signaling pathway. However, the clinical use of curcumin is limited owing to its low potency and poor pharmacokinetic profile. In this study, an attempt was made to achieve more potent Wnt inhibitory activity in osteosarcoma cells by carrying out synthetic chemical modifications of curcumin. We synthesized a total of five series consisting of 43 curcumin analogs and screened in HEK293T cells for inhibition of beta-catenin transcriptional activity. Six promising analogs, which were 6.5- to 60-fold more potent than curcumin in inhibiting Wnt activity, were further assessed for their anti-invasive activity and Wnt inhibitory mechanisms. Western blot analysis showed disruption of beta-catenin protein nuclear translocation following treatment with analogs 2f, 3c and 4f. Using transwell assays, we also found that these compounds were more potent than la (curcumin) in impeding the invasion of osteosarcoma cells, possibly through suppressing MMP-9 activity. Structure-activity-relationship studies revealed that Wnt inhibitory effects could be enhanced by shortening and restraining the flexibility of the 7-carbon linker moiety connecting the terminal aromatic rings of curcumin and substituting both rings with appropriate substituents. Our results demonstrate that the synthesized curcumin analogs are more potent Wnt inhibitors in osteosarcoma cell lines as compared to parental curcumin and are good lead compounds for further development. Future in vivo tests with these compounds will define their therapeutic potentials as promising drug candidates for clinical treatment of osteosarcoma. (C) 2013 Elsevier Masson SAS. All rights reserved.
• US9365486B2
  申请人：——

  公开号：US9365486B2

  公开（公告）日：2016-06-14
• [EN] INHIBITION OF THE GROWTH OF TUMOUR CELLS<br/>[FR] INHIBITION DE LA CROISSANCE DE CELLULES TUMORALES
  申请人：UNIV PRETORIA

  公开号：WO2008135886A2

  公开（公告）日：2008-11-13

  (EN) The invention provides the use of a compound selected from compounds of the formula (2) and pharmaceutically acceptable salts thereof in which: R1 is halogen; either R2 is H and R3 is XR4 or R3 is H and R2 is XR4; X is -COCH=CH- or -CH=CHCO-; and XR4 is Formula (I) in which: R5, R6, R7, and R8 are independently H, halogen, OR9 or CH2- NR10R11 in which R9 is H or C1-C3 alkyl and R10 and R11 are together or independently H, pyrrolidinyl, piperidinyl, morpholinyl, -CH2 - morpholine, 1 -ethyl-1 -piperizinyl, t- butylamino, dimethylamino or diethylamino, in the manufacture of a medicament for the inhibition of the growth of tumour cells.(FR) L'invention concerne l'utilisation d'un composé choisi parmi des composés de la formule (2) et des sels pharmaceutiquement acceptables de ceux-ci, dans laquelle : R1 est halogène; soit R2 est H et R3 est XR4, soit R3 est H et R2 est XR4; X est -COCH=CH- ou -CH=CHCO-; et XR4 est représenté par la formule (I) dans laquelle : R5, R6, R7 et R8 sont indépendamment H, halogène, OR9 ou CH2- NR10R11, R9 étant H ou alkyle en C1-C3 et R10 et R11 étant ensembles ou indépendamment H pyrrolidinyle, piperidinyle, morpholinyle, -CH2- morpholine, 1-éthyl-1-piperizinyl, t-butylamino, diméthylamino ou diéthylamino, cette utilisation étant dans la fabrication d'un médicament pour l'inhibition de la croissance de cellules tumorales.