1-[2-hydroxy-3-(2-propenyl)-4,6-bis(methoxymethoxy)phenyl]ethanone | 118056-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-hydroxy-3-(2-propenyl)-4,6-bis(methoxymethoxy)phenyl]ethanone
• 英文别名: 1-[3-allyl-2-hydroxy-4,6-bis(methoxymethoxy)phenyl]ethanone；2-hydroxy-3-allyl-4,6-dimethoxymethoxy-acetophenone；2'-hydroxy-4',6'-bismethoxymethoxy-3'-(2-propenyl)acetophenone；2'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(2-propenyl)acetophenone；1-[2-hydroxy-4,6-bis(methoxymethoxy)-3-prop-2-enylphenyl]ethanone
• CAS: 118056-13-6
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: FRHGAFREYMSVBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[2-hydroxy-3-(2-propenyl)-4,6-bis(methoxymethoxy)phenyl]ethanone 以 乙醇 为溶剂， 以obtained in Production Example 6 and 13.7 g of the p-methoxymethoxybenzaldehyde的产率得到4-methoxymethoxy-benzaldehyde
  参考文献：
  名称：

  Anti-ulcer agent comprising chalcone derivative

  摘要：

  本发明涉及一种抗溃疡剂，其包括以下通式I所表示的化合物作为有效成分，以及包含在该通式I所表示的化合物中的一种新的查尔酮衍生物： 其中，X和Y独立地代表氢原子或共同形成单键，R1代表羟基、乙酰氧基、羧甲氧基或甲氧羰基甲氧基，R2代表氢原子、异戊烯基、异戊基或丙基，R3代表羟基或甲氧基，R4代表氢原子、羟基或甲氧基，R5代表氢原子、羟基、甲氧基或异戊基，R6代表羟基、甲氧基或羧甲氧基，R7代表氢原子或甲氧基。

  公开号：

  US05234951A1
• 作为产物：
  描述：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 29.0h， 生成 1-[2-hydroxy-3-(2-propenyl)-4,6-bis(methoxymethoxy)phenyl]ethanone
  参考文献：
  名称：

  三叶草冠外消旋苯乙酮单体的全合成及体外抗肿瘤活性

  摘要：

  六苯乙酮衍生物，acronyculatins我（1），J（2），K（3），L（4），N（5）和O（6），最近从Acronychia trifoliolata，和已知的acronyculatin的结构中分离出来。B（7）被修改。由于分离产品的数量有限，以及它们的结构相似性，所以外消旋的肩甲素I–L，N，O和B（1 – 7合成）以确认其结构并获得足够的材料用于生物学评估。通过羟基保护，烯丙基化或烯丙基化，环氧化和环化的各种顺序，将三羟基苯乙酮转化为目标化合物。Ç -Prenylations通过直接加入异戊烯基或通过1,3-或3,3-σ重排进行。通过在Raji细胞中由12 - O-十四烷酰phorbol-13-乙酸酯诱导的爱泼斯坦-巴尔病毒早期抗原（EBV-EA）活化，在抗肿瘤促进试验中评估了合成的外消旋化合物。所有测试的化合物均显着抑制EBV-EA活化。尤其是外消旋顶体素I（1）显示出最有效的抑制作用，IC

  DOI：

  10.1021/acs.jnatprod.6b00646

文献信息

• Anti-ulcer agent comprising chalcone derivative as effective ingredient
  申请人：Tsumura & Co.

  公开号：US05106871A1

  公开（公告）日：1992-04-21

  The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: ##STR1## wherein X and Y independently stand for a hydrogen atom or together form a single bond, R.sub.1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R.sub.2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R.sub.3 stands for hydroxyl group or a methoxy group, R.sub.4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R.sub.5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R.sub.6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R.sub.7 stands for a hydrogen atom or a methoxy group.

  本发明涉及一种抗溃疡剂，其包括以下一般式I所代表的化合物作为有效成分，以及包含在由该一般式I所代表的化合物中的一种新的查尔酮衍生物：##STR1## 其中X和Y独立地代表氢原子或共同形成一个单键，R.sub.1代表羟基、乙酰氧基、羧甲氧基或甲氧羰基甲氧基，R.sub.2代表氢原子、异戊二烯基、异戊基或丙基，R.sub.3代表羟基或甲氧基，R.sub.4代表氢原子、羟基或甲氧基，R.sub.5代表氢原子、羟基、甲氧基或异戊基，R.sub.6代表羟基、甲氧基或羧甲氧基，R.sub.7代表氢原子或甲氧基。
• Synthesis and Antifungal Activity of Chromones and Benzoxepines from the Leaves of <i>Ptaeroxylon obliquum</i>
  作者：Modibo S. Malefo、Thanyani E. Ramadwa、Ibukun M. Famuyide、Lyndy J. McGaw、Jacobus N. Eloff、Molahlehi S. Sonopo、Mamoalosi A. Selepe

  DOI：10.1021/acs.jnatprod.0c00587

  日期：2020.8.28

  showed moderate to good activity. 12-O-Acetyleranthin (8) had the highest activity against C. albicans, with an MIC value of 9.9 μM, while 12-O-acetylptaeroxylinol (9), the compound present in Ptaeroxylon obliquum, had the highest activity against C. neoformans, with an MIC value of 4.9 μM.

  该研究报告了具有生物活性的 oxepinochromones 12- O-乙酰基白质素 ( 8 )（角异构体）和 12- O-乙酰基ptaeroxylinol ( 9 )（线性异构体）的首次全合成。测定了这些化合物及其衍生物对白色念珠菌和新型隐球菌的抗真菌活性。大多数化合物在两种真菌之间具有良好的选择性，并显示出中等至良好的活性。12- O-乙酰基花青素 ( 8 ) 对白色念珠菌的活性最高，MIC 值为 9.9 μM，而 12- O-乙酰基丁二烯酚 ( 9 )，其存在于Ptaeroxylonobliquum对新型隐球菌的活性最高，MIC 值为 4.9 μM。
• Design, Synthesis, and Biological Evaluation of Prenylated Chalcones as Vasorelaxant Agents
  作者：Xiaowu Dong、Jing Chen、Chaoyi Jiang、Tao Liu、Yongzhou Hu

  DOI：10.1002/ardp.200800229

  日期：2009.7

  Five prenylated chalcones and one allylated chalcone were prepared according to the analysis based on support vector machine (SVM) classification model. Most of the synthesized chalcones showed potent vasorelaxant activities through evaluation in aortic rings with the endothelium pre‐contracted by phenylephrine (PE), indicating that the experimental activities were in good agreement with the theoretical

  根据基于支持向量机(SVM)分类模型的分析，制备了5个异戊二烯化查耳酮和1个烯丙基化查耳酮。大多数合成的查尔酮通过评估主动脉环与去氧肾上腺素（PE）预收缩的内皮显示出有效的血管舒张活性，表明实验活性与理论活性非常吻合。这些化合物的构效关系表明，取代基模式和羟基的数量对其血管舒张活性至关重要，并且用烯丙基取代异戊二烯基保留了有效的活性。
• ANTI-ULCEROUS AGENT CONTAINING CHALCONE DERIVATIVE AS EFFECTIVE INGREDIENT AND NOVEL CHALCONE DERIVATIVES
  申请人：TSUMURA & CO.

  公开号：EP0292576A1

  公开（公告）日：1988-11-30

  An anti-ulcerous agent containing a compound represented by general formula (I) as effective ingredient and novel chalcone derivatives included by the compounds. In the disclosed formula X and Y each represents a hydrogen atom or, when taken together, they represent a direct bond, R1 represents a hydroxy, acetoxy, carbomethoxy or methoxycarbonylmethoxy group, R2 represents a hydrogen atom or an isoprenyl, isopentyl or propyl group, R3 represents a hydroxy or methoxy group, R4 represents a hydrogen atom or a hydroxy or methoxy group, Rs represents a hydrogen atom or a hydroxy, methoxy or isopentyl group, R6 represents a hydroxy, methoxy or carbomethoxy group, and R7 represents a hydrogen atom or a methoxy group.

  一种抗溃疡剂，含有通式(I)代表的化合物作为有效成分，以及由该化合物包含的新型查尔酮衍生物。在所公开的式中，X 和 Y 各代表一个氢原子，或当它们结合在一起时，代表一个直接键，R1 代表羟基、乙酰氧基、羰基甲氧基或甲氧基羰基甲氧基，R2 代表一个氢原子或异丙基、异戊基或丙基、R3 代表羟基或甲氧基，R4 代表氢原子或羟基或甲氧基，Rs 代表氢原子或羟基、甲氧基或异戊基，R6 代表羟基、甲氧基或羰基甲氧基，R7 代表氢原子或甲氧基。
• Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents
  作者：Xiaowu Dong、Tao Liu、Jingying Yan、Peng Wu、Jing Chen、Yongzhou Hu

  DOI：10.1016/j.bmc.2008.11.052

  日期：2009.1

  A series of flavonoid derivatives were designed, synthesized. Their vasorelaxant activities were evaluated experimentally against rat aorta rings pretreated with phenylephrine (PE). Among them, 6-hydroxy-8-allyl- 4'-chloro-flavanone 8q exhibited the highest vasodilatory activity (EC50 = 4.6 mu M, E-max = 95.1%). The 3D-QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method, and a statistically reliable model with good predictive power (r(2) = 0.872 and q(cv)(2) = 0.496) was established. The contour plots of CoMFA model provide a good insight into the structure-activity relationships of these compounds and may be used to design more potent flavonoids derivatives as vasorelaxant agents. (C) 2008 Elsevier Ltd. All rights reserved.