1-(2-hydroxy-4-(methoxymethoxy)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one | 78316-23-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2-hydroxy-4-(methoxymethoxy)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one
• 英文别名: 2'-Hydroxy-4,4'-bis(methoxymethoxy)chalcone；1-[2-hydroxy-4-(methoxymethoxy)phenyl]-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 78316-23-1
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: RVWNCGYNBUZJLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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-4-(methoxymethoxy)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以82.3%的产率得到7,4'-di(methoxymethoxy)flavan-4-one
  参考文献：
  名称：

  Synthesis and antitumor activity of liquiritigenin thiosemicarbazone derivatives

  摘要：

  In an attempt to develop potent and selective antitumor agents, a series of liquiritigenin thiosemicarbazone derivatives were designed and synthesized. The cytotoxicities of these compounds were evaluated in vitro against K562, DU-145, SGC-7901, HCT-116 and Hela cell lines. The pharmacological results showed that most of the prepared compounds displayed excellent selective cytotoxicity toward K562 and DU-145 cells. From the structure activity relationships we may conclude that the introduction of a thiosemicarbazone functional group at the 4-position in the skeleton of liquiritigenin is associated with an increase in cytotoxicity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.036
• 作为产物：
  描述：

  4-methoxymethoxy-benzaldehyde 、 1-[2-羟基-4-(甲氧基甲氧基)苯基]乙酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(2-hydroxy-4-(methoxymethoxy)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  A novel 4′‐brominated derivative of fisetin induces cell cycle arrest and apoptosis and inhibits EGFR / ERK1/2/STAT3 pathways in non‐small‐cell lung cancer without any adverse effects in mice

  摘要：

  DOI：

  10.1096/fj.202200669rr

文献信息

• Anti-ulcer agent comprising chalcone derivative
  申请人：Tsumura Juntendo, Inc.

  公开号：US05234951A1

  公开（公告）日：1993-08-10

  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 a 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。
• 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： ##STR1## 其中，X和Y独立地代表氢原子或形成单键，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。
• Synthesis and antitumor activity of liquiritigenin thiosemicarbazone derivatives
  作者：Kun Hu、Ze-hua Yang、Sha-Sha Pan、Hua-jin Xu、Jie Ren

  DOI：10.1016/j.ejmech.2010.04.036

  日期：2010.8

  In an attempt to develop potent and selective antitumor agents, a series of liquiritigenin thiosemicarbazone derivatives were designed and synthesized. The cytotoxicities of these compounds were evaluated in vitro against K562, DU-145, SGC-7901, HCT-116 and Hela cell lines. The pharmacological results showed that most of the prepared compounds displayed excellent selective cytotoxicity toward K562 and DU-145 cells. From the structure activity relationships we may conclude that the introduction of a thiosemicarbazone functional group at the 4-position in the skeleton of liquiritigenin is associated with an increase in cytotoxicity. (C) 2010 Elsevier Masson SAS. All rights reserved.
• A novel 4′‐brominated derivative of fisetin induces cell cycle arrest and apoptosis and inhibits <scp>EGFR</scp> / <scp>ERK1/2/STAT3</scp> pathways in non‐small‐cell lung cancer without any adverse effects in mice
  作者：Akash Sabarwal、Jaco C. van Rooyen、Jeremy Caburet、Moscos Avgenikos、Arpit Dheeraj、Mansoor Ali、Deepali Mishra、Joséphine S. B. de Meester、Saskia Stander、Willem A. L. van Otterlo、Catherine H. Kaschula、Rana P. Singh

  DOI：10.1096/fj.202200669rr

  日期：2022.12