1-(2-hydroxy-4,6-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-one | 118062-57-0

• 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-4,6-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-one
• 英文别名: 2-hydroxy-3-(3,3-dimethylallyl)-4,4',6-trimethoxymethoxy-3'-methoxy-chalcone；2'-Hydroxy-3-methoxy-4,4',6'-tris(methoxymethoxy)-3'-(3-methyl-2-butenyl)chalcone；1-[2-hydroxy-4,6-bis(methoxymethoxy)-3-(3-methylbut-2-enyl)phenyl]-3-[3-methoxy-4-(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 118062-57-0
• 化学式: C₂₇H₃₄O₉
• 分子量: 502.562
• InChiKey: MMRISUDCBWMNHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-4,6-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-one 在 盐酸 、 双氧水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 14.0h， 生成 racemoflavone
  参考文献：
  名称：

  NLRP3炎症小体抑制活性天然异戊烯基黄酮类化合物的全合成/半合成

  摘要：

  炎症是身体对刺激的防御反应。当体内平衡受到干扰时，可能会导致疾病。黄酮类化合物具有明显的抗炎作用，异戊烯基显着增强黄酮类化合物的药理活性。因此，异戊烯基黄酮类化合物有潜力作为抗炎药物开发的先导化合物。本研究共合成了 8 个天然化合物，包括 5,7-二羟基-4'-甲氧基-8-异戊二烯类黄酮 ()、4'-O-甲基阿兰黄酮 ()、Kushenol W () 和消旋黄酮 ()，并已全合成首次。此外，三种黄酮醇：Licoflavonol ()、3,5,7,3',4'-五羟基-6-异戊二烯黄酮醇 () 和 Macarangin ()，可以通过直接异戊烯化一步合成。在此过程中，还同时探索了一种经济高效的β-异戊烯基化方法，以促进天然产物的高效合成。通过 NLRP3 信号通路评估这些化合物的潜在抗炎活性。值得注意的是，Macarangin ()表现出最有效的抑制作用。 SAR（结构-活性关系）还表明异戊烯

  DOI：

  10.1016/j.bmcl.2024.129777
• 作为产物：
  描述：

  1-[2,4,6-三羟基-3-(3-甲基丁-2-烯基)苯基]乙酮 在 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 24.33h， 生成 1-(2-hydroxy-4,6-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  NLRP3炎症小体抑制活性天然异戊烯基黄酮类化合物的全合成/半合成

  摘要：

  炎症是身体对刺激的防御反应。当体内平衡受到干扰时，可能会导致疾病。黄酮类化合物具有明显的抗炎作用，异戊烯基显着增强黄酮类化合物的药理活性。因此，异戊烯基黄酮类化合物有潜力作为抗炎药物开发的先导化合物。本研究共合成了 8 个天然化合物，包括 5,7-二羟基-4'-甲氧基-8-异戊二烯类黄酮 ()、4'-O-甲基阿兰黄酮 ()、Kushenol W () 和消旋黄酮 ()，并已全合成首次。此外，三种黄酮醇：Licoflavonol ()、3,5,7,3',4'-五羟基-6-异戊二烯黄酮醇 () 和 Macarangin ()，可以通过直接异戊烯化一步合成。在此过程中，还同时探索了一种经济高效的β-异戊烯基化方法，以促进天然产物的高效合成。通过 NLRP3 信号通路评估这些化合物的潜在抗炎活性。值得注意的是，Macarangin ()表现出最有效的抑制作用。 SAR（结构-活性关系）还表明异戊烯

  DOI：

  10.1016/j.bmcl.2024.129777

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, biological evaluation of prenylflavonoids as vasorelaxant and neuroprotective agents
  作者：Xiaowu Dong、Lingling Qi、Chaoyi Jiang、Jing Chen、Erqing Wei、Yongzhou Hu

  DOI：10.1016/j.bmcl.2009.04.120

  日期：2009.6

  A series of prenylflavonoids with multiple hydroxyl groups were synthesized and evaluated for their vasorelaxant activities against rat aorta rings pre-contracted by phenylephrine (PE), as well as their neuroprotective effects against OGD induced PC12 cell injury. The results indicated that the prenyl group at A-ring of prenylflavonoids, as well as hydroxyl groups at B-ring was important for their activities. (+/-)Leachianone G 1b, bearing 8-prenyl and 2',4'-dihydoxyl groups, exhibited the most potent vasorelaxant and neuroprotective effects. (C) 2009 Elsevier Ltd. All rights reserved.
• Identification of SVM-based classification model, synthesis and evaluation of prenylated flavonoids as vasorelaxant agents
  作者：Xiaowu Dong、Yujie Liu、Jingying Yan、Chaoyi Jiang、Jing Chen、Tao Liu、Yongzhou Hu

  DOI：10.1016/j.bmc.2008.07.031

  日期：2008.9

  Support vector machine (SVM) was applied to predict vasorelaxation effect of different structural molecules. A good classification model had been established, and the accuracy in prediction for the training, test, and overall datasets was 93.0%, 82.6%, and 89.5%, respectively. Furthermore, the model was used to predict the activity of a series of prenylated flavonoids. According to the estimated result, eleven molecules 1-11 were selected and synthesized. Their vasodilatory activities were determined experimentally in rat aorta rings that were pretreated with phenylephrine ( PE). Structure-activity relationship (SAR) analysis revealed that flavanone derivatives showed the most potent activities, while flavone and chalcone derivatives exhibited medium activities. (C) 2008 Elsevier Ltd. All rights reserved.