3-(3,4-bis(methoxymethoxy)phenyl)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one | 112772-60-8

• 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: 3-(3,4-bis(methoxymethoxy)phenyl)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one
• 英文别名: 2'-Hydroxy-3,4,4',6'-tetrakis(methoxymethoxy)chalcone；3-[3,4-bis(methoxymethoxy)phenyl]-1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 112772-60-8
• 化学式: C₂₃H₂₈O₁₀
• 分子量: 464.469
• InChiKey: QFHIMBFWWKHSJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-(3,4-bis(methoxymethoxy)phenyl)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one 在 盐酸 、 水 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 24.5h， 生成 金色草素
  参考文献：
  名称：

  A One-Pot Synthesis of Aurones from Substituted Acetophenones and Benz­aldehydes: A Concise Synthesis of Aureusidin

  摘要：

  A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations.

  DOI：

  10.1055/s-0031-1291153
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 3-(3,4-bis(methoxymethoxy)phenyl)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  新型骨架黄烷-生物碱的全合成

  摘要：

  本研究描述了新型骨架天然化合物 kinkeloids A 和 B 的首次全合成，这是一组从非洲植物 Combretum micranthum 中分离出的新发现的黄烷生物碱。关键和最后一步是通过曼尼希反应实现的，通过该反应，哌啶部分与黄烷部分偶联。通过使用 LC/MS 与植物叶片提取物中的那些进行比较，进一步确认了合成的kinkeloids 的身份。

  DOI：

  10.3390/molecules25194491

文献信息

• Biological Properties and Absolute Configuration of Flavanones From Calceolariathyrsiflora Graham
  作者：Ernesto Valdés、César González、Katy Díaz、Yesseny Vásquez-Martínez、Carolina Mascayano、Claudia Torrent、Francisco Cabezas、Sophia Mejias、Margarita Montoya、Marcelo Cortez-San Martín、Marcelo A. Muñoz、Pedro Joseph-Nathan、Mauricio Osorio、Lautaro Taborga

  DOI：10.3389/fphar.2020.01125

  日期：——

  Flavanones (–)-(2S)-5,4’-dihydroxy-7-methoxyflavanone (1) and (–)-(2S)-5,3’,4’-trihydroxy-7-methoxyflavanone (2) were isolated from the extracts of Calceolariathyrsiflora Graham, an endemic perennial small shrub growing in the central zone of Chile. The absolute configuration of these compounds was resolved by optical rotation experiments and in silico calculations. Three analogs (3, 4, and 5) were synthesized

  黄烷酮（–）-（2小号）-5,4'-二羟基-7-甲氧基黄酮（1）和（–）-（2小号）-5,3'，4'-三羟基-7-甲氧基黄酮（2）从 钙藻锡兰Graham，一种生长于智利中部的地方性多年生小灌木。这些化合物的绝对构型通过旋光实验和在计算机上计算。合成了三个类似物（3、4和5），以与所研究的生物学方法进行构效关系。生物学测试表明，仅黄烷酮2对耐甲氧西林的菌株具有中等抑制作用小号。 金黄色MRSA 97-77（MIC值为50 µg / ml）。此外，黄烷酮2对5-hLOX表现出有效，选择性和竞争性抑制作用，这支持该植物在呼吸道疾病中作为抗炎药的传统用途。另外，2表现出对B16-F10（8.07±1.61 µM）的细胞毒性和选择性作用，但活性比依托泊苷和紫杉醇少4.6和17倍。
• 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。
• 金色草素在制备治疗神经退行性疾病及延缓衰老药物中的应用
  申请人：常州大学

  公开号：CN117771230A

  公开（公告）日：2024-03-29

  本发明属于药物技术领域，具体提供了一种金色草素在制备治疗神经退行性疾病及延缓衰老药物中的应用。实验证明，金色草素可显著提高对神经损伤细胞的保护作用；对秀丽隐杆线虫寿命及衰老生理指标相关参数(褐脂质、抗氧化能力、自噬等)有正向影响；对秀丽隐杆线虫帕金森症病理模型具有明显的治疗作用；显著改善阿尔茨海默症模型小鼠的学习记忆障碍和运动功能障碍。提示金色草素具有治疗神经退行性疾病的作用，且可能通过提高线虫的抗氧化能力和自噬水平延缓衰老，能够用于制备治疗神经退行性疾病及延缓衰老的药品。
• Antibacterial and Antioxidant Activity of Synthetic Polyoxygenated Flavonoids
  作者：Mauricio Enrique Osorio-Olivares、Yesseny Vásquez-Martínez、Katy Díaz、Javiera Canelo、Lautaro Taborga、Luis Espinoza-Catalán

  DOI：10.3390/ijms25115999

  日期：——

  Flavonoids are an abundant class of naturally occurring compounds with broad biological activities, but their limited abundance in nature restricts their use in medicines and food additives. Here we present the synthesis and determination of the antibacterial and antioxidant activities of twenty-two structurally related flavonoids (five of which are new) by scientifically validated methods. Flavanones (FV1–FV11) had low inhibitory activity against the bacterial growth of MRSA 97-7. However, FV2 (C5,7,3′,4′ = OH) and FV6 (C5,7 = OH; C4′ = SCH3) had excellent bacterial growth inhibitory activity against Gram-negative E. coli (MIC = 25 µg/mL for both), while Chloramphenicol (MIC = 25 µg/mL) and FV1 (C5,7,3′ = OCH3; 4′ = OH) showed inhibitory activity against Gram-positive L. monocytogenes (MIC = 25 µg/mL). From the flavone series (FO1–FO11), FO2 (C5,7,3′,4′ = OH), FO3 (C5,7,4′ = OH; 3′ = OCH3), and FO5 (C5,7,4′ = OH) showed good inhibitory activity against Gram-positive MRSA 97-7 (MIC = 50, 12, and 50 µg/mL, respectively), with FO3 being more active than the positive control Vancomycin (MIC = 25 µg/mL). FO10 (C5,7= OH; 4′ = OCH3) showed high inhibitory activity against E. coli and L. monocytogenes (MIC = 25 and 15 µg/mL, respectively). These data add significantly to our knowledge of the structural requirements to combat these human pathogens. The positions and number of hydroxyl groups were key to the antibacterial and antioxidant activities.