tetrakis(O-methoxymethyl)butein | 124775-23-1

• 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: tetrakis(O-methoxymethyl)butein
• 英文别名: 2',3,4,4'-tetrakis(methoxymethoxy)chalcone；(E)-1-(2,4-Bis(methoxymethoxy)phenyl)-3-(3,4-bis(methoxymethoxy)phenyl)prop-2-en-1-one；(E)-1-[2,4-bis(methoxymethoxy)phenyl]-3-[3,4-bis(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 124775-23-1
• 化学式: C₂₃H₂₈O₉
• 分子量: 448.47
• InChiKey: ADKHVJZZDAHAAW-WEVVVXLNSA-N

物化性质

• 沸点：
  589.4±50.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 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：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tetrakis(O-methoxymethyl)butein 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 19.0h， 以77%的产率得到(2R^*,3S^*)-tetrakis(O-methoxymethyl)butein epoxide
  参考文献：
  名称：

  Takahashi, Hiroshi; Kubota, Yumiko; Igushi, Mieko, Heterocycles, 1986, vol. 24, # 2, p. 369 - 377

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.5h， 生成 tetrakis(O-methoxymethyl)butein
  参考文献：
  名称：

  Potential application value of hydroxychalcones based on isoliquiritigenin in agricultural plant diseases

  摘要：

  为了提高领先化合物异黄酮的杀真菌活性，设计并制备了33种羟基查尔酮。

  DOI：

  10.1039/d2nj03261a

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 PPAR-.GAMMA. Ligand-Binding Activity of the New Series of 2'-Hydroxychalcone and Thiazolidinedione Derivatives
  作者：Sang Hoon Jung、Soo Young Park、Youngmi Kim-Pak、Hong Kyu Lee、Kyong Soo Park、Kuk Hyun Shin、Kazuo Ohuchi、Hyun-Kyung Shin、Sam Rok Keum、Soon Sung Lim

  DOI：10.1248/cpb.54.368

  日期：——

  Fifteen chalcones and three thiazolidinedione (TZD) chalcones were prepared to evaluate their peroxisome proliferator-activated receptor-γ (PPAR-γ) ligand-binding activities. Among the three TZDs, one compound possessed PPAR-γ transactivation potential, while the others showed antagonistic activity against PPAR-γ transactivation. Among the chalcones, compound 5 was the most potent, and structure–activity relationship studies indicated that a methoxyl group in position C-4 and hydroxyl group in position C-4′ or 5′ in chalcone plays a key role in determining the potency of PPAR-γ activation.

  研究人员制备了十五种查耳酮和三种噻唑烷二酮（TZD）查耳酮，以评估它们的过氧化物酶体增殖激活受体-γ（PPAR-γ）配体结合活性。在这三种 TZDs 中，一种化合物具有 PPAR-γ 转激活潜力，而其他化合物则对 PPAR-γ 转激活具有拮抗活性。结构-活性关系研究表明，查尔酮中 C-4 位的甲氧基和 C-4′ 或 5′ 位的羟基对 PPAR-γ 的激活效力起着关键作用。
• 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。
• Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers
  作者：Emily Hofmann、Jonathan Webster、Thuy Do、Reid Kline、Lindsey Snider、Quintin Hauser、Grace Higginbottom、Austin Campbell、Lili Ma、Stefan Paula

  DOI：10.1016/j.bmc.2015.12.024

  日期：2016.2

  In this study, we evaluated the abilities of a series of chalcones to inhibit the activity of the enzyme xanthine oxidase (XO) and to scavenge radicals. 20 mono-and polyhydroxylated chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and then tested for inhibitory potency against XO, a known generator of reactive oxygen species (ROS). In parallel, the ability of the synthesized chalcones to scavenge a stable radical was determined. Structure-activity relationship analysis in conjunction with molecular docking indicated that the most active XO inhibitors carried a minimum of three hydroxyl groups. Moreover, the most effective radical scavengers had two neighboring hydroxyl groups on at least one of the two phenyl rings. Since it has been proposed previously that XO inhibition and radical scavenging could be useful properties for reduction of ROS-levels in tissue, we determined the chalcones' effects to rescue neurons subjected to ROS-induced stress created by the addition of beta-amyloid peptide. Best protection was provided by chalcones that combined good inhibitory potency with high radical scavenging ability in a single molecule, an observation that points to a potential therapeutic value of this compound class. (c) 2015 Elsevier Ltd. All rights reserved.
• US5106871A
  申请人：——

  公开号：US5106871A

  公开（公告）日：1992-04-21