E-3-(4-苄氧基)-1-(2.4-二苄氧基-6-羟基)苯基)丙烯酮 | 88607-79-8

• 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
• 中文名称: E-3-(4-苄氧基)-1-(2.4-二苄氧基-6-羟基)苯基)丙烯酮
• 英文名称: (E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one
• 英文别名: (E)-3-(4-(benzyloxy)phenyl)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)prop-2-en-1-one；E-3-(4-benzyloxyphenyl)-1-(2,4-bisbenzyloxy-6-hydroxyphenyl)prop-2-en-1-one；4,2',4'-tris(benzyloxy)-6'-hydroxychalcone；4,4',6'-Tribenzyloxy-2'-hydroxychalcone；4,4',6'-tribenzyloxynaringeninchalcone；E-3-(4-benzyloxyphenyl)-1-(2,4-bisbenzyloxy-6-hydroxyphenyl)propenone；E-3-(4-Benzyloxy)-1-(2.4-bisbenzyloxy-6-hydroxy)phenyl)propenone；(E)-1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-3-(4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 88607-79-8
• 化学式: C₃₆H₃₀O₅
• 分子量: 542.631
• InChiKey: POBAJWKYWOQRCS-DYTRJAOYSA-N

物化性质

• 熔点：
  127-129°C
• 沸点：
  756.0±60.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  E-3-(4-苄氧基)-1-(2.4-二苄氧基-6-羟基)苯基)丙烯酮 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以1.3 g的产率得到根皮素
  参考文献：
  名称：

  Jain, A. C.; Paliwal, Poonam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 416 - 418

  摘要：

  DOI：
• 作为产物：
  描述：

  溴甲苯 、 (S)-柚皮素 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以81%的产率得到E-3-(4-苄氧基)-1-(2.4-二苄氧基-6-羟基)苯基)丙烯酮
  参考文献：
  名称：

  Synthesis of a Potent and Selective Inhibitor of p90 Rsk

  摘要：

  The synthesis of the naturally occurring kaempferol glycoside SL0101 has been accomplished, as has its biochemical evaluation. SL0101 exhibits selective and potent p90 Rsk inhibitory activity at nanomolar concentrations without inhibiting the function of upstream kinases such as MEK, Raf, or PKC. The synthesis verified the structural assignment of the natural product and has provided access to material sufficient for detailed biological evaluation.

  DOI：

  10.1021/ol0500463

文献信息

• De Novo Asymmetric Syntheses of SL0101 and Its Analogues via a Palladium-Catalyzed Glycosylation
  作者：Mingde Shan、George A. O'Doherty

  DOI：10.1021/ol062076r

  日期：2006.10.1

  upon a diastereoselective palladium-catalyzed glycosylation, ketone reduction, and dihydroxylation to introduce the rhamno-stereochemistry. The asymmetry of the sugar moiety of these kaempferol glycosides was derived from Noyori reduction of an acylfuran. An acetyl group shift from an axial (C-2) to equatorial position (C-3) under basic conditions was also described. [reaction: see text]

  天然山ka酚糖苷SL0101（1a）及其类似物1b-e及其对映异构体的对映选择性合成已通过7-10个步骤完成。这些途径依赖于非对映选择性钯催化的糖基化，酮还原和二羟基化以引入鼠李糖立体化学。这些山emp酚糖苷的糖部分的不对称性源自酰基呋喃的Noyori还原。还描述了在基本条件下乙酰基从轴向（C-2）转移到赤道位置（C-3）。[反应：看文字]
• NOVEL ANALOGUES OF EPICATECHIN AND RELATED POLYPHENOLS
  申请人：SPHAERA PHARMA PVT. LTD.

  公开号：US20160039781A1

  公开（公告）日：2016-02-11

  The present invention provides novel analogues of epicatechin and related polyphenols, their variously functionalized derivatives, process for preparation of the same, composition comprising these compounds and their method of use.

  本发明提供了表儿茶素及相关多酚的新颖类似物，它们的各种官能化衍生物，以及它们的制备方法、包含这些化合物的组合物和它们的使用方法。
• Synthesis of (±)-Lotthanongine, a Novel Natural Product with a Flavan-Indole Hybrid Structure
  作者：Keisuke Suzuki、Keisuke Hatakeyama、Ken Ohmori

  DOI：10.1055/s-2005-868485

  日期：——

  First total synthesis of lotthanongine (3), a natural product with a flavan-indole composite structure, has been achieved via the Lewis acid-catalyzed C-C bond formation between the catechin and the indole units.

  首次完成了具有黄烷-吲哚复合结构的天然产物洛坦农(3)的全合成，这一过程是通过路易斯酸催化的儿茶素和吲哚单元之间的C-C键形成实现的。
• Practical Synthesis of a<i>C</i>-Glycosyl Flavonoid via<i>O</i>→<i>C</i>Glycoside Rearrangement
  作者：Toshihiro Kumazawa、Kazuhito Ohki、Mitsuo Ishida、Shingo Sato、Jun-ichi Onodera、Shigeru Matsuba

  DOI：10.1246/bcsj.68.1379

  日期：1995.5

  The C-glycosylation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride and 2-acetylphloroglucinol 3,5-bis(alkyl ether) in the presence of boron trifluoride etherate as an activator stereoselectively gave the β-C-glucoside in a good yield via O → C glycoside rearrangement. Subsequently, aldol condensation of the C-glucoside with benzaldehyde afforded the corresponding β-C-glucosyl chalcone in a good

  2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基氟和2-乙酰间苯三酚3,5-双（烷基醚）在三氟化硼醚化物作为活化剂存在下的C-糖基化立体选择性地得到通过 O → C 糖苷重排，β-C-糖苷的产率很高。随后，C-葡萄糖苷与苯甲醛的羟醛缩合以良好的收率提供相应的β-C-葡萄糖基查耳酮。
• Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin
  作者：The-Huan Tran、Thi-Thu-Hien Vo、Thi-Quynh-Nhi Vo、Thi-Cam-Nhung Cao、Thai-Son Tran

  DOI：10.1155/2021/4817900

  日期：2021.11.30

  Alzheimer’s disease (AD) is an irreversible neurodegenerative disease that affects many older people adversely. AD has been putting a huge socioeconomic burden on the healthcare systems of many developed countries with aging populations. The need for new therapies that can halt or reverse the progression of the disease is now extremely great. A research approach in the finding new treatment for AD that has attracted much interest from scientists for a long time is the reestablishment of cholinergic transmission through inhibition of acetylcholinesterase (AChE). Naringenin is a flavonoid with the potential inhibitory activity against AChE. From naringenin, many other flavonoid derivatives, such as flavanones and chalcones, can be synthesized. In this study, by applying the Williamson method, nine flavonoid derivatives were synthesized, including four flavanones and five chalcones. The evaluation of AChE inhibitory activity by the Ellman method showed that there were four substances (2, 4, 5, and 7) with relatively good biological activities (IC50 < 100 μM), and these biological activities were better than that of naringenin. The molecular docking revealed that strong interactions with amino acid residue Ser200 of the catalytic triad and those of the peripheral region of the enzyme were crucial for strong effects against AChE. Compound 7 had the strongest AChE inhibitory activity (IC50 13.0 ± 1.9 μM). This substance could be used for further studies.

  阿尔茨海默病（AD）是一种不可逆的神经退行性疾病，严重影响许多老年人。随着人口老龄化，AD已经给许多发达国家的医疗保健系统带来了巨大的社会经济负担。现在非常需要新的治疗方法来阻止或逆转疾病的进展。一种在寻找AD新治疗方法上引起科学家长期关注的研究方法是通过抑制乙酰胆碱酯酶（AChE）来重新建立胆碱能传递。柚皮素是一种具有潜在抑制AChE活性的类黄酮。从柚皮素中可以合成许多其他类黄酮衍生物，如类黄酮和香豆素。本研究采用Williamson方法合成了九种类黄酮衍生物，包括四种类黄酮和五种香豆素。通过Ellman方法评估AChE抑制活性，发现有四种物质（2、4、5和7）具有相对较好的生物活性（IC50 <100μM），这些生物活性比柚皮素更好。分子对接揭示了与催化三联体氨基酸残基Ser200和酶的周围区域的强相互作用对于强烈的AChE抑制效果至关重要。化合物7具有最强的AChE抑制活性（IC50 13.0 ± 1.9μM）。这种物质可以用于进一步的研究。