6-prenylpinocembrin | 55051-77-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-prenylpinocembrin
• 英文别名: isoglabranin；(2S)-5,7-dihydroxy-6-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
• CAS: 55051-77-9
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: UOWOIGNEFLTNAW-KRWDZBQOSA-N

物化性质

• 熔点：
  214-216 °C(Solv: hexane (110-54-3))
• 沸点：
  552.2±50.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-prenylpinocembrin 在 三氟乙酸 作用下， 以75%的产率得到5-Hydroxy-8,8-dimethyl-2-phenyl-2,3,7,8-tetrahydro-6H-pyrano[3,2-g]chromen-4-one
  参考文献：
  名称：

  类黄酮等成分与胰岛素分泌活性Pseudarthria木莲

  摘要：

  从Pseudarthria hookeri中分离出三个新的黄酮类化合物，即pseudarflavones A（1）和B（2）和6,7-（2⿳，2⿳-二甲基二甲基铬烷）黄酮（3）和13种已知化合物：Boeravinone L（5），gancaonin P（4），dorsamin F（10），大黄素（6），6-异戊烯基pinocembrin（7），hiravanone（11），dorsmanin I（12），6,8-二异戊烯基间烟酸（13），6-异戊烯基3⿲-甲氧基香dict酚（14），扁豆酚（15），乳脂醇（16），原儿茶酸（17）和α-叔噻吩基（18）。通过IR，MS，1D和2D NMR光谱技术并与文献报道的数据进行比较，阐明了它们的结构。化学转化也被用来确认一些任务。化合物的胰岛素分泌活性（1，3 ⿿ 18）上分离的小鼠胰岛进行评价。化合物（1，3，5和12）显示出温和的效果对葡萄糖刺激

  DOI：

  10.1016/j.phytol.2016.07.015

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• Cytotoxic Evaluation of (2S)-5,7-Dihydroxy-6-prenylflavanone Derivatives Loaded PLGA Nanoparticles against MiaPaCa-2 Cells
  作者：Berenice Andrade-Carrera、Beatriz Clares、Véronique Noé、Mireia Mallandrich、Ana Calpena、María García、María Garduño-Ramírez

  DOI：10.3390/molecules22091553

  日期：——

  The search for new alternatives for the prevention and treatment of cancer is extremely important to minimize human mortality. Natural products are an alternative to chemical drugs, since they are a source of many potential compounds with anticancer properties. In the present study, the (2S)-5,7-dihydroxy-6-prenylflavanone (semi-systematic name), also called (2S)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-2-phenyl-2,3-dihydro-4H-1-Benzopyran-4-one (CAS Name registered) (1) was isolated from Eysenhardtia platycarpa leaves. This flavanone 1 was considered as the lead compound to generate new cytotoxic derivatives 1a, 1b, 1c and 1d. These compounds 1, 1a, 1b, 1c, and 1d were then loaded in nanosized drug delivery systems such as polymeric nanoparticles (NPs). Small homogeneous spherical shaped NPs were obtained. Cytotoxic activity of free compounds 1, 1a, 1b, 1c, and 1d and encapsulated in polymeric NPs (NPs1, NPs1a, NPs1b, NPs1c and NPs1d) were evaluated against the pancreatic cancer cell line MiaPaCa-2. The obtained results demonstrated that NPs1a and NPs1b exhibited optimal cytotoxicity, and an even higher improvement of the cytotoxic efficacy was exhibited with the encapsulation of 1a. Based on these results, NPs1a were proposed as promising anticancer agent candidates.

  寻找预防和治疗癌症的新方法对于降低人类死亡率极其重要。天然产物是化学药物的替代品,因为它们是许多具有抗癌特性的潜在化合物的来源。在本研究中,从Eysenhardtia platycarpa叶子中分离出(2S)-5,7-二羟基-6-戊烯基黄烷酮(半系统名称),也称为(2S)-5,7-二羟基-6-(3-甲基-2-丁烯-1-基)-2-苯基-2,3-二氢-4H-1-苯并吡喃-4-酮(CAS注册名)(1)。这种黄烷酮1被视为生成新的细胞毒性衍生物1a、1b、1c和1d的先导化合物。然后将这些化合物1、1a、1b、1c和1d装载在聚合物纳米粒子(NPs)等纳米级药物传递系统中。获得了小的均匀球形NPs。对游离化合物1、1a、1b、1c和1d以及包封在聚合物NPs中的化合物(NPs1、NPs1a、NPs1b、NPs1c和NPs1d)对胰腺癌细胞系MiaPaCa-2的细胞毒性活性进行了评价。结果表明,NPs1a和NPs1b表现出最佳的细胞毒性,而1a的包封则表现出更高的细胞毒性效果。基于这些结果,NPs1a被提出作为有前景的抗癌药物候选物。
• PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  申请人：McMaster University

  公开号：US20210380513A1

  公开（公告）日：2021-12-09

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
• Flavonoids and other constituents with insulin secretion activity from Pseudarthria hookeri
  作者：Joseph Tchamgoue、Rahman M. Hafizur、Jean Claude Tchouankeu、Simeon F. Kouam、Achyut Adhikari、Abdul Hameed、Ivan R. Green、Mohammad I. Choudhary

  DOI：10.1016/j.phytol.2016.07.015

  日期：2016.9

  Three new flavonoids viz., pseudarflavones A (1) and B (2) and 6,7-(2⿳,2⿳-dimethylchromano)flavanone (3), were isolated from Pseudarthria hookeri together with thirteen known compounds: boeravinone L (5), gancaonin P (4), dorsamin F (10), emodin (6), 6-prenylpinocembrin (7), hiravanone (11), dorsmanin I (12), 6,8-diprenyleriodictyol (13), 6-prenyl-3⿲-methoxyeriodictyol (14), oblonginol (15), orobol

  从Pseudarthria hookeri中分离出三个新的黄酮类化合物，即pseudarflavones A（1）和B（2）和6,7-（2⿳，2⿳-二甲基二甲基铬烷）黄酮（3）和13种已知化合物：Boeravinone L（5），gancaonin P（4），dorsamin F（10），大黄素（6），6-异戊烯基pinocembrin（7），hiravanone（11），dorsmanin I（12），6,8-二异戊烯基间烟酸（13），6-异戊烯基3⿲-甲氧基香dict酚（14），扁豆酚（15），乳脂醇（16），原儿茶酸（17）和α-叔噻吩基（18）。通过IR，MS，1D和2D NMR光谱技术并与文献报道的数据进行比较，阐明了它们的结构。化学转化也被用来确认一些任务。化合物的胰岛素分泌活性（1，3 ⿿ 18）上分离的小鼠胰岛进行评价。化合物（1，3，5和12）显示出温和的效果对葡萄糖刺激