2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate | 3162-03-6

• 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: 2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate
• 英文别名: 4-(7-acetoxy-5-hydroxy-4-oxochroman-2-yl)phenyl acetate；7,4’-O,O-diacetoxynaringenin；4',7-di-O-acetylnaringenin；diacetyl-7,4' naringenine；4',7-diacetylnaringenin；(+/-)-7-acetoxy-2-(4-acetoxy-phenyl)-5-hydroxy-chroman-4-one；[4-(7-acetyloxy-5-hydroxy-4-oxo-2,3-dihydrochromen-2-yl)phenyl] acetate
• CAS: 3162-03-6
• 化学式: C₁₉H₁₆O₇
• 分子量: 356.332
• InChiKey: PPTNIBIWQQIJJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate 在 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 、 偶氮二甲酸二异丙酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 potassium hydroxide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 黄腐酚
  参考文献：
  名称：

  柚皮素合成黄腐酚和黄腐酚-d3

  摘要：

  报道了从容易获得的柚皮素中六步合成黄腐酚 ( 1a ) 及其 d 3 -衍生物 ( 1b )。通过 Mitsunobu 反应引入异戊二烯侧链，随后铕催化的 Claisen 重排和碱基介导的色原酮打开得到 α,β-共轭酮系统。化合物1b用作两种波兰啤酒中1a的稳定同位素稀释测定的内标。

  DOI：

  10.1039/d1ra05443k
• 作为产物：
  描述：

  (S)-柚皮素 生成 2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate
  参考文献：
  名称：

  CHANDRA, SURESH;SASTRY, M. S., INDIAN J. PHARM. SCI., 50,(1988) N, C. 321-322

  摘要：

  DOI：

文献信息

• Selective C-6 Prenylation of Flavonoidsvia Europium(III)- Catalyzed Claisen Rearrangement and Cross-Metathesis
  作者：Sandra Tischer、Peter Metz

  DOI：10.1002/adsc.200600454

  日期：2007.1.8

  Starting from the readily available parent flavonoids, the flavanone 6-prenylnaringenin, the isoflavone 6-prenylgenistein (wighteone, erythrinin B) and a protected derivative of the flavonol 6-prenylquercetin (gancaonin P) have been synthesized in short reaction sequences featuring the title processes as key steps.

  从容易获得的母体类黄酮开始，以标题过程为特征的短反应序列，合成了黄烷酮6-异戊烯基柚皮素，异黄酮6-异戊二烯异黄酮（Wighteone，赤藓素B）和黄酮醇6-异戊二烯槲皮素（gancaonin P）的受保护衍生物。作为关键步骤。
• Reduction de flavanones par le cyanoborohydrure de sodium dans l'acide trifluoroacetique - I/
  作者：Guy Lewin、Maryse Bert、Jean-Claude Dauguet、Corinne Schaeffer、Jean-Luc Guinamant、Jean-Paul Volland

  DOI：10.1016/s0040-4039(01)93420-3

  日期：——

  Reduction of natural flavanones with NaBH3CN in CF3COOH gives, depending on substituents 7 and 4′, either flavanes or 1,3-diaryl propanes.

  在CF 3 COOH中用NaBH 3 CN还原天然黄烷酮，取决于取代基7和4'，产生黄烷或1,3-二芳基丙烷。
• An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement
  作者：Sven Gester、Peter Metz、Oliver Zierau、Günter Vollmer

  DOI：10.1016/s0040-4020(00)01078-4

  日期：2001.2

  enin (2) have been prepared in racemic form using prenyl ether 5 as a general intermediate. While a domino Claisen–Cope rearrangement of 5 was the key step in the synthesis of 1, the cytotoxic compound 2 was additionally secured via a europium(III)-catalyzed Claisen rearrangement of 5 at low temperature. Both 1 and 2 display strong estrogenic activities.

  从市售的柚皮素（3）开始，使用异戊二烯醚5作为一般中间体，以外消旋形式制备了类黄酮8-异戊烯基柚皮素（1）和6-（1,1-二甲基烯丙基）柚皮素（2）。尽管多米诺克莱森-应对的重排5是在合成中的关键步骤1中，细胞毒性化合物2通过铕（III）被加催化的固定的克莱森重排5在低温下。既1和2显示强雌激素活性。
• Molecular Docking and Panicolytic Effect of 8-Prenylnaringenin in the Elevated T-Maze
  作者：Mariane Cristovão Bagatin、Camila Santos Suniga Tozatti、Layara Akemi Abiko、Diego Alberto dos Santos Yamazaki、Priscila Rebeca Alves Silva、Leonardo Martins Perego、Elisabeth Aparecida Audi、Flavio Augusto Vicente Seixas、Ernani Abicht Basso、Gisele de Freitas Gauze

  DOI：10.1248/cpb.c14-00569

  日期：——

  The purpose of this study was to investigate the effects of the chronic administration of a racemic mixture of 8-prenylnaringenin (8-PN) on rats submitted to the elevated T-maze (ETM) model of generalized anxiety and panic disorders. The selective serotonin (SERT) reuptake inhibitor fluoxetine was used as a positive control. Rat locomotion was assessed in a circular arena following each drug treatment. The administration of racemic 8-PN for 21 d in rats increased one-way escape latencies from the ETM open arm, indicating a panicolytic effect. To evaluate the interactions of 8-PN with monoamine transporters, a docking study was performed for both the R and S configurations of 8-PN towards SERT, norepinephrine (NET) and dopamine transporters (DAT). The application of the docking protocol showed that (R)-8-PN provides greater affinity to all transporters than does the S enantiomer. This result suggests that enantiomer (R)-8-PN is the active form in the in vivo test of the racemic mixture.

  本研究旨在探讨长期服用 8-异戊烯基柚皮素（8-PN）外消旋混合物对大鼠广泛性焦虑症和恐慌症高架 T 型迷宫（ETM）模型的影响。选择性血清素（SERT）再摄取抑制剂氟西汀被用作阳性对照。每次用药后，在圆形迷宫中对大鼠的运动能力进行评估。外消旋 8-PN 给药 21 天后，大鼠从 ETM 开放臂的单向逃逸潜伏期延长，这表明它具有缓解恐慌的作用。为了评估 8-PN 与单胺转运体的相互作用，对 8-PN 的 R 和 S 构型与 SERT、去甲肾上腺素（NET）和多巴胺转运体（DAT）进行了对接研究。对接协议的应用表明，(R)-8-PN 与所有转运体的亲和力均高于 S 对映体。这一结果表明，在外消旋混合物的体内试验中，(R)-8-PN 对映体是活性形式。
• Ability of Prenylflavanones Present in Hops to Induce Apoptosis in a Human Burkitt Lymphoma Cell Line
  作者：Reinhard Diller、Herbert Riepl、Oliver Rose、Corazon Frias、Günter Henze、Aram Prokop

  DOI：10.1055/s-2007-981545

  日期：2007.7

  The identification of effective cancer preventive compounds from hops has become an important issue in public health-related research. We compared the antiproliferative and apoptosis-inducing effects of side chain variants of prenylflavanones, e. g., 8-prenylnaringenin (7) and 8-geranylnaringenin (10), which have been identified in hops (Humulus lupulus), and their synthetic variations 8-furanmethylnaringenin (8) and 8-cinnamylnaringenin (9). These were accessible by a Mitsunobu reaction and Claisen rearrangement. Flavanones 9 and 10 showed cytotoxic and apoptotic activities. Apoptosis was induced in a mitochondrial dependent manner. 8-Cinnamylnaringenin (9) displayed noticeably improved apoptotic effects when compared to 8-prenylnaringenin. The potential of 8-prenylnaringenin (7) is shown in an ex vivo experiment on a multi-drug resistant leukaemia blast.

  从啤酒花中鉴定有效的癌症预防化合物已成为公共健康相关研究的一个重要课题。我们比较了已在啤酒花（Humulus lupulus）中发现的8-prenylnaringenin (7)和8-geranylnaringenin (10)等prenylflavanones侧链变体及其合成变体8-furanmethylnaringenin (8)和8-cinnamylnaringenin (9)的抗增殖和诱导细胞凋亡作用。通过 Mitsunobu 反应和 Claisen 重排，可以获得这些化合物。黄烷酮 9 和 10 具有细胞毒性和细胞凋亡活性。诱导细胞凋亡的方式依赖于线粒体。与 8-异戊烯基柚皮素相比，8-肉桂基柚皮素（9）的凋亡效果明显提高。8 -异戊烯基柚皮素（7）的潜力体现在对具有多种抗药性的白血病细胞进行的体内外实验中。