7-8-二羟基-2,3-二羟芴 | 51876-18-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 7-8-二羟基-2,3-二羟芴
• 英文名称: 7,8-dihydroxyflavanone
• 英文别名: 7,8-dihydroxy-2-phenyl-chroman-4-one；7,8-Dihydroxy-2-phenyl-chroman-4-on；7,8-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one
• CAS: 51876-18-7
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: OXEDXEXEXGPMOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  7-8-二羟基-2,3-二羟芴 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以98%的产率得到7,8-二甲氧基-2-苯基-2,3-二氢色烯-4-酮
  参考文献：
  名称：

  Selective and efficient oxidative modifications of flavonoids with 2-iodoxybenzoic acid (IBX)

  摘要：

  2-Iodoxybenzoic acid (IBX), a mild and efficient hypervalent iodine oxidant, has been utilised in different reaction conditions to perform several efficient oxidative modifications of flavonoids. Fine-tuning of the reaction conditions allowed remarkably selective modifications of these compounds. At room temperature, IBX proved to be an excellent reagent for a highly regioselective aromatic hydroxylation of monohydroxylated flavanones and flavones, generating the corresponding catecholic derivatives showing high antioxidant activity. At 90 degrees C, IBX efficiently dehydrogenated a large panel of methoxylated flavanones to their corresponding flavones exhibiting anticancer activity. IBX polystyrene has also been utilised to increase the recovery of highly polar compounds. Following the first oxidation, the reagent was recovered and reused in several runs without loss of efficiency and selectivity. The first example of an application of IBX polystyrene in a dehydrogenation reaction has been described. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.014
• 作为产物：
  描述：

  7-羟基黄烷酮 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以84%的产率得到7-8-二羟基-2,3-二羟芴
  参考文献：
  名称：

  Selective and efficient oxidative modifications of flavonoids with 2-iodoxybenzoic acid (IBX)

  摘要：

  2-Iodoxybenzoic acid (IBX), a mild and efficient hypervalent iodine oxidant, has been utilised in different reaction conditions to perform several efficient oxidative modifications of flavonoids. Fine-tuning of the reaction conditions allowed remarkably selective modifications of these compounds. At room temperature, IBX proved to be an excellent reagent for a highly regioselective aromatic hydroxylation of monohydroxylated flavanones and flavones, generating the corresponding catecholic derivatives showing high antioxidant activity. At 90 degrees C, IBX efficiently dehydrogenated a large panel of methoxylated flavanones to their corresponding flavones exhibiting anticancer activity. IBX polystyrene has also been utilised to increase the recovery of highly polar compounds. Following the first oxidation, the reagent was recovered and reused in several runs without loss of efficiency and selectivity. The first example of an application of IBX polystyrene in a dehydrogenation reaction has been described. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.014

文献信息

• Flavonoids: structural requirements for antiproliferative activity on breast cancer cells
  作者：Christelle Pouget、Fabienne Lauthier、Alain Simon、Catherine Fagnere、Jean-Philippe Basly、Christiane Delage、Albert-José Chulia

  DOI：10.1016/s0960-894x(01)00617-5

  日期：2001.12

  Several classes of flavonoids (flavones, flavanones, 2'-hydroxychalcones and flavan-4-ols) having a variety of substituents on A ring were investigated for their antiproliferative activity against MCF-7 human breast cancer cells. Structure-activity relationships of these compounds were discussed. 2'-hydroxychalcones and methoxylated flavanones were found to be potent inhibitors of MCF-7 cells growth

  研究了在A环上具有各种取代基的几类类黄酮（类黄酮，黄烷酮，2'-羟基查耳酮和黄烷-4-醇）对MCF-7人乳腺癌细胞的抗增殖活性。讨论了这些化合物的构效关系。发现2'-羟基查耳酮和甲氧基黄酮是MCF-7细胞生长的有效抑制剂，而黄酮和flavan-4-ols除7,8-二羟基黄酮外似乎是弱抑制剂。
• Shinoda, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1928, vol. 48, p. 35
  作者：Shinoda

  DOI：——

  日期：——
• Starkov, S. P.; Polyanskaya, N. L.; Volkotrub, M. N., Journal of general chemistry of the USSR, 1982, vol. 52, # 6, p. 1214 - 1217
  作者：Starkov, S. P.、Polyanskaya, N. L.、Volkotrub, M. N.

  DOI：——

  日期：——
• Ishwar-Dass et al., Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 599,608
  作者：Ishwar-Dass et al.

  DOI：——

  日期：——
• [EN] NUCLEIC ACID COMPOUNDS FOR INHIBITING FOS GENE EXPRESSION AND USES THEREOF<br/>[FR] COMPOSÉS D'ACIDE NUCLÉIQUE POUR INHIBER L'EXPRESSION DU GÈNE FOS ET UTILISATIONS DE CEUX-CI
  申请人：MDRNA INC

  公开号：WO2008109454A2

  公开（公告）日：2008-09-12

  (EN) The present disclosure provides meroduplex ribonucleic acid molecules (mdRNA) capable of decreasing or silencing FOS gene expression. An mdRNA of this disclosure comprises at least three strands that combine to form at least two non-overlapping double-stranded regions separated by a nick or gap wherein one strand is complementary to a FOS mRNA. In addition, the meroduplex may have at least one uridine is a 5-methyluridine, a nucleoside is a locked nucleic acid, or optionally other modifications, and any combination thereof. Also provided are methods of decreasing expression of a FOS gene in a cell or in a subject to treat a FOS-related disease.(FR) L'invention concerne des molécules d'acide ribonucléique méroduplex (ARNmd) pouvant diminuer ou étouffer l'expression du gène FOS. Un ARNmd de cette description comprend au moins trois brins qui s'associent pour former au moins deux régions double brin non chevauchantes séparées par une encoche ou un espace dans lequel un brin est complémentaire à un ARNm FOS. De plus, le méroduplex peut avoir au moins une uridine qui est une 5-méthyluridine, un nucléoside qui est un acide nucléique bloqué, ou éventuellement d'autres modifications, et toute combinaison de ceux-ci. Sont également proposés des procédés de diminution de l'expression d'un gène FOS dans une cellule ou chez un sujet pour traiter une maladie liée au FOS.