4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone | 898550-56-6

• 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: 4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone
• 英文别名: 4,2',4'-tris(benzyloxy)-6'-hydroxy-5'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone；(E)-1-[2-hydroxy-4,6-bis(phenylmethoxy)-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]phenyl]-3-(4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 898550-56-6
• 化学式: C₇₀H₆₄O₁₀
• 分子量: 1065.27
• InChiKey: RTMAKQJDKFKZRN-QTJABEQRSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  80
• 可旋转键数：
  26
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone 在 吡啶 、 4-二甲氨基吡啶 、 thallium(III) nitrate 作用下， 以 甲醇 为溶剂， 反应 68.0h， 生成 染料木素8-C-葡萄糖苷
  参考文献：
  名称：

  Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-β-d-glucopyranosides

  摘要：

  Genistein and orobol 8-C-beta-D-glucopyranosides (1 and 3) were firstly synthesized in overall yields of 39% and 41% from 2,4-di-O-benzylphloroacetophenone (4), as follows: (1) the formation of the chalcone (6, 7) by aldol condensation of the benzyl-protected C-glycosylphloroacetophenone (5), a key intermediate of the total synthesis of I and 3 and synthesized by a C-glycosylation method involving the O -> C glycoside rearrangement of 4 in 96% yield; (2) the formation of isoflavones (10, 11 and 12, 13) by the formation of acetals by oxidative rearrangement of the protected chalcones (8 and 9) using TI(NO3)(3), followed by acid-catalyzed cyclization: (3) a final debenzylation by hydrogenolysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.038
• 作为产物：
  描述：

  甲基-Alpha-D-吡喃葡糖苷 在 吡啶 、 硫酸 、 sodium hydride 、 溶剂黄146 、 sodium hydroxide 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 1,4-二氧六环 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 79.0h， 生成 4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone
  参考文献：
  名称：

  Exploiting the Therapeutic Potential of 8-β-d-Glucopyranosylgenistein: Synthesis, Antidiabetic Activity, and Molecular Interaction with Islet Amyloid Polypeptide and Amyloid β-Peptide (1–42)

  摘要：

  8-β-d-Glucopyranosylgenistein (1), the major component of Genista tenera, was synthesized and showed an extensive therapeutical impact in the treatment of STZ-induced diabetic rats, producing normalization of fasting hyperglycemia and amelioration of excessive postprandial glucose excursions and and increasing β-cell sensitivity, insulin secretion, and circulating insulin within 7 days at a dose of 4 (mg/kg bw)/day. Suppression of islet amyloid polypeptide (IAPP) fibril formation by compound 1 was demonstrated by thioflavin T fluorescence and atomic force microscopy. Molecular recognition studies with IAPP and Aβ1-42 employing saturation transfer difference (STD) confirmed the same binding mode for both amyloid peptides as suggested by their deduced epitope. Insights into the preferred conformation in the bound state and conformers' geometry resulting from interaction with Aβ1-42 were also given by STD, trNOESY, and MM calculations. These studies strongly support 8-β-d-glucopyranosylgenistein as a promising molecular entity for intervention in amyloid events of both diabetes and the frequently associated Alzheimer's disease.

  DOI：

  10.1021/jm501069h

文献信息

• 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。
• Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-β-d-glucopyranosides
  作者：Shingo Sato、Kaoru Hiroe、Toshihiro Kumazawa、Onodera Jun-ichi

  DOI：10.1016/j.carres.2006.03.038

  日期：2006.7

  Genistein and orobol 8-C-beta-D-glucopyranosides (1 and 3) were firstly synthesized in overall yields of 39% and 41% from 2,4-di-O-benzylphloroacetophenone (4), as follows: (1) the formation of the chalcone (6, 7) by aldol condensation of the benzyl-protected C-glycosylphloroacetophenone (5), a key intermediate of the total synthesis of I and 3 and synthesized by a C-glycosylation method involving the O -> C glycoside rearrangement of 4 in 96% yield; (2) the formation of isoflavones (10, 11 and 12, 13) by the formation of acetals by oxidative rearrangement of the protected chalcones (8 and 9) using TI(NO3)(3), followed by acid-catalyzed cyclization: (3) a final debenzylation by hydrogenolysis. (c) 2006 Elsevier Ltd. All rights reserved.
• Exploiting the Therapeutic Potential of 8-β-<scp>d</scp>-Glucopyranosylgenistein: Synthesis, Antidiabetic Activity, and Molecular Interaction with Islet Amyloid Polypeptide and Amyloid β-Peptide (1–42)
  作者：Ana R. Jesus、Catarina Dias、Ana M. Matos、Rodrigo F. M. de Almeida、Ana S. Viana、Filipa Marcelo、Rogério T. Ribeiro、Maria P. Macedo、Cristina Airoldi、Francesco Nicotra、Alice Martins、Eurico J. Cabrita、Jesús Jiménez-Barbero、Amélia P. Rauter

  DOI：10.1021/jm501069h

  日期：2014.11.26

  8-β-d-Glucopyranosylgenistein (1), the major component of Genista tenera, was synthesized and showed an extensive therapeutical impact in the treatment of STZ-induced diabetic rats, producing normalization of fasting hyperglycemia and amelioration of excessive postprandial glucose excursions and and increasing β-cell sensitivity, insulin secretion, and circulating insulin within 7 days at a dose of 4 (mg/kg bw)/day. Suppression of islet amyloid polypeptide (IAPP) fibril formation by compound 1 was demonstrated by thioflavin T fluorescence and atomic force microscopy. Molecular recognition studies with IAPP and Aβ1-42 employing saturation transfer difference (STD) confirmed the same binding mode for both amyloid peptides as suggested by their deduced epitope. Insights into the preferred conformation in the bound state and conformers' geometry resulting from interaction with Aβ1-42 were also given by STD, trNOESY, and MM calculations. These studies strongly support 8-β-d-glucopyranosylgenistein as a promising molecular entity for intervention in amyloid events of both diabetes and the frequently associated Alzheimer's disease.