β-D-glucopyranosiduronic acid 4-formyl-2-methoxyphenyl methyl ester triacetate | 704885-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-glucopyranosiduronic acid 4-formyl-2-methoxyphenyl methyl ester triacetate
• 英文别名: 4-Formyl-2-methoxyphenyl beta-D-glucopyranosiduronic acid triacetate methyl ester；methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-formyl-2-methoxyphenoxy)oxane-2-carboxylate
• CAS: 704885-44-9
• 化学式: C₂₁H₂₄O₁₂
• 分子量: 468.414
• InChiKey: QTHPZBHVIGLWPP-VDRZXAFZSA-N

物化性质

• 沸点：
  549.1±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮、氯仿、二氯甲烷、二甲基甲酰胺、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  149.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  β-D-glucopyranosiduronic acid 4-formyl-2-methoxyphenyl methyl ester triacetate 在 O₂B₆ 、 硼酸三丁酯 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 curcumin β-D-glucopyranosiduronic acid 2,3,4-tri-O-acetyl methyl ester
  参考文献：
  名称：

  Curcumin glucuronides: Assessing the proliferative activity against human cell lines

  摘要：

  A gram scale synthesis of the glucuronide metabolites of curcumin were completed in four steps. The newly synthesized curcumin glucuronide compounds 2 and 3 along with curcumin 1 were tested and their anti-proliferative effects against KBM-5, Jurkat cell, U266, and A549 cell lines were reported. Biological data revealed that as much as 1 mu M curcumin 1 exhibited anticancer activity and almost 100% cell kill was noted at 10 mu M on two out of four cell lines; while curcumin mono-glucuronide 2 as well as di-glucuronide 3 displayed no suppression of cell proliferation. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.11.006
• 作为产物：
  描述：

  香草醛 、 乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 喹啉 、 silver(l) oxide 作用下， 反应 2.0h， 以49%的产率得到β-D-glucopyranosiduronic acid 4-formyl-2-methoxyphenyl methyl ester triacetate
  参考文献：
  名称：

  EP3479828

  摘要：

  公开号：

文献信息

• [EN] EPOTHILONE ANALOGS FOR SITE SPECIFIC DELIVERY IN THE TREATMENT OF PROLIFERATIVE DISEASES<br/>[FR] ANALOGUES D'EPOTHILONE PERMETTANT L'ADMINISTRATION SPECIFIQUE D'UN SITE DANS LE TRAITEMENT DE MALADIES PROLIFERATIVES
  申请人：SCHERING AG

  公开号：WO2004050089A1

  公开（公告）日：2004-06-17

  Conjugates of epothilones and epothilone derivatives (as effectors) with suitable saccharides or saccharide derivatives (as recognition units) are described. Their production is carried out by the recognition units being reacted with suitable linkers, and the compounds that are produced are conjugated to the effectors. The pharmaceutical use of the conjugates for treating proliferative or angiogenesis-associated processes is described.

  本文描述了用适当的糖或糖衍生物（作为识别单元）与紫杉醇类和紫杉醇衍生物（作为效应物）的共轭体。它们的生产是通过将识别单元与适当的连接剂反应，然后将产生的化合物与效应物共轭。本文还描述了共轭体在治疗增殖或血管生成相关过程中的药物用途。
• Effector conjugates, methods for their preparation and their pharmaceutical use
  申请人：——

  公开号：US20040167083A1

  公开（公告）日：2004-08-26

  Conjugates of epothilones and epothilone derivatives (as effectors) with suitable saccharides or saccharide derivatives (as recognition units) are described. Their production is carried out by the recognition units being reacted with suitable linkers, and the compounds that are produced are conjugated to the effectors. The pharmaceutical use of the conjugates for treating proliferative or angiogenesis-associated processes is described.

  描述了具有适当的糖或糖衍生物（作为识别单元）的紫杉醇和紫杉醇衍生物（作为效应物）的共轭物。它们的制备是通过将识别单元与适当的连接剂反应，然后将产生的化合物与效应物共轭。描述了共轭物在治疗增殖或血管生成相关过程方面的药物应用。
• New effector conjugates, methods for their preparation and their pharmaceutical use
  申请人：Bosslet Klaus

  公开号：US20060276413A1

  公开（公告）日：2006-12-07

  Conjugates of epothilones and epothilone derivatives (as effectors) with suitable saccharides or saccharide derivatives (as recognition units) are described. Their production is carried out by the recognition units being reacted with suitable linkers, and the compounds that are produced are conjugated to the effectors. The pharmaceutical use of the conjugates for treating proliferative or angiogenesis-associated processes is described.

  本文描述了与适当的糖或糖衍生物（作为识别单元）结合的依泊单酮及其衍生物的共轭物（作为效应物）。它们的生产是通过将识别单元与适当的连接剂反应，然后将产生的化合物与效应物结合而完成的。本文还描述了这些共轭物在治疗增殖或血管生成相关过程中的药物用途。
• EP3479828
  申请人：——

  公开号：——

  公开（公告）日：——
• EPOTHILONE ANALOGS FOR SITE SPECIFIC DELIVERY IN THE TREATMENT OF PROLIFERATIVE DISEASES
  申请人：Schering AG

  公开号：EP1581218A1

  公开（公告）日：2005-10-05