7-benzyloxy-6-β-D-glucopyranosyloxy-coumarin | 34340-36-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-benzyloxy-6-β-D-glucopyranosyloxy-coumarin
• 英文别名: 7-Benzyloxy-6-β-D-glucopyranosyloxy-cumarin；7-O-Benzyl-aesculin；7-phenylmethoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• CAS: 34340-36-8
• 化学式: C₂₂H₂₂O₉
• 分子量: 430.411
• InChiKey: NUYWJVQUOKZELZ-MIUGBVLSSA-N

物化性质

• 熔点：
  182 °C
• 沸点：
  715.5±60.0 °C(Predicted)
• 密度：
  1.489±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-6-β-D-glucopyranosyloxy-coumarin 在 甲醇 、 Pd-BaSO₄ 作用下， 生成 秦皮甲素
  参考文献：
  名称：

  Über einige Benzylderivate des 6,7-Dioxykumarins und die Synthese des Aeskulins

  摘要：

  DOI：

  10.1002/ardp.19442820114
• 作为产物：
  描述：

  6,7-二羟基香豆素-7-苄醚 在 甲醇 、 alkaline solution 、 氨 、 丙酮 作用下， 生成 7-benzyloxy-6-β-D-glucopyranosyloxy-coumarin
  参考文献：
  名称：

  Über einige Benzylderivate des 6,7-Dioxykumarins und die Synthese des Aeskulins

  摘要：

  DOI：

  10.1002/ardp.19442820114

文献信息

• Esculetin derivatives, method for manufacture thereof, and
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：US05731293A1

  公开（公告）日：1998-03-24

  A compound of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are, independently, --CON(R.sup.4)R.sup.5, or a monosaccharide, or acylated monosaccharide group, with the proviso that at least one of R.sup.1 and R.sup.2 is --CON(R.sup.4)R.sup.5, and R.sup.4 and R.sup.5 are, independently, a hydrogen atom, or a hydroxyl, alkyl, aryl, or aralkyl group, or R.sup.4 and R.sup.5 together with the nitrogen atom attached thereto form a 3- to 7-membered saturated cycloaliphatic amino group, and R.sup.3 is a hydrogen atom, or a hydroxyl, alkyl, aryl, aralkyl, or --COOR.sup.8 group, and R.sup.3 is at 3- or 4-position, and R.sup.8 is a hydrogen atom or an alkyl group, or a salt thereof is disclosed. The compound has a function to inhibit a matrix metalloproteinase.

  化合物的化学式为（I）：##STR1## 其中R.sup.1和R.sup.2独立地为--CON(R.sup.4)R.sup.5，或单糖或酰化单糖基团，但至少其中一个为--CON(R.sup.4)R.sup.5，而且R.sup.4和R.sup.5独立地为氢原子，或氢氧基，烷基，芳基或芳烷基，或R.sup.4和R.sup.5连同其所连接的氮原子形成3到7个成员的饱和环脂肪族氨基基团，而R.sup.3为氢原子，或氢氧基，烷基，芳基，芳烷基或--COOR.sup.8基团，且R.sup.3位于3或4位，R.sup.8为氢原子或烷基，或其盐。该化合物具有抑制基质金属蛋白酶的功能。
• Esculetin derivatives, method for manufacture thereof, and pharmaceutical composition
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：EP0719770A1

  公开（公告）日：1996-07-03

  A compound of the formula (I): wherein R1 and R2 are, independently, -CON(R4)R5, or a monosaccharide, or acylated monosaccharide group, with the proviso that at least one of R1 and R2 is -CON(R4)R5, and R4 and R5 are, independently, a hydrogen atom, or a hydroxyl, alkyl, aryl, or aralkyl group, or R4 and R5 together with the nitrogen atom attached thereto form a 3- to 7-membered saturated cycloaliphatic amino group, and R3 is a hydrogen atom, or a hydroxyl, alkyl, aryl, aralkyl, or -COOR8 group, and R3 is at 3- or 4-position, and R8 is a hydrogen atom or an alkyl group, or a salt thereof is disclosed. The compound has a function to inhibit a matrix metalloproteinase.

  式 (I) 的化合物： 其中 R1 和 R2 独立地为-CON(R4)R5，或单糖，或酰化单糖基团，但 R1 和 R2 中至少有一个为-CON(R4)R5，且 R4 和 R5 独立地为氢原子，或羟基、烷基、芳基或芳烷基、或 R4 和 R5 与相连的氮原子一起形成 3 至 7 元饱和环脂族氨基，且 R3 是氢原子，或羟基、烷基、芳基、芳烷基或 -COOR8 基团，且 R3 位于 3 位或 4 位，且 R8 是氢原子或烷基，或公开了其盐。该化合物具有抑制基质金属蛋白酶的功能。
• Inhibition of Monoamine Oxidases by Functionalized Coumarin Derivatives:  Biological Activities, QSARs, and 3D-QSARs
  作者：Carmela Gnerre、Marco Catto、Francesco Leonetti、Peter Weber、Pierre-Alain Carrupt、Cosimo Altomare、Angelo Carotti、Bernard Testa

  DOI：10.1021/jm001028o

  日期：2000.12.1

  A large series of coumarin derivatives (71 compounds) were tested for their monoamine oxidase A and B (MAO-A and MAO-B) inhibitory activity. Most of the compounds acted preferentially on MAO-B with IC50 values in the micromolar to low-nanomolar range; high inhibitory activities toward MAO-A were also measured for sulfonic acid esters. The most active compound was 7-[(3,4-difluorobenzyl)oxy]-3,4-dimethylcoumarin, with an IC50 value toward MAO-B of 1.14 nM. A QSAR study of 7-X-benzyloxy meta-substituted 3,4-dimethylcoumarin derivatives acting on MAO-B yielded good statistical results (q(2) = 0.72, r(2) = 0.86), revealing the importance of lipophilic interactions in modulating the inhibition and excluding any dependence on electronic properties. CoMFA was performed on two data sets of MAO-A and MAO-B inhibitors. The GOLPE procedure, with variable selection criteria, was applied to improve the predictivity of the models and to facilitate the graphical interpretation of results.
• Amiard; Nomine, Bulletin de la Societe Chimique de France, 1948, p. 476,478
  作者：Amiard、Nomine

  DOI：——

  日期：——
• Esculetin derivatives and method for manufacture thereof, use thereof, and pharmaceutical composition
  申请人：KUREHA CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0654479B1

  公开（公告）日：2000-03-15