10-(3-hydroxy-4-methoxy-phenyl)-9-(4-{4-[10-(3-hydroxy-4-methoxy-phenyl)-2,4,5,7-tetraoxo-1,3,4,5,6,7,8,10-octahydro-2H-1,3,8,9-tetraaza-anthracen-9-yl]})-10-(3-Hydroxy-4-methoxy-phenyl)-9-phenyl-9,10-dihydro-1H,8H-1,3,6,8,9-pentaaza-anthracene-2,4,5,7-tetraone | 1465917-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 10-(3-hydroxy-4-methoxy-phenyl)-9-(4-{4-[10-(3-hydroxy-4-methoxy-phenyl)-2,4,5,7-tetraoxo-1,3,4,5,6,7,8,10-octahydro-2H-1,3,8,9-tetraaza-anthracen-9-yl]})-10-(3-Hydroxy-4-methoxy-phenyl)-9-phenyl-9,10-dihydro-1H,8H-1,3,6,8,9-pentaaza-anthracene-2,4,5,7-tetraone
• 英文别名: 9-(3-Hydroxy-4-methoxyphenyl)-2-[4-[4-[5,7,11,13-tetrahydroxy-9-(3-hydroxy-4-methoxyphenyl)-2,4,6,12,14-pentazatricyclo[8.4.0.03,8]tetradeca-1(10),3(8),4,6,11,13-hexaen-2-yl]phenoxy]phenyl]-2,4,6,12,14-pentazatricyclo[8.4.0.03,8]tetradeca-1(10),3(8),4,6,11,13-hexaene-5,7,11,13-tetrol；9-(3-hydroxy-4-methoxyphenyl)-2-[4-[4-[5,7,11,13-tetrahydroxy-9-(3-hydroxy-4-methoxyphenyl)-2,4,6,12,14-pentazatricyclo[8.4.0.03,8]tetradeca-1(10),3(8),4,6,11,13-hexaen-2-yl]phenoxy]phenyl]-2,4,6,12,14-pentazatricyclo[8.4.0.03,8]tetradeca-1(10),3(8),4,6,11,13-hexaene-5,7,11,13-tetrol
• CAS: 1465917-69-4
• 化学式: C₄₄H₃₂N₁₀O₁₃
• 分子量: 908.797
• InChiKey: AAUWUPVKKGSIIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  67
• 可旋转键数：
  8
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  307
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  异香兰素 、 巴比妥酸 、 4,4'-二氨基二苯醚 在 phosphotungstic acid 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以86%的产率得到10-(3-hydroxy-4-methoxy-phenyl)-9-(4-{4-[10-(3-hydroxy-4-methoxy-phenyl)-2,4,5,7-tetraoxo-1,3,4,5,6,7,8,10-octahydro-2H-1,3,8,9-tetraaza-anthracen-9-yl]})-10-(3-Hydroxy-4-methoxy-phenyl)-9-phenyl-9,10-dihydro-1H,8H-1,3,6,8,9-pentaaza-anthracene-2,4,5,7-tetraone
  参考文献：
  名称：

  Synthesis of new pyrimidine-fused derivatives as potent and selective antidiabetic α-glucosidase inhibitors

  摘要：

  The synthesis of a set of pyrimidine-fused derivatives (L1-L8), resulting from the incorporation of different fragments on the pyrimidine-fused heterocycle (PFH) of the earlier reported alpha-glucosidase (alpha-Gls) inhibitor (C1-C5), allowed the discovery of new ligands with modest and selective inhibitory activity. The PFH core (substructure 2) was proved to play a significant role in their inhibitory properties. Additionally, the substituent on substructures 1 and 3 of the heterocyclic ring was demonstrated to be important in the enzyme inhibitory action of the pyrimidine-fused derivatives. Moreover, these ligands show selective inhibitory properties for alpha-Gls over porcine pancreatic alpha-amylase (alpha-Amy) which is important in terms of their reduced susceptibility for the possible development of intestinal disturbance side effects. Therefore, low to moderate alpha-Amy inhibition with effective alpha-Gls inhibitory action may offer a better therapeutic strategy. Overall, these compounds can potentially offer a new opportunity to develop novel antidiabetic drugs with selective inhibitory action against alpha-Gls. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.07.008

文献信息

• Synthesis of new pyrimidine-fused derivatives as potent and selective antidiabetic α-glucosidase inhibitors
  作者：Farhad Panahi、Reza Yousefi、Mohammad Hossein Mehraban、Ali Khalafi-Nezhad

  DOI：10.1016/j.carres.2013.07.008

  日期：2013.10

  The synthesis of a set of pyrimidine-fused derivatives (L1-L8), resulting from the incorporation of different fragments on the pyrimidine-fused heterocycle (PFH) of the earlier reported alpha-glucosidase (alpha-Gls) inhibitor (C1-C5), allowed the discovery of new ligands with modest and selective inhibitory activity. The PFH core (substructure 2) was proved to play a significant role in their inhibitory properties. Additionally, the substituent on substructures 1 and 3 of the heterocyclic ring was demonstrated to be important in the enzyme inhibitory action of the pyrimidine-fused derivatives. Moreover, these ligands show selective inhibitory properties for alpha-Gls over porcine pancreatic alpha-amylase (alpha-Amy) which is important in terms of their reduced susceptibility for the possible development of intestinal disturbance side effects. Therefore, low to moderate alpha-Amy inhibition with effective alpha-Gls inhibitory action may offer a better therapeutic strategy. Overall, these compounds can potentially offer a new opportunity to develop novel antidiabetic drugs with selective inhibitory action against alpha-Gls. (C) 2013 Elsevier Ltd. All rights reserved.