(Z)-N,N'-<5-<<1-(5-acetyl-4-hydroxy-2,6-dioxo-2H-pyran-3(6H)-ylidene)ethyl>amino>-1,3-phenylene>bis<2(R),3-dihydroxypropanamide> | 130548-54-8

• 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: (Z)-N,N'-<5-<<1-(5-acetyl-4-hydroxy-2,6-dioxo-2H-pyran-3(6H)-ylidene)ethyl>amino>-1,3-phenylene>bis<2(R),3-dihydroxypropanamide>
• 英文别名: (2R)-N-[3-[[(1Z)-1-(5-acetyl-4-hydroxy-2,6-dioxopyran-3-ylidene)ethyl]amino]-5-[[(2R)-2,3-dihydroxypropanoyl]amino]phenyl]-2,3-dihydroxypropanamide
• CAS: 130548-54-8
• 化学式: C₂₁H₂₃N₃O₁₁
• 分子量: 493.427
• InChiKey: MUCXEEMPNRCCGJ-XPWVWULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.56
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  231.82
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal 水 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 (Z)-N,N'-<5-<<1-(5-acetyl-4-hydroxy-2,6-dioxo-2H-pyran-3(6H)-ylidene)ethyl>amino>-1,3-phenylene>bis<2(R),3-dihydroxypropanamide>
  参考文献：
  名称：

  Synthesis of chiral and achiral pyranenamine derivatives. Potent agents with topical ocular antiallergic activity

  摘要：

  The SS, RR and meso stereoisomers of pyranenamine SK&F 84210 (2) were synthesized stereospecifically starting from commercially available (R)-(-)- or (S)-(+)-2,2-dimethyl-1,3,dioxolane-4-methanol (3). In addition, two achiral pyranenamines 19 and 26 were also synthesized. When evaluated by intravenous and topical routes in the rat passive ocular anaphylaxis (POA) assay, (SS)- and meso-2 as well as achiral compounds 19 and 26 were found to be more potent antiallergic agents than (RR)-2.

  DOI：

  10.1021/jm00105a060

文献信息

• Synthesis of chiral and achiral pyranenamine derivatives. Potent agents with topical ocular antiallergic activity
  作者：Charles Gluchowski、Trudy E. Bischoff、Michael E. Garst、Lester J. Kaplan、Steven W. Dietrich、Angelika S. Aswad、Mary A. Gaffney、K. Roger Aoki、Carlos Garcia、Larry A. Wheeler

  DOI：10.1021/jm00105a060

  日期：1991.1

  The SS, RR and meso stereoisomers of pyranenamine SK&F 84210 (2) were synthesized stereospecifically starting from commercially available (R)-(-)- or (S)-(+)-2,2-dimethyl-1,3,dioxolane-4-methanol (3). In addition, two achiral pyranenamines 19 and 26 were also synthesized. When evaluated by intravenous and topical routes in the rat passive ocular anaphylaxis (POA) assay, (SS)- and meso-2 as well as achiral compounds 19 and 26 were found to be more potent antiallergic agents than (RR)-2.