methyl 5-acetamido-4-(3-(2-methoxyphenyl)thioureido)-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate | 1392415-10-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 5-acetamido-4-(3-(2-methoxyphenyl)thioureido)-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
• 英文别名: methyl (2R,3R,4S)-3-acetamido-4-[(2-methoxyphenyl)carbamothioylamino]-2-[(1S,2R)-1,2,3-triacetyloxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1392415-10-9
• 化学式: C₂₆H₃₃N₃O₁₁S
• 分子量: 595.628
• InChiKey: IXRXZBSGVKHSCU-PCYHMHGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  209
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-4-(3-(2-methoxyphenyl)thioureido)-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以81%的产率得到5-acetamido-4-(3-(2-methoxyphenyl)thioureido)-6-(1,2,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of C-4-modified zanamivir analogs as neuraminidase inhibitors and their anti-AIV activities

  摘要：

  With the introduction of bioisosteres of the guanidinium group together with scaffold hopping, 35 zanamivir analogs with C-4-modification were synthesized, and their inhibitory activities against both group-1 and group-2 neuraminidase (H5N1 and H3N2) were determined. Compound 026 exerts the most potency, with IC50 values of 0.58 and 2.72 mu M against N2 and N1, respectively. Further preliminary anti-avian influenza virus (AIV, H5N1) activities against infected MDCK cells were evaluated, and D5 exerts similar to 58% protective against AIV infection, which was comparable to zanamivir (similar to 67%). In a rat pharmacokinetic study, compound D5 showed an increased plasma half-life (t(1/2)) compared to zanamivir following either intravenous or oral administration. This study may represent a new start point for the future development of improved anti-AIV agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.033
• 作为产物：
  描述：

  异氰酸2-甲氧苯酯 、 扎那米韦 以 二氯甲烷 为溶剂， 以69%的产率得到methyl 5-acetamido-4-(3-(2-methoxyphenyl)thioureido)-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate
  参考文献：
  名称：

  Synthesis of C-4-modified zanamivir analogs as neuraminidase inhibitors and their anti-AIV activities

  摘要：

  With the introduction of bioisosteres of the guanidinium group together with scaffold hopping, 35 zanamivir analogs with C-4-modification were synthesized, and their inhibitory activities against both group-1 and group-2 neuraminidase (H5N1 and H3N2) were determined. Compound 026 exerts the most potency, with IC50 values of 0.58 and 2.72 mu M against N2 and N1, respectively. Further preliminary anti-avian influenza virus (AIV, H5N1) activities against infected MDCK cells were evaluated, and D5 exerts similar to 58% protective against AIV infection, which was comparable to zanamivir (similar to 67%). In a rat pharmacokinetic study, compound D5 showed an increased plasma half-life (t(1/2)) compared to zanamivir following either intravenous or oral administration. This study may represent a new start point for the future development of improved anti-AIV agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.033