2-[3-[(3R,4R,5S)-4-acetamido-5-(diaminomethylideneazaniumyl)-3-pentan-3-yloxycyclohexene-1-carbonyl]oxypropoxycarbonyl]naphthalen-1-olate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[3-[(3R,4R,5S)-4-acetamido-5-(diaminomethylideneazaniumyl)-3-pentan-3-yloxycyclohexene-1-carbonyl]oxypropoxycarbonyl]naphthalen-1-olate
• 化学式: C29H38N4O7
• 分子量: 554.6
• InChiKey: OXCMWNOFPUTYNN-ISJGIBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  176
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-羟基-2-萘甲酸 在 吗啉 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 36.0h， 生成 2-[3-[(3R,4R,5S)-4-acetamido-5-(diaminomethylideneazaniumyl)-3-pentan-3-yloxycyclohexene-1-carbonyl]oxypropoxycarbonyl]naphthalen-1-olate
  参考文献：
  名称：

  Intramolecular ion-pair prodrugs of zanamivir and guanidino-oseltamivir

  摘要：

  Zanamivir (ZA) is a potent anti-influenza drug, but it cannot be administrated orally because of the hydrophilic carboxylate and guanidinium groups. Guanidino-oseltamivir (GO) is another effective neuraminidase inhibitor with polar guanidinium group under physiological conditions. The ester prodrugs ZA-HNAP (5) and GO-HNAP (6) were prepared to incorporate a 1-hydroxy-2-naphthoic (HNAP) moiety to attain good lipophilicity in the intramolecular ion-pairing forms. ZA-HNAP resumed high anti-influenza activity (EC(50) = 48 nM), in cell-based anti-influenza assays, by releasing zanamivir along with nontoxic HNAP. Under similar conditions, the hydrolysis of the GO-HNAP ester was too sluggish to show the desired anti-influenza activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.080

文献信息

• Intramolecular ion-pair prodrugs of zanamivir and guanidino-oseltamivir
  作者：Kung-Cheng Liu、Pei-Shan Lee、Shi-Yun Wang、Yih-Shyun E. Cheng、Jim-Min Fang、Chi-Huey Wong

  DOI：10.1016/j.bmc.2011.06.080

  日期：2011.8

  Zanamivir (ZA) is a potent anti-influenza drug, but it cannot be administrated orally because of the hydrophilic carboxylate and guanidinium groups. Guanidino-oseltamivir (GO) is another effective neuraminidase inhibitor with polar guanidinium group under physiological conditions. The ester prodrugs ZA-HNAP (5) and GO-HNAP (6) were prepared to incorporate a 1-hydroxy-2-naphthoic (HNAP) moiety to attain good lipophilicity in the intramolecular ion-pairing forms. ZA-HNAP resumed high anti-influenza activity (EC(50) = 48 nM), in cell-based anti-influenza assays, by releasing zanamivir along with nontoxic HNAP. Under similar conditions, the hydrolysis of the GO-HNAP ester was too sluggish to show the desired anti-influenza activity. (C) 2011 Elsevier Ltd. All rights reserved.