(2R,3R,4S,2'R,4'R,5'S)-3-Acetylamino-4-guanidino-4',5'-dihydroxy-3,4,3',4',5',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2R,3R,4S,2'R,4'R,5'S)-3-Acetylamino-4-guanidino-4',5'-dihydroxy-3,4,3',4',5',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-carboxylic acid
• 英文别名: (2R,3R,4S)-3-acetamido-2-[(2R,4R,5S)-4,5-dihydroxytetrahydropyran-2-yl]-4-guanidino-3,4-dihydro-2H-pyran-6-carboxylic acid；(2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(2R,4R,5S)-4,5-dihydroxyoxan-2-yl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• 化学式: C₁₄H₂₂N₄O₇
• 分子量: 358.351
• InChiKey: PIBTYJJAYFVZOW-XIIWAEAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  190
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,2'R,4'R,5'S)-4',5'-Diacetoxy-3-acetylamino-4-(2,2-dimethyl-propionyloxy)-3,4,3',4',5',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-carboxylic acid methyl ester 在 Lindlar's catalyst sodium hydroxide 、 sodium azide 、 Dowex 50W (H⁺) 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (2R,3R,4S,2'R,4'R,5'S)-3-Acetylamino-4-guanidino-4',5'-dihydroxy-3,4,3',4',5',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-carboxylic acid
  参考文献：
  名称：

  Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir

  摘要：

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01039-9

文献信息

• Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir
  作者：Takeshi Masuda、Satoshi Shibuya、Masami Arai、Shuku Yoshida、Takanori Tomozawa、Akiko Ohno、Makoto Yamashita、Takeshi Honda

  DOI：10.1016/s0960-894x(02)01039-9

  日期：2003.2

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.