(4S,5R,6R)-4-azido-5-methanesulfonylamino-6-(1S,2R,3-triacetoxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester | 171241-97-7

• 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: (4S,5R,6R)-4-azido-5-methanesulfonylamino-6-(1S,2R,3-triacetoxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3R,4S)-4-azido-3-(methanesulfonamido)-2-[(1S,2R)-1,2,3-triacetyloxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 171241-97-7
• 化学式: C₁₇H₂₄N₄O₁₁S
• 分子量: 492.464
• InChiKey: BXOBBPLSHRGBFR-CWCFIDOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  183
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R)-4-azido-5-methanesulfonylamino-6-(1S,2R,3-triacetoxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 sodium methylate 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 246.0h， 生成 (4S,5R,6R)-4-guanidino-5-methanesulfonylamino-6-(1R,2R,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and influenza virus sialidase inhibitory activity of analogues of 4-guanidino-Neu5Ac2en (GG167) with modified 5-substituents

  摘要：

  Analogues of 4-guanidino-Neu5Ac2en (GG167) have been prepared containing alternative amide and sulfonamide substituents at the 5-position. (4S,5R,6R)-4-guanidino-5-(2,2,2-trifluoroacetylamino)-6-(1R,2R,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 5 and (4S,5R,6R)-4-guanidino-5-methanesulfonylamino-6-(1R,2R,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 6 were the only analogues which approached the activity of GG167, showing potent inhibition of influenza virus sialidases and good antiviral activity in vitro.

  DOI：

  10.1016/0223-5234(96)80447-8
• 作为产物：
  描述：

  methyl 5-[acetyl(tert-butoxycarbonyl)amino]-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate 在 吡啶 、 盐酸 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 (4S,5R,6R)-4-azido-5-methanesulfonylamino-6-(1S,2R,3-triacetoxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and influenza virus sialidase inhibitory activity of analogues of 4-guanidino-Neu5Ac2en (GG167) with modified 5-substituents

  摘要：

  Analogues of 4-guanidino-Neu5Ac2en (GG167) have been prepared containing alternative amide and sulfonamide substituents at the 5-position. (4S,5R,6R)-4-guanidino-5-(2,2,2-trifluoroacetylamino)-6-(1R,2R,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 5 and (4S,5R,6R)-4-guanidino-5-methanesulfonylamino-6-(1R,2R,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 6 were the only analogues which approached the activity of GG167, showing potent inhibition of influenza virus sialidases and good antiviral activity in vitro.

  DOI：

  10.1016/0223-5234(96)80447-8

文献信息

• [EN] DERIVATIVES OF 2-DEOXY-2,3-DEHYDRO-N-ACETYLNEURAMINIC ACID (DANA)<br/>[FR] DERIVES DE L'ACIDE 2-DESOXY-2,3-DESHYDRO-N-ACETYLNEURAMINIQUE (DANA)
  申请人：BIOTA SCIENTIFIC MANAGEMENT PTY LTD

  公开号：WO1995018800A1

  公开（公告）日：1995-07-13

  (EN) (4S, 5R, 6R)-4-Guanidino-5-methanesulphonylamino-6-[(1S,2R)-1,2,3-trihydroxypropyl-5,6-dihydro-4H-pyran-3-carboxylic acid and its physiologically acceptable derivatives and solvates are inhibitors of viral neuraminidase.(FR) L'acide (4S, 5R, 6R)-4-guanidino-5-méthanesulfonylamino-6-[(1S, 2R)-1,2,3-trihydroxypropyl-5,6-dihydro-4H-pyranne-3-carboxylique, ses dérivés ainsi que ses solvates physiologiquement tolérables sont des inhibiteurs de la neuraminidase virale.

  (4S,5R,6R)鸟苷二胺-5-甲基砜氨基-6-[(1S,2R)-1,2,3-三羟基丙基-5,6-双氢-4H-pyran-3-酸]及其生理可接受的衍生物和可溶化衍生物是抑制病毒神经元酶的化合物。