methyl (3R,4R,5R)-4-(acetylamino)-3-isopropoxy-5-vinyl-1-cyclohexene-1-carboxylate | 335418-35-4

• 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 (3R,4R,5R)-4-(acetylamino)-3-isopropoxy-5-vinyl-1-cyclohexene-1-carboxylate
• 英文别名: methyl (3R,4R,5R)-4-acetamido-5-ethenyl-3-propan-2-yloxycyclohexene-1-carboxylate
• CAS: 335418-35-4
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: ZQYQBEUVPLXNGM-IACUBPJLSA-N

物化性质

• 熔点：
  132-133 °C
• 沸点：
  427.9±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (3R,4R,5R)-4-(acetylamino)-3-isopropoxy-5-vinyl-1-cyclohexene-1-carboxylate 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以96%的产率得到(3R,4R,5R)-4-(acetylamino)-3-isopropoxy-5-vinyl-1-cyclohexene-1-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm

  摘要：

  Structure-based design has led to the synthesis of a novel analogue of GS-4071. an influenza neuraminidase inhibitor, in which the basic amino group has been replaced by a hydrophobic vinyl group. An X-ray co-crystal structure of the new inhibitor (K-i = 45 nM) bound to the actin e site shows that the vinyl group occupies the same subsite as the amino group in GS-4071. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00732-1
• 作为产物：
  描述：

  (1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one 在 吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 四氧化锇 、 sodium azide 、 N-甲基吲哚酮 、 偶氮二异丁腈 、 三丁基膦 、 三氟化硼乙醚 、 双氧水 、 potassium carbonate 、 氯化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 生成 methyl (3R,4R,5R)-4-(acetylamino)-3-isopropoxy-5-vinyl-1-cyclohexene-1-carboxylate
  参考文献：
  名称：

  Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm

  摘要：

  Structure-based design has led to the synthesis of a novel analogue of GS-4071. an influenza neuraminidase inhibitor, in which the basic amino group has been replaced by a hydrophobic vinyl group. An X-ray co-crystal structure of the new inhibitor (K-i = 45 nM) bound to the actin e site shows that the vinyl group occupies the same subsite as the amino group in GS-4071. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00732-1

文献信息

• Neuraminidase inhibitors
  申请人：Abbott Laboratories

  公开号：US06593314B1

  公开（公告）日：2003-07-15

  The present invention provides compounds of formula Ia and Ib or a pharmaceutically acceptable salt, prodrug, or ester thereof, useful in the inhibition of neuraminidase enzymes from disease-causing microorganisms, especially influenza neuraminidase, pharmaceutical formulations containing same, processes and intermediates for preparing said compounds, as well as methods of using said compounds, including preventing and treating diseases caused by microorganisms having said neuraminidase enzyme.

  本发明提供了公式Ia和Ib的化合物，或其药用可接受的盐、前药或酯，用于抑制疾病引起微生物的神经氨酸酶，特别是流感神经氨酸酶，含有相同化合物的药物配方，用于制备所述化合物的过程和中间体，以及使用所述化合物的方法，包括预防和治疗由具有所述神经氨酸酶酶的微生物引起的疾病。
• Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm
  作者：Stephen Hanessian、Jianchio Wang、Debra Montgomery、Vincent Stoll、Kent D. Stewart、Warren Kati、Clarence Maring、Dale Kempf、Charles Hutchins、W.Graeme Laver

  DOI：10.1016/s0960-894x(02)00732-1

  日期：2002.12

  Structure-based design has led to the synthesis of a novel analogue of GS-4071. an influenza neuraminidase inhibitor, in which the basic amino group has been replaced by a hydrophobic vinyl group. An X-ray co-crystal structure of the new inhibitor (K-i = 45 nM) bound to the actin e site shows that the vinyl group occupies the same subsite as the amino group in GS-4071. (C) 2002 Elsevier Science Ltd. All rights reserved.