3,4-O-ethylpropylidenequinic acid-1,5-lactone | 374687-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3,4-O-ethylpropylidenequinic acid-1,5-lactone
• 英文别名: (1R,2R,6R,8S)-4,4-diethyl-8-hydroxy-3,5,10-trioxatricyclo[6.2.1.02,6]undecan-9-one
• CAS: 374687-78-2
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: BLBATLZXHPGXQK-SDNRWEOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-O-ethylpropylidenequinic acid-1,5-lactone 在 吡啶 、 重铬酸吡啶 、 3 A molecular sieve 、 sodium methylate 、 sodium hydride 、 二异丁基氢化铝 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 40.0h， 生成 (1R,2S,3S)-3-O-benzyl-5-(benzyloxymethyl)-1,2-ethylpropylidene-4-cyclohexene-1,2,3-triol
  参考文献：
  名称：

  A New Synthesis of Valienamine¹

  摘要：

  DOI：

  10.1021/jo010202t
• 作为产物：
  描述：

  右旋奎宁酸 、 3-戊酮 在 磷酸 作用下， 反应 12.0h， 以25%的产率得到3,4-O-ethylpropylidenequinic acid-1,5-lactone
  参考文献：
  名称：

  Carbocycles Related to Oseltamivir as Influenza Virus Group-1-Specific Neuraminidase Inhibitors. Binding to N1 Enzymes in the Context of Virus-like Particles

  摘要：

  We report here the exploitation of the 150-cavity in the active sites of group-1 neuraminidases for the design of new triazole-containing carbocycles related to oseltamivir. Inhibition studies with virus-like particles (VLPs) containing the influenza virus neuraminidase-1 (NI) activity indicate that several candidates are inhibitors, with K(i) values in the 10(-5)-10(-8) M range. In contrast, a known candidate that preserves the free amino group and a new candidate containing a guanidine function are better inhibitors, with K(i) values of 1.5 x 10(-9) and 4.6 x 10(-10) M, respectively. The most active inhibitor of the N1 enzyme in the triazole series was selective for the N1 class and showed significantly less inhibition (K(i) = 2.6 mu M vs 0.07 mu M) of the free influenza virus neuraminidase-2 (N2). In addition, saturation transfer difference (STD) NMR spectroscopic studies with this compound and the VLPs show that the entire molecule forms contacts with residues in the active site. These data taken together support our proposed binding mode in which the active site and the adjoining 150-cavity are both occupied.

  DOI：

  10.1021/jm100822f

文献信息

• Compositions for preventing and/or treating degenerative disorders of the central nervous system and/or lysosomal storage disorders
  申请人：Amicus Therapeutics, Inc.

  公开号：US11358926B2

  公开（公告）日：2022-06-14

  The present invention provides novel compounds as well as compositions and methods using the same for preventing and/or treating degenerative disorders of the central nervous system and/or lysosomal storage disorders. In particular, the present invention provides methods for preventing and/or treating Parkinson's disease, Alzheimer's disease and/or Gaucher's disease.

  本发明提供了用于预防和/或治疗中枢神经系统退行性疾病和/或溶酶体贮积症的新型化合物以及使用这些化合物的组合物和方法。特别是，本发明提供了预防和/或治疗帕金森病、阿尔茨海默病和/或戈谢病的方法。
• [2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons
  作者：Gordon L. Lange、Craig C. Humber、Jeffrey M. Manthorpe

  DOI：10.1016/s0957-4166(02)00339-7

  日期：2002.7

  Three chiral 2,5-cyclohexadienone synthons bearing different chiral auxiliaries were examined in [2+2] photoadditions with cyclopentene. Regeneration of the 'masked' double bond in the adducts resulted in the preparation of optically active 5-4-6 adducts. The enantiomeric purity of each adduct was found to be >95% using comparative C-13 NMR analysis of the appropriate ketals. The asymmetry induced in the cycloaddition step of our methodology indicated that the facial selectivity was directly correlated to the degree of steric bulk of the chiral auxiliary oil the synthon. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Novel Compositions For Preventing And/Or Treating Degenerative Disorders Of The Central Nervous System And/Or Lysosomal Storage Disorders
  申请人：Amicus Therapeutics, Inc.

  公开号：US20200055810A1

  公开（公告）日：2020-02-20

  The present invention provides novel compounds as well as compositions and methods using the same for preventing and/or treating degenerative disorders of the central nervous system and/or lysosomal storage disorders. In particular, the present invention provides methods for preventing and/or treating Parkinson's disease, Alzheimer's disease and/or Gaucher's disease.
• Carbocycles Related to Oseltamivir as Influenza Virus Group-1-Specific Neuraminidase Inhibitors. Binding to N1 Enzymes in the Context of Virus-like Particles
  作者：Sankar Mohan、Sarah McAtamney、Thomas Haselhorst、Mark von Itzstein、Brian Mario Pinto

  DOI：10.1021/jm100822f

  日期：2010.10.28

  We report here the exploitation of the 150-cavity in the active sites of group-1 neuraminidases for the design of new triazole-containing carbocycles related to oseltamivir. Inhibition studies with virus-like particles (VLPs) containing the influenza virus neuraminidase-1 (NI) activity indicate that several candidates are inhibitors, with K(i) values in the 10(-5)-10(-8) M range. In contrast, a known candidate that preserves the free amino group and a new candidate containing a guanidine function are better inhibitors, with K(i) values of 1.5 x 10(-9) and 4.6 x 10(-10) M, respectively. The most active inhibitor of the N1 enzyme in the triazole series was selective for the N1 class and showed significantly less inhibition (K(i) = 2.6 mu M vs 0.07 mu M) of the free influenza virus neuraminidase-2 (N2). In addition, saturation transfer difference (STD) NMR spectroscopic studies with this compound and the VLPs show that the entire molecule forms contacts with residues in the active site. These data taken together support our proposed binding mode in which the active site and the adjoining 150-cavity are both occupied.
• A New Synthesis of Valienamine¹
  作者：Stanton H.-L. Kok、C. C. Lee、Tony K. M. Shing

  DOI：10.1021/jo010202t

  日期：2001.10.1