(2S,3R,4R)-1-methyl-2,3-isopropylidenedioxy-4-hydroxymethyl-1-pyrroline | 909703-52-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R)-1-methyl-2,3-isopropylidenedioxy-4-hydroxymethyl-1-pyrroline
• 英文别名: 1-methyl-2,3-O-isopropylidene-1,4-dideoxy-1,4-imino-1-N-dehydro-D-ribitol；(3S,4R,5R)-2-methyl-3,4-isopropylidenedioxy-5-hydroxymethyl-1-pyrroline；[(3aS,6R,6aR)-2,2,4-trimethyl-6,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-6-yl]methanol
• CAS: 909703-52-2
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: IGDMTPDMUXULRK-GJMOJQLCSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  278.2±40.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R)-1-methyl-2,3-isopropylidenedioxy-4-hydroxymethyl-1-pyrroline 在 palladium on activated charcoal 甲醇 、 氢气 、 溶剂黄146 作用下， 生成 ((3aR,4R,6R,6aS)-2,2,6-Trimethyl-5-nonyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-methanol
  参考文献：
  名称：

  exo-Imino to endo-Iminocyclitol Rearrangement. A General Route to Five-Membered Antiviral Azasugars

  摘要：

  A facile synthesis is reported for five-membered iminocyclitols which allows for variation in stereochemistry at all the chiral centers, diverse C-1- and N-substitution, and the potential for a three-component combinatorial process. The key step is inversion at the C-4 stereocenter (L-lyxo sugar -> D-ribono azasugar). The exo-imino to endo-iminocyclitol process was extended to the D-lyxo and the D- and L-hexose series. Some analogues were found to be more potent than N-butyl DNJ and N-nonyl DNJ in antiviral activity.

  DOI：

  10.1021/ol061071r
• 作为产物：
  描述：

  (3aR,6S,6aR)-6-(methanesulfonyl)tetrahydro-2,2,4-trimethylfuro[3,4-d]-1,3-dioxol-4-ol 在 氨 作用下， 以 乙醇 为溶剂， 以34%的产率得到(2S,3R,4R)-1-methyl-2,3-isopropylidenedioxy-4-hydroxymethyl-1-pyrroline
  参考文献：
  名称：

  exo-Imino to endo-Iminocyclitol Rearrangement. A General Route to Five-Membered Antiviral Azasugars

  摘要：

  A facile synthesis is reported for five-membered iminocyclitols which allows for variation in stereochemistry at all the chiral centers, diverse C-1- and N-substitution, and the potential for a three-component combinatorial process. The key step is inversion at the C-4 stereocenter (L-lyxo sugar -> D-ribono azasugar). The exo-imino to endo-iminocyclitol process was extended to the D-lyxo and the D- and L-hexose series. Some analogues were found to be more potent than N-butyl DNJ and N-nonyl DNJ in antiviral activity.

  DOI：

  10.1021/ol061071r

文献信息

• Combinatorial library approach to iminocyclitols with biological activity
  申请人：Moriarity M. Robert

  公开号：US20070088164A1

  公开（公告）日：2007-04-19

  A method of synthesizing stereochemically defined iminocyclitol comprises replacing an intraring oxygen in a cyclic sugar by an intraring imine to form an iminocyclitol, wherein said iminocyclitol has a defined stereochemical configuration different from a stereochemical configuration of the cyclic sugar. The invention also provides combinatorial libraries of iminocyclitol compounds, allowing for diverse C1 and N-substitution. In addition, provided are methods of treating viral infections with iminocyclitols compounds.

  合成立体化定义的亚胺环糖醇的方法包括通过在环糖中替换环内氧原子为环内亚胺来形成亚胺环糖醇，其中所述亚胺环糖醇具有与环糖不同的定义的立体化配置。该发明还提供了亚胺环糖醇化合物的组合库，允许多样的C1和N取代。此外，还提供了使用亚胺环糖醇化合物治疗病毒感染的方法。
• Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring
  作者：Venkata L.A. Malladi、Adam J. Sobczak、Tiffany M. Meyer、Dehua Pei、Stanislaw F. Wnuk

  DOI：10.1016/j.bmc.2011.07.043

  日期：2011.9

  LuxS (S-ribosylhomocysteinase) catalyzes the cleavage of the thioether linkage of S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione (DPD), the precursor to a small signaling molecule that mediates interspecies bacterial communication called autoinducer 2 (AI-2). Inhibitors of LuxS should interfere with bacterial interspecies communication and potentially provide a novel class of antibacterial agents. In this work, SRH analogues containing substitution of a nitrogen atom for the endocyclic oxygen as well as various deoxyriboses were synthesized and evaluated for LuxS inhibition. Two of the [4-aza] SRH analogues showed modest competitive inhibition (K-I similar to 40 mu M), while most of the others were inactive. One compound that contains a hemiaminal moiety exhibited time-dependent inhibition, consistent with enzyme-catalyzed ring opening and conversion into a more potent species (K-I* = 3.5 mu M). The structure-activity relationship of the designed inhibitors highlights the importance of both the homocysteine and ribose moieties for high-affinity binding to LuxS active site. (C) 2011 Elsevier Ltd. All rights reserved.
• <i>exo</i>-Imino to <i>endo</i>-Iminocyclitol Rearrangement. A General Route to Five-Membered Antiviral Azasugars
  作者：Robert M. Moriarty、Carmen I. Mitan、Norica Branzǎ-Nichita、Kenneth R. Phares、Damon Parrish

  DOI：10.1021/ol061071r

  日期：2006.8.1

  A facile synthesis is reported for five-membered iminocyclitols which allows for variation in stereochemistry at all the chiral centers, diverse C-1- and N-substitution, and the potential for a three-component combinatorial process. The key step is inversion at the C-4 stereocenter (L-lyxo sugar -> D-ribono azasugar). The exo-imino to endo-iminocyclitol process was extended to the D-lyxo and the D- and L-hexose series. Some analogues were found to be more potent than N-butyl DNJ and N-nonyl DNJ in antiviral activity.